how do I change careers?

by Alison Green on November 19, 2020

It’s the Thursday “ask the readers” — and this week we have two questions on a similar theme: changing careers. Here’s the first letter:

I daydream about doing “something else” — but I’m not sure if it’s just “grass is greener” or if I should plan to do something about it!

My job (software engineering manager) has lots of good qualities (so I’m quite spoilt in a way) –good pay and benefits, mostly reasonable hours, nice colleagues, intellectual challenge, good commute (and I am getting good feedback). But I’m not passionate about the work and I also get chronic stress migraines. I can’t blame that entirely on the job, but it’s definitely a contributing factor (and has been particularly bad this last month where I feel like I’ve lost most of my weekends stuck on the sofa, hence impetus to write this).

I’m passionate about property and have considered estate agency, becoming an architectural technician or similar, or maybe some sort of property management. (I would love to do property development but don’t currently have the capital or let’s be honest, the experience.) I have a mathematics degree from an elite university but no property (or even sales) experience.

Any of those would involve a significant pay cut, especially if I needed to retrain and then start in a very entry level role. How does one work out if it’ll be worth it? It seems a very plausible outcome that I retrain for a different career and it’s just differently stressful *and* not paid as well… so I’m feeling a bit stuck. I can’t really imagine being in my industry for another 30 odd years until I retire. Advice please!

And here’s the second letter:

I’m a 22-year veteran of public education — I teach high school. We’ll soon be going back to a combination of in-person and distance learning, and I’m beginning to realize that I may not be able to do this job anymore — as it is now, but possibly even when circumstances are more “normal.” Like many teachers, I don’t have the usual highs/successes that often balance out the lows/failures. Just lows right now.

I’m considering my options: drastically lowering my expectations of myself, therapy, taking a leave, quitting entirely.

I’ve been teaching for so long; I’m not even sure what jobs are out there. The few websites I’ve gone to (“Thinking of Quitting Teaching? Here’s Ideal Jobs for Former Teachers”) suggest jobs that either take prohibitively more education and money than I can invest, or are simply not currently viable because of COVID. I’ve started making a list of my skills and my strengths (and then probably buying your book), but I was wondering if your readers had suggestions for where to start when you’ve been doing something as long as I have and need to start fresh.

I’d love to hear from people who are former teachers, but any general advice on how to start from scratch would be appreciated.

Readers, what advice do you have on changing fields generally and for these two letter-writers specifically?

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{ 298 comments }

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  1. different seudonym*

    Current, not former, teacher, and no actionable advice, but I just wanted to tell LW 2 that I get it. I”m not as burnt as you, but plenty of fine colleagues are. This is just so bad, all the time.

    1. AnotherTeacher*

      Every teacher I know is at least lightly pondering leaving teaching. I am very concerned about the future of education in the US.

      1. AnotherTeacher*

        Sorry, hit send too soon:

        The toll this year has taken on teachers cannot be overestimated. I’m so glad the OP asked this question because I had the same one!

        1. Firecat*

          Yeah I everyone I know who teaches has quit this year. I’m not sure what education will look like if I have kids.

          Teaching shouldn’t be a field that chews through new hires like rat through the cheese cuboard.

      2. Sharrbe*

        Can confirm. Everyone is stressed out and demoralized. They’re having problems getting their students motivated, especially distance learners.

      3. Idril Celebrindal*

        Same for librarians in my experience. It seems like everyone is either thinking about a career change or wondering why they spent all that money on their degree.

      4. Humble Schoolmarm*

        Not just the US, sadly. I’m in a spot that has been close to ideal as far as covid for the past weeks, but the burnout throughout my staff is terrifying. I’ve cried every day this week and if one more overpaid ‘expert’ blabs about ‘doing it all for the kids’ I’m flipping some tables.

        Also parents out there, please, please, please be kind to your teachers. If we’re not communicating in the way and volume you prefer, it’s because we can’t. And for the love of all that’s holy, teach your kids some self-regulation and resilience when it comes to peer relationships and don’t expect the teachers to do it instead. (It’s been a drama filled week in grade 7)

      5. Flower necklace*

        I’m a teacher. I love teaching. It is truly amazing to watch my students grow and change. Before this year, I never thought I would ever want to stop teaching.

        But I hate teaching virtually so much. I don’t think there’s a safe alternative right now, but I miss the movement and the energy of the classroom. And the thought of leaving has crossed my mind. I know my coworkers (all dedicated, caring teachers) have thought about it, too.

      6. Rainbow Brite*

        I’m not in the US, and this is the first time in my teaching career I’ve almost wished I were. Schools where I live have been back full-time at full capacity since August (and no, I don’t live somewhere the virus is under control — in fact, the rest of the country is under near-complete lockdown). I had a position that ended in April, so I had a couple of weeks of virtual teaching and then I decided to pivot to freelance writing. The original plan was to supplement that with casual teaching days, but I’ve done that once since schools returned and I can’t say it made me keen to do more — no masks, no social distancing, no personal shields, no modification of instruction in terms of not having the whole class group right in front of teachers on the floor, etc. And there are cases in most schools right now, it just isn’t being reported.

    2. Kali*

      SO of a current teacher here, and if it weren’t for the number of years’ experience, he could have written that second letter (I could have written the first with a different industry, lol). He fell into teaching but ended up loving most of it – he has never spoken seriously about leaving until this year. He sleeps about 4 hours per night these days. Everyone at his school is the same, and everyone is wondering how long this can feasibly go on. For a career that’s known to be for long-haulers (past a few years’ experience), it’s frightening.

      OP, there are many skills that you can leverage. I know a former math teacher who is now a supply chain specialist. My SO has a hobby of building computers and knows so much about it that he could go into sales. (I actually know several teachers that went into sales – the organizational skills are already there, and you’ve been “selling” to kids for years!) There’s also an editor of textbooks, a yogi, and a curriculum specialist.

      1. Miss Characterized*

        So clear I’m not alone here. I didn’t think I was, but I’m so grateful for the support!

    3. Hydrangea McDuff*

      I left the classroom for school communications a few years ago after nearly 20 years teaching. It was a strange and diagonal move but I am so happy. I still feel like I am making a difference and serving kids. And I’m also keeping my certificate up to date in case I ever want to return.

      I had another short lived career in marketing before reaching so I knew I had other options. I loved teaching but it was time for a change. I did take a pay cut, but so far it has been an ok trade off for the work life balance.

    4. NYC Teacher*

      I also have no advice to offer, but you’re not alone in this LW #2. It’s my 2nd year at an elementary school in NYC, and I’m losing my mind trying to teach these kids through a screen.

      If you’ve always loved teaching before, I would try to hold on at least for this year. Every single teacher I work with is overworked and overwhelmed right now. We’re doing double duty on all of the most draining parts of teaching without the payoff of actually getting to interact and bond with the kids. It’s terrible for morale and unsustainable overall for the school system.

      If it helps, I try to remind myself that my lessons, even if not my personal best, are unequivocally better than whatever my students will end up with if a sub takes my place. If my 400 students and their families deserve grace and understanding, then I try to remind myself that I deserve it too. It’s not the most inspirational mantra I’ve ever had, but it’s what gets me through the day sometimes.

  2. MJ*

    LW 2: look into instructional design. Still working in education, but not directly teaching. It’s a great field, and Covid has only made instructional designers more in demand.

    1. Web Crawler*

      I don’t have advice, LW1, but as somebody else with chronic stress migraines, you have my sympathy. Whatever you do, I hope they clear up!

    2. Ms. Characterized*

      LW2 here (for little while until the day starts and I have to teach Zoom kids and room kids) — thanks.

      1. bleh*

        Both at once is pedagogically unsound. So sorry you (and all of us teaching Zoom & room simultaneously) have to make up the difference for bad covid policy and bad educational funding.

        1. Peter Piper Picked a Peck of Pickled Peppers*

          I have a question about this. Not in the US. My kids are back at school based on our lockdown levels, etc. Some families have opted to keep their kids at home because of individual risk factors, but those kids still need schooling, so the teachers are teaching in the classroom and “zooming” for the at-home kids. I realise this is difficult and not ideal for teachers or kids, but what are the alternatives when there is no budget for running separate classes?

          1. Beth Jacobs*

            I think you can run separate classes without extra cost, it’s just challenging logistically. We’ll be doing this for a while, so there’s no reason to stick to normal class groups. You can put 20 4th graders from the district into one zoom class regardless of their prior class or even school.

            1. Quinalla*

              Yes, this is what my school did, the teachers actually went on strike when the school board went back on their agreed way to do this and proposed zoom and in class simultaneous instruction with teacher’s liable for anything that happened on zoom. (They had a few other issues they were striking about too, but that was the main one, holy cow I am still so pissed at our school board!!!)

              I am beyond stressed with everything I have going on in my life, but I do not envy any teacher right now, ugh. My kids’ teachers have been doing a great job with what they have available, but distance learning sucks for K-12. I’m glad my kids are in elementary school where I feel like the impact is lessoned, though still significant, but I am supplementing their teaching a LOT and many parents are not able to do that. Can’t imagine having a middle schooler or high schooler during this…

          2. Kimmybear*

            Do you have enough kids staying home to combine classes at different schools into one “all virtual” class for that grade level? Our class is kids from 5 different schools with one completely online teacher. Not ideal but better than splitting the teacher’s attention between in-person and online at the same time

            1. Properlike*

              That would not be up to the teachers or even the schools. District administrations and Boards of Ed decide these things, and as we’re seeing across the US, many of them have no earthly clue what teaching involves as they set out their plans. For most teachers I know, it has been one long year of initiaties imposed downward with little to no input from teachers. If you’d put the teachers in charge, all this would’ve been taken care of long ago — but no one wants to hear the truth about what it would really take.

          3. PhysicsTeacher*

            The school district could have (and should have) grouped these kids into different classes based on the option they chose. So Zoom kids are in a class of ALL Zoom kids, and in-room kids are in a class of ALL in-room kids.

            Let’s say 1/3 of the students are staying home and my school district has 10 classes of 1st grade. They could run 3 classes of remote first grade and 7 classes in-person. No budgetary difference.

            1. uncivil servant*

              My experience is that class size has been capped to allow physical distancing, so they can’t put the same 25 kids in the same classroom, but you can have 15 kids present and 10 virtual.

              1. PhysicsTeacher*

                Okay, so make your virtual classes bigger and your in-person classes smaller.

                This is a problem that would still exist, and more so, with all students in-person. We’re in a pandemic. Something has to happen at the institutional level. There are situations where the school district just needs to figure it out without dumping everything on the teachers (and, like most districts, they’re not used to solving problems themselves without just dumping them on the teachers).

                1. Red*

                  District admin here….I may be out of touch too :) but I will say that it is soooo hard to find a version of this that everyone likes. Some of the teachers I work with much prefer simultaneous teaching to losing half their class. Others would prefer to rearrange classes. In some situations, based on the numbers, you’d have to reassign school placements to make it work. We have schools where almost all students want to be f2f and others that are the flip – and across all of them, large numbers of teachers who can’t return to face to face. We’ve spent a bunch of time working with teachers to try to develop options that serve them and students/families well and still have situations that are…. Not good. I think there are only better and worse options without substantial significant funding and any kind of thoughtful fed/state plan. Definitely some places just gave up on trying, but I’m not convinced there are any really easy solutions.

                2. just a random teacher*

                  I’m a district that is attempting a version of this (more complicated and less sensible than this, but that’s beyond the scope of this comment). As an online-only teacher, I have almost 300 students (secondary, so teaching multiple levels of one subject) and am so burnt out. Parents and students are constantly angry at me for not responding to messages from them quickly and for not grading things faster.

                  It’s not sustainable past a certain class size if you want to give kids actual feedback and anything but too-easy multiple choice quizzes. (I also have the “fun” of having curriculum that assumes that they got through all of last year’s standards last year and will be getting through all of this year’s standards this year and the reality that last spring was a mess, so demand for extra support/clarification/tutoring/revision attempts on assignments is high.)

                  I don’t think there is a solution that doesn’t involve vast sums of money. I have several ideas that might work, but they’d all be too expensive for my district or state to afford.

            2. Diahann Carroll*

              So Zoom kids are in a class of ALL Zoom kids, and in-room kids are in a class of ALL in-room kids.

              This is how my niece’s school district did it (she’s in virtual kindergarten and seems to love it).

          4. allathian*

            I’m not in the US, our numbers are getting worse, although they’re still pretty good compared to most of Europe or the US (incidence per 100,000 inhabitants is around 50), so my son’s at school in person. But his school had a case of some 25 kids and some teachers getting exposed to the virus. These people had to quarantine, but they rearranged the classes so that those teachers who were quarantining but healthy taught online classes for the kids in quarantine (and exceptionally kids who were at home recuperating from some other illness) and the teachers who weren’t in quarantine taught in-person. It seemed to work pretty well, even if some teachers in school had to teach two classes at once, in separate rooms. My son (5th grader) said that it worked well enough for two weeks, although he also said he wouldn’t want to do it for much longer than that.

        2. NotAnotherManager!*

          Yes, it is, and our school district is proposing it, which I am deeply unhappy about. Our kid is in the class with the homeroom teacher who is designated all virtual/all year, so I am hoping it doesn’t affect us. But I was steamed when I go the email because there are different strategies for online and in-person learning, and if the school district doesn’t realize that, it makes me wonder what sort of distance learning professional development they’ve been offering. I can’t imagine asking the teachers to do that – it’s not the right approach for them or the kids.

          My district has nearly 200K students, and the largest (public) university within the school district boundaries has an excellent instructional design/technology department. You’d think someone could make a call.

    3. Lyudie*

      Seconding this. I moved into ID a couple of years ago after 20+ years in writing. And even doing training of adults (corporate onboarding, for example) might suit you better than working with high schoolers.

      1. Kicking-k*

        Yeah. My mother transitioned to adult education (pre-college level) from high school and never regretted it. The learners weren’t that much older than highchoolers, often, but they had a choice about whether to be there and that helped a lot.

        1. Lyudie*

          Yeah, I have never taught kids but I imagine there’s a lot of overlap in the theory. There are certainly lots of resources available to get the basics of adult learning theory. You are totally right about choosing to be there being a big advantage with adults, honestly adults are probably easier to teach because there are factors around motivation and focus that are different than even high schoolers. I’ve heard from professors that students who return after being in the workforce are more self-motivated, better prepared, etc. because of the experience from meeting deadlines in a job and because they want to be there. Kids usually are only there because adults make them lol and it makes a big difference.

      2. CupcakeCounter*

        I was going to suggest corportage training and education.
        And I second the suggestion for adult ed – GED candidates can be some of the best students because most aren’t taking the opportunity for granted. My aunt is a teacher and she also said she got more fulfillment teaching a summer ESL and US history/civics classes to a groups of newly arrived immigrants and those going for their citizenship test than any other class.

        1. Properlike*

          Unfortunately, GED and ESL do not tend to pay living wages. A lot of that is adjunct-level at community colleges. Most adjuncts have to work at three or four different ones to make an actual living (with no benefits, no insurance, no job protection) and that’s IF you get classes/hours that semester.

      3. Elizabeth West*

        Yep. My CompTIA instructor just said in our weekly Zoom today that he loves his work. Also, I’ve been seeing quite a few job posts lately looking for people to set up LMS courses.

        The LMS jobs make me kinda wish I’d finished my master’s in Education. I didn’t want to teach kids, but I could have gone into this or corporate training.

    4. Norelle*

      Second This! And depending on what it is that you DO like about teaching, adult education in a business setting can pull from your favorite parts. Instructional Design, On-the-Job Training, Leadership and Career Development Training, HRD and Evaluation systems.
      In my position, I focused my Adult Education credentials into an Onboarding position – like a transition between HR functions and job training – my team works to host new hire orientation each week and also to connect new hires with the different HR/Benefits/Payroll/IT teams during their first couple weeks.

    5. GothicBee*

      This is a really good suggestion. I worked at a university that had a large online presence as an editor for the instructional design department, and it was a great field, though I didn’t stay long because of the management in that particular department. Since it was at a university, you could get a degree as part of the education benefit, so that could potentially be something to look for if you would be interested in getting another degree if it was paid for by your employer.

    6. A Red Panda*

      Yes, this. I’m a former teacher who moved into an ID role this summer at a university and I love it. I’m able to use my education skills without the classroom stress. Besides higher ed, you could check with local nonprofits (I was also offered a Training Coordinator role with the library system in my county) and the private sector (might look at Corporate Trainer roles as well as ID). If you have a military base in your area, there may also be contract opportunities for civilians–another ID in my office did that with our local AF base for 8 years.

      1. K.*

        How do you go about transitioning from education to instructional design? I am a high school teacher (with a PhD. in my subject area) and dual-credit instructor who has written all of my own curriculum, curriculum for my school’s department, and also been hired by outside organizations to write online 9-12 curriculum, so I have what seems to me is relevant experience. So far when I apply for instructional design jobs, I have not gotten any responses. Do you need to get another degree? Contacts in the industry? Start at a more junior level? (If so, what would those junior-level roles be called?) Thank you!

