I feel horrible about reporting my boss’s tax fraud, limits on employee computer monitoring, and more

by Alison Green on April 10, 2023

It’s five answers to five questions. Here we go…

1. I feel horrible about reporting my boss’s tax fraud

I recently left a job I loved dearly because my boss stopped paying me. We had a great relationship leading up to that, so when she said she couldn’t pay me and then flipped out because I told her I was leaving, I was pretty surprised. She said some ugly things that really hurt, then tried to act like we were best friends and asked me not to tell anyone else in our profession about what happened. Just a few days later, I realized that even though she’d classified me as a 1099 worker for a year and a half, I really should have been a W-2. My tax bill was astronomical and my tax preparer told me I’d been misclassified. I reached out to my old boss and asked if she could fix this. She refused and said that even if she did, I would have to pay her back for “overpayment.” I already talked to a lawyer who told me that’s insane.

I know I need to report her for tax fraud and request reclassification from the IRS. I also know that the consequences could be very bad for her. I still feel some weird need to protect her or fix her mistakes. We’d been fairly close and I know she’s going through a very difficult time in her personal life right now, but so am I, and it’s her fault. How do I get over the guilt of feeling like I am betraying a boss who already betrayed me?

You’re not betraying her by expecting her to act ethically and legally. And you’re not betraying her by filling the appropriate paperwork to correct your own tax obligations. She is betraying you by expecting you to eat thousands of dollars to cover for her violation of the law … as well as by attacking you when you declined to work for free (!) and by threatening you with (fake) repayment consequences.

You’re not requesting reclassification from the IRS to get revenge on your boss; you’re doing it because it’s a necessary step to straightening out your taxes — a situation that she created.

Frankly, you’d need to do that even if she were being lovely to you. But she’s not being lovely; she’s being a complete jerk. That sucks — this is a job you loved and someone you were close to — but that’s on her, not on you, and you can’t let it deter you from protecting your own finances.

Read an update to this letter.

2. Are there any limits on employee computer monitoring?

I have reason to believe my employer is planning to install desktop monitoring software on at least some computers within our organization. The particular program is one that’s, as I understand it, incredibly invasive (to the point of being a keylogger), and the management responsible for this project is being very tight-lipped. Even most of IT hasn’t been told this is being done, which has definitely raised eyebrows since they’d have to support whatever it runs on; from talking with them, I can’t imagine they’d be deploying this particular program if it were their choice. All in all, it sounds incredibly shady if we aren’t being told what will be monitored, and why.

While I’m sure employers have the legal right to monitor the computers they own, are you aware of any limitations on what they’re allowed to monitor, or how they’re allowed to use the information they gather? I’m prepared to accept that I won’t like the answer, and I suspect that even though I’m opposed to these programs on principle, there isn’t much I can do since nobody who’s worked on this project is aware that I know about it. If I have to find another job, I will, but I’d rather it not come to that.

Legally, employers can monitor anything done on their devices or their networks. Assuming these are work computers being operated on their networks, they can monitor literally every action you take down to every key you press. Some programs let them watch your screen while you work or see randomly taken screenshots of what you’re doing at any given time. (To be clear, most employers don’t do this! But some do, and legally they can.)

Restrictions on what they can do with the info they gather: They can’t use it to discriminate against you for your health, religion, or other protected class (for example, if they saw an email to your doctor about a medical issue or saw you browsing a web page from your religious institution, they can’t use that to discriminate against you). If their keylogger logs the password to your personal email account, they can’t take that password and use it to log in to your personal email and go rooting around in it later. And they can’t use their surveillance to interfere with unionizing or other organizing.

But they can monitor it all if it’s on their devices or networks. A small number of states require that employers provide notice to workers that they’re doing this kind of monitoring, but most don’t.

3. My boss asked if I regret accepting my job

I’m in my early thirties and spent most of my professional career at the same job. The work was engaging and I loved my colleagues, but it took a serious toll on my mental and physical health. My former manager left a year ago for a job in a more conventional office environment. When there was an opening in her office early this year, she encouraged me to apply. I did and got the job. Naturally, I was thrilled—not only was I leaving a job I’d grown to dread, I’d also be working under a manager I really connected with.

It’s been two months now and I fear I’ve made a huge mistake. I had a sense going in that my new colleagues wouldn’t be as warm and expected the work to feel less meaningful, but I didn’t realize how adversarial some people were or how unfulfilling the work would be.

My manager’s style is still friendly and encouraging, but many of the people at her level or above are shockingly petty and spiteful, the kind of people who’ll ice you if they think you have a nicer office than them or who misstate your title in a way that makes you appear inferior (think “assistant” instead of “administrator”). One person in particular has been driving me up the wall – for example, whenever they decide I’ve made a mistake, they’ll send me a critical email and copy leadership, including the big boss. Oftentimes, these “mistakes” are actions someone else took or they lack critical information to understand why I took a particular action and why their solutions wouldn’t have worked.

My responsibilities also aren’t what was suggested in the job description. I’m ostensibly implementing systems and processes to improve office efficiency — turns out that mostly means calendar management and making sure the fridge is stocked with the bosses’ favorite snacks.

In my last check-in with my manager, she asked me whether I regretted taking the job. As I hadn’t expressed my dissatisfaction to her, I was surprised and wasn’t sure how to respond. While I mentioned that I’d appreciate having more substantive duties, I didn’t feel like I could share negative feedback about people who outrank my manager, especially when she can’t do much to change their behavior.

I also can’t see an upside to admitting you regret taking a job. Her asking me that felt like she was admitting to pulling a bait-and-switch on me with this position in an effort to fill a vacancy with someone she knows she works well with. I’m not sure what to do and I’m also feeling a little betrayed. Is there any point in sharing some version of these feelings with my manager or am I better off adopting a head down, mouth shut approach until more time passes and I can start job hunting in earnest?

I don’t think her question is necessarily an acknowledgement that she pulled a bait-and-switch. It’s possible, but it’s also possible that she didn’t intend this but things changed from the way she expected them to play out, she’s aware of that, and she’s checking in on how you’re feeling.

I do think there’s value in having a more candid conversation since you knew her before taking the job and she recruited you for it. Don’t just tell her you’d “appreciate having more substantive duties” (as it sounds like you did); tell her that the job is fundamentally different from what you came on board to do and ask if, realistically, that will change. Focus there rather than on feeling betrayed, since this is the actionable piece.

Also, you mentioned needing to wait until more time passes before you can job search. You don’t need to do that. There’s no reason you need to stay at a job that isn’t what you signed up for, and if you leave quickly enough, you can keep this off your resume entirely. Job search now.

4. Can I contact a CEO who offered me a job previously to ask about job openings now?

I am starting my job search after two years at Company A. Last time I was on the market, I had great interviews with Company B and got an offer from them that was initially my top choice, in part because of how much I liked Company B but also because the role at Company A was a lateral move on a team that wasn’t that interesting to me. Ultimately Company A gave me an offer for a much more exciting team and for a higher level, so I accepted. After the dust settled, the CEO of Company B (who had interviewed me) sent me a very kind email saying essentially, “I’m sorry to hear we won’t be working together in the short-term. But careers are long, keep in touch.”

Now that I’m in the job market, I’d love to revisit Company B. I’ve been watching their jobs page and they are hiring, but they haven’t posted any good matches for me. I can just keep an eye on the jobs page and apply if they post a good fit. But would it be out of line to email the CEO letting her know I’m in the market and would love to explore any opportunities they may have? Would it be better to email asking to catch up with her? Option 1 feels more honest, but I don’t want to come off like I’m saying “give me a job.” Option 2 may be more tactful, but I also have no idea how to network with a CEO! I worry about taking up her time without really having anything to talk about.

Email the CEO and don’t beat around the bush — say right up-front what you’re hoping to connect about. That’s more respectful of her time, and it’s a normal thing to do. If you just ask to “catch up,” you could be waiting weeks for there to be room on her schedule, whereas if you just tell her why you’re writing, she’ll be able to take action on that immediately.

You can simply say, “You interviewed me a couple of years ago and offered me the X role on your Y team. I ultimately took another offer, but you encouraged me to keep in touch. I’m now looking for my next step and, given how much I liked what I learned about Company last time, I’d love to talk about any opportunities you have that might be a good fit.” You could add, “I’ve been watching your jobs page and haven’t seen the right opening there, but wanted to connect with you as well.”

Read an update to this letter. 

5. As a manager, how much credit should my resume take for team accomplishments?

I’m a program director at a nonprofit and have started thinking about my next step and working on my resume. In the program that I manage, a team of people all work closely together to deliver results. I’m never sure how to reflect this in a resume — I don’t want to take credit for work that was delivered by 10 people, but if I manage those 10 people, is that what I ought to be doing?