        1. Lyudie*

          K, you might want to check out ATD (Association for Talent Development). Even without being a member, there are a lot of resources and they have good classes (though they are not cheap). I started by taking some classes through LinkedIn Learning, then graduate-level courses online (I’m now in a master’s program but took several classes as a non-degree student). I doubt you need to get another degree but looking into some specific classes on adult learning theory and instructional design might be helpful. In particular see if you can find something about ADDIE, which is a very common model used for creating training. There is probably a lot of overlap between what you already know but having some of those specific buzzwords might help you. Good luck <3

          1. anon e. miss*

            seconded! it’s legit hard to hire an instructional designer or technologist right now in my area because they’ve all been snapped up!

            1. anon e. miss*

              ack nested in the wrong place, sorry. But since I’m here, i was just on a hiring committee for a new ID and demonstrating the theoretical knowledge to back up the practical experience, knowledge of trends in the field, best practices, etc. was the biggest factor for us.

        2. JobHunter*

          Search the careers portals of professional societies for instructional design positions, too. Some associations have a designated position to lead the membership training or certification courses.

        3. Anhaga*

          K., I’m another former educator (I was a college-level instructor) who was making a move into instructional design, and what I did was to wrangle enough money to do an instructional design series of courses through edX (the University College at the University of Maryland course). It was great and helped me fill in my knowledge gaps in learning theory and models of instructional design, as well as prompting me to start learning some course authoring software (Storyline360) and building a portfolio. I was getting interviews for ID jobs after completing that additional training, though I eventually ended up going in a totally different direction where I still use those skills along with my main line of work, digital accessibility.

        4. NotAnotherManager!*

          I am still on the job postings listserv for the program where I got my M.Ed, and most of the postings are looking for experience with content creation tools like Captivate, Articulate, Storyline, or Camtasia, storyboarding, and accessibility compliance (section 508/ADA). LinkedIn Learning (formerly Lynda) may have training/exercise files for some of these tools, and your library may have a subscription.

          You may want to look and see if your local universities have an ID or learning technologies certificate program. The one closest to me has a 15-credit certificate that covers the theory of ID, methods of content delivery, and practical classes in accessibility in course content design and specific software.

      2. Daria*

        Seconding instructional design. But you could also look at ed tech companies that are focused on K-12 education. For many roles (like teacher trainers, liaisons with school staff, and content developers) your teaching experience would be a huge asset. I’m thinking of companies like Better Lesson, Panorama Education, Curriculum Associates, or IXL learning.

    7. _ID_*

      I’m an Instructional Designer and I agree – this is a good fit for recovering teachers! I have my M.A. but there are easier ways to get started. Look at the ATD website – Association for Talent Development. They have great options to get started. Good luck!

    8. Syl*

      I second this! I am a former teacher that transitioned to ID and I love it. Way less stress but still get to be creative and in education. Bonus: even with Covid, I get daily calls/emails from recruiters so jobs are plentiful.

      1. Ms LikesWork*

        Do you mind if I ask where to find the jobs? I have classroom teaching and instructional design/ e-learning experience at my current job and want to transition to that being my full time gig bc I love it!

    9. Music Teacher Here*

      So, I am a music teacher and I’ve also been considering that maybe K-12 teaching isn’t for me for forever. But the career choices I always see as options are things like Instructional Design and Curriculum type jobs…which I don’t think I would be hired for considering that I don’t have a background in elementary or secondary general ed.

      Any ideas for us non-classroom teachers?? (And please don’t say teach private lessons or play for money…that’s a side gig. Would not come anywhere near my current income and would have no benefits, to boot.)

      1. FORMER Music Teacher Here!*

        For a music teacher, I wouldn’t write off instructional design! You have the background in HOW students learn, and even if you don’t have the same type of curriculum as classroom teachers, you do have training and experience in building knowledge in your classes. At a really high level, the job of an instructional designer is to take information from the experts and put it into a format that works for students. As a music teacher, you would likely bring ideas to the table that other teachers wouldn’t!

        I ended up working in university academic records. I’m responsible for reviewing for degree clearance, a lot of staff training, and project management-type things. My office has several former teachers who have found their home in higher ed. I love the exposure to education from another angle, and I’ve crafted my role to include a lot of training. My department loves me for it, because I’ve created clearer documentation and I’m great at training presentations. I also do a ton of outreach to train other departments in our systems, so my office has built some great relationships throughout the university.

        Teachers so often get stuck thinking they ONLY know how to teach, but it’s not true at all! Everything we do in the classroom relates to working on an office, and so many offices are in desperate need of people who are good at understanding a technical process and breaking it down into the important stuff in relatable ways.

        1. Music Teacher Here*

          Thank you so much for your insightful reply! You’re right- I am exceptionally good at breaking down something really technical. I teach eight and nine year olds how to play instruments, for goodness sake! You can’t be good at that without being able to understand and break down the process and anticipate where they could go wrong. You got me thinking. Thanks! :)

        2. Gloucesterina*

          I might be too late to your discussion of university academic records roles – would this be a plausible transition for someone with a fairly jack-of-all-non-highly-technical-trades background in nonprofit membership-based organizations (by this I mean, a professional association with a membership database, and experience that includes things ranging from maintaining member records using different membership database systems to managing accreditation of the organization’s programming by external accrediting bodies, which has a project-managery component).

          I am not sure if I am using any recognizable general terminology here, apologies!

      2. Accidental Itenerate Teacher*

        You can check if any local museums have education programs – before I got my current job (teaching/writing curriculum for professional development type classes) I worked for a local museum doing educational programs when schools visited for field trips.

        You can also look at programs that do continuing or professional education type things. My last few jobs have specificly mentioned that they weighted teaching experience higher than industry experience because it was much easier to teach me the material than it was to teach someone how to teach.

        For background – I have no experience/education as a elementaty/secondary/any school type teacher. I’ve just wound up with alot of nontraditional teaching or teaching adjacent jobs.

        1. Music Teacher Here*

          My local museums are the Smithsonian Institution and they, as far as I know, usually want folks with museum adjacent degrees :)

          Thanks for the ideas! I appreciate it!

          1. NotAnotherManager!*

            And the competition for those jobs is intense! I looked into it when I did my instructional design degree, and I think the Smithsonians basically have people lining up to work for less than entry-level staffers on the Hill.

        1. Music Teacher Here*

          I don’t think I would enjoy Music Therapy, (plus I don’t have the money to go back to school) but thank you!

      4. ObserverCN*

        Music Teacher Here — I’m not sure how old you are, but there are jobs in the military for musicians. (I had a friend who played in the West Point Band and made a pretty good living.)

    10. pandora366*

      LW2 – I am former teacher headed towards instructional design/education administration. :) I am in Canada though so not sure about climate in USA, but demand is great and I work at a nonprofit managing learners and instructors on Zoom, GoToWebinar etc. I started off doing administrative work at nonprofits that offer continuing education so translate all the community service/field trips you did as project management, and see if you did any admin work eg. student records, receipts, reports to convince them that you did assessment, evaluation and certification work. Toastmasters also helped me in getting that part done. Life is awesome here and despite less holidays, I enjoy my 9-5!

    11. NotAnotherManager!*

      I have an master’s in instructional design, and it is super cool and is a growing field due to the proliferation of online degrees, MOOCs, and sites like Lynda (LinkedIn Learning), Khan Academy type sites, etc. Most of my classmates worked either in K-12 schools and wanted to shift out of the classroom or worked for a government contractor (because the government uses a lot of computer-based learning). It did involve a number of education theory and research classes (and the teachers definitely had a leg up on me and the other non-educator folks in terms of knowledge and practical experience).

      I do not work in instructional design because the paycut from what I do now was too much for this stage of my life, but it’s what I’m hoping to do as my second career when I can afford to take the improved work/life balance for the dollars. I really enjoy the process and have used it to do a few volunteer/hobby projects.

    12. Sleepytime Tea*

      THIS is a great idea. I would also add being a trainer in a learning and development department for a company. If you still enjoy the teaching aspect of things, that is. But the hours are wildly better, as is the pay. Significantly less stress. I worked with trainers who trained electrical technicians in things like new company software, but had no background in that area – it wasn’t needed specifically. They needed good teachers, and they would hire people and give them the resources they needed by training them on the software (or getting the trained by the vendor) and then they would train the technicians on it.

        1. NotAnotherManager!*

          Trainer, Corporate Educator, Learning Coach, Content Delivery Technician/Specialist – all sorts. Start with a search for training in the job description on Indeed or Monster or something and you’ll get a sense of what titles are being used most often. (I work in an industry without standardized titling, and I have to do this once a year to make sure I’m up on current titles and am posting new positions in a way that will get them clicked on.)

    13. Skeeder Jones*

      This was going to be my suggestion as well, or learning and development in general. It uses the same skills just on a different age group.

    14. DBOHGA*

      I too am leaving education after 10 years and can recommend two trainings that don’t require you to go back to school, but are an investment Idol Academy and elearning launch. I am in both and have learned Ssooooo much.

  3. Working Hypothesis*

    I needed to change careers radically at midlife, and choose to go back to school, but not in the way most people probably think about it. I looked at professions which required licensing — especially in the health care range because there’s almost always work in anything health care related and because there’s a wide range of state-licensed professions in that category.

    The thing about state-licensed positions is that, for the most part, to get an introductory level job in one, *all* you need is your license and the ability to show by hands-on examination what you can do. An EMT, a massage therapist, a hairdresser, a phlebotomist, an X-ray technician… all those are just the tip of the iceberg in professions that can be won with a state license and the ability to pass a “hands-on interview,” or a practical exam by your prospective employer.

    Most of these aren’t things you’d want to start doing right now because of the pandemic, but with two vaccines ready to start rolling as early as December and training periods ranging from a few months to two years depending on the profession, that may well not be a concern when you’re ready to look for a job after training. And a good trade school will not only teach you to pass the licensing exam but help you connect with employers in their network and continue to support you in finding work, even long after you graduate.

    Can any given former teacher or techie find something in the range of licensed trades which will suit them? Maybe and maybe not, but I switched from a white-collar field to licensed massage therapy and have never been happier. It might be worth exploring.

    1. Beth*

      Not to sound like a Debbie Downer — but for any career move of that type, it’s vital to make sure that there really is a demand for the target occupation, in your area, and that the demand is ongoing.

      I used to live in a place where LMTs were already ten a penny, and there were three schools in the area turning out a hundred brand new LMTs every year. Nobody could make a living as one unless they were incredibly good at business, and also good at selling themselves in a saturated market. And the schools did not provide suggestions of where else in the country they might need to move to in order to get a job (not that the typical new licensee was likely to want to move to another part of the country).

      1. Sola Lingua Bona Lingua Mortua Est*

        This describes programmers in my market. It hard not to steer others away when they look to me for advice on the career.

      2. anon24*

        Also make sure the field you are going into actually pays well. I’m an EMT, I love what I do, its a certification that’s easy to get and there’s a massive nationwide shortage so jobs are easy to come by, but there’s a reason for that. It’s not an easy job in the best of times and pay is terrible – the national average is around $29,900 a year according to zip recruiter. Probably not a change many are going to want to make mid-career.

        1. #nonprofitlife*

          My partner (former EMT) calls it making $15 an hour the hard way. While proud of what he did, he definitely has some residual trauma from the work itself.

  4. OrigCassandra*

    I strongly recommend the work of Herminia Ibarra, especially Working Identity (2003). In contrast to many career-management books, which assume you have to figure everything out to the ninth decimal place before you dare type the first letter into your new résumé, Ibarra plants her flag on “try things and let them change you and your sense of self.” She has also published shorter pieces in Harvard Business Review and elsewhere.

    Even if you don’t completely subscribe to this idea, I found it something of a relief at the time I read it, a time when (like both OPs) I wasn’t sure about the first decimal place, much less the ninth. I think it also better fits the peripatetic career directions common today than the like of the parachute books.

    Good luck, OPs. OP2, thank you for your dedication to your work, and don’t let anyone guilt-trip you about changing careers.

      1. OrigCassandra*

        You’re welcome, and thank you back! I hadn’t seen that, and it’s a very good summary of Working Identity.

  5. Vanessa*

    LW1 – you seem to be in a fairly comfortable position, can you delve into other business opportunities on the side? Take an architecture class, study for and take your realtors license? That sort of thing. Typically you’ll get a feel for if you have an aptitude just by doing the basics, and all the while you’ll be making your current high salary.

    1. MK*

      That’s a good idea, as long as you also try to find out about the everyday reality of any profession you choose. In my own field, I have known people who loved the study of law and/or law school, but detested working as a lawyer/notary/prosecutor/judge/any practical application of law.

      1. Elizabeth I*

        Networking can be an especially helpful component early on in a career transition for this reason – to learn before its’ too late whether you would really like this new role or not.

        After doing some basic research about your target role for context, reach out to a few people who do that kind of work (I have found LinkedIn very helpful for this). Tell them you are looking to transition into the industry/role they are in, and ask if they would be willing to answer 3-5 questions for you over a quick phone call or email. Most people are flattered to be asked and will say yes, in my experience.

        Come to the call/email with intelligent, thoughtful questions – not the kind of questions a simply google search could answer for you (otherwise, you’re just wasting their time). Ask things like: What are the unexpected bests and worsts of this job? What are qualities that make a candidate stand out for this kind of role – what qualities are hiring managers looking for that are hardest to find? You can also ask their advice on what someone with your experience could do to break into this new career. Also ask whether they have any other recommendations for you (such as books/blogs to read, other people to talk to, etc) – when I’ve asked this question, people have often volunteered to introduce me to others in the industry, which has led to more networking with industry people – and sometimes directly to job opportunities. (But don’t ever directly ask for a job in these networking conversations (it comes across as tacky) – just ask for their advice. That leaves it open for them to suggest that you apply for a job at their company or to recommend that you talk to their friend who is hiring, etc).

        Then, assuming you are still interested in transitioning to this role based on the new information you’ve gathered, you can tailor your cover letter and resume based on what you learned from the industry-knowledgeable sources you talked to. For example, if you know that hiring managers are especially looking for people with x and y qualities which are hard to find, you can demonstrate how your previous career gives you excellent transferable skills in those areas – or seek out training/experience in those areas to become a valuable candidate.

    2. e*

      This is what I did! I transitioned from an investment management job into software development by learning and volunteering in my free time. In my case this was doubly helpful because one of the key signs for me that I wasn’t cut out for investment management was that I had a hard time bringing myself to proactively study things on my own time, and doing things on the side kind of forces you into that situation.

      This may seem hard because you are spending your weekends on the sofa recovering from stress! Especially in March/April of this year, I was working probably 70 hours a week and also just miserable. Quite frankly, I did not accomplish very much on my transition during this period, and the whole process took maybe a year. I got through it by setting myself a personal timeline at the end of which I was just going to quit and go to grad school, which was a) something I felt confident in because of all the time I’d spent learning on the side, and b) something I was in a financial position to consider, because I had been setting money aside for some sort of grad school for some time and also had gotten married to someone supportive. Grad school is probably not… super helpful for getting into property management, but you can (and I did at various points) sub in the concept of boot camps, certifications, and just taking time off and thinking about making the career change as my full time job.

    3. Cascadia*

      A teacher friend of mine got her real estate license last year in online/evening classes just because she was really interested in it. She continues to teach, but has gotten the license now and is with a brokerage. Since she has summers off she started doing her first sales and has a great client base of everyone in our school. I’m not sure what her long term goals are for it, but it definitely seems do-able to get the license and get your feet wet while still working your other job.

      1. Glitsy Gus*

        Granted this was *mumble mumble* years ago, but when I was a kid my dad, who’s a teacher, got his real estate license and did exactly this. He worked part time with a friend who owned her own agency and worked very part time during the school year and more over the summer. That would be a good option to give it a shot and see if it’s something you want. Or see if there is an agency that could use a little help over the weekends for someone in the process of studying for their license. I know in my area markets are really active right now, so it is very possible agencies could use a bit of part time help.

    4. SpringIsForPlanting!*

      Seconding this… for what you’re looking at, you might want to try becoming a small-time landlord; in many locations it’s not *too* hard for a professional who’s financially comfortable to pick up a single rental property. That can be a way to gain low-key experience with real estate, property management, and property development all at once. Especially if you’re able to pick up something at foreclosure/tax auction/short sale.

    5. LW1 here*

      Thank you! This is a good idea (I’d looked into architecture qualifications but real estate looks maybe a bit more tractable) and something I will look into. I do struggle with motivation to do stuff after a long week but with the pandemic I’m not doing lots else and it would be good to have a focus. Plus I think I’d actually enjoy it (and as you say – I should definitely find out sooner rather than later if I don’t :p)

  6. 3DogNight*

    Teacher–I have only 1 semester of college education, and I have a great career in Tech Sales. The market may not be amazing right now, but that will likely change in about 6 months, with the vaccine, slow down of the pandemic, and the elections being behind us. There really aren’t any pre-requisites for sales, other than being personable, and passionate about your products. The product knowledge will be taught to you by your employer. At the larger companies you then have a jillion options for career paths, including education! It is genuinely rewarding work at good organizations.
    All of that to say, more education is not a requirement to change careers. Good luck!

  7. old curmudgeon*

    My spouse was a high-school teacher for the first ten years of his professional career. When he decided that he had to make a change, the single most important thing he did that helped him decide on his next direction was to go to a place called Johnson O’Connor for a two-day battery of aptitude tests.

    J-O’C has been doing aptitude testing for about a century now, which means that they have a huge wealth of data about what aptitudes people have and how they feel about their careers. For example, if people with aptitudes X, Y and Z love being a business analyst but hate being a call-center worker, that establishes a probability that if you have X, Y and Z in your aptitudes, you probably won’t want to pursue a call-center job.

    The tests they perform range from hand-eye coordination (picking up tiny pins with your fingers and with tweezers) to inductive reasoning, logic and memory. One test I recall my spouse describing was that the tester folded up a piece of paper in a certain way, then asked “If I poke a hole through all these layers and then unfold the paper, where would the holes appear on the unfolded page?”

    At the end of the process, there was a lengthy interview where the person from J-O’C went through every single aptitude that was tested, discussed where the person fell in the range of all the hundreds of thousands of people they’ve ever tested for that aptitude, and then, most importantly, discussed the different career types that would (and would not) play well to the person’s strongest aptitudes. That was the point when my spouse found out that one reason he hated grading his students’ work was that he scored in the lowest 10 percentile for graphoria (clerical speed and accuracy) of everyone they had ever tested for it. (That, by the way, is also why I maintain the checkbook in our family!)

    Does that mean that everyone who goes through aptitude testing automatically winds up in a field they love? Of course not! But the process does give them insights into the types of careers that will play to their strengths, and why other types of careers might not be a great choice.

    Good luck to both OPs – I hope you find something that is more rewarding than your current gigs!

    1. old curmudgeon*

      Obligatory post script – No, I do not work for J-O’C, nor for any other aptitude testing place.

      Also, it’s not cheap, which I recognize is a barrier for many. In my spouse’s case, the cost was worthwhile in terms of what he got out of it, but it’s a pretty spendy thing to do.

    3. Guacamole Bob*

      My grandfather was a big believer in Johnson O’Connor and paid for me to be tested in my early 20’s. I wasn’t really ready to do the work of finding a real career path and getting the training to get there, so I basically forgot about it.

      I found the report several years later when packing for a move to grad school – to discover that I was going to school for a job that they had identified as a top fit for me. And I love it.

      One thing I remember is that they broke down mathematical ability into a few different pieces. I scored very highly on a couple of them, but no better than average on the kind of number fluency that makes it easy to do things like calculate restaurant tips in your head. As a math major who was always being asked to do that kind of math by others who expected me to be good at it, this was a small but very valuable “aha” moment.

      1. Guacamole Bob*

        I should add that when I was finally ready to figure out my career stuff in my late 20’s, the book The Pathfinder helped me a lot. You have to actually do the exercises, but it was helpful framing for all the different aspects that go into a job. For example, some people know they want to be an accountant, but they don’t much care what kind of organization they work for. Others are happy doing a wider variety of jobs as long as they’re working for, say, an organization focused on the environment or the natural world. Some people like being at a desk all day, some want to be out in the field, etc.

        For OP2 in particular – teaching is very different than many office jobs. You’re on your feet much of the day, forming meaningful relationships with dozens if not hundreds of people you see daily, doing a ton of clerical work (from what I hear from my teacher friends about grading and grade database systems), and have very little control over your schedule. When setting out to find a job outside the field, it might help to walk through a guide like The Pathfinder to help you think about what characteristics a job might need to have to be a good fit for you.

        Might be helpful for OP1, too. A real estate agent has a very different day to day than a property manager, and both are very different than a job in an architecture office. If you do decide to take the leap and the pay cut to change careers, the more work you can do ahead of time to be confident it will be a good fit, the better.

    5. OtterB*

      I can also recommend an organization called Career Vision in the Chicago area (although working remotely now) that does a similar testing. Full disclosure: I worked in their research department years ago but don’t have an ongoing relationship with them. Both my husband and daughter went through testing and found it helpful. The thing that I remember from going through the testing as a new employee is that I’d always wondered why I test highly on mechanical aptitude but am unable to fix things … turned out I have very low finger dexterity.

      http://www.careervision.org

    7. Peonies*

      I think it’s the most useful comment Ive ever read on the internet.
      I didnt know that I needed that.

      Thank you so much. Beyond grateful

  8. Peter Piper Picked a Peck of Pickled Peppers*

    OP1, have you considered looking for a software engineering job in the property sector?

    Pros:
    – make contacts
    – get industry experience
    – see what it’s actually like to work in the industry and what the different roles look like
    – possibly make a transition within your new company to a more property focused role

    Cons
    – if you’ve started to hate software development, you might still hate doing it for the property sector

    You could make this type of move with your current experience and maybe a short course that would give you an advantage over other “vanilla” software engineers.

    1. e*

      Seconding this. I work at a real estate company on the software side, and one of the things I’ve found very striking is how invested management has been in keeping employees happy and finding the right roles for them, even across departments. I know someone that’s gone from analytics to finance, and we just brought someone over from acquisitions to investments, and management has moved responsibilities between groups based on what individual people have been interested in picking up. That obviously comes down to company culture, but I guess my point is that it’s something possible within this industry – in my previous roles in investment management, that kind of transition was pretty unimaginable between groups.

      1. Donna Meagle*

        I was coming to comment many of the same points.

        Commercial Real Estate has many opportunities for things like product development within different sub-markets and sub-specialties. For example, do you want to manage accounts? Help occupiers assess and manage their utility load and costs? Help owners track waste management? Work on moves and mergers? Occupancy planning?

        There is so much you can do, and many of the CRE firms are large, global companies with some resources for employee development and retention that you might not find in other sectors.

    2. TiffIf*

      I was going to say this! I work as a quality analyst for software that is used in the property management, real estate data (similar to MLS data), construction and property insurance (personal and commercial lines) industries.

    3. Peter Piper Picked a Peck of Pickled Peppers*

      Just wanted to add that my suggestion for a short course was a property related course. Glad to see that others have the same idea!

    4. Anhaga*

      Oooh, this is a good suggestion, because there *are* software companies that specialize in this! We have one locally that I myself was eyeing as a place I might want a job–they have a good reputation for being a sane, employee-friendly workplace.

      Honestly, this whole idea of “look for something in your current field that is related to your ambition” was how I started making my career transition. I was moving out of higher ed and focused on looking for instructional design positions. I ended up making a bigger leap (into a specialized type of QA for websites and apps), but the smaller initial steps toward ID got me started.

    5. Generic Name*

      This is a great idea. I’m also wondering if you hate managing people (it’s so stressful!) and would be happy going back to an individual contributor role, or if it’s the whole industry.

      1. LW1 here*

        I don’t hate managing people actually – I think the worst thing about my job is that it can feel a bit relentless. There’s always things that are broken or that someone is unhappy about and it can be disheartening to feel like you’re putting in a lot of effort and it’s not getting anywhere. But my positivity varies ;)

        1. Cc*

          Product manager here, so in same field but adjacent role. I’ve found the book “How to have a good day” really helpful to recharacterize to myself how much control I have over my schedule and feeling happier about what was accomplished each day. My point is that possibly the need is to adjust your relationship with work, not necessarily that you need to change fields or careers.

    6. LW1 here*

      Definitely a good idea :) my experience is fairly niche (specifically lots of the property related companies I can think of run websites and I know basically nothing about web development) but ya know, I could learn so that’s probably really just my imposter syndrome talking :)

  9. Pink Dahlia*

    Going into property management to reduce stress would be like going into restaurant ownership to support fasting.

    2. bunniferous*

      This. What I would recommend to the op is-what exactly about these types of jobs seem appealing to you? Is it human interaction, or something else? The answer to THAT question would give a better idea of the next step to take.

      1. LW1 here*

        It’s literally the property, I find it super interesting. I am totally aware that it’s a high stress job and that my job is probably considered not that high stress by some (!) so that’s a strong factor against.

        I think if I was back at school choosing I would try to be an architect, but in my country at least that’s like a 7 year degree and starting salaries are like half of what I earn now (or less). So that just doesn’t really feel obtainable.

    3. violet04*

      The term “property management” caught my eye because my husband is currently looking for jobs in this area. He has commercial facility management experience and applied for a job for an apartment management company. If this is the type of work OP is looking into, then be prepared to take a pay cut and be on call.

      For this specific job, the work would entail having a normal 8-5 workday, but he would be on call 24/7 one week a month. He was told he would definitely get called multiple times. He had to take a test to gauge his knowledge of basic electronics, HVAC, plumbing, etc. The pay is in the $18-20 range.

      I work in software development (not management) and wouldn’t trade this job for anything. I can WFH, have a flexible work schedule and the salary to pursue my hobbies in my off time.

  10. Alton Brown's Evil Twin*

    OP1 – you say you’re “passionate about property”. So what concrete things have you done to explore or satisfy that passion? You have to do more than armchair stuff.

    I was in engineering, and after a number of personal and professional crises (and the dotcom crash + 9/11), I turned my wine hobby into a 5-year career in wine retail (I eventually went back to engineering). But I had been a serious student of wine for some time – my parents had a hobby vineyard when I was a kid. And it took a bunch of fits and starts before I was at all settled, and even then it was still a significant step back in income. So don’t go into a career change expecting it to be trouble-free.

    Since you say you have reasonable hours, have you considered getting a real estate sales license and working part-time in the field while you see if it appeals to you? You can also do part-time property management – plenty of people who own just a handful of rental properties could use somebody to do some of the grunt work, like managing applications and credit checks, doing cleanup and minor repairs when the property is vacant, etc. As an immediate action item, I’d suggest you go to every open house you can and taken careful notes of what you think the agent & owner have done well to sell the property, and what they could improve on.

  11. Aly_b*

    For LW1: if what you are interested in is property development, there are lots of large developers who hire people – project managers or coordinators, various kinds of admin and executive staff, etc. It’s not just the money person that does everything. So there might be something there that’s more of a job type job. Some of the developers are starting to get smarter about computers and might see some value in a manager who knows more deeply what software can do. However: working for a developer is a somewhat high stress environment, at least where I live. I would say likely more so than software, though perhaps not depending on where you work. Architectural technologist, likewise, is a lot of hours and some pretty hairy deadlines at least at first. I’m sure these depend on the area, the individual company, etc, but would be worth asking around about locally before you dive in. There are definitely fun parts of the construction industry and I do enjoy working in my piece of it (sustainability stuff) but it is deadline driven and can definitely be stressful.

  12. Colette*

    For the first letter, I have many questions!
    You say you aren’t passionate about the work – but software engineering is a big field. Would you be happier doing a similar job in a property-related environment (i.e. software used to take/display pictures of home for sale, mapping software, architectural software, etc.)?
    Were you ever passionate about your current field? If so, is there something you can do to get that back – e.g. a new job?
    What kind of property-related skills do you have? (Can you do basic repairs, such as fixing a leaking tap or replacing a light? Have you done any renovation work? Have you given thought to floor plans and traffic patterns, and can you recognize issues when you see them?)
    Are you willing to make the lifestyle changes you’d have to make to start over in a field that pays either less or more erratically?
    What kind of skills do you think you’d need in the paths you’re interested in? How do they map to the skills you already have?

    1. Keyboard Jockey*

      I came here to say something similar! Presuming you didn’t get into software to be a manager, could it be the management piece that’s burning you out, and not the actual field?

      Also, managing developers is very different across different kinds of organizations (say, matrixed orgs vs. siloed ones). It could be that your current organization isn’t a great fit for your style or your personality

    2. LW1 here*

      All good questions. I don’t think I’ve ever been passionate about my job, it was a second career choice after physical injury forced me out of the first. I don’t *dislike* it though and I do value all of the good things I mentioned – I’m certainly not planning to quit tomorrow. I just don’t know if I want to be here for a long time. I don’t think the company is the problem and (unusually?) I don’t really dislike management.

      I (slightly embarrassingly?) basically dream in floor plans and yes, I can recognise problems with them. Architecture is a big draw but there’s a huge training cost to get there (though tbh I would be quite happy designing residential extensions for the rest of my life, so maybe I should think harder about taking the plunge.). I’ve only done renovation work on my own house and don’t have a bunch of practical skills tbh, but I could tell you a bunch about planning permission and building regs.

      1. Designer Girl*

        Hey, as an architect, one thing I recommend looking into is what the daily job of an architect entails, and how that is impacted by the job market/types of architects needed in your area. It will depend a lot on the company, but in many jobs, it is not uncommon to be doing a lot of things that they never mention or teach in architecture school, and that many people do not associate with the profession. In my job as an architect, I actually spend about 80% of my work time running projects, meetings, speaking with clients and contractors, reviewing work and addressing questions by the team, doing paperwork required to get and keep a project moving. I do get to do a bit of drawing and designing, but it is maybe 10-20% of what I do.

        That is not to say architecture isn’t great! I love architecture and have never imagined doing anything else, but before investing a huge amount of time and money into it, I recommend looking into what working as an architect entails, to make sure you will enjoy all of the job. Best of luck!

  13. archangelsgirl*

    For the 22 year veteran of education: You have both my congratulations and my sympathy and my complete awe at what you do. I taught for 18 years, and then quit. During the last year I taught, I made a list of what I loved about teaching and what wasn’t working for me anymore. I discovered, to my surprise, that what I was done with most was all the people whose emotions and expectations I had to manage. I’m not even talking about the kids. It was mostly the other myriad adult stakeholders.

    For me, most of the jobs on those, “what should ex-teachers do,” lists are very people-oriented, but I discovered that I’m … not that anymore. So I work from home. I love the peace and quiet. I take breaks to drink coffee, throw dinner in the oven, and read Ask a Manager. I’m not getting rich, but the peace of mind is so worth it.

    My partner also quit teaching this year after 25 years. What HE didn’t like about teaching was the conflict between doing what was good for kids (like giving them work they could do and be successful at) versus all the testing mandates. The final straw of course was ‘rona. BUT he’s very social. So he works retail now. Also, not getting rich, but happy.

    I found that when I hit 50, I was empowered to say, “No thank you,” to something that I found actually, quite frankly, impossible. Education is like that these days.

    All that to say … maybe make that list I suggested. This list can’t be done in an afternoon. It takes a few months. Also, I found it helpful to do some online aptitude tests. I just did freebies and after awhile, they all began to recommend sort of a top 10 list. Finally, maybe don’t rely on what Internet articles say teachers might like to do or be good at. I tried that at first, but the actual interest inventories helped me a lot more.

    Good luck! I really feel your pain. It’s hard to jump off, but you’ll make it. Think more about what YOU would like to do than what “a teacher” would like to do. Know yourself. That’s probably the best advice for any kind of career change.

    1. Ms. Characterized*

      Thanks for your thoughtful response. I’m glad you’re both doing well. We, too want to be happy, not rich — but we also really dig health insurance, and the years I’ve paid into the retirement fund…well, it’s obvious I need to have a conversation with HR, too, to see what my options are. Better to make that list knowing more of the variables.

      1. ThatOnePlease*

        Would administration be an option? I know someone who transitioned from being a college professor to curriculum director at a middle school, and they’re much happier.

        1. Miss Characterized*

          For me, no. I’d miss the kids. I hate fundraising AND excessive meetings. The act of teaching is the part I enjoy the most, so looking into other ways to do that is the goal.

      2. Teachers Kid*

        When my dad was looking at retiring from teaching, he made an appointment with the state teacher retirement people and sat down to figure out exactly what quitting at this time vs that time would mean. He found it very helpful.

        Once he decided that working until X date was worth it, he has his timeline and could focus on making it that long.

        1. Sara without an H*

          Yes, this. Make an appointment with a rep at your retirement plan, whatever it is. They should be able to calculate the impact of several different retirement dates on your future retirement income. Then you can compare the cost and impact of a career change against retirement by X date.

          I’ve been doing this for a couple of years now with my own retirement company. I went back (remotely) this summer and based on what they told me, decided I could get out next May. That knowledge has made an amazing difference in my morale.

      3. archangelsgirl*

        I’m glad you brought up pension. I didn’t bring it up in my original post, because I didn’t know if you had one. But since you did … Here’s two ways to look at pension. A) You’re leaving X% of your pension on the table. Lots of teachers see it that way. I don’t. I see it as: My pension is free money that subsidizes me to do something I like to do better. Simplistically, if I work for $10 dollars an hour, my pension makes it like I’m getting paid $15 an hour to do that work, if that makes sense, because the pension is “free money.” As a friend who also left teaching early pointed out, “They pay me X amount to get out of bed in the morning.” Of course, if you leave pension on the table, it makes it trickier when you get to the point where you don’t want to work at all, and you can’t gloss over that. You have to obviously have enough financial resources to keep you at 60 or 80 or 90 or whatever. Nobody but you can decide what that looks like, though.

      4. BadApple*

        In my state working at a community college has the same retirement system as the public schools, I believe. If you have a master’s, that may be something to look into. Best wishes :-)

    2. Rachel in NYC*

      OP 2: I’m not a teacher- I opted against it because of the parents when I was in school. But I would add to think about whether there is short-term goal you can focus on or possibly something that can be changed at your current job that would still be a change but would make you happier.

      One of my mom’s best friend has been a teacher for close to 30 years now, so while she’s been burned out more years then not, I know that she’s been focused on the goal of her upcoming retirement. At the same time, she was able to change what grade she was teaching (she’d been moved from K to 1st to 2nd). Being moved back to teaching kindergarten was reinvigorating for her. She likes teaching the youngest kids.

    3. Gamer Girl*

      I quit teaching after 10 years and have since radically switched careers–one of the hardest decisions I’ve ever made!