For example, say my team successfully advocated for an increase in the state’s education budget, from $10b to $20b. In that case, which approach is better: (a) “Successfully advocated for a budget increase from $20 to $40 billion in 2024,” which I think best emphasizes the outcome, or (b) “Worked with a team of five to develop a campaign strategy that secured a budget increase to $20b” — in other words, giving others credit and being more specific about what my contribution was. I’m always conscious about not wanting to take credit where it isn’t do, but also don’t want to do myself a disservice when I know I played an important role.

To some extent, it depends on exactly what your role was. If you were taking a lead on, say, the lobbying, it makes sense to write, “Led successful lobbying campaign that resulted in a budget increase from $20 to $40 billion in 2024.” On the other hand, if you were managing the people doing the lobbying, I’d do it this way: “Managed a team of five to successfully lobby for a budget increase from $20 to $40 billion…”

In general, though, “managed a team that achieved X” is nearly always a reasonable formulation.

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{ 182 comments }

{ 182 comments… read them below }

  1. PollyQ*

    #1 — Your former boss is no better than a thief. If she didn’t want to get in trouble, she shouldn’t have broken the law.

    1. Limdood*

      If OP feels this strongly about protecting their boss after already being screwed over on several accounts (wage theft, abused for quitting, tax fraud, double down on the tax fraud, and then monetary threats – if you’re reading this, OP, this isn’t exaggeration, these are multiple CRIMES committed against you), then I really question just how rosy of a relationship there actually was. the “great relationship, then ‘flips out’ at bad news, then acts all buddy buddy, then threats when called out”….that sounds like a seriously dysfunctional relationship, and it might be worth taking a HARD look back at the past of that relationship….AFTER you get your back pay and correct taxes that she legally owes you.

      And just because after all this it feels like you’re still seeing someone who shifted their financial burden onto you illegally without permission (which is theft at best and fraud at worst) as someone who needs YOUR help….I might suggest taking a step back and seeing if you’re being taken advantage of anywhere else in your life…

      1. Falling Diphthong*

        I think we often have a mental image of a manipulative person as sitting atop the success heap, radiating confidence. Swanning around in a cloak while cackling.

        It can be harder to recognize when the manipulative person is writhing around wailing that the only thing preventing the consequences of their own actions from falling on them is that you haven’t yet reported those actions to anyone.

        1. Wintermute*

          You make a SUPER good point not just for work but life in general– manipulation and control don’t necessarily imply competence or success. That friend whose life is always abject chaos (often self-inflicted) and you cannot for the life of you figure out why you’re so invested in protecting them from the predictable consequences of their actions or how you keep finding yourself roped into putting more effort into fixing their life than they do– they just might be a manipulator too.

          1. AnonForThis*

            Someone also doesn’t need to be a manipulator (or at least not intentionally) to cross all reasonable boundaries and impose on you. The person may genuinely need a heart transplant, but it’s still not good to offer your own while you still need it.

        3. AbruptPenguin*

          Yes, this is so well-put. Playing the victim is a way for people to avoid being accountable for their actions. It’s manipulation and an attempt to control you for their benefit.

          OP’s boss’s logic reminds me of Bob Loblaw’s TV ad from Arrested Development: “Why should you go to jail for a crime someone else…noticed?”

      2. JSPA*

        I’ve seen it happen within a family. It was an over-stretch to create the position in the first place, done to launch a hard-luck grand-nephew. Add in miscommunication…ignorance of terms on both sides…ignorance of the law on the part of the employer (common when the business owner has previously been a one- person operation / had never had a longer-term employee / is defaulting to what was acceptable 30+ years ago when they were young)… and add in that the nephew was talked into taking the job by protestations of how essential they would be (when the actual primary goal was to get them out of the deep funk playing video games in the basement after a couple of arrests for weed possession) such that both parties believed they were doing a good deed, and it’s not surprising that all parties felt screwed. Including the middle generation, who’d begged both parties to make it happen, and bought services they didn’t really need, to be supportive.

    2. LG*

      I agree. I’m still struggling with why the OP would feel guilty at all when the boss screwed them over so badly.

      1. Violet Rutherford*

        I think the guilt comes from this being a situation where it feels like Boss didn’t do the initial bad actions *intentionally*. (Maybe she’s a lot nastier than she seemed to be and it was intentional all along, but we don’t know that.) But the guilt should be assuaged by her horrible actions afterwards. She doesn’t deserve sympathy after a reaction like that.

        1. Wintermute*

          That’s a fair point, honestly I think it’s important to separate out those two things, too, in your mind. There’s the thing that was done wrong, and there’s the behavior around it.

          The misreporting just has to be fixed. Any reasonable person who made a mistake like that would want to correct it as soon as possible (and lets be clear, our tax system is mostly concerned about getting their money, if you make a mistake and then go back and get everything in order, file amended paperwork, pay anything owed, that’s often as far as things go in terms of consequences, possibly with some fines or penalties).

          Then there’s the… just not wanting to do that because it is not convenient for her? And the threats, misbehavior and so on around not wanting to pay what’s owed either to LW or the state.

          There is no Form 1040 FEEL-Z where they ask how bad you feel about not paying employee’s taxes, it’s a simple matter of did you pay or not.

        2. learnedthehardway*

          I’d argue that the nastiness is a dead giveaway that the boss knows EXACTLY what she did, and expected to never have to deal with the consequences or expected to have time to clean things up, or something else.

          Remarkably short-sighted and stupid of the boss.

      2. Ellis Bell*

        It’s for sure an overly invested relationship for a business connection, but I think that was done to OP on purpose. The boss uses charm, overshares, and lies very easily. It would be a walk in the park for her to get an overly close relationship going with the OP. While OP was still getting paid, what reason would they have to be suspicious of this great boss, who sees them as an equal and trusts them so much? There would be no point in picking at that – though I’m sure it struck them as a little odd on occasion. Now that the money’s ran out, OP knows it’s logically weird to still feel this connection, but this stuff comes with an emotional hangover that you can’t just sever. Their boss is already under the skin. I imagine OP has a lot of processing to do about what they were told, versus what was true (Like, I imagine this person really does have a problematic personal life but I don’t think they’re blameless if this is anything to go on). I think that when OP is done sorting through it all, they are going to be just as angry about the emotional manipulation as they are about being left to pick up a fraud bill. My advice to OP is to hold onto the rope of logic and ignore the feelings and emotions of responsibility and friendship implanted by a liar, until you get through. OP, this isn’t a healthy boss-employee relationship; I trust my boss, and really like her but I wouldn’t give her a second thought while being truthful to tax authorities! She’s never made me feel responsible for her life decisions, because I’m not.

        1. AnonForThis*

          One of my early jobs had a very charismatic CEO who love bombed me so much in the first stages that I accepted a ridiculously low hourly rate. Then, when he threatened to stop paying me because my work “wasn’t even half as good as [coworker]’s work”, I was so upset that thought I was being unreasonable and greedy for asking him to pay me for my hours worked. I put my foot down, but it still felt like his threats were somehow my fault.

          It wasn’t until I realized that [coworker] hadn’t been paid in months that I understood how abusive the guy was. It’s so much easier to see a dynamic like that clearly from the outside.

        2. LW1*

          This is it exactly. I’ve had bosses screw me over before, but this has felt much weirder. She definitely overshared and told me so much about her personal life and I thought at the time that she didn’t have anyone else to talk to, but now I see that she was laying the groundwork. It was unfair for her to cross those boundaries, and I feel ashamed that I let her but I’m holding onto the rope of logic!

          1. Ellis Bell*

            I think it happens to us all. Either romantically, or personally you meet that person for whom every relationship is a con. The benefit of the doubt only works 99 per cent of the time. Eventually you meet that one person in a hundred who shouldn’t be trusted. It’s definitely easier to spot after a personal, lengthy experience. It’s fairly impossible to do so otherwise.

      3. Irish Teacher*

        I do understand. If you’ve been friends with somebody for a long time, it can be hard to acknowledge to yourself that they were really a bad person who was taking advantage of you. It’s very easy to think, “well, maybe she just made a mistake. I’m sure she wouldn’t deliberately steal from me.”

        And then society often emphasises loyalty and “standing by your friends” so I can understand why somebody would feel guilty about getting somebody “in trouble,” especially as the former boss seems to be trying to manipulate her and make her feel like she has betrayed the boss. In some ways, the boss sounds like she is behaving in a similar way to domestic abusers, saying things that really hurt, then acting like you are friends and asking you to keep their “secret.”

        And a lot of people don’t like conflict and I don’t think it would be at all surprising if the former boss started sending abusive messages or something once the information comes out.

        1. Shiba Dad*

          Yes, when you work with/for friends you often will give them the benefit of the doubt. I’ve been there.

      4. Smarty pants*

        A former co-worker of mine turned in two of our bosses for wage theft at different times. They skimmed from her tip share. The first time was a boss she hated. She had no problem turning the first one in and literally watching him get fired. She liked the second boss. She felt guilty about turning him and blamed herself for his firing. I pointed out it was no different from when the first boss stole from her, and he was always preaching personal responsibility but had the gall to blame her when the consequences of his own actions found him. Didn’t make a difference to her. I’m no longer in touch with her so I don’t know if she ever made peace with it.

        1. Wintermute*

          tip positions tend to be restaurant and service jobs– and those come with a whole other set of baggage. Someone who only steals from you a moderate amount could indeed be the best boss you’ve ever had in that space, given how horrifyingly prevalent all other forms of worker abuse are. And that causes a funny sort of “better the devil I know” rubric.

          1. Smarty pants*

            It took me years to deprogram from restaurants. I still have certain gut reactions from the toxic environment and bosses. My “normal” compass is far better calibrated these days.

      5. Totally Minnie*

        I’ve been in a similar position where a supervisor I trusted and respected – and truly believed those feelings to be mutual – did something really hurtful to me. When you’re emotionally invested in this job and this relationship, it can be really hard to just turn off the “I trust this person” switch. It can be like the stages of grief. You go through denial (I’m sure they didn’t mean to hurt me), bargaining (if I do everything right, surely we’ll get that trusting respectful relationship back), and several other stages before you get to the place where you can accept that the relationship isn’t what you thought it was and you were taken advantage of.

      6. She of Many Hats*

        Manipulators are usually very charismatic when they want something or getting what they want from you. Their true colors show when they’re foiled or called out. And for the victims, it can be very difficult to see past the Faerie Glamourie when they’re trying to reconcile reality with what they “knew” about someone.

        1. Jules the 3rd*

          My friends know that if I describe someone as “charming”, they should take that as a red flag. I’ve seen way too many abusive people hide it.

          I almost think that Lundy’s _Why Does He Do That_ should be required reading in about the 7th grade, right as kids start to get cynical / suspicious.

      7. SmithsonianLaurie*

        I wonder what industry they work in. I’ve found that in high-stakes jobs like childcare, medical care, immigration or family law, etc there’s an attitude of “you’re not just letting ME down, you’re letting THEM down.” throw in some trauma bonding if underserved communities are involved and a dash of good old fashioned “we’re all a family here” shenanigans and you’ve got a recipe for OP having a skewed sense of what’s reasonable for an employer to expect of them. OP’s boss could have easily pulled out “if you don’t help me/work for free/protect me from my own lawbreaking people could DIE” which isn’t going to help the guilt complex

        1. LW1*

          You absolutely hit the nail on the head lol, I’m an immigration lawyer and it was exactly like that.

    3. rebelwithmouseyhair*

      And she was only nice to you while there were no problems. That’s what we call a hypocrite. She was probably hoping you’d like her too much to want to report her.

  2. Limdood*

    #2 – stop doing ANYTHING not DIRECTLY job related on those company machines….no personal email AT ALL, no calendar sync, etc. That’s information that your employer has no need to know, is illegal if they use some of it, but is often very difficult to prove they used it.

    So don’t give them the chance. Make sure everything personal is off the machine and encourage all your coworkers to do the same.

    2. Bit o' Brit*

      This really should be standard operating procedure on any company-owned device. Any half-decent IT department will have the ability to remotely access and control a company-owned computer. And while they may not be able to see your password without a keylogger, they can reset it to whatever they want if they need access (though this is generally an after-you’ve-left-the-company action, lay-offs can happen at any time). Nothing on a work laptop should be personally private.

      1. T2*

        Going further, make absolutely certain that your personal accounts use a different unrelated password than your work accounts.

        And do not use your work account as a backup or emergency password reset tool for anything related to your digital identity.

        Everything at work can be taken away from you. Everything. Just keep it separate as standard operating procedure.

      2. Observer*

        And while they may not be able to see your password without a keylogger, they can reset it to whatever they want if they need access

        That’s only true for passwords on accounts they control. Not your personal accounts.

        1. Bit o' Brit*

          Right, I meant that in the sense that they could access any files, both in user-specific areas as well as any cloud storage services that you might have syncing to the device.

    3. T2*

      Guys I have be clear here. I have been working in IT for 25 years.

      Never ever ever do anything personal on a company device. I carry two laptops for this reason. This also goes for your phone.

      1. KatEnigma*

        Yes. LW and the commenters are naive to believe this hasn’t already been happening. And that they ARE told about it in the onboarding literature under “anything you do on a company device or network may be monitored” And yes, that goes back decades now…

        1. JustaTech*

          This is true, but then it’s hard when, say, your 401K bank for work happens to be your personal bank as well, so if you need to do a work-related thing to your 401K you either have to risk your personal banking, or try to do it at home after hours.

          1. Observer*

            What does that even mean? Your employer doesn’t have any access to your 401k any more than they have access to your personal bank account, even if you have direct deposit for your paycheck.

            Anything to do with you personal accounts, including your 401K should be done after hours, unless it’s something like filling out your election form or changing your withholding. Regardless of what bank your company uses, that doesn’t touch your personal accounts.

      2. rayray*

        Just out of curiosity, how often do companies really dig in to what people are doing? I am generally pretty careful to not log on to personal stuff on my desktop at the office, but sometimes I have logged on to email to check something, but I always log out when I am done. I do keep my spotify logged in because I just can’t get through the workday without having something to listen to.

        I guess what I am wondering is, do companies actively monitor employees activity, or is it more of a thing where they’ll dig in if they feel they have reason to?

        1. Keymaster of Gozer*

          Only do it when we need to or something looks really suspicious (like finding malware, torrent clients, private VPNs etc)

          We simply do not have the time or staff to read the server logs for every single user. Also, insider knowledge: reading server or access logs is really, really boring.

          1. IrishMASMS*

            Speak for yourself keymaster. I (used to be) one of those security analysts that enjoyed looking through the logs, looking for the bad actors…

          2. Reluctant Mezzo*

            Ha, yes, flipping through the fuel logs for company trucks? The word ‘unleaded’ sort of stands out. Snicker.

            1. Splendid Colors*

              Because the company trucks use diesel, so the only reason someone would use unleaded was if they fueled their personal car on the company card?

        2. Observer*

          I guess what I am wondering is, do companies actively monitor employees activity, or is it more of a thing where they’ll dig in if they feel they have reason to?

          It depends on the company. Smart companies don’t actually look at much of anything unless they need to. (With some exceptions for heavily regulated industries, etc.) That said, many are recording everything so they CAN look if they need to. And there are often automated systems that will monitor for certain types of usage and ping the appropriate person if something problematic comes through. Also, sometimes you get spot checks or your stuff gets looked at as a byproduct of a different investigation.

      3. Double A*

        I have a question about what you mean about phones. I definitely wouldn’t use a company phone for anything personal, but I do sometimes log in to my company Google account on my personal phone. Could that compromise other things on my phone? (I work for a school I am honestly not that worried about it but am curious).

        1. I Need Coffee*

          Especially challenging since so many companies have gone to “bring your own device” for phones, neither providing or reimbursing for a separate company-only device.

      4. Jules the 3rd*

        YEP.

        My company offered lots of support for people who wanted to use their personal phones to access work tools / emails. No, thank you, nope. If you, company, want to get me a phone and pay for the line, ok, but otherwise? Nope.

    4. BatManDan*

      Not just off the machine, but off the network. Don’t connect your personal devices to their network for the wi-fi or anything. Use your cellular data plan. Lots of y’all are missing the fact that they can legally monitor any company DEVICE or NETWORK. Network includes their wi-fi.

      1. Peanut Hamper*

        Yep, this. Found this out at my last job when a former employee liked to lock himself in the bathroom and watch….movies.

      2. InsufficentlySubordinate*

        IT here. Agree, I log into nothing personal on the company machine, and I don’t use their WIFI for personal things. I actually try not to use any WIFI except ones I know are Password protected and it’s private. SOmetimes you have to, but I do a minimal amount on public WIFI. I have post-its over my work laptop and shut the camera on my personal computer unless it is specifically needed. I try not to use my personal phone for company business and I will not install any software solely for work on my phone. I’ve been thinking about getting a phone to use as a work phone so I can install that stuff. I also do not give my work email-address for any personal business.