      For me personally, the things I loved about teaching were:
      -being at school and the school environment (always been a nerd!)
      -the rush of constantly adapting to changing needs and parameters within the same base lessons
      -developing relationships with students and kids (I taught primary school but also university
      -supportive colleagues and highly collaborative relationships but also the total independence with running my own classroom
      -working with both very challenging kids and very gifted kids and creating a supportive environment for all
      -the performance-based aspects: gives me a huge rush to be up in front of 30 kids and know that I have to keep their attention the whole time!

      The things that were not good:
      -endless, endless paperwork and admin
      -constantly changing timeslots, and the requirement to do the exact same amount of reqs but with half the time
      -endless admin (yes, I said it twice–because there’s always some task I forgot to do! Did I mention that I found out a couple years ago that I actually have ADD? There are so many things that make sense in my life now!)
      -the pay (abysmal in one case–pay bracket set up in 1992 and hadn’t changed since!)
      -constant stress from all the work after the school day and no time to relax (so many essays to grade!)

      I first shifted to private tutoring (I had been building up a tutoring side gig for about 4 years and had constant demand. Before I shifted entirely, I called all the people on my waiting list, asked if they were interested, and lined up contracts.), Due to a major life change, I had to stop after a few years. It was really sad, since the schedule was perfect for me (free morning and early afternoon to do whatever I wanted, easily schedule medical appts, meet up with people, volunteer…) and then work for around 6 hours every afternoon/evening. Plus, I loved working with each child, helping them (and their parents!) find the part of my subject that they were really talented at, and then using those strengths to build up the rest. (I didn’t do any homework help in most cases, as I actually find that more difficult to do dynamically, and I strongly believe that kids should simply do their homework themselves. Just my own lesson plans.)

      I then got an extremely lucky break in a hard-to-break-into industry where good language skills are scarce. And this is what I feel I must mention: you probably have a lot of subject-based skills that are already highly valuable, but combined with your nearly 20 years teaching? If you do your cover letter up right, you will have people absolutely begging you to come work for them. In the hard sciences, business, etc, finding people who can really teach and explain things but can also do the work is difficult! Don’t sell yourself short! Add to that that you have two decades of managing crazy-making admin (all of those papers to grade, attendance records, participation records, standards tracking–all things I’m fairly confident that you, as a math teacher, are far more capable at than I!) Plus managing hundreds of students in person? People who can consistently captivate and keep their audience for 45mins at a stretch is vanishingly rare, except among teachers!

      Now, I also do a tiny bit of teaching on the side–about one university level course per year, and I just love it. It satisfies that teaching itch! I love giving students the confidence that comes with deep knowledge and understanding of my subject in a trusting environment, but I could never, ever go back to teaching full time unless there were a radical change in admin responsibilities and renewed trust in teachers to simply plan lessons and standards that suit their students, rather than so much testing pressure.

      If I had to change jobs again (who knows!), I would probably choose a role that required a lot of fundraising. I’ve always been good at it, even as a kid and when I was in university I did it for a lot of orgs, and it ticks nearly every box of what makes me tick (quick responses to situations, working with lots of people, can be very hands-on, though I’m not so sure about the admin side!) So, think over your skills and what really makes you tick with teaching, and then go for it and start applying. You will definitely miss the students, but once you find another career path, that doesn’t have to be the end of teaching. So many volunteer programs need good, qualified teachers to help people, and there are so many ways to be a teacher! Good luck!

  14. Regina Phalange*

    For the second letter writer, it probably depends where you live, but in my city there’s lots of work in education foundations/non-profits. I work for a foundation where there are lots of former teachers (myself included) who do coaching work, or program management, or other admin work. It’s well paid and flexible and people are generally happy. But if you’re not in an urban area, it may be tougher to find orgs like the one I work for.

    2. BeckaBeeBoo*

      I was going to say this, I work in in the non-profit sector with a Master’s in Education (but have not ever been in the classroom/educational setting). A lot of jobs I look at for education based nonprofits require classroom experience and pay well. Additionally, a lot of our staff are former teachers/educators– our Director of Impact who works on building relationships with schools and school districts, our grant writer, and some of our program mangers. Check out Idealist and PhilanthropyNewsDigest, as both list jobs that often are looking for people with teaching experience for nonprofit jobs.

    3. Teaching skills are versatile*

      To add to this: I’m an Education Program Manager and I work for a Public Utility. I live in a semi-rural community. I run field trips, outreach and work with 5 different school districts.My classroom teaching experience means I know how to work with teachers, I “get” it, I know how to prepare materials and activities that get 9-year olds excited about conserving water. I get to support fantastic teachers. The pay and benefits are great, and I work 40-50 hours a week.

      Teachers also tend to make good bosses; they are good at assessing progress in staff and take on a mentorship approach to management.

  15. Popcorn Burner*

    General advice: Find a certificate program and network, network, network. (Even virtually, on phone calls, and on social media.) Join a few local job board groups on Facebook—whatever you think you might be interested in. My local industry-specific job board (on FB) allows jobseekers to introduce themselves and to ask pertinent questions about how best to enter our industry.

    I know tons of people have moved away from Facebook, but there’s a ton of connection happening on it via groups.

  16. Powerthirteen*

    As someone who tried and failed to switch careers: I think it’s doable. But the most important thing you can do, that I *didn’t*, is make connections with people in your target occupation/industry before you even start and get a realistic sense of how you’ll start a new career. Where’s your toehold? My experience trying to switch into a new career was that even if you have a credential, even with a great cover letter someone in their 30’s is not an appealing candidate for entry-level jobs in a career path unless people *know* you.

  17. The Rural Juror*

    LW1 – I work in construction, and I see a big difference between weeks where I’m at a job site often versus weeks where I’m in front of my computer working on drafting. Technical drawings that you might work on as a architectural technician are very draining. Sometimes if I’m working on something for a while, I have to set alarms to get up and walk outside for a bit to let my eyes rest. I enjoy working on construction documents, I just have to remind myself to be proactive about comfort.

    That’s not to dissuade you from pursuing a career that takes you in that direction, just be wary. I’ve never had a migraine (knock on wood), but I do get tension headaches if go down a rabbit hole and sit too long staring at CAD.

    A saving grace for me is that there are days where I can split my time between the office and the sites. I might spend a couple of hours on a drawing, then go to a site and need to get measurements, then come back and input that information into the drawing in progress. You might also benefit from an arrangement where you can split your time a little more (like property management!). I hope that would help with your overall health and well-being.

    1. not owen wilson*

      I also get headaches when I look at computers for too long, but I’m a chemical engineer so that’s usually when I get up to go do labwork. LW, if you can alter your work flow at all to involve more time away from screens I would highly recommend it. Even just printing things out vs. reading them on a screen helps me. I would also say to look into blue light glasses. Working on making the migranes better may make a big difference in how much you generally like your job, at least in the short term while you figure out your next steps.

      1. sb51*

        Was going to say something similar. I was having major ergonomic/pain issues a few years back; fixed those plus finding out and fixing thyroid issues, plus saying to myself “if I spend the amount additional I get in my next raise on monthly massages, would I be happier? yes” (obviously this was not during a pandemic). *poof* The expectations/pressure/workload didn’t change but I went back to mostly finding my work “fast-paced/exciting/etc” rather than stressful. Also double-check your vision — at some point most of us staring at a computer screen may need a “screen-distance” prescription rather than a reading-book (traditional close-up).

        This is absolutely not to say a change might not be the right move, but you don’t want to switch fields only to find out the migraines followed because they were more physiological than stress.

        1. The Rural Juror*

          My poor mother figured out she needed bi-focal contacts when she went to the chiropractor for neck/back pain and he asked her a series of questions leading to – “Ma’am, sounds like you’re looking down to see over your reading glasses…which is causing your neck pain. I think you need to go see your optometrist!”

          It’s amazing how little things that make us more comfortable can make such a big difference. She said she’s actually been much happier at work overall since her neck/back pain has gone away. And she’s the court clerk at a courthouse…which isn’t exactly a stress-free job!

  18. DataGirl*

    I’m in a similar situation. I’m in my mid-40s and I have a 12 year old Master’s degree in a field I’ve never used (library science) because right before I graduated I got offered a job at a non-profit doing IT stuff. I’ve been doing IT since then, and I don’t enjoy it, but I do enjoy the paycheck. I can’t think of any way to get out of IT and back to anything I’d enjoy without either a) taking a significant pay cut or b) getting another degree. I have teenagers whose college I need to pay for so I can’t really justify getting another degree right now- especially as I still owe a ton on my student loans from my first degree. I can’t really afford a major pay cut for similar reasons. And I feel the clock ticking on my age for starting over.

    Additionally, 3 years ago I took a job which by the title and job description looks like IT work- but isn’t. I don’t hate what I do, but it’s not sustainable as a position that will last until retirement. The problem is if I try to move laterally to a new company doing what I used to do/what my title says I can do- I would need retraining as all my skills are out-of-date and rusty. I’ve been at a lost for a couple years now, no options seem viable. The most logical thing would be to take some IT classes and get certifications, then move to another company, but my heart isn’t in it.

    Sorry, I know it’s not supposed to be all about me, and I have no advice to give, just commiseration from someone stuck in a similar way.

    1. Peter Piper Picked a Peck of Pickled Peppers*

      Library science + IT could be a good for for Information Architecture and UX Content Strategy?

      1. DataGirl*

        I took a class on IA as part of my program, but I don’t remember much. I’m not sure what kind of job that would be?

        I’ve looked into data science too, but even those jobs would be about a 30% pay cut.

        1. Peter Piper Picked a Peck of Pickled Peppers*

          Information Architecture is part of UX that deals with taxonomy, and the like. That’s not a great explanation—if you Google it, you’ll find lots of better definitions
          and references. Peter Morville (sp?) has written some good stuff.

          But it might not be a good option for you—I don’t think it pays as well as data science. Not in my area anyway.

      2. Oaktree*

        This. I’m a librarian currently, and there’s quite a few jobs in metadata management, systems librarianship, UX/UI/digital content management, etc. A lot of library school graduates come from a humanities background and their skills are in social sciences rather than STEM, so qualified librarians who also have compsci or IT experience are pretty desirable.

        1. DataGirl*

          Interesting, I’ll do some research. I figured since my degree is so old and I never actually used it in my employment that it was basically useless at this point.

  19. irritable vowel*

    I left my job and previous career at the end of last year and have been kind of stuck in a limbo for this whole year. Part of that is because of the pandemic – it’s really tough to start a new career when everything is so weird and lots of places aren’t hiring. But I’ve also learned something about myself that I’m not sure I realized before – I have a sense of how much my time is worth that is…kind of rigid. I’ve found that there’s a big gap between understanding theoretically that starting a career in an adjacent industry would mean taking a pay cut, and being able to stomach that much of a pay cut when it comes down to it. I’ve learned that I just can’t go back to earning what I did 20 years ago, or go back to being at an assistant level and having no agency – it’s silly in some ways, but it’s connected to my sense of self-worth in a way I didn’t fully acknowledge before I left my previous job. I’ve been applying and interviewing since the spring, and when I was finally offered a position last month, I ended up turning it down. So, I’m stuck trying to figure out if I want to keep doing the part-time and freelance work I’ve been doing this year, or go back to my previous industry in a way that’s palatable to me.

    I guess the bottom line here is: it may be harder than you realize to change careers, in ways that you hadn’t fully considered. That doesn’t mean that you shouldn’t do it, but think about whether you can *really* take a big pay cut, etc., in ways other than the financial implications.

    1. AnotherAlison*

      This is a really good comment. I’m not a big house/fancy car person, but I probably value my financial security a little more than my work happiness. I wouldn’t work in an abusive situation or stay working in a field where my mental health was really suffering, but a job that is 40% likeable and pays well is probably going to win out for me vs. one that is 75% likeable and pays half. If I could get back to my old salary in the next 5 years, I’d consider it, but if it was say, going from software engineer to teacher, I’d have to a lot of money banked to make that switch. I’d also have a hard time doing something very uncertain. . .like if I really wanted to be executive management for a sports team but had to give up a 6 figure accounting job and start out in box office ticket sales to do that. It would be fabulous if it worked out, but not a lot of people make it to the top of that field.

    2. LW1 here*

      This is a very good point, I do acknowledge that at the moment I am both well paid and generally respected (which you know, feels good?) and I’d need to be ready to lose both of those to start something completely different.

  20. MsMaryMary*

    LW2, I have a client in the library software industry. I won’t name names, but if you use an app to borrow books from your local public library there’s a good chance it’s their app. They hire a ton of teachers for the educational version of their app. Sales, account management, customer service, software development, etc. I know other makers of educational software and materials do the same.

    Good luck!

    2. MsMaryMary*

      And the educational side of their business is growing like crazy right now, as everyone tries to come up with electronic versions of materials for students to access through remote learning.

    3. Anon for this*

      Similar but not exactly the same thing: I am not affiliated with LibraryThing, but they are hiring into several big positions right now, and they seem like pretty awesome people. More details on their blog!

    4. Another idea*

      Yes, I work at a company that makes software for K-12 schools and they like to hire former teachers into a lot of roles.

    5. Kimmy Schmidt*

      This is a great suggestion! A lot of the library vendors I work with are either former librarians or former educators, and they opt for many different paths at the vendor company – sales and training, but also research and development, UX, customer service, and analysts.

    6. BetsCounts*

      The next time you speak with your client perhaps you could tell him/her THANK YOU FROM THE BOTTOM OF MY HEART. I was traveling throughout California last January, and ended up with literally a dozen different library cards that all have ebook access through an app and I am ROLLING in reading material.

  21. Peter Piper Picked a Peck of Pickled Peppers*

    OP2, there are lots of fields where your background in education is an advantage. You don’t say what you enjoy doing, or have an interest or aptitude in. Don’t make any decisions while you are trying to get out of teaching but have no idea where you want to end up.

    E-learning might be a good option
    – designer for an e-learning platform (do a short UX course and see if you enjoy it)
    – creating online learning material
    – online tutoring

    Someone else suggested instructional design which is a similar idea.

    1. Ms. Characterized*

      I’ve definitely started my list of my aptitudes/strengths, and I’m pretty sure online curricular design one of them (this whole year has been trying to learn how to ride a horse while running after it, trying to get on). But I am good at creative solutions — I enjoy problem solving and troubleshooting when it comes to education.

      1. Peter Piper Picked a Peck of Pickled Peppers*

        Good luck! I think there are lots of opportunities.

        UX is all about problem solving, and I’d guess so is instructional design. There is quite a big overlap.

        Curricular design also sounds really interesting. I’m sure you will find something that works for you, without having to start all over again.

  22. JelloStapler*

    LW2- I’m feeling the same in higher education; but at the same time, I have earned a lot of flexibility and reputation at my institution so I don’t want to start over. I just wish I was paid more! This has been my struggle for the last year or so.

    1. Ms. Characterized*

      My college and grad school profs are such a huge part of my career and general personhood. I don’t have any $$ to offer — just my sincere thanks for doing what you do, and for doing what you CAN do right now in the middle of *gestures broadly at everything* this.

  23. LDN Layabout*

    I realise this is more likely advice for people outside the US, however, for LW#2 and other people who have been in certain careers for a long time such as education or health care, regulatory jobs might be an option.

    If it’s a sector where regular inspections or site visits are carried out, a lot of them are done by former professionals from that sector.

    1. Jay*

      Yup. I have a friend who was a teacher and then principal and moved states when she remarried. She didn’t want to deal with trying to transfer her license. She went to work for the accrediting agency and was really happy there for about five years (until her husband retired and they moved again). I’m in healthcare and I know a number of people – mostly nurses – who have gone to work for the various accrediting agencies at the state and Federal level.

      1. Gumby*

        Bonus: you can ease into it while still a teacher. Either working on putting together your own school’s report or by serving on a visiting committee. It is likely to be a fair amount of work – but it is a way to try it out before having to commit 100%. (Also, if you volunteer once TPTB will ask you back over and over again, assuming you were not terrible, which makes you a known entity if you do decide to switch careers.)

  24. Juniantara*

    The one piece of advice I can offer is that sometimes it’s easier to pivot inside an organization that already likes you and already knows your strengths and weaknesses. Does the company you do software management for have a property department or property manager? Does your school district need an accountant or tech support? Managers will often take a known good employee/good culture fit and help you learn new specific skills, and they might even let you keep your pay rate (or a good percentage thereof) while doing it. Then in a couple of years you have a resume with the right words you can take out to other employers.

  25. MsFieryWorth*

    LW2- This depends a lot on what you’ve taught for the last 20+ years and where you are located, however you may find opportunities in museum education, science center education, environmental/park education, or similar places. Think about where you’ve taken the students on field trips, as those places will have a need for educators to develop those student programs in ways that tie into the curriculum and speak to both teachers and students.

    I think someone has already commented that there may be opportunities in test development and curriculum development, education policy work, and even text book development or sales.

    2. Skippy*

      I hate to be a downer, but earlier this year I was laid off from a position in museum education after 15 years in the field and the job market is absolutely dire right now, even for those of us with lots of experience. The field may come back eventually, but not until sites can re-open at full capacity. It’s a great field, and your classroom experience would certainly serve you well, but there’s not a lot out there right now.