      3. I'm Just Here for the Cats!!*

        I wonder how this works for public universities. I work at a state university and I use the guest wifi for my phone since I don’t want to use all of my data. I use the guest wifi not the wifi for employees that require your password to log in. What does IT do with the information the monitor. Most student use the guest wifi too, and I’m sure there are all sorts of interesting things.

    5. Miette*

      Also note that they can monitor what’s on their NETWORK, which means anything you access over wifi on your phone and other personal devices.

    6. Nekussa*

      I keep being baffled by news reports about government agencies banning TikTok from government phones. If your employer gave you that phone, they absolutely do have the right to ban any app they don’t like! (That’s a separate issue from whether you should or should not install TikTok at all.)

      1. jj*

        A lot of government agencies use tik tok as a big part of their public relations strategy, so part of what makes it a big deal is it functionally prevents government agencies from effectively disseminating information to demographics that don’t have strong presence on other social media platforms

      2. IrishMASMS*

        The TikTok “controversy/hype” is to help get Senate Bill 686 The RESTRICT Act passed. Unfortunately in its current form the RESTRICT Act [sic] grants sweeping authority for the U.S. government to prosecute, fine, and imprison any person whom–among *many* other things–uses a VPN to access any “app” operated by a “foreign adversary” of the U.S. The wording of the bill is so broad and vague that it can criminalize a wide range of technologies, and potentially even ensnaring U.S. citizens for conspiracy simply on the basis that they use a VPN that the USG can’t snoop on and see what they’re doing with it.

        As am InfoSec & Privacy professional, this is some _scary_ shit, and I have already communicated to my congresspeople to kill this bill with fire.

        1. Twix*

          I 100% agree about the RESTRICT Act, but the concerns around TikTok are neither new nor baseless. I’m a software engineer at a Fortune 100 subsidiary that handles a lot of classified and otherwise access-restricted data. I don’t personally work with classified stuff, but I have access to plenty of information it would be very illegal to share with a foreign government. As a result, we go through a lot training on data security, including in-person presentations from agents from our local FBI field office. The most common form of espionage in today’s world is cultivating inside sources in companies like mine through social engineering, which has been the case since long before TikTok existed.

          The first step of that is identifying employees who are sympathetic to a foreign adversary, have a grudge against their employer or the USA, or would be susceptible to bribery or blackmail. The Chinese government has no problem whatsoever with exerting direct control over Chinese companies in furtherance of their geopolitical agenda, so the idea of China having direct access to a vast database of data about Americans’ day-to-day lives, including data they may not be aware they were sharing, that can be mined for that kind of information is a major concern in that sense. (To say nothing of the fact that with direct access to the authentication code it would be trivial to log raw passwords and 70% of people use the same passwords across most of their personal accounts, or the fact that control over the algorithms that decide what content people are exposed to on a daily basis can be abused in come incredibly scary ways.)

          I wholeheartedly support killing the RESTRICT Act with fire, but while I don’t know what the right solution is, ignoring that very real issue is not a good idea. We all saw how much turmoil the Russian government was able to cause in our last two elections just with user-level access to social media and scraping publicly available content.

          1. Anon For Now*

            I like the idea of a gdpr style regulation for the United States that restricts what kind of data *any* social media (or otherwise) apps can collect/store/transmit. Facebook via Cambridge Analytica has already done what we’re pretending to be afraid Tik Tok has the potential to do.

    8. danmei kid*

      The only thing not directly job related I do on the company computer is read AAM – I consider this Personal Development time!

    9. Lauren*

      Also, block your camera because they can remote in whenever they feel like it or default camera on for every Teams meeting. Hello breastfeeding mamas! IT is full of some less than great people who might remote in whenever they feel like without any legit reason to. So yeah, have that laptop closed at night and facing a wall during the day if you use your camera often vs any family in the background.

      1. eyes are burning*

        I have been in IT for 30 years – the only time I have investigated anything on our network has been when something bad is happening already (malware, virus etc – which often came because of porn sites) or someone reported something. Believe me I wish I could UNSEE some of the things I’ve seen – there is NO way I’m going looking for it.

        D*** pics of a married guy in our warehouse taken by our Dir of HR on her company phone – saw when we were offloading her photos that she demanded we do before we swapped her phone……

    10. IrishMASMS*

      As others have mentioned and discussed at length: use your company issued equipment only for work related activities; and unless absolutely required never use your own equipment for work related activities. If you must use personal equipment for work, I would strongly urge you to have a separate laptop/phone for those and only those activities. Use encryption (like Signal) for your SMS (text) messaging.

      Depending on the company and the technology they have deployed, we can see what web sites you go to, what emails you send, what text messages (outside of Signal) you send/receive. Depending on the maturity of the information security program and team at the employer, they may only look at the alerts we receive – or there may be a “threat hunting team” that goes into the logs we receive looking to find malicious or suspect activity the monitoring systems did not alert upon. We are looking for criminal elements, nation state actors, the real malicious folks – but if we come across someone so blatantly violating company policies, it is hard for us to turn a blind eye and not pass it along per our organizational policies.

      Also, for some of us the risk of legal action against the employer/company is potentially impactful. There is a legal practice called a “notice of discovery” where opposing council demands all data and devices that may have data on them pertinent to the case. Guess what happens if that includes your personal laptop or phone (they go to opposing council for analysis)? Guess who has to retain & pay the lawyers regarding the involvement of your personal devices (you do unless the employer is willing to cover the costs). It is so much easier if company work is on company provided devices, and none of your personal dealings are exposed in that notice of discovery. You manage people, you interview or hire people, and are using your personal devices for these business activities? I would alter your approach and only use company provided.

      This concern regarding your privacy by LR#2 and many AAM readers is great to read. May I suggest the book “The Smart Girl’s Guide to Privacy: Practical Tips for Staying Safe Online” by Violet Blue to help guide your concerns?

  3. Grizabella the Glamour Cat*

    Gotta agree with this, especially considering all the awful things she’s done to you, LW:

    – stopped paying you (!)
    – flipped out because you told her you were leaving
    – said ugly things to you that really hurt
    – misclassified you as a 1099 worker for a year and a half, when you should have been a W-2
    – flatly refused to fix the problem and expected you to eat the resulting enormous tax bill
    – threatened to make you pay her back for “overpayment” (HOW???) if you took any action to get it fixed yourself

    LW, this woman has treated you TERRIBLY. You have absolutely NOTHING to feel guilty about. You have done nothing wrong, and you won’t be doing anything wrong when you report her for this. Meanwhile, she has done all sorts of things wrong, including defrauding you AND the government, and she deserves to be held to account.

    Please realize that no matter what kind of relationship you may have thought you had with her in the past, it was an illusion. This is a person who would cheerfully throw you under the bus without a second thought, and has in fact already thrown you under there and is trying hard to convince you to stay there.

    This is who she is, and she has ALWAYS been this person, regardless of how well she may have been hiding it. You were actually never close to her; you were close to someone you THOUGHT she was. The whole time you felt you were close to her, she was using and abusing you and lying to the IRS.

    You have NO obligation to protect her, fix her mistakes, or shelter her from the consequences of HER OWN miss doings. No matter how harsh those consequences may be, she EARNED them through her own terrible choices.

    I hope Alison gets an update from you soon saying that you reported this. I’d love to also hear that you’ve gotten over any mixed feelings about reporting her, but I know that may take a little longer.

    Any time you feel so much as a twinge of guilt or uncertainty, try repeating the following:

    “This is an unethical, lying, individual who defrauded the government and wanted me to be her accomplice in doing so. She threw me under the bus, expected me to stay there, and was outraged when I resisted. She does not have my best interests at heart and never has. Any consequences she experiences are the result of HER choices, and it’s not my job to protect her from them.”

    Good luck, LW!

    3. AnonForThis*

      One of my bosses threatened to 1) stop paying me, and 2) sue me if I stopped working because of that. He somehow had me thinking this was my fault (because I just wasn’t good enough at my job) until I found out that my highest-performing coworker hadn’t been paid in months.

      What would you say to a friend whose boss “only” misclassified her, resulting in a tax bill of several thousand dollars? How about one who “only” stopped paying her? Advocate for yourself like you would for your friend.

    4. goddessoftransitory*

      And remember, LW, her threats mean no more than her lying friendship pose ever did. She’s trying not to go to prison, which is where she belongs. She has no more power over you and cannot demand one thin dime.

  4. AcademiaNut*

    For LW1 – if your ex-boss can’t make payroll, and has been committing fraud to keep expenses down (ie, deliberately misclassifying you to save money), her business is going to fail, and it’s probably going to get messy. Paying thousands of dollars in extra taxes to protect her is going to hurt you, but isn’t going to save her.

    2. Snow Globe*

      Good point. That also means the LW needs to get things rolling ASAP if they want to get any kind of payment from the ex-boss, because there will very likely be other creditors trying to get to her money as well.

      1. RagingADHD*

        Yeah, unpaid wages are next priority in bankruptcy after secured debt, but that isn’t going to help you if there is literally no money left and nothing to sell.

        1. Aitch Arr*

          What Raging said.

          When a former employer went bankrupt, I only got 60 cents on the dollar of monies owed me, because they laid me off and then hired me back as a 1099.

          (I was in my mid-20s and didn’t know any better. Also it was the dot-bomb era.)

    3. Keymaster of Gozer*

      Yeah, this is what started the process that ended up with me reporting my employer to the authorities. First they couldn’t pay me, then it got worse.

    4. Double A*

      Yes, could these “tough times” she’s going through possibly also be referred to as “the consequences of her own actions”?

    5. Lenora Rose*

      As a supporting point, I worked for a failing business once, years and years ago (I was there during 9/11). I did quit once it became clear that the temporary blip of staff paycheques being late was not temporary and was going to get worse. BUT, while it was a few months late, my boss made good on all employee pay owing before he shut down, and he respected, not insulted, those who would not go down with the sinking ship. Even a business failing is not an excuse for the mistreatment this person put you through, never mind the tax fraud.

  5. Terminal Reader*

    To LW1, you may have been your ex-boss’ friend but she was not yours. Friends do not deceive, use and betray friends. You owe her nothing but you always owe yourself self-respect.

    1. The Prettiest Curse*

      This ex-boss is the definition of a person that you shouldn’t feel bad about turning in for tax fraud.

    2. I Wrote This in the Bathroom*

      This woman literally sees LW as a walking ATM and throws fits and/or threatens LW when called out on it, that’s not a friend.

  6. Violet Rutherford*

    I’m sure the tax fraud boss didn’t wake up one day and say “I’ma ruin my business and break a bunch of laws, for funsies”. I’m sure a lot of stuff happened that snowballed into this mess. But it’s not YOUR mess, LW1. You can’t fix it and it doesn’t matter whose fault it was. You have to protect yourself and your household (even if your household is just you and the dust bunnies in the corner). I understand why it feels bad. It would be a lot easier to turn her in if she broke into your house and stole from you, right?

    But whatever circumstances led her to this situation, it doesn’t matter. Please do right by yourself. You don’t deserve to pay for her mistakes or carelessness or whatever the heck is going on here.

  7. Lead Balloon*

    LW1, being in a bad place doesn’t give someone a free pass on the consequences of their actions.

    There is a lot of evidence that your former boss is prepared to act unethically (and even break the law) in order to further her interests. It is not unethical for you to do what is legally your right to do in this situation and report her.

  8. DyneinWalking*

    LW1, a lot of times people soften moral obligations for the people they know (and like) – probably because they know their good sides and it can be hard to accept that people who have good sides can have bad sides, too. But the thing is, very few people are unlikable and bad throughout; most of the “bad” people you read and hear about have their good sides, just like your boss does.

    Which basically means that, if your boss doesn’t deserve consequences for her tax fraud, NO ONE EVER deserves consequences for tax fraud (at least, the kind of tax fraud that she did). It also means that if you feel like you ought to eat the costs of her misclassifying you, then every misclassified employee should do that, too.
    But I’m pretty sure that your moral compass objects to that idea… hold on to that feeling. That’s the feeling that tells you that you’re doing the right thing despite knowing the crime-committing person personally.

  9. Emma*

    I also own a business, and let me tell you, LW1: Your boss knew from the get go that this stuff was her responsibility to get right. When you set up a business you understand that a big part of your job is finding out what the law requires and making sure you follow it. It’s a lot of responsibility, there are a lot of resources available to help you, and that responsibility is one of the reasons why business owners tend to pay ourselves more than we pay our employees. Your boss has failed to meet the basic requirements of her job, and regardless of what happened or why, she’s decided to try to push the consequences onto you instead of facing up to them herself. You don’t owe her anything.

    1. Splendid Colors*

      Yeah, I’m sure part of the reason the SBA funds so many “how to run your own business” groups is that the taxes paid by businesses that are prospering AND not doing business under the table outweigh the cost of paying people to give advice and create webinars.

  10. Miss C.*

    I’m confused about LW1’s situation and the W2 vs 1099 situation. Obviously as a 1099, LW1 would now be responsible for paying both employer and employee parts of taxes owed. But if employer had LW1 as a 1099, doesn’t that mean she wasn’t taking money out of her paycheck for said taxes, and wouldn’t LW1 have noticed? Or did employer take money out but not use it to pay the employer part of LW1’s taxes?

    1. rudster*

      This what I am confused about too. It sounds like OP thought she was a W2 employee but only found that she was classed by the employer as independent contractor when she received a 1099 instead of a W2. Unless the boss is pocketing the employer share of the payroll taxes, that should definitely have been obvious from amount of deductions the payroll statement.

      1. Marni*

        I got the impression that LW one didn’t understand the implications of being a 1099 employee, and trusted that the employer knew what they were doing. I certainly would have done the same in my 20s. But then when they went to a tax preparer to do their taxes, they were shocked by what they would owe, and that’s when the tax preparer explained to them the difference between a W-2 and a 1099 employee and how they’d been misclassified to their detriment.

        1. Ama*

          I was misclassified at my first job out of college even though the bookkeeper at that job was a family friend and my dad’s a CPA. I did know up front it was a 1099 position and was able to pay my taxes correctly (thanks to my dad) — but neither he nor my family friend were actually familiar enough with the rules governing 1099 classification to recognize that my job was misclassified; the bookkeeper was correctly classified as a 1099 employee (she did not work in the office and worked hours she chose) and just didn’t realize that what made my receptionist job different from hers (I had to work set hours, in the office) was what should have reclassified me.

          Years later, I worked a job where I hired a lot of 1099 contractors and that employer had a formal checklist you had to fill out each time you hired a new contractor to make sure you were classifying people correctly — which was the point at which I realized I had been misclassified previously.

    3. Sloanicota*

      I guess in a smallish business between friends, it’s possible OP didn’t understand the distinction or didn’t realize; I wonder if it’s possible for an employer to switch classification methods in the middle of the year without mentioning it! That’s really terrible, if so.

    4. Rosemary*

      Yes I was confused about this too. I have worked as a 1099, and my paychecks were obviously substantially larger than they would have been had my employer been withholding taxes – but I knew I was responsible for paying my own taxes. Surely OP would have realized that taxes were not being withheld and she was responsible for them? I can see being surprised about the amount owed, however – not realizing that as a 1099, you are 100% responsible for SS etc (that typically the employer covers if you are W2). I.e. if you previously had a W2 job with a 50K salary, you might assume your taxes would be the same – but if you make 50K as a 1099, you are ultimately taking home less because you have to cover more taxes (which is why, as a 1099 worker, I charged more than I would expect if I were salaried)

    5. Sara without an H*

      “Just a few days later, I realized that even though she’d classified me as a 1099 worker for a year and a half, I really should have been a W-2. My tax bill was astronomical and my tax preparer told me I’d been misclassified.”

      Based on this statement, it looks to me ask though Fraud Boss set up the Letter Writer as a 1099 worker and convinced her that this was correct. LW believed her — why shouldn’t she? A lot of people don’t really understand the distinction.

      Now she knows, of course, and needs to take appropriate action for her own benefit.

    6. Ginger Cat Lady*

      That’s NOT “obvious” to a lot of people who have never worked as a 1099 contractor before. Plus, it’s entirely likely the business owner lied to her about the tax implications! Literally just had this conversation with my nephew at Easter dinner yesterday. He’s just started a new job and his boss told him she would be paying him as a 1099 contractor because “it saves us both a bunch of taxes”
      And I was horrified. He had NO idea. It most certainly was not obvious to him.
      Please remember that people are not stupid for not knowing what you think is “obvious”. And that sometimes people like this business owner lie and mislead people.

      1. Samwise*

        Right. First full time job after college: I discovered I was a “contractor” and not an employee when I got audited. I had no idea. The IRS agent was actually very kind and helped me set up a payment plan and waived the penalties. I think he was pleased to get the info about my by then ex-boss, The Crook, and I suspect I got audited because he was such a crook — they were looking at him and picked up anyone else involved in his business.