      1. Rara Avis*

        Yeah, the museum where my husband worked laid off 44% of their workforce in July, and they have no reopening plans on the horizon.

        1. Miss Characterized*

          “Do something with a museum” is one of the top items on the general web advice list. I’d hate to flail about at something that’s not my field when experts are out of work. Right now I’m just donating to museums to help try to keep them operating when the world starts up again.

          1. Disco Janet*

            Yeah, I got a lot of “work at a museum!” suggestions when I was looking for non-teaching education work. The thing is, unless you are a director or other high up position, most museum jobs pay very little. And as others said, now is a very rough time for all museums.

  26. Lily Rowan*

    I have spent a lot of time thinking I should change careers, and then just changing jobs instead because it’s so much easier. Finally I shifted my field just a little, and now am a small cog in a huge machine and I LOVE IT. I am surprised at how much I love it, how little stress I have, etc. I know I lucked out in a lot of ways, but I wonder if either of you can think about smaller shifts that might be enough of a change without having to blow everything up and start over.

    1. CamJansen*

      I identify with this comment a lot. I did more of a lane switch than an entire career switch. In the same job family with many identical responsibilities but shifted in burden and culture enough that it really bettered my quality of life (and I’m not getting stress migraines anymore, and my hair stopped falling out). Figuring out the core of what I liked and thrived in and looking across industries to see where I could apply that helped significantly.

      1. Lily Rowan*

        Yes! Exactly — I was idly looking through job postings and saw one that included all of the things I liked about my previous work with none of the ones that stressed me out. I figured what the heck, and here I am.

    2. Lavender Gooms*

      Interesting! This was the exact change I made LAST WEEK. I’m in my second week at my new job where I am doing/focused on a single aspect (maybe two once I’m fully trained) of my previous job—but for a much larger organization. Without having to juggle alllllllll those other pieces, my stress level is already shrinking.

  27. reject187*

    LW 2, I might not be the best person, but I realized that, after being the English department and burning myself out on three different extracurricular activities, all I really needed was a break. So I took a sabbatical this year and I’m hoping to get back into education, but I would encourage you to take a rest period before you start trying to pursue something else, no matter what it is. Teaching is tough cookies! We all need rest and we don’t often get it.

    1. Ms. Characterized*

      A sabbatical could be an option — I’m afraid of not getting to be at my home school after I come back (they make you go where you’re needed/there’s an opening), and I’m afraid of what other losses might accrue. A professional version of FOMO, if you will. It’s not particularly rational, but it is what I’m feeling.

      1. Double A*

        This could be something to talk to your union about. My teaching position was eliminated, and I was indeed offered a job that I in no way wanted, and that was my only option due to the union contract, so I resigned.

  28. AnotherAlison*

    LW1: I sympathize, but I think you need to take a hard look at your skills, strengths, and passions. I wonder if your property/real estate interest is a fun escapist fantasy, or a real thing you could do? I would worry about you making a leap into something that is a bad fit.

    For example, my own career has been in mechanical engineering and project management. On my own chuck-it-all and start-over days, I would tell you my dream job is being a game warden. There are some TV series here about game wardens, and I love these shows so much. Realistically, though, if in my job, I had to go confront some dudes about illegal turkey hunting, I would probably pee my pants. I score high on career tests in analytical professions, not service professions or working with the public.

    For you, if you have not ever taken action on doing anything hands-on building/design or real estate related before, I would question if it’s what you should really move towards. Do you have an aptitude for it? I think you might look into careers that leverage your software and math talents and reapply them somewhere else. Another poster mentioned software for real estate. Could you work for Bentley and design CAD software (or a place like my engineering company where we have software engineers on staff customizing all the CAD software)? Could that put you in proximity to the drafting world and maybe you do go that route? Seems like that would baby-step you into something you have more passion about without taking you out of the area of your greatest skill.

  29. EEB*

    For the second letter-writer: I work in the training/learning & development field, and it’s full of former K-12 teachers. It’s a nice field for former teachers because a lot of the skills overlap (so teachers generally don’t need to pay for further education/certification), but a lot of the stressors present for K-12 education, especially this year, are much less prevalent. Google searches for “teaching to training” or “teachers to trainers” should pull up a bunch of good resources, if you’re interested in learning more.

  30. Four lights*

    I worked for a year as a teacher and then realized it was definitely not for me I ended up working as a paralegal which I really liked. The book that really helped me figure out what kind of job I would want to do is the What Color Is Your Parachute Book. It has a self inventory that I think does a good job of not just figuring out what transferable skills you have, but also what you’re looking for in a job in terms of what level of passion do you want to have, what type of hours, what type of responsibilities, if you want to work on big teams or not, a whole lot of different things. And then from there you take that and look for something that could fit your profile. So once you know what you’re looking for and some of these job sectors, you can start informational interviews with people to find out more specifically what type of job has those qualities in that industry.
    I knew that I liked writing, research, working independently but being responsible for myself, office environments, 9 to 5 jobs. Paralegal fit all of those things.

  31. Bopper*

    For Software Engineer… another idea is to look into adjacent careers…like Project Manager or Training or Solutions Architech/Systems Engineer/Integration Engineer/Analyst/Sales Engineer

    For the latter you can learn more about/work with the application/industry and have it be less about the coding.

    2. LW1 here*

      This would be a good suggestion if it were coding I disliked (I don’t :p) – I think most other jobs within my industry I’d enjoy less! Certainly I don’t fancy product management. (But the suggestion of looking for software roles within a property company that’s come up is a good one).

  32. Ms. Characterized*

    I’ll have to sign off, Commentariat, because classes are starting. I’ll come back to read at the end of the day and comment if it’s relevant. Thank you for all who’ve offered support, advice, or just a friendly howdy. It’s sometimes just nice to be seen.

  33. voluptuousfire*

    For LW #2–consider Edtech! I’d wager there are companies that would love a veteran teacher like yourself on their team. I’d check out job sites like Built In dot com to see what edtech companies may be in your area.

  34. LabRat*

    The first time I changed careers, I was OTJ trained, but needed a credential, which I could only test for with a degree, but that degree wouldn’t have added to my knowledge base much. I sat down and thought about what career really made me excited to think about – and then I had the luxury of doing an internship to test it out.

    The second time, I had a graduate degree and big dreams of changing the field, or at least my little corner of it. Unfortunately, the field isn’t ready in any sort of perceptible fashion to make the changes that I think are important. So, I had to figure out how my current skills and knowledge could land me a job that I would enjoy and be good at. I thought about the things I DO enjoy (organizing, tracking, synthesizing and distilling information, learning new things) and landed a job where I can do all those things AND still occasionally use my subject matter expertise!

    I won’t lie, that second job search in particular was very nearly a solid year of looking and applying and interviewing. It has turned out to be very worth it, though I would never in a million years have imagined ending up here!

  35. Didi*

    I’ve changed careers not once but twice and I’m 50.

    My advice is to think of yourself differently in two days:

    1. not as a profession (“a teacher,” or “a software engineer”) but as a set of skills (such as, “I have a great eye for detail” or “I am very empathic” or “I write very well”). These skills are in demand by other industries and professions.
    2. by listing all the things you like and all the things you don’t like about what you do now. Do you like or loathe meetings? Travel? Quiet heads-down time? Deadlines?

    Next, research all the industries in your area. You can get this data from the labor statistics bureau where you live (state or federal). Most areas tend to have concentrations of industries, such as health care, or manufacturing etc.
    See how what you like to do and what you’re good at mesh with industries in your area.

    Finally, make a list of trade-offs. Are you willing to take a pay cut or do you need to maintain pay? What kind of commute and hours are you willing to put in? Do you need to be a manager, or are you OK being an individual contributor? Do you need a fancy title or some other “ego” boosting aspect of a new job, or are you OK with something less flashy? Do you think you’d prefer a large or a small company?

    Think of all these variables and you’ll focus on a few that are really right for you. That’s how I got both my career changes, and they have worked out well. They all have a common thread around what I am good at and what I like, but they’re in different industries and different types of roles.

  36. Bananie*

    You are not alone! Adam Davidson’s book, The Passion Economy, is so inspiring and full of stories about people taking risks and changing careers. Highly recommend it, along with Guy Raz’s podcast “How I Built This”. They both emphasize that intrinsic motivation and resilience in the face of setbacks can matter more than being an expert and having it all figured out from the start.

  37. AndreaC*

    My friend is also trying to get out of teaching, and I always advise her to look for jobs at places that value educators: namely universities and colleges. There are always a variety of jobs available, and you should be able to find something that speaks to your interests and abilities.

    This is definitely only a piece of the solution, but it’s somewhere to start.

    1. Sleepy*

      I don’t agree that universities and colleges value educators, especially K12 educators, in my experience. I would suggest looking at education-related nonprofits.

    2. AnotherAlison*

      Universities and colleges are extremely hard-hit by the pandemic. It would not be my first recommendation right now. The administrators and faculty I know locally had their only raise in ~5 years last year and are now getting pay cuts if they make over ~$50k. Maybe in normal times.

      1. Properlike*

        Even in normal times, you’re brought on as an adjunct, for minimal hours at minimal pay, teaching the exact same classes as full-time faculty but making $15K/year instead of $50K/year (if you’re lucky to get the hours.) A “part-time” teaching load (two-three classes) is still full-time work.

        1. Sleepy*

          Exactly, and competing against people with PhDs, which most universities value more than classroom teaching experience.

    3. Esmeralda*

      K-12 gives you some great skills that are useful in many college/university jobs. However, working with college age students is not the same as working with k-12 age students. You need to have actual experience working with this population.

      Many k-12 teachers appply for our academic adjacent positions, but most lack experience working w college students. So they never make the first cut. The ones who do have actual substantial experience.

      If you’re interested in moving into positions at a college or university: learn what kinds of jobs there are. Network/info interview to learn about the job AND to find out what qualifications you need to get those jobs.

  38. yamikuronue*

    If you have the right kind of brain for it, one of the easiest and most lucrative careers to switch into is software development. You can be self-taught and still get in, so you don’t need more education, and you don’t even need certification or anything either. What you would need to do is start taking self-paced lessons in some programming language (see what’s needed in your area, Ruby or Python or Javascript are usually good ones to learn) and learn as much as you can. If you find it relatively easy, as in, you’re not fighting your brain for it, just picking up new skills, you might be able to switch careers and become a junior programmer. I’m at a Senior level now and making six figures, though I picked up some specialty skills along the way on the job that helped with the compensation aspect.

    If you want to learn Javascript, this is my favorite resource: https://nodeschool.io/#workshoppers . It’s a series of little tutorials where you get hands-on training and learn the basics, and by the time you’ve finished them all you’re learning some quite advanced concepts. Plus it’s 100% free and it runs on any computer.

    1. J.B.*

      I’m curious where the dev jobs someone can be self taught come in? You would likely need to get a job at a small business as most of the larger ones are more rigid about platforms.

  39. Ali G*

    One option for both LWs would be to look into the community/adult education resources in your area. When I was toying with a career change, I took a bunch of classes from my county. They were cheap, on evenings and weekends, and gave me just enough info to be able to explore a topic. You could get a good idea if a new focus is a good idea for you with relatively low investment. Then, if you get serious about something, you have contacts in your community via your instructors (most I met were very willing to meet with me outside of class).

  40. Not trying to be rude, just good at it*

    I can totally relate to the teachers dilemma. After bouncing around my urban school district on one year assignments I was sent to my first long term school where I spent 10 years. A new principal arrived and she dismantled my department and I was transferred to second long term school for 10 years. Same principal was appointed and again, my department was dismantled and I was out. I was so done with teaching but a wise owl whispered in my ear, “You are 5 years away from a 75% lifetime pension.” I survived for 6 more years until there were no more high school jobs for me and I was a terrible elementary school teacher.

    I don’t know how your pension works, but try to make it a few more years. The agony is short term, the pension payments are forever.

    1. Music Teacher Here*

      Pension is one major reason I don’t want to change careers. I’m 11 years in and I actually do love my job. Just not right now amidst budget cuts and coronavirus. Music doesn’t go with either thing.

      1. Not trying to be rude, just good at it*

        Think about how much fun it must be to teach welding or cooking online to high school students.

  41. notMichelle*

    Both my partner and I have switched careers and I’m currently in the process of trying to switch again. The biggest advice I can give is to really highlight your transferrable skills. My partner was an elementary school teacher and he got a job teaching skills to adults and now he’s the CRM admin for that company. Someone mentioned instructional design and I would echo that.

    For both, definitely take classes or further your education somehow in those fields. I’m personally trying to move into CRM administration from basic office work and I have spent the better part of a year and half learning as much as I can and I’m volunteering with this particular skillset. Also try to work with recruiters. My first transition came from working retail and going into an office environment and I was able to get that through a temp agency (it turned perm within a month). Good luck!

  42. Cori S*

    FOr LW2 -I am a former teacher and I leveraged my knowledge into a career in technical writing. Teachers know how to break difficult concepts into terms their audience understands. Technical writing does the same thing. Teachers develop curriculum (even within the standard curriculum taught in their school) and can be flexible in how it is presented.

    I started off developing technical manuals for the automotive industry, then banking. Currently I am a technical writer for a cyber-security company. I have discovered that the ability to write clearly, concisely and logically is what is most needed. The content can be learned (and a good SME who can refine the content is awesome) but the ability to take the concepts and make them easily learnable is what is truly needed to excel in Technical Writing.

  43. 867-5309*

    Look at tech companies (EdTech is huge right now) who would love to have a former teacher as part of their customer success or sales teams. We’re a meeting management solution and we get excited when someone with an executive assistant background applies for one of our jobs on those teams because they have deep domain knowledge (coordinating executive and board meetings) that is tough to teach. I imagine it would be the same in education.

  44. Gav*

    The book “Designing Your Life” by Bill Burnett and Dave Evans is a really great tool for contemplating and planning next steps in your career. In a nutshell – you don’t have to suddenly change everything all at once. Rather than doing a 180, sometimes it’s best to start by rotating just 20 degrees. If that goes well, rotate 20 more. Treat your life as a series of experiments – try something new that is tangential to your current path, and if it works, venture farther. Completely upending your life or career because you crave newness is not the path for everyone.

  45. KB*

    To LW2, I haven’t been teaching as long as you or (it seems) in the same country as you, but lockdown made me see how burned out I was. I was so happy that I didn’t have to go teach in person. I woke up happy for like a good month. I recognise that that is an odd response to a pandemic and I realised I needed out and got a job teaching in an additional needs school. It was intimidating at first but I love it! I have 10 kids, a team in the room with me, I don’t feel like I have to do all the things all the time, the kids learn at their own pace and there is no expectations on them achieving certain grades by certain dates. Having a team makes behaviour management much less stressful and the behaviour isn’t actually much worse than I had from kids in mainstream (in my country anyway). The kids arrive on buses so I no longer get shouted at daily by parents. Also: extremely little marking! I don’t feel pulled in so many directions and like I’m dropping the ball all the time anymore. And I get the same salary as a mainstream teacher (in my country it’s standardised). It is not the job for everyone, but is there something you enjoy in education you can pivot into? Like teaching English as a second language (to adults or in schools) or courses at community colleges?

    1. Miss Characterized*

      I’m so glad that worked out for you! Many comments are about slow or slight pivots, and they’ve been good for me to write down. Thanks for adding to my list!

  46. cosmicgorilla*

    I just have a comment on the stress migraines.

    My neurologist told me that an ungodly percentage of headaches come from our necks. We know that we have a tendency to tense up our shoulders when we’re stressed. We don’t always realize how much tension we’re putting on our upper backs when we lean over a laptop all day. This upper back/shoulder tightness will pull on your neck, which will help trigger or exacerbate a migraine.

    I say this as someone who suffered for years before someone did some hardcore work on my trapezius muscle. Proactively foam roll and tennis ball roll your upper back. Shrug your shoulders during the day to release tension. Look up trapeziuw and other upper back stretches. Find someone who does myofascial release. This could help more than you think. It helped me, despite my multiple migraine triggers.

  47. Coco*

    I have general advice based on my own experience, and mine is different because my new career path is still part of my overall industry, but definitely a separate path that took intentional and ongoing effort to move into. I specifically chose my last job because it put me “in between” 2 tangentially related career paths. I then took an after work certificate course to solidify my new career path I wanted to get into. Not to brag, but I was a bit of a “star student” and I ended up teaching part time after work for the school after completing my course. I also volunteered and went to networking events in the new career path I wanted to be in. My point is I specifically sought these out. I presented my new knowledge to my colleagues at work and I was named a budding expert in the new path. This eventually led to more opportunities at work where I could do work in my new career path — my job didn’t really have these opportunities before (an acquisition made it possible) so it was a huge surprise. When I felt ready to make the full career switch, I felt like I built up a wealth of knowledge and experience (whether through the part time teaching or the unpaid, volunteer experience). The new job and career didn’t fall into my lap. It was the result of several years of hard work, and choosing opportunities intentionally.

  48. A Teacher*

    Same. I’m also battling admin in my building throwing teachers under the bus and the amount of false positivity and “growth mindset” coupled with the amount of PDs and “grace” we are supposed to give has me side eyeing my career at this point.

    No advice. Take it one day at a time and know a lot of us are right there with you.

    1. Miss Characterized*

      Are you sure we don’t work together? :) Your lingo seems familiar!