        I have since warned many of my students about this particular fraud. If you don’t have a W-2, there’s something shady going on — either your wages are not being reported, or you’ve been deliberately misclassified.

      2. Splendid Colors*

        A lot of people who don’t actually run businesses have Dunning-Kruger syndrome about 1099 vs. W2. I STILL, in 2023, in California, where we had a ginormous ballot proposition in the last election about redefining employee vs. contractor, still tell me I can save money by hiring people as 1099s who would never, ever, fit the definition. If I hire students to come work at the studio on grunt work, they’re NOT 1099 independent contractors.

        Working only at my location, check.
        Working using my equipment, check.
        Working under my direct supervision, check.
        Don’t have their own business where they provide this service to multiple clients, check.

        No, this is NOT like having the bookkeeper come in to look at my receipt collection at my office instead of going to theirs. Or having the caterer bring in sandwiches and fruit trays.

        At least I haven’t heard “send your piecework to a sheltered workshop and get stuff done for pennies on the dollar” in a while. If the cost per piece is less than it would be for a regular worker, they’re cheating the disabled employees. The lower hourly wage is supposed to be proportional to lower productivity. (Which is still exploitive, at least from the perspective of they have to work there and can’t try to get a job that suits their skills better at a competitive wage.)

    7. Happy meal with extra happy*

      I had a crappy boss who, when I started working for him, asked if I wanted to be a W2 employee or 1099, and he was somewhat pushing for me to be 1099. Fortunately, I knew enough to know he was being shady (and I said I wanted to [properly] be a W2 employee), but it was my first full time job, and if I didn’t know better, I can see how easily it would have been to say ok to being 1099.

      (To make it worse, this was my first job as an attorney and my attorney boss owned the firm.)

    8. Thornus*

      My first professional attorney job, I was misclassified. I noticed no withholdings in my first paycheck. Boss said “oh we think it’s easier for people to file their own taxes, but don’t worry, we still pay employer-side.” Which, well, they didn’t. It was a lie. They 1099’d to save on their own tax bill and passed it along. LW1 might have been new, might not have known anything about taxes beyond filling out a 1040, etc. It happened to me even with all the schooling I had. Sometimes people don’t know what they don’t know.

  11. LW5*

    Hi! I’m LW4, and was so happy to see my question taken (long time reader, of both the posts and the comments section!). I really appreciate the advice. I have always wanted to be careful about not overselling myself, but also not wanting to be overly modest. I know it’s always up to the individual case, but I like the suggested formulations. If anyone else has suggestions or views on this, I’m all ears.

    And, because it will drive me crazy unless I fix it: I should’ve said ‘credit DUE,’ not ‘credit do’. And got my numbers wrong in the first example. Sorry!

    1. peacock limit*

      LW4, Alison’s phrasing was good – and then be prepared in your cover letter or the interview to expound on HOW your managing made that a successful bid/project/etc.

      I had an old boss who gave all of my successes as successes for HIS review, and then simply said “peacock did all of those things, and I hired her, so…” because he truly did not know how I did all of the things I did on behalf of our department and he didn’t have a whole lot to do with it (besides staying out of my way, lol).

      1. AnonForThis*

        Well, clearly deciding to hire you and staying out of your way were both very successful!

    2. Mockingjay*

      I always find the responses to questions like yours interesting. How do you build credentials when you work in a collaborative environment?

      For instance, I am a tech writer and work as a federal contractor. Whether I collaborate on a document or work alone, the government “owns” all the work (it’s in the contract), which means I have no samples to offer. So I have to have similar phrasing in my resume to describe the work I do and its outcomes. I can’t provide a copy of a doc, but I can tell you the research methodology used to produce the document, and how that method supports a team or unilateral approach. (It took me a while to figure this out – my resume “pre-AAM” was limited to a list of doc types in my very specific program subset. “I edited these doc types: A, B, C…” Ugh.)

      1. quercus*

        Mockingjay — Generally, documents produced by the US government are public domain and can be copied by anyone. So a federal employee wouldn’t own their work, but (unless classified or otherwise secret) the employee could freely share a copy of the final version as an example of their work. If you haven’t, I’d check your contract carefully, keeping in mind that for the government, there’s a difference between ‘owning ‘ and ‘being able to prevent someone from copying’

        1. Splendid Colors*

          When I worked for government contractors, no way would I have been allowed to share documents related to nuclear reactor design. Not everything is like NASA Mars photos or maps of national parks.

    3. Filthy Vulgar Mercenary*

      My sense is that you’re overthinking it a bit, because something is activated for you and that is why you’re overthinking it :)

      If I was a CEO, I’d very much prefer the direct route. My former Soldiers reach out to me all the time asking for references and letters of recommendation out of the blue, and I’m always happy to do it. However, if someone reached out to me to ‘catch up’ and then when we caught up, I discovered they were looking for a reference/job in my company, I’d feel taken advantage of – not because they wanted a job, but because they weren’t upfront with me about it.

      I also second Alison’s point about making time for things. If I’m busy I will prioritize catching up much lower than I will prioritize a business transaction.

      Also, remember you’re also doing this CEO a potential favor. You’re filling a potential business need she has. Just because it also works out for you, by filling a need YOU have, doesn’t make it manipulative. You don’t have to play the game of pretending we are all in this for passion and don’t need the money and oh look, a job? aw, why you shouldn’t have, for me?

      If it helps, try to reframe it as project management; each person has a thing to contribute to the project as well as a way their participation benefits them. Being upfront about all of it sets better conditions for things to work out successfully.

      1. Artemesia*

        Really good point. The ‘catch up’ ploy feels manipulative and insincere. The ‘you once offered me a job and I am on the market again’ approach seems straightforward. Alison’s phrasing was perfect.

    4. learnedthehardway*

      For any accomplishment you claim, just make sure that it is accurate how you describe it. The example Allison gave of whether you personally led or managed a team to make something happen is a good one. A good interviewer will ask follow up questions to find out what your personal contribution was. If it was that you personally did all the things, that’s great. If it was that you set the strategy, delegated the work, kept the team on track, did the reporting – ie. provided the oversight – that’s great too.

  12. ItsOftenAChoice*

    OP1 do you live in California? Because in most of the rest of the US there isn’t a clear cut line that says “this must be 1099 and that must be w-2”. It’s common for contractors to be asked which they want and there are financial pros and cons to both (1099 means you can deduct expenses from your taxes whereas that has increasingly disappeared from w-2, for example, and for some people that would overcome the extra FICA taxes you have to pay).

    I don’t know your specific situation and am not saying you weren’t misclassified, but it’s often not a cut and dried thing and in at least some cases in many locations it’s up to the the parties involved to agree on the classification.

    1. BatManDan*

      The IRS has some pretty clearcut guidelines on the 1099 / W-2 differential. If you work WHERE you are told to work, WHEN you are told to work, with equipment provided by the company, then you are an employee. IANAL, but the IRS dot GOV website is pretty easy to read. As an aside, the LW uses the words “boss” and “job,” which are words that only apply to employers. Not saying the LW knows / should know the differences, but she clearly thought of it as a traditional job, which means it looks like a duck and it walks like a duck.

      2. doreen*

        Whether it’s clearcut or not depends – if you are told where to work and when to work with equipment provided by the company you are almost certainly an employee. But suppose you are told where and when to work using your own equipment – you might be an employee or you might be a contractor depending on other factors. (Maybe you’re a mechanic who works set shifts with their own tools. Or maybe you clean my office every other day between 5 and 7 PM and you have other customers you work for at different times) Even the IRS says that all the factors have to be taken into account and there isn’t any single factor or magic number of factors that make the determination.

      3. Wintermute*

        You make it sound a lot clearer than it is, because in this day and age basically no job except traditional freelancing has ALL of the features of one or all of the other.

        It’s increasingly common for someone to work flex time from home– they do not work when they’re told, or where, but they do it using employer-provided equipment, the employer has intimate and constant control over their work product and they have minimal independence when it comes to how the job is done or to what standard. Even though they meet half the requirements for I-9 they’re a W-2 employee, most likely.

        But if they use their own equipment, but work hours as specified by the employer, using strictly controlled policies and procedures, that’s often I-9, despite the fact it meets less criteria for I-9 employment than an IT engineer working from home.

    2. Peanut Hamper*

      This is simply not true.

      As BatManDan points out, the IRS does indeed make this a pretty cut and dried thing.

      1. Riot Grrrl*

        Not really. As others have pointed out, the IRS provides guidelines but ultimately acknowledges that the entirety of the relationship has to be taken into account as a whole to determine what is an employee vs. what is a contractor. It’s an acknowledgment that there’s some room for interpretation here. I do think ItsOftenAChoice’s comment implies a level of discretion that isn’t exactly right. (I don’t know that I’d say it’s “common” for a contractor to be asked to choose.) But it’s equally inaccurate to state that all distinctions are clear everywhere. That also is not true.