      Sending you strength, and sarcasm for the ‘growth mindset’ — you should have that looked at. ;)

    2. Miss Characterized*

      Are you sure we don’t work together? :) Your lingo seems familiar! Sending you strength, and sarcasm for the ‘growth mindset’ — you should have that looked at. ;)

  49. Please make it stop*

    LW #2 –

    I have worked in Ed Tech for the last 10 years, and have seen a lot of former teachers hired. Sometimes as trainers teaching teachers how to use the software, sometimes as customer support or even sales, and sometimes as the resident expert for the best way the software should work. Both of the companies I have worked for are working from home now and one of them has already made the decision to be remote from here on out. The other company is still making a decision.

  50. Alex B.*

    My current employer offers an education assistance benefit (tuition reimbursement), but it has some conditions attached to it and I’m wondering if all of those are common or not (first employer, not familiar with other places). The conditions are:
    1. Minimum time employed before being eligible.
    2. Must be in good standing from last performance review.
    3. There’s a cap to the amount of assistance per year.
    4. The company has to approve the course plan.
    5. If you leave the company within 6 months of the last tuition reimbursement you have to pay it back.

    Are all of these conditions common for this sort of benefit? Most of them seem fairly straightforward but I was curious. Conditions 4 and 5 in particular make it seem like this benefit would not be helpful in making a significant career change.

    1. InfoGeek*

      Condition #5 is more lax than the equivalent at the companies I’ve worked for.
      Where I work now, you have to work 2 years or pay it back.

      This benefit is meant to help you move up or over WITHIN this company, not to help you leave.

  51. Rapid Roy (The Stock Car Boy)*

    I’m in the middle of trying to figure out my own path and both OP’s situations resonate. I like what I do, and I’m well paid to boot, but Covid-19 and working remotely have both amplified some pain points in the work culture and also added another layer of stress and uncertainty because I’m working in a mode that I don’t like at all – I’m just more effective when I work with my team and my colleagues in person.

    To the OP Engineer: I totally get it. Lots of reasons to stay in your current role, but no p fulfillment. I too am seeing my stress levels rise and I sympathize with your migraines. I hate when my job stress follows me home and my anxiety keeps me up at night. They don’t pay me enough to think about work 24 x 7 or lose out on my free time because work is insane!

    The only advice I can share is that I try really hard to put my work in a box and disconnect from work at the end of the day. I aim to focus on stuff outside of work to find meaning and purpose and fulfillment. The job is where I go to make money. I agree to do stuff, and they agree to pay me money for my efforts. If the agreement gets out of balance (too much BS, too many demands, too much stress, not enough money, etc) then I can always look for the next opportunity.

    To the OP teacher: Thanks for doing your job. My dad is a retired (30+ years) teacher and I saw first hand what it takes to do that job well. I sense that you love your students and can’t imagine ‘phoning it in’. You know the ‘highs’ of connecting with a student and, quite literally, changing someone’s life. I can imagine that not being able to do what makes teaching awesome is especially draining. I wish I had more advice but I am hoping you can press on until you can find something awesome in your current role or find a new awesome role.

  52. Cubular Belles*

    There is a lot of cross over between education and the business world. Being able to distill it down to “what is the business question?” then using all resources to address it is a vital skill, it’s called being a Business Analyst.

    Corporate Training comes to find, or teaching software applications or platforms? or HR (confidentiality) maybe?

    If you want inelastic demand for your labor supply, get into IT. IT can be self taught and if you are teaching online you could also teach yourself online after hours while you make the transition. There are online IT courses as well.

    The internet is full of little side gigs writing or editing so that’s one route to explore too, or start a YouTube channel.

    Make a list of all the things you enjoy doing, then see if any of them can become side gigs to keep you afloat while you make your break from academia. Best of luck to you!

  53. Em*

    LW#2, my spouse transitioned from teaching middle school to working as a community college advisor. Like when he was teaching, he gets to work directly with students and help them figure out how to navigate their educational paths, but unlike when he was teaching, he gets to leave thoughts of work at work. Plenty of his colleagues over the years had also transitioned in from other fields (even post-retirement). Unfortunately, many colleges have hiring freezes at the moment, but you could start looking at student services roles and see if anything interests you for the future.

    1. Miss Characterized*

      This resonates with me: I like working with students, I like problem solving, and I’d really, really, like to leave my work at work and be home when I’m home.

  54. Disco Janet*

    I was in a similar situation to you a couple years ago, although I was a preschool teacher. I wanted to still be in education, and had just got my masters, but was getting burned out after 18 years in the classroom. I was able to get a job writing curriculum for a franchise based childcare company. What about a non-teaching role in a school? I have a friend who taught high school Spanish for a number of years, but recently because a guidance counselor. It still has its challenges to be sure, but does not have the clenching, neverending exhaustion of day to day teaching. So there are other options out there, though they are less of them and therefore more competitive.

  55. triplehiccup*

    LW2 – I am a former teacher who has found success branching into adjacent fields that are different than what have been mentioned upthread. My first job after I left the classroom was as a research analyst at an education nonprofit – the pay was better, but the hours and stress level were still pretty high. I now work in consumer education and outreach at a federal financial regulatory agency, which is a better fit. Very good pay, I work exactly 40 hours a week, I get to do a lot of the creative work that I enjoyed with teaching, and there’s actually budget to do it well! I even got to contract a former teaching colleague to do some writing for us during her summer break this year. The internal bureaucracy and mismanagement do rival the extremely incompetent principals I worked under, but my immediate management is wonderful – there are a lot of smart and passionate people working in government. And your years of teaching should count in your favor for pay-setting – it’s hard to know exactly but I believe I got an additional $10k for my measly 5 years in the classroom. There are a range of federal job types that might work for you, many of them are virtual, and many of them explicitly count volunteer/unpaid experience if you have any non-work activities that you’d want to expand on – for example, check out this listing: https://www.usajobs.gov/GetJob/ViewDetails/583922200

  56. Quickbeam*

    Career changer here….went from a criminal justice career (master’s prepared) , retrained and re-degreed for nursing at 31. I am now 65 so have some perspective.

    1. I grossly underestimated how much I liked a nice weekday schedule, no OT, weekends off, civilian clothes
    2. My major goal was portabiltiy which nursing did provide, absolutely. My prior job had a rigid residency requirement and zero portability.
    3. Nursing for all its demand is extremely “blue collar” in the physicality and hourly nature of work. It was a shock to have to fight for a weekend or a holiday off. I was definitely naive.

    With 34 years of expereince I have no regrets but I was very cluless as to the negatives of the career I was jumping into. To people considering career changes, look hard at what you want to have vs what you already have. Ask people in those jobs what they dislike. If possible, can you do your desired job as a sie gig for a while to geet a better understanding?

  57. Some Lady*

    I left teaching after 5 years. I wanted to stay in education or at least in the subject area I taught, but for non-profits rather than in schools. I got nowhere when I first started applying to nonprofit positions, even though I can say in retrospect that I would have been fine at the jobs I was applying to if hired, my resume just wasn’t as competitive because I had zero office experience. I was finally able to make the switch by going back to school for a second master’s, as part of which I got an internship at a nonprofit doing stuff much more related to what I hoped to be doing. Then, I took a job that was a pay cut and a sorta entry level, but that would build the parts of my experience that were still missing and open doors through industry recognition. I did a LOT of research and a LOT of work to find a school and scholarship opportunities that would make this feasible and qualify for them, and I worked 2 jobs to make ends meet when first starting out in the new position (and still now, because job 2 is fun and gives me a big financial pillow). It was hard and definitely some people would not consider it worth it, but it was for me 1,000%. In this pandemic I am so, so relieved to not be teaching (those of you who are, you’re heroes, I see you).

    My suggestion is to haunt the job search sites, especially industry-specific ones for anything that interests you, and read the descriptions of jobs that seem interesting to you. Be broad in your approach because there could be positions you would like that you don’t realize exist/you might like yet. See what skills and experience you have and are missing for those jobs, and map out a plan to build your resume and references in that area through volunteering, side jobs, classes, or whatever else you need. You’ll likely learn from that skill building even more about yourself and what would make a good fit for you. It might take a few years but they will be more bearable with an exit strategy in place. Good luck!

  59. Corporate Goth*

    Do your research.

    I direct production topics, analyze, write, and edit technical teapot analysis. I’m in the top 4% of my career field nationally and in the top 1% at my organization. I am well-paid, well-respected, am running a lot of gamechanging changes in the tea industry…and long to write novels about crime fighting dragons, sword-fighting professors, and spacefaring spies.

    So I’m doing exactly that, in my spare time.
    – I’m studying craft: How to plot, how to write, how to edit for fiction rather than teapots, exploring software that can help, reading books and studying them for effectiveness.
    – I’m making connections: Joining a writing critique group, networking online, going to virtual conventions and training, joining a weekly prompt group.
    – I’m building habits: Writing the weekly prompts, undergoing edits and reviews, building a daily writing habit, coming up with ideas, writing when I don’t want to or am distracted (accountability!), and working on projects with clearly outlined goals.
    – I’m learning the business side: What things cost money or don’t, advertising and marketing, what covers work for which genres, how to run a website or a newsletter.

    This has let me write my first book, though it’s not yet published, and I’m working on others. It also gives me a number of ideas on what I need to learn, how to build a career more slowly but with skills to make it successful, allows for a plunge to even see if I like it before a major career move, and saves my sanity when I have a bad day with the teapots.

    1. Corporate Goth*

      It also helps that my skills in technical writing and editing are applicable to my desired career path. I’ve just broadened the aperature. So thinking seriously about what you can do easily – say, in a time of crisis or unexpected layoffs – really helps think about viable career paths.

      Research is even more important if you want to do a total shift to something brand new with zero or low applicability.

    2. Corporate Goth*

      One more addition. I’ve also been able to incorporate new ideas on how to think about problems, different types of editing, and training material from the side gig to the day job. It’s had far more crossover than I ever anticipated.

  60. HealthAnalyticInsights*

    Maybe consider a side hustle as a way to test the waters of a new career you are interested in. Starting a youtube channel or blog to investigate this field might be a way to test if you want to jump shift permanently.

  61. Hotdog not dog*

    LW 2, no advice, just appreciation from the bottom of my heart for teachers this year! I can’t imagine how I’d deal with things if my ENTIRE job shifted so completely. So many teachers I know (including the ones currently teaching my son) are doing an outstanding job in spite of the obstacles. I don’t blame you for wanting out, but thank you for struggling through this far!

  62. Kat Em*

    I transitioned from teaching to marketing. All those parent newsletters, the culture building, the event planning, and the “customer” service dealing with cantankerous parents really translated well. I was also able to talk about documenting learning, keeping abreast of a huge and shifting body of government regulations, and staying engaged and creative in a sometimes stressful environment. That being said, I started blogging when I was still teaching, then began freelancing as a writer on the side before making the full leap. I can definitely appreciate that it would be more difficult to go cold turkey, so to speak.

  63. EngineerMom*

    I’m in the midst of this myself. Still trying to figure out what to do. I don’t *hate* my job, and it pays well and has transitioned fairly seamlessly to 100% remote work, but the really excellent manager that hired me has since moved on to another position, and the person I have now is almost completely hands’-off as a manager, and it’s… not a good fit. I prefer a manager who actually knows what my job entails and can make helpful suggestions beyond “I don’t know, who do you think would be a good person to talk to?”

  64. Sleepy*

    I am a former teacher–taught high school for four years.

    I transitioned out of teaching by taking a job at an after school program where I was working with students for part of the time (after school), and doing administrative tasks in the morning (while the kids were in school). Later, building on the administrative skills I developed, I transitioned to managing the program. My teaching background makes me a valuable manager for the program; my direct reports know they can look to me for advice on working with youth, and I’ve been able to win the respect of our funders which is super important for a nonprofit. I actually moved to a new state where I am not certified, but I would add that being a certified teacher can add credibility for a nonprofit, school-adjacent program.

    I took a pay cut to do this, but my mental health is much better.

    Another friend who taught middle school transitioned to nannying. It was a huge pay cut, but her mental health improved like 1000%.

    Throwing it out there–would teaching in a different situation make things better for you at all? Transitioning to private school from public school or vice versa? Teaching international students English?

  65. Gertrude Thompson*

    LW1: Change management has 5 phases: 1) precontemplation, 2) contemplation, 3) decision, 4) action, and 5) maintenance. You are clearly somewhere between the first two phases, so it’s quite normal that you don’t feel ready to make a decision. (I advise not to make a decision until the pandemic is over). In the meantime, try a few online career assessments (the Holland Assessment is a good one!) You have plenty of time to write plans, think about them, and rewrite them while we’re all waiting out the pandemic. Then, if you try on a new profession for size, I recommend volunteering to get some experience and to see if it’s a good fit. I hope that helps!

  66. 1234*

    Like some others on this thread, I’m also trying to figure out my own path and both these letters resonate with me. I have a bachelor’s in business and have worked in different fields related to marketing. I love event planning/tasks related to event planning/putting together timelines and working to secure vendors. I now work for an adult education company and am the coordinator for their trainings, which uses the same/similar skills as event planning. It’s hard because I love the actual event planning itself – the work interests me. However, with my current job, I realized how much I valued:

    1 – A 9-5 schedule (or something similar). I hated the long hours that event planning took; I ate ramen for dinner many nights because I was too tired to cook. I also had no energy or time to work out during the week so I spent weekends at the gym/taking fitness classes. I now have time and energy to exercise after work and cook myself a healthy meal.

    2 – “Team bonding” events to be few and far between. I like that my current job doesn’t do things like “city wide scavenger hunt” or celebrate St. Patty’s day with day drinking, although those stories amused my friends. There are small get-togethers for holidays (not this year) and birthdays and that’s it. No “happy hour at the office” or “Zoom happy hours.”

    3 – People who communicate clearly about what their needs/wants are. I can make (most things) happen but you have to tell me directly what you want. I am not very good at reading between the lines. I learned that with managers who communicated more in a roundabout way but I guess you can find that in almost any field.

    OP #1 – What attracted you to property management? A friend of mine recently got into it but she also has a sales background and has a similar personality to the LW awhile back who got jobs higher than the level she applied. She is just very personable and people like her. I will say, property management does not seem easy whatsoever. I have an idea of it based on the property management company that my apartment building uses and my friend’s experiences. You seem to deal with lots of complaining people.

    OP #2 – What are your strengths? What do you like most about teaching? I agree with the other comments about looking into education non-profits and instructional design. Both seem like they could be good fits.

  67. F.I.R.E*

    This may seem a bit extreme for LW1 but have you considered aggressively saving for “retirement” aka financial independence, whereby you’d be financially comfortable enough to pursue other career options but also not feel like you are compromising your financial future? You mentioned that you are paid well. My husband and I have reframed our thinking and have been putting about half of our earnings toward savings. We are both 30 and believe if we continue this way, we could be financially independent in the next 15 years. We’ve also decided that it wouldn’t mean that we quit our jobs immediately but that if we wanted to take time off from work to explore other things, we could. We also don’t have children nor do we plan to so YMMV in that respect but just a thought.

    1. LW1 here*

      Yes I have, and my partner and I sound similar-ish to you guys :) one option I would definitely consider is just aggressively saving to pay off the mortgage and considering a career switch only at that point, where I have the cushion of being able to have fairly low outgoings.

  68. Kara S*

    I was in the middle of changing fields before COVID. My former field (coincidentally also software project management) played well to my skills, paid well, and had promising abilities to move up. But the work was not interesting and I wasn’t interested in being promoted. I decided to get a degree in an open ended, adjacent field (digital design). This would allow me to not start totally from square one once I was done school because I did have experience and connections in the field. My plan was to find some way to eventually transition full time into the design aspects of the industry, potentially moving away from software altogether and eventually starting my own WFH web design business. School was not a necessity for this but it was the right choice for me.

    Once COVID hit, I ended up getting a job in software design that was made possible by my (partially finished) degree and my past experience as a manager. I plan to eventually finish the degree and follow through on moving out of software and designing a job where I work for myself. The main reason I made the career switch was I wanted a job where I was in charge of my own schedule and I was doing creative work. That would never have been possible as a manager so I knew the change was the right choice.

    Some questions that I found super helpful to ask when I was planning all of this:
    – What do you want out of a career and day job?
    – Which aspects of your current job do you like and not like? Is there some variation of this job you do want (either through promotion or through finding a similar yet different position somewhere else?
    – If you need education to get your new job/career path, is that something you can afford and are willing to do? Can you work school into your existing work schedule? Do you even want to?
    – Is there any way you can make moves within your industry to eventually get out of it?

    I would also do so much research. Not just into what your new career path might pay but into the day to day aspects. Make sure these align with what you are looking for. I’d also advise not overly romanticizing the end result of your new field but instead focus on all the steps it would take to get there and ask yourself if you really want to take them.

    Good luck!

  69. Lizzo*

    General advice: making a career change is awesome, and it’s never too late! But please consider the very real financial implications of making the change–not just costs for retraining, but how recession-proof the new career is. Look at data for the industries you’re interested in and see what the potential trends are for the next 10 years.

    Also, are you retraining for a very specific thing, or will the new skills be transferrable to other industries? Can you combine skills from your old career with skills from retraining?

    Being happy in your career is important, but financial stability and security are also connected to happiness.