    5. Dilly*

      It is not up to the person doing the work or the person/entity hiring for the work to “pick” which one to use. It’s either 1099 or it’s W2. The federal government decides by creating regulations which describe the differences between the two. If it meets Criteria A it’s W2 and if it meets Criteria B it’s 1099. No matter what either party “want” or “prefer”.

      1. Reality Biting*

        Well, yes, but the distinction between those two things is not necessarily straightforward. There’s a lot of gray area and sometimes some negotiation is required. Here’s what the IRS says about its independent contractor criteria:

        There is no “magic” or set number of factors that “makes” the worker an employee or an independent contractor and no one factor stands alone in making this determination. Also, factors which are relevant in one situation may not be relevant in another.

        It’s not impossible to imagine cases that are gray enough that the employer might take into account the worker’s preference (how they see themselves) as one data point in making a decision about which way to go.

    6. doreen*

      in at least some cases in many locations it’s up to the the parties involved to agree on the classification.

      Not exactly – it’s not going to be up to the parties to agree to any classification they want. There are some “positions” that can be structured in different ways and the structure will determine whether the person is an employee or not , and some of those “not employees” may be independent contractors (while others will be their own separate business) and the parties will agree on that structure but that’s not the same as the classification being subject to agreement.

    7. I am Emily's failing memory*

      Others have already pointed out that the determination is based on the way the employment is structured (hours, location, equipment, degree of autonomy), but I want to point out that even in a situation where an employer and a worker might choose whether to structure the role as an employee or a contractor, what’s “making up for FICA taxes” should be that the 1099 employee is paid at a higher enough rate that their net after taxes is comparable to the net compensation the W2 employee receives after taxes, including the value of employer-paid benefits like paid leave, healthcare, and unemployment insurance.

      Tax deductions are generally not free money. They reflect actual losses you incurred. Deducting expenses saves you on taxes only because the IRS is acknowledging that you didn’t really earn as much as you were paid on paper, so you’ll only be taxed on the amount you really did earn. The ability to reduce your taxable income does not make up for being taxed at a higher rate, to say nothing of the issue of benefits and unemployment eligibility.

    8. KatEnigma*

      This used to be more true. But the IRS cracked down on “contractors” a few years ago (10 now? I am old. LOL) and with that put out clear guidelines.

  13. TeapotNinja*

    OP1, before you report anything to IRS, make sure you have your former boss blocked on any communication channel (email, phone, LinkedIn, Facebook, etc.) you might’ve communicated with her before or that you suspect she knows otherwise. It’ll prevent you from heap of abuse coming your way afterwards.

    1. Sara without an H*

      For email, I’d recommend setting up a rule to send all incoming letters, unread, straight to a Fraud Boss folder. If Fraud Boss escalates, LW1’s attorney might be interested.

      Or not. But I always figure that it’s better to have documentation and not need it, than need it and not have it.

  14. sswj*

    OP1, if you’re reading, I’d love to know how this turns out. It sounds like a really stressful, sad, and infuriating scenario – I hope it all works out well for you in the end.

  15. Irish Teacher*

    LW3, I wouldn’t necessarily assume your boss is admitting she pulled a bait-and-switch on you. For one thing, it sounds like the two of you worked together for a while and knew each other pretty well? In which case, it is very likely she would notice if you seemed less happy than previously. Or as Alison says, it could be that the job turned out to be different than she expected too, for whatever reason and it’s occurred to her you might not be happy with that. Or she may have noticed that some other people are her level are being nasty to you, which she probably wouldn’t have predicted. Or…she might just be second-guessing herself, feeling she put pressure on you to apply for the job and it might be sheer coincidence that she is right. She may have asked the same question even if the job was perfect and you loved it, just because some people feel responsible for anything that happens after they recommend something. It’s possible she just wanted reassurance that “I gave you good advice, didn’t I? You don’t regret following it?”

    1. Alanna*

      I agree, and am a little surprised that LW’s assumption was that the boss had done a bait-and-switch — it suggests a toxic work environment could be warping everyone’s thinking a little bit.
      My first thought was whether the boss regrets her own move — since it sounds like her peers and managers are jerks! — and is also regretting bringing LW into this situation. I’m curious if she gave LW a heads up about any of this when she was onboarding her into this job.

      I think Allison’s suggestion for an honest conversation is a good one. Since you both opted in to working with each other again, and come from a shared context, you can be a little more open and honest than you normally would be with a boss two months in. (To be clear, I’m not recommending going into that conversation with a goal of just venting, which can happen when two people trust each other in an untrustworthy environment — keep the focus on fact-finding and problem-solving.)

  16. Lilo*

    So I haven’t seen it explicitly written down, so to say it as clearly as possible:

    LW1, your boss stole money from you. Not paying you for work is theft. Misclassifying you so you pay taxes she should be paying is fraud and theft from YOU. Don’t protect someone who stole money from you.

  17. Ash*

    LW1, you should also file a wage claim with your state department of labor for the time that you worked without being paid. You deserve to have every dime that you earned through your work.

    1. Not your typical admin*

      LW 1 – when you first started did you fill out a W-4 or W-9? If you don’t remember, try to get that document if at all possible. A w-4 is typically used for those who get a w-2, and lists your dependents and how much withholding you want, a w-9 is typically used for those who get 1099s and just lists your reporting information since the employer doesn’t do any withholding. This would be an easy way to show what your bosses intentions are.

      I’m so sorry you’re going through this. I know tax problems can be overwhelming and stressful.

      1. Not your typical admin*

        Sorry – didn’t realize I was replying to someone instead of making a new thread.

  18. HonorBox*

    Op1- loyalty is a great human trait but also can betray us. You and your boss had a great relationship and you’re feeling a sense of loyalty to her. But please reread everything you wrote like you’re one of us reading it for the first time.

    She couldn’t pay you and then flipped out because you said you were leaving? Loyalty to a boss/job only needs to go as far as the paycheck. If there’s no paycheck, you owe them nothing. Did she expect you to stick around, work as normal and not get compensation for that? That’s a bridge far too far.

    And you also have an accountant and lawyer telling you that you have good standing to report the misclassification to the IRS. Do it. Again you owe your former boss nothing. You have the right and responsibility to take care of yourself first. If there’s some sort of challenge the boss faces, remember that you asked for their assistance first.

  20. SimpleAutie*

    lw5:

    Thank you so much for asking this question! I’ve been wrestling with this same thing and it’s honestly a relief that I’m not the only one!

    Alison, thanks for answering it!

  21. One HR Opinion*

    LW1 – Unfortunately you will still be responsible for the “employee” taxes that she didn’t take out of your pay, but getting properly classified will take off the burden of the “employer” taxes. You don’t owe your boss special consideration, but there is a program through the IRS called Voluntary Classification Settlement Program that she may be able to use to make this easier on her that you could tell her about.

    Also, don’t forget that you’ll want to reach out to your state dept of revenue as well unless you live in a state with no state taxes (I’m sure you’re lawyer told you that to, but just wanted to be sure).

    1. EPLawyer*

      I wouldn’t tell her a darn thing. All boss has done if blame OP for the mess boss created. Boss can find out about the voluntary settlement program on her own AFTER OP reports her.

      OP, your loyalty to your boss ended when she stopped paying you as noted above. The ONLY part of this hot mess that is your problem now is paying your share of the not withheld taxes. That’s it. The rest is hers. You don’t want for her anymore so its not your responsibility to fix it.

  22. Gary Patterson’s Cat*

    I used to work for a small dysfunctional startup that fired a worker they had classified as a freelance 1099.
    She filed for unemployment, which the owner fought of course, to be smug (there was also some gross affair stuff going on).
    Well, this resulted in a full tax investigation by the state, the former employee won because she was misclassified, and it was found the owner was not paying many other payroll taxes too! That place was ridiculous and the owner so toxic.

  23. RagingADHD*

    LW1: it wasn’t a mistake. She was doing it on purpose.

    She expected you to work for free, and got mad when you said no. SHE WAS INTENDING TO EXPLOIT YOU FOR FREE LABOR.

    Sorry, but it’s worth shouting about.

    The tax misclassification may have started out as a sincere misunderstanding of the law (maybe. I doubt it, but maybe). It stopped being a mistake when she doubled down and threatened you.

    You realize, right, that she was trying to make you pay her taxes? Not only was she expecting you to work for free, she expected you to subsidize her business. Essentially, to pay her for the privilege of working there.