  70. IT Heathen*

    LW #2:

    If there is a health related reason (mental or physical) that could prevent you from returning to work full time, you might be eligible for vocational rehabilitation, which would pay for you to go back to school.

  71. Mayflower*

    LW No. 1, I am a retired software engineer with a dozen investment rental units. When I saw that you are looking to avoid stress AND you are considering becoming a property manager, I nearly choked.

    Please, please, please do not go into property management. Half your tenants will be good, reasonable people but the other half will be unimaginable jerks, or have serious mental health issues, or both. In the past couple weeks alone, I have been:

    1) Yelled at by a tenant for not fixing a problem he’s been having “this whole year”. This was the first time he told me about it, and he’s moved in last month.

    2) Yelled at by a tenant for spying on her through FAKE security cameras. She is a single mom so I offered her to purchase and install automatic flood lights and fake security cameras on the front and back of the house ($500 out of my pocket for something I didn’t have to do) which she happily accepted.

    3) Yelled at by a tenant for not fixing her oven. I’ve had a handyman “fix” it 3 times, and every time she forgets how to use it and logs a complaint again.

    4) Yelled at by a tenant for not refunding the full amount of security deposit. These tenants haven’t paid any rent for 4 months (she quit her job to “focus on being a SAHM”) and left the house in such bad condition that I had to install a new kitchen ($5k out of my pocket) and left so much stuff behind that I had to hire movers and junk haulers ($1k, then two days of cleaning by me and my husband).

    5) Yelled at by a tenant for mold and holes in the walls in the basement. Every handyman/electrician/plumber/rental inspector who went through it told me there is no mold or holes in the walls; her own social workers went down there twice to check out her complaint and said they didn’t see anything.

    I am stopping here in the interest of time but trust me, you do not want to become a property manager. The professional property managers that I know personally are either tough as nails, or so preternaturally relaxed that I suspect they are just always stoned. If you get stress migraines, this is the last profession you want to go into.

    1. Sara without an H*

      I believe all your examples — some of them, I think, have been my neighbors.

      You bring up an important point — before making the leap to a new career, it’s important to talk with people who are actually in the field and find out negatives, as well as positives. The actual job rarely matches your mental picture of it.

  72. AnotherAlison*

    Throwing out some “what not to do” advice, although I think the OPs are pretty safe. My brother-in-law is a career changer in his mid-30s, only he never had much of a career. He had a series of random jobs and spent ~5 years in manufacturing and was moving up the ladder there. He quit his job and went back to community college and is pursuing a general associates, to be followed by a general bachelors, and will be in his late-30s with a multi-year work history gap when he’s finished. This is absolutely not what I would be looking for in hiring a career changer.

    Do:
    – Keep a steady work history, unless you have a very specific educational program that would not allow you to work part-time.
    – Know specifically what you’re going to. If he knew where he wanted to go, he could try to get applicable work now and have a better chance at getting a foot in the door later. What would you think of, let’s say, a guy who finished a teaching degree in his 30s and had no history working with kids vs. one who had been a para for a few years?
    – Try to bring something from your past experience to your next job. You’re competing with younger, lower-cost people. It’s going to be easier if you can offer something more than the average entry-level person.

  73. Anona*

    I was a teacher for 3 years and it wasn’t for me.

    I took an admin job (basically an administrative assistant job) at a university, and worked my way up from there.

    It helped that after teaching I did some campaign volunteering and volunteering as office staff in a free clinic, just to have some non teaching experience. I also networked pretty hard with people I knew who worked at the university.

    I definitely took a pay cut ($7k), but it was worth it to me. I now make more than I do teaching but my teaching salary wasn’t huge ($39k). I’m an assistant director of an office and make $60k, that took around 10 years.

    As someone who has done some hiring at our state university, because it’s a state organization, there are a lot of regulations. Like we have to make sure everyone has the required qualifications listed in the job description before we interview them. So for us, it’s important that job candidates be specific about stuff (like if a position references needing technology skills, it’s something you need to reference in you resume or cover letter), which a lot of candidates don’t always do.
    Teaching is so niche, but I think what helped me is that I explained how my experience fit the position, and also referenced my volunteer experience. I had experience doing parent teacher conferences im another language and also got a small grant at the school, just stuff that’s not just planning lessons. So any experience leading committees, etc, just stuff that can be relevant elsewhere.

    I love working in higher ed. We’re facing budget constraints right now, but I love working with students, while still (pre pandemic). having a really clear separation between work and home. Good benefits and leave. It was amazing to me that they would order staples for me, and I didn’t have to buy them like in a classroom.

    Good luck!!!!!!

  74. SnapCrackleSloth*

    LW1, I’m in a similar position to you–successful ‘professional’ job but with dreams of being in home design/renovation. You don’t mention your current skills and resources, but what I’ve been able to do is begin to build the beginnings of a side business–with one investment in a fixer-upper, some latent handy skills, and VERY creative and dedicated mortgage brokers (cannot emphasize that factor enough), my husband and I were able to turn a home we lived in into a strong sale, which then funded multiple other opportunities, and we now have 6 properties that we’ve refurbished and are renting until we see enough capital to start a legitimate business that can allow me to go half-time/freelance writing and marketing, half-time home renovation. In the meantime, I’m getting an online certification in interior design so I can feel solid on selling myself, and I’ve shifted my thinking on my current job into the means by which we can afford this (expensive, intense) hobby-for-now.

  75. Anona*

    And I definitely wouldn’t get a new degree to get into higher ed. Degrees are nice but experience trumps all, at least in the non- teaching positions. We’ve had PhD people apply to some positions with no practical experience. They typically haven’t gone far.

  76. Like 12 Cats On Acid*

    Former teacher here, I quit this year (after 22 years) and became a baker. The pay cut is huge but at the time I had a plan that involved a list of food banks, washing my clothes in the park restroom, sleeping in my car, and using the library for internet – whatever it took. Luckily I got a job. My state has free classes for technical education, including things like car repair and HVAC, and I took culinary arts until COVID shut the schools down. I waited a while until it became clear that the lockdown wasn’t going to be a two or three week thing and started applying everywhere and trying to get experience. I volunteered as a cook at a homeless shelter and applied to grocery stores and nursing homes because I figured they would stay open no matter what. I let the chefs at the shelter know I wanted a job and they gave me different tasks to do so I could add something to my resume every week, basic stuff like “experience using a Hobart mixer” and “maintained time/temperature logs”. The great thing about shelter workers is that they’re used to helping people get jobs, so the chefs were very direct about saying “write this on your resume tonight”. I kept refining my cover letter and cover email paragraph because a lot of food service jobs are just on Craigslist and don’t want a full cover letter. I applied to a job almost every day (there weren’t a lot out there so some days I didn’t apply anywhere, but I checked religiously). After I applied, I tried to forget about it and move on to the next job. In two months I had one interview, with a Very Nice Chef who said he’d love to hire me but couldn’t until full capacity dining was allowed. I put it out of my mind and kept applying. Then another month and two of the first places I applied called me, and then Very Nice Chef called to ask if I’d found a job because business was picking up and all of a sudden I had a week with two first interviews, two second interviews, a third interview, and two job offers. Very Nice Chef is now my Very Nice Boss and we’re doing fantastically with outdoor dining so fingers crossed that this keeps working out.

    I think those websites on what to do after you’ve been teaching are only useful if you still want to be connected to teaching on some level – they just aggravated me because I was pretty much done with white collar work and human contact. If they have a website for what to do if you’re running screaming out of the classroom and want to do the opposite of teaching, that would’ve been helpful. Now it’s just me in my corner of the kitchen baking away, and I haven’t been this happy in years. It’s heaven. My experience has been that the pay cut isn’t as drastic as it looks, because you’re probably spending so much money on classroom supplies, and when you factor in the unpaid hours you spend grading, emailing/calling/meeting with parents, planning and preparing lessons, cleaning your classroom and making it look cheerful and educational, making copies, etc, my actual loss is $2 an hour. I could surely use the $2 but not enough to go back to the classroom. Every paycheck I get is enough, and it turns out that enough….is enough. In my interviews I kept Alison’s most common phrases in mind, and kept reminding myself to be matter of fact about everything and that people leave jobs all the time. I had my answers prepared about why I was switching careers, but it turned out no one wanted to know why I was leaving the classroom; as soon as I said I used to be a teacher all of my interviewers said some version of ugh, now that’s an awful job. I wasn’t ready to sleep in bushes, but I had a car and once I was at the point where sleeping in it was a viable option, the whole world opened up.

  77. Duckles*

    I found a “bridge” job— one that required my experience from my old job but a different role/industry. They’re rare but can be a good way to get your feet wet trying something new.

  78. Youth*

    I got stress migraines at my last job (and they almost completely went away when I switched to a new company).

    Is there any way you could transfer to a new position where you could use your software engineering skills but in a different way? I took a job that used my same skills but doing something completely different. It’s a lot less stressful for me.
    Same thing goes for teaching. My aunt was a teacher who switched to teaching English to Chinese students online for a while.

  79. Former Educator*

    I made a career change a few years back and while I did not land my ultimate dream job, I did land a job I love and adore which is crazy-busy and fulfilling and wonderful. I was a college professor and now I work in media/press/pr. My overall story is just too long to type here but a few tidbits worth knowing: 1) I began working toward a career change about a decade before I actually could make the switch. I did not know it would take so long. 2) I did every single thing you see in career change articles but even with that it was a huge challenge to switch: volunteering in my field, going back to school, networking, working for free, interning, working part time, etc. 3) The truth is employers don’t need look for somebody different in their pile of resumes; if they have 50 people who came up the traditional way, your resume with a slightly different path, is easy to pass by. I hope you will pursue your next thing and I am living proof that it can happen and persistence pays off. But I also wanted to share the reality that it can be a tough journey in contrast to all the articles out there that make it sound like a snap.

  80. Lizh*

    I can’t comment on the IT part of property management. However being an actual property manager onsite is tough. Property management can be s tough job and very stressful. You can’t please everyone. And now that people are home and seeing things the demands are even worse. I am in property management and the amount and intensity of verbal abuse we have to deal with is through the roof this year. I am seriously thinking of looking for something else. I can’t speak as to teaching but property management can be very very stressful. And it doesn’t pay much for all the abuse after hours emergencies etc. that we put up with.

  81. Work work work work work*

    LW 2: I’m a former teacher who transitioned out after 8 years of being school-based. I currently work at an education non-profit – it was a step down for me in terms of responsibility/managing a team, but I didn’t take a pay cut (admittedly, mostly thanks to moving to a blue state), I’m getting developed in technical skills I wasn’t previously, and the impact on my personal life has been absolutely worth it. I’ve also seen people make the jump from teaching to edtech pretty frequently, often because you can be a product rep while you’re still in the classroom. I haven’t seen a ton of people directly make the jump to instructional design without doing some course or degree work beforehand, but there are definitely independent contracting opportunities with K-12 education companies to develop materials. Quick plug for the EdSurge job board if you’re at all interested in edtech or ed nonprofits – they have a lot of postings that are in the education sector, but don’t involve classroom teaching.

  82. Ash Bash*

    My spouse is a former teacher (he left earlier, after about 5 years), but here’s how he did it:
    -He invested in some serious career counseling (including a four hour aptitude test that found he would be terrific in the tech sector, but would be an awful teacher. It gave him hope and direction.)
    -He realized that he had built skills in the classroom and outside of it that would work well in an IT environment – he ran a computer lab and has incredible patience with users.
    -He applied for a job within our public school system about a year ago, but on the IT side instead of the teaching side. It’s not an entry level job, but it’s relatively junior. This isn’t his forever job, but it has given him space to remember what he is good at and a direction for where he could go next. The classroom is very different from other offices and so this year has been a “buffer” to give him space to learn how to be in new environments.
    -He is happier, which makes his career seem more achievable. He’s not making a huge amount of money, but he wasn’t before either. He has more time/space now to focus on getting excited, rather than just trying to survive.

  83. Haha Lala*

    For OP#1-
    Volunteer for Habitat for Humanity! (Or a similar organization). You can get involved with the construction process, maybe make some contacts, and get a better idea if that is something you’d want to try as a career.

    Also, look into SketchUp! It’s similar to the drafting software’s you’d likely use as an architectural technician, but you can use the free version and find tutorials to follow online. If you really enjoy that, then you can find classes to take to learn more.

  84. Educator-Adjacent*

    LW#2: Consider looking at the various LMS (learning management system) providers like Blackboard, Canvas, D2L, etc.. We hire a ton of former educators as Customer Success Managers, Learning Strategy consultants, Instructional Designers, Implementation Consultants, Trainers, etc.

  85. L*

    LW2, I work in education policy and former teachers are the gold standard here. We get a lot of Teach for America and City Year grads, but there are also those who worked as a teacher/administrator for a long time and then switched to the policy side of things. So if you’re at all interested in that sort of macro-level work, look into education nonprofits in your area. Of course, nonprofits have been hit hard by COVID, but there are some that are still hiring, and it’s at least worth a look!

  86. AcovidRN*

    I don’t have any advice for the second letter write but I can certainly empathize. I am a nurse who switched into this field and now desperately want to leave. The danger and poor treatment is unreal. I am having a real tough time showing a track record of achievement in this job and I have not received any callbacks from my job submissions either.

    1. Miss Characterized*

      I’m so sorry you’re going through this. I hope that you’ve found some resources in this thread, even if they’re not profession-specific.

      I see you. I’m thinking of you.

  87. Anonosaurus*

    So much great advice here. My two cents’ worth is to find out what the day to day life in the job is like – whether that’s through volunteering, finagling some work experience, talking to people in similar roles, all of the above. I’m not talking about the corporate culture – I’m talking about the core job tasks. What is it like to do this every day and what do you spend your time on? Is the job repetitive or varied? How much human contact is involved and what kind of humans?

    The reason I think this is important is because I switched from working in charity management to practising law about 15 years ago. I worked as a legal secretary when I was in college so I knew what I was getting into (actually, if possible, temping in admin roles in the chosen field can be helpful) but I have frequently encountered work experience students and interns who have no clue what the everyday job is like because law school is all about the theory and not the practice. TV legal dramas don’t help. We sometimes kid around in the office that a realistic drama series about attorneys would involve filming a room full of people quietly looking at pieces of paper all day. Maybe making some calls. A coffee now and then. And this is coming from someone who does trials! (OK, court is a bit more exciting, but still nothing like TV courts). You do apply the knowledge you have acquired through studying law but the practical tasks involved in doing the job are difficult to discern until you start spending time in a law office, and they also vary significantly across different legal specialisms. A lot of the core skills for my job I learned in other contexts (such as calming down upset and angry people – retail and customer service jobs FTW).

    Don’t get me wrong I love my job and have never regretted it. However, it took me about six or seven years to get my pay back on track after starting back at the absolute bottom of the pile – had I stayed where I was, I would be much better off financially, but I had gotten to the point where I would feel physically nauseous and tearful every morning when I turned into the block where my old office was. So I feel you and I would encourage you to go for it but also to be real about what a day in the life looks like.

  88. Properlike*

    Must be in the air, because I sent a similar question to Alison last week! When you’ve worked in “traditional” occupations for so long (two separate, sequential careers in education and creative), how do you know where your skills fit in the general outside world? I’m several decades in the workforce, I know exactly what I’m good at, what I’m not, and what I want from a job situation… all I need is this ellusive List of Jobs that match my skills.

      1. Properlike*

        I’m being quite literal with that, but this whole thread has provided it! I now have two single-spaced pages of job titles, companies, industries, and websites that are a good match for my specific skill sets. All the other job advice I’ve gotten has been along the lines of “curriculum writer” and “editor” (or, even worse, the dreaded “sales” and “marketing.”) Those were the parts of my jobs that I liked the least.

        Thank you, Alison, and posters, and especially OP#2 for putting the teacher-specific question forward!

  89. NonEngineerInTech*

    To LW1 — I’d follow the advice of others to keep your cushy job and pursue your interests as a hobby. I moved from analytics in a non-tech to tech, and software engineers (both ICs and managers) are some of the most coddled employees I’ve ever seen. Maybe I’ve just had bad luck where I’ve worked, but while they obviously do very useful work, they are overwhelmingly lacking in soft skills or business sense, not held to professional standards (eg refusing to take meetings before 11am because they want to sleep in, but expecting responses at midnight; rude to the point that they drive others to quit–think constantly excluding relevant stakeholders from meetings and taking over then messing up other people’s work after declaring it “trivially east”–but nobody cares because their “skills” are worth it. Meanwhile non-engineers are expected to bend over backwards to make up for the engineers’ incompetence at basic soft skills), and convinced of their own brilliance in all areas, including those well outside their domain. If I were hiring for a non-SWE role, I would be extremely reluctant to consider an engineer without a lot of evidence that this person wasn’t an arrogant jerk. Software engineering is a magical combo of high salary, great benefits, and extremely low performance standards (I’ve never taken a CS class in my life, but have debugged our programmers’ code based on knowledge I’ve picked up on the job. It’s not the intellectual challenge engineers make it out to be). Why leave it? It’s a serious question — I’m obviously bitter about the crappy software engineers I’ve worked with, but only because I wish I too could be paid more to do less AND act like a jerk at work whenever I’m having an off day!

    1. LW1 here*

      I don’t disagree that engineers are often well paid in comparison to other careers that are equally stressful or difficult. But… you clearly have a very skewed view here. I assure you at my company is it not acceptable to refuse meetings at 11am, to ignore business needs, or to be incompetent at soft skills. We also do not have ‘extremely low performance standards’ :) it does sound like your place is unusually bad!

  90. JJ*

    1. I’d imagine many people will disagree, but I think being “passionate” about your work is both super over-rated and can be discouraging, as good passion jobs are rare and hard to find. Plus, monetizing your passions/hobbies can be a total drag that ruins the hobby, especially if it is one that serves an audience (like art or music). Find an industry you’re interested in, intrigued and challenged by, and keep your passions as your own thing you get to do your own way.

    2. Bad (or even meh) jobs can make you feel like you want to quit the whole field. If the prospect of taking a big pay/status cut to change industries is too much, maybe find a new job, one with more flex to it where you can pursue the field you’re interested in on the side, gain experience, etc.

    3. Things are crazy right now, I think we all want to quit everything from time to time! Be gentle with yourself and try not to stress over it if you can.

    1. HelenOfWhat*

      I agree that being passionate about work or “doing what you love” is overrated. I realized a lot of the blocks I’ve had on creative work have been due to thinking it has to be good enough to sell. Any time I approach a creative hobby without expectation of needing to sell it later (or thinking I truly don’t care if no one ever buys my work) I end up overflowing with ideas and actually following through! It’s made me realize I don’t need anyone to pay me for that part of me.

  91. HelenOfWhat*

    Transitioning careers is tough, and though I haven’t technically done so I have known others who have to varying degrees of success. I agree with many that research and informational interviews will get you prepared no matter what your interests. I briefly considered a change that would require a new degree and was wisely given the advice to take a class on it first to see if I actually like it.
    LW#1, you mention not having sales experience, that seems like something you might be able to dip into at your current job or next one since most companies have sales teams. See if you can shadow a training session or access those materials, consider whether you can build something small to help with the sales process (a chance to work cross-functionally and get to know the process). It’s also worth looking into tech jobs where you work on real estate related products, so that you gain industry knowledge while using skills you already have. Apparently mortgage companies are doing extremely well right now due to the appeal of low interest rates. There are lots of tech companies that serve real estate in different areas of the process and it’s amazing how much you learn by creating a product for that customer (and you can often leverage that into using professional development funds to gain deeper knowledge). My husband works at a company where clients are largely from real estate development/architecture and I would also note that real estate, especially on the property end can be very stressful and the personalizes involved are very different from software industry personalities. (Not universally but again, talking to people who do what you want to do is key.)
    LW#2, I echo a lot of the comments above on transferring skills gained from teaching. I have a colleague who started her career as a teacher, moved into customer support for our tech company, and rapidly progressed into project management. You don’t mention what you want to do in particular but I’ve also worked at nonprofits where a background in education would have been useful (even in non-program delivery areas like finance/administration, grants management, HR, project management, etc).

    Good luck!

  92. Ladybugger*

    Book Recommendation: Pivot by Jenny Blake. I found this so helpful as a “how not to throw the baby out with the bathwater” guide to finding and pursuing your next career move – really whether you stay in the same industry or not! She’s the creator of Google’s Career Guru Program, and she profiles lots of people in the book with real situation which I found so helpful (and the solution is not “give it all up and follow your dreams!”, advice which gives me heart failure).

  93. Tzatziki*

    LW 2: My mom was a teacher for many years and she got a job transcribing police calls after she retired. Maybe something involving editing or transcribing? I know she was well set up to deal with grammar and such going in.

    LW 1: After I got my bachelor’s, I worked in my (low-paying) field for a bit before going back to school to retrain. What worked for me is really knowing what I wanted out of a job. I didn’t focus on what I was passionate about. I wanted the job itself to be halfway decent and interesting enough that I didn’t dread it, but the most important was I never wanted to send out 50+ resumes per job ever again, and I wanted to be appreciated. I really put a lot of thought into my second career that I didn’t in my first. I did have to get loans to go back to school, but this time I knew I would get a well-paying job immediately after so it wasn’t that bad. I guess my advice is think about things you want out of a job beyond just what you like doing. What kind of pay do you want? What kind of colleagues do you want? How much flexibility do you want? For me, there was no job I would enjoy more than sitting on my couch cross stitching, so I pretty much chose something that would let me do my hobbies a lot, would pay well, and I wouldn’t have to do a big job search for.

  94. Karlee*

    LW#2: I’ve worked in K12 education companies for my entire career (decades) and there is a very high value placed on experience in the classroom. In my company, a full third of staff are former teachers. One of the easiest entries into the field is as a educational or learning consultant. The big publishers hire them to do presentations and to answer questions from districts and schools that are evaluating their products. If you’ve ever been on a curriculum evaluation committee, you’ve seen these people at work. It’s a great entry to begin to understand the business side of education. Other places where I’ve seen teachers hired directly from the classroom include item writers for assessment companies, content writers and jr. editors (lower level than instructional designers) for any curriculum company. Product trainers are often recruited from schools, whether its training on how to use software or how to use curriculum. Almost every product company has a service team that provides related professional learning and teachers are great candidates for this work. And lots of companies hire teachers who have used their products as sales people. Sales has a bad name for a lot of educators but most education companies do needs-based selling so you aren’t being asked to persuade an unwilling decision maker into making a purchase. It’s really a relationship-based job and not what most people expect.

    Use edtech as a keyword in your searhes. Check the job listings of companies whose products you have used. Your familiarity with at least one of their products is an advantage. Reach out and ask for informational interviews to get a better understanding of the roles available (but not in pursuit of a specific job at a company). And don’t hesitate to apply to jobs where you don’t meet the requirements for business experience (ex: 2 years experience in sales). Lots of companies post their ideal job requirements but will hire an enthusiastic educator without that experience given how much they value is derived from the candidate’s time in the classroom.

  95. Exhausted Trope*

    To the 22 year veteran teacher… I taught public and private school 7-12 students for 10 years and went on to work in university for 3 years. Then I got the opportunity to write curriculum. You might want to consider it. I love to write so it was a natural fit for me.

  96. Kelly Brown*

    For the teacher: I follow “Teacher Misery” on Instagram. I haven’t explored the options but the person behind the account offers ways to transition out of education.

  97. LW1 here*

    Thank you so much for all the responses, I will read them all.

    I do know that property management is stressful and not well particularly well paid, I admit to trying to come up with things that I could do in property without a huge amount of new qualifications, and potentially reusing the project management skills I already have.

    I also did write this at the end of a 3 day migraine when I was feeling particularly low, and I’ve also found wfh during Covid hard. So I think folks who said to ensure it’s not just temporary and to look at my relationship to the job before I tear everything up give good advice :)

    Longer term I’m going to focus on saving so finances don’t have to be a determining factor so much and will also look into real estate courses, I kinda hadn’t even realised these were a thing and they look interesting even if it does end up more a hobby.

    Thanks Alison for publishing my letter and good luck to all other potential career changers out there!

  98. Anongineer*

    For the first letter (and in general): if you’re thinking of taking a job that pays less and this is a concern, figure out what that would mean for your standard of living.

    Research salaries and find what would you can expect to be paid for your experience. Make a budget with this new salary, including rent/mortgage, food, debts/loans, etc. Then try living on that budget for 1-3 weeks and see if it’s reasonable for your lifestyle. This has always helped me when considering taking a pay cut. Is it something I can feasibly do?

    Disclaimer: the pandemic may have drastically changed your lifestyle and spending, so take that into account when looking into future proposed expenses.

  99. Argh!*

    I know two former teachers who went to work in libraries. One earned an MLS and one used her MEd to get a job that was one step lower than being a librarian (though still working with teens and doing much of the same work – just more of the programming side and less on the collection building side). If there’s a shortage of school librarians where you are, maybe you could get your employer to pay for some or all of the master’s degree.

    re: tech to anything — we all need tech expertise, so I could see using that as an entré into the desired field as their local tech guru, and then branching out once in the professional orbit.

  100. Jennifer Juniper*

    LW1, since your migraines are triggered by stress, you may want to focus on getting your migraines under better control before making any decisions. Job-hunting, taking a pay cut, and starting over all sound stressful enough in normal times. During a pandemic? Even more so!

    Please tell your doctor what is happening to you and see if you can get FMLA if necessary to deal with this health issue. This sounds really bad! You should not be losing every weekend to these damn things.

  101. Tracey*

    This is general advice, but I have switched careers 5 times so far. Now I’m very happy with both my job and industry, and I’m really grateful for the winding path. My suggestion to is to review your skill-set and go after different jobs in the same industry,
    or a similar position in a different industry, but don’t try to do both at once. It will be much easier for hiring managers to see you in a new position this way.
    I’m of the opinion that if you look ahead to the career paths your current role would lead to and you find that vision depressing, make a change. There is simply no way of knowing what else is happening out there if you don’t change your view. Of course, you don’t want to be needlessly job hopping, but if you’re in a job for several years, it’s usually not difficult to explain why a move in a particular direction is strategic.

  102. Green Goose*

    Former teacher here:

    I only taught for a couple of years before I knew that it would not be something that I wanted to do long-term, but I wanted to stay in education. I started looking at admin jobs at colleges, community colleges and education nonprofits. I applied a whole bunch of places and eventually got an entry-level role at an education nonprofit. The starting salary was low but I was able to move up fairly quickly and I’d say that about 30% of the people at my organization used to teach as well.

  103. Katrinka*

    For anyone who’s looking to change careers or shore up their skills for job hunting or in their current job, I cannot recommend Coursera enough. They have a lot of top colleges involved and offer a lot of online courses.I took the Johns Hopkins Covid Tracing class for free, but I am currently on the $50/month subscription, which allows me to take any offered classes I want. I am currently taking a University of Michigan Intro to Python class, and because it’s self-paced I’m moving through the course quicker than their suggested minimum (3 hours/week). I am trying to find an analyst position and cannot afford any regular classes (I’m currently unemployed), so this is a great way for me to get some additional training to make me more marketable to employers.

    In addition to peer-reviewed assignments, there are message boards and online groups to work and connect with to discuss classwork or just socialize. I haven’t even finished exploring everything on their site.

    Even if you just wanted to take something for fun, this is an affordable way to take well-regarded courses from anywhere.

  104. Krakatoa*

    I did a complete 180 in careers when my first company started annual rounds of layoffs that I barely survived. They still exist, but are a shell of what they were when I worked for them. It is a huge leap of faith, but one I’m really glad I took. Now I make more, and am happier with my job, and my job is stable (-ish… Covid made us go part time for a while, but my industry will always be in demand).

    My advice is, first, make a list in what your current job is lacking that you want in a new career. Define your priorities. If you can’t define them clearly, it may be that you’re more just burned out on work in general and need a break or a new job versus really needing to change industries (which can be especially problematic if you have to pay for school/training to break into a new industry).

    Then, really look at what the careers you’re looking at entail. A lot of things sound good on paper, but the reality of the job doesn’t really match that. If possible, reach out to people in the industry you’re looking out to try to shadow them on their day and ask them what it takes to have that career and what he realities of their day to day life really are.

  105. LPUK*

    In my last corporate role, I too got stress migraines 2-3 times a week and spent my weekends and most evening in bed. It happened gradually so that I mistook for normal and soldiered through. It’s only when HR/ first wider/ office manager/health&safety manager all ganged up on me and got the Company Doctor involved ( who promptly signed me off for six weeks as unfit to work) that I realised how conditioned I was to always feeling ill. Now I do much the same thing as. Consultant instead – yes it’s still sometimes busy, but I can control my hours much better, and go for a nap/rest whenever I need it, and my migraines have almost disappeared. So maybe it isn’t the job but the environment you need to change?

  106. Ellen Ripley*

    Late to comment but for #1: you have a uniquely desired skillset and I wouldn’t entirely change your profession; instead I’d decide what was most important to you and look for positions that will give you that. I worked in tech for a few years and had many friends and a spouse who were software engineers. If you are a decent coder and can communicate with people, you will always be wanted somewhere. What you may have to do is ‘downgrade’ yourself back to an individual contributor role which will give you more flexibility. Then you can figure out what your priorities are: a particular set of working times or circumstances? The kind of projects/software you help on? The people you work with?

    Then I’d also look at what you can do in the rest of your life to give you the engagement and reward you’re looking for. You may be able to start a side hustle that you enjoy, or keep it a hobby, but either way, don’t expect your job to give you all your fulfillment all the time (I’ve changed careers several times now, and as the old saying goes, wherever you go, there you are.)

  107. TeacherLady*

    I’m a teacher who is mid-career change. I was in the same boat as LW2, with the major difference being it was my 2nd year of full-time teaching.

    I’m not sure if my approach is transferable, but what I did was to move to on-call teaching, and work on my 2nd career on the side. Being on-call gives me the flexibility to devote more time to my 2nd career as it grows, or if I have a busy month with it. It also gives me the security of knowing (most of the time – COVID is not great for this) that I’ll be able to pay my bills if 2nd career has a slow month.

    I’m lucky that career #2 is both remote and flexible.

    The tradeoff for pursuing a career I’m really passionate about is having less security and an income that varies from month to month, but it works for me.

  108. Azelma*

    Former teacher here. Left about a year ago due to burnout and insane stress, so I can’t imagine how difficult it is at the moment.

    I now work for a company that makes educational resources, and I absolutely love it. Loads of opportunities to be creative, flexible hours and still using my skills in education.

    I’m not US based, but I bet there will be similar companies in the US :)

  109. Ms. Enigma*

    My mother made a career switch to education in her 50’s. She started out in a teaching assistant program where she worked for 3 years while getting her Masters (for free) and then had her own classroom after graduating (with a 4.0!). She continued taking graduate classes at a local university which was relatively inexpensive and now has over 100 credits over and above the MEd and her principal certification. She figured out pretty quickly that classroom management was not one of her strengths–she worked in a district where there would be 30+ kids in a class–but she likes educational theory and feeling like she’s making a difference. She was able to get a part-time position within her school doing testing coordination, scheduling, leading professional development etc., so she was only teaching a half load. She eventually transitioned into full-time work in the administrative office and did that for several years before retiring.

    You should also consider looking for nonprofit jobs. There are SO MANY educational nonprofits and I’m sure your classroom experience would be valuable, and you would have transferable skills. You could be a program manager, grant writer, instructor, lobbyist, union representative, etc.!

  110. Fezziwig*

    I can identify with both of these letters!

    I worked in an public education adjacent field (social services) and burned out quickly. I made a career change and I’ve felt really happy with this change mentally, but my career is still not in a good place. I no longer deal with the mental and emotional burn out of my previous field. I even received a higher ed degree with several professional internships in my new field, but I’ve never had another full-time, stable job. Now that the pandemic is upon us, it’s even worse.

    I would caution anyone who would be leaving a stable, full-time with benefits position from doing so. The stress in the current social and political moments make unhappiness at work seem even greater. But I can’t emphasize enough how little it matters that you “love” or even like the work you do if you can’t get any. Stressing about paying rent and having health benefits in the current moment is not worth any of that.

    If things are more stable next year, go for it! I wish I could say relevant experience and education in your new field is enough to guarantee a job (it hasn’t been for me) but I’ve never regretted the switch as far as knowing this is the career I’d like to pursue moving forward.

    1. 1234*

      You message about stressing about paying rent and having health benefits resonates so much with me. Do you have any tips on staying engaged even though you don’t “love” what you currently do?

  111. LPC*

    Therapist here! It might be worth making an appointment with your local community college and taking a career assessment then working with one of the academic counselors to review results and consider options (required classes, training costs, etc.) You might be surprised at the feedback – it’s helpful learn what’s recommend for your skills/interest/personality and also in demand in your area…

  112. Dee*

    Hiii – I’m currently considering my career options, and trying to figure out the right way to pivot. I’ve been in my current role for 3ish years, but in this general line of work for longer. (For background, I work in tech/ as a Salesforce Admin).

    Being home the past few months, I’ve had more time than I’d normally give myself to think about this. And as I’ve started research my options, I realize that the big thing limiting my options is me! And it’s not even about lacking confidence or being self-deprecating. It’s about adjusting how I approach things.

    For ex…I’m an analytical person who likes to make decisions based on what’s black-and-white. So if I know I lack knowledge in x, I’ve told myself that it means I prob can’t do y. And that’s not always the right way to approach careers…which I should know, since I definitely did not start my career in tech. Empirical evidence!!

    So I hope this advice doesn’t sound hokey. But I think the best things you can do to *start* this process, based on what I’ve started to do:
    1) take advantage of your time away from the office (if that’s your situation)
    2) do TONS of research on people’s paths & pivot stories (which helped me realize that I could do more than I originally thought)
    3) Expand your social networks with like-minded professionals, especially during covid. I’ve joined Facebook and LinkedIn groups just to take inspiration from other people’s ideas
    4) Actively try to free yourself from those automatic, limiting beliefs. Unless it’s something rigid like law or medicine, or you’ve found evidence that says otherwise, there’s no reason to think you can’t switch into a line of work that’s different from what you’ve done in the past. Just making that cognitive shift has changed how I approach things, and it’s given me ideas I would’ve completely written off a year ago.

    p.s. If anyone happens to be specifically interested in a Salesforce career – they’re known for having people from all walks of life transition! You can find it online, but also happy to answer some qs if I can help.

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