    I am sorry that you got fooled by a con artist who made you think you were friends. Unfortunately, con artists are very good at that.

  24. Slow Gin Lizz*

    I hope LW4 updates us soon on the email they sent to the CEO of Company B and how it led to LW getting an awesome new job!

  25. TotesMaGoats*

    OP#5
    Agree with Alison’s advice and add this. Whatever you put make sure you can back it up. By some sort of weird planetary alignment I was able to interview my former boss for a role at my institution. So color me shocked when reading his resume and seeing him take credit for things I had done all by myself. It wasn’t “led a team that….”, it was “secured a partnership with…” whic I know he didn’t do because I did it. I promptly alerted the search chair to the conflict of interest and the inaccurate information.

  26. WantonSeedStitch*

    OP #1, for handling the emotional side of things, my approach in this kind of situation would be to talk to yourself like you’d talk to a friend who was in the same situation and came to you to talk about it. Would you be telling that friend, “well, you two DID get along really well, and I’m sure she wasn’t TRYING to make your life hard and cheat you out of money you earned?” No, you’d say, “hey, no matter how nice she may have been at times, she was your BOSS and she CHEATED you. You don’t owe her any guilt over this. You have to do what’s right–for you and legally speaking.”

    1. Filthy Vulgar Mercenary*

      Right – it actually makes it worse, because this boss took advantage of and committed crimes against someone she got along well with, someone who was dependent on her and trusted her, and someone to whom she had an obligation.

      LW1, I wonder if there is some kind of traumatic bonding going on here for you.

  27. Michelle Smith*

    LW1 you seem like a deeply kind and empathetic person so don’t take what I’m about to say too personally but…you are being way, way, way too overly deferential to your boss’ situation and feelings in this moment. Like to a degree that I am shocked and appalled. Please read and reread Alison’s advice and then go make that report. This is a business matter, it’s not personal, and it needs to be handled. If you won’t do it for yourself, do it for anyone who is still working for and being scammed by her (yes scammed – because she is pushing her tax burden onto others, that’s literally stealing from her employees and fraud to the government) and anyone who she employs in the future.

  28. logicbutton*

    LW1, there’s a framing I learned from, I believe, Captain Awkward that I’ve found to be helpful in reducing feelings of guilt that you know are irrational. Try reminding yourself that you are actually *uniquely unqualified* to have sympathy for her right now. There will be other people in her life whose role it is to have sympathy for her and help her, and you are the one person on the planet whose role that absolutely shouldn’t be.

    1. RagingADHD*

      I think that if you believe (consciously or unconsciously) that having sympathy for someone as a human being means you are obligated to willingly submit to a person with power over you committing crimes against you, and enable them to cover up those crimes…

      Then I think your concept of “sympathy” needs some work, because that is not what most people mean by sympathy.

      1. logicbutton*

        Sorry, is this directed at me? I specifically said LW1 *didn’t* owe their boss sympathy. That was the whole point of the comment.

  29. JustMe*

    OP1 – you sound like a very kind and conscientious person, and that is wonderful. Unfortunately, it sounds like your old boss doesn’t want to extend any kindness our courtesy to you, let alone do what she is ethically and legally required to do. Worse, it sounds like she’s doubling down when called out on her bad behavior and is making it seem personal as a means of manipulation. It’s not personal–you literally quit because you were owed money and realized that she had committed fraud, which negatively affected you. Tons of people go through personal difficulties and still pay their employees and correctly issue W2s. She’s failing to do the bare minimum and acting like it’s not her fault to deflect blame, when it’s probably affecting all of the other employees at your old job as well. If she didn’t want it to happen, she should have made different choices. You have nothing to be sorry about. Period.

  30. Venus*

    LW4:
    When I am returning to an email exchange from years ago I try to find the email where they said “Please reach out in future” and reply to that one (often with a new subject line) because I hope that it creates some goodwill on their part. They likely get a lot of requests and if you make it easy for them to see that they were keen on you two years ago then that should help. I agree completely with Alison to be direct, and I would definitely include the last part about saying that you had been looking at their postings but hadn’t yet found the right fit. That shows you have put in effort before contacting them, and will improve their opinion of you. Good luck!

  31. Sara without an H*

    Hi, LW#3– Alison is right, you really don’t need to wait to start job hunting. Job searches usually take longer than you think, so you might as well get started. Read everything in the AAM archives about resumes, cover letters, and interviews.

    I don’t think your manager consciously pulled a bait & switch on you. It’s possible that she, too, misread this company and is now doing things she wasn’t actually hired for. (Maybe she also regrets her new position, who knows?) When you start getting interviews, have some well-thought-out questions you can ask about job duties, promotional opportunities, and workplace culture, so that you don’t get stung again.

    If interviewers ask why you’re moving on so quickly, you can say something like: “The job developed into something different from what I’d been told it would be when I was hired. I’m really interested in doing A, and the thing that excites me about this job is the chance to develop my skills in A.” (Adjust as needed.)

    Since your manager knows you, see if you can persuade her to help you identify some projects that would let you add to your skills. Meanwhile, do your job well, be polite and professional to everyone, and start looking for your next employer.

    1. JustaTech*

      I also read it as the manager also regretting her decision to move to this company and maybe wanting a gut-check with LW3, since they’d been at the same stressful place before.
      Heck, maybe the manger had realized this place was a mess, is about to leave and wants to offer to take LW3 with her to some place better.
      Only the LW knows the manager well enough to be able to guess if this is a “haha, I’ve screwed you over!” or a “I have made a terrible mistake” kind of situation.

  32. kiki*

    re LW2– I am curious about employers being able to access webcams and microphones without the explicit consent of the user. In an office or other work setting, I suppose there are likely security cameras around, but in a remote setting, it seems different? While I try to be careful about blocking my webcam physically if it’s not in use, I know not everyone does. And working from home, it seems especially invasive to have company cameras peering in.

    If anyone is knowledgeable about this area, I’d be really interested in learning more. Thank you!

    1. OP #2*

      That’s my concern as well honestly. Like, if they want to watch what I’m doing on the company network, that doesn’t bug me (within certain limits; part of why my IT contact is concerned is that he says HR should ever be able to see the nitty-gritty of the configuration he works on, for security purposes). I just don’t want them snooping via webcam/microphone.

  33. Violet Fox*

    LW 2: Are you in the US? The legal framework for this is *really* different inside and outside of the US.

    1. OP #2*

      I am, yes. The corp is a decently-sized international one (other offices are mostly in Europe, with a couple in Asia or Australia), which makes me wonder how they’re handling this for folks outside the US…

      1. Violet Fox*

        Well a lot of that is flat illegal in most of Europe. A lot of companies have different standards for people who are in different places in order to follow local laws, but anywhere in GDPR-land, that is just not legal.

        Granted they could also be ignoring local labour and privacy laws, since that does happen too.

        Where I work is big enough that we have our own IT lawyers that we can consult if needed (they’re seriously amazing people), as well as privacy and GDPR officers.

  34. KatEnigma*

    LW2: Somewhere in your onboarding material, and probably repeated, offhandedly, in your annual stuff, there is almost always a line that anything done on company equipment or the company network may be monitored. That was your warning. It also has been true for over 2 decades now. So always assume your company CAN see your keystrokes, has always been able to see your keystrokes, as well as any traffic that goes over their network if you connect your personal cellphone or laptop, and any company you quit and move to will be able to do the same.

    1. OP #2*

      Yeah, I vaguely recall seeing something to that effect. If I didn’t, well, it’s probably coming. My concern was more if there was anything they just aren’t allowed to monitor (like, to the point where court cases/etc. have held “you must configure your monitoring system to not watch X”), but I’m guessing not.

  35. Jane*

    OP3: “One person in particular has been driving me up the wall – for example, whenever they decide I’ve made a mistake, they’ll send me a critical email and copy leadership, including the big boss. Oftentimes, these “mistakes” are actions someone else took or they lack critical information to understand why I took a particular action and why their solutions wouldn’t have worked.”

    omg, I hear you on this and am so sorry you’re going through it. I left a job last year over a co-worker who did that exact kind of thing, and it’s like I am on another planet now. I couldn’t be more grateful to my current boss and to the team of six I manage for being kind, professional, and cheerfully willing to help.

    Something is wrong with your co-worker, your manager, and your workplace altogether. I hope you’re able to find a much better situation, OP.

  36. OP #2*

    Hi folks, OP #2 here; I realized there was a bit of detail I forgot to include in the letter, so I wanted to clarify:

    The concern among folks I’ve talked to, given the reputation of this program and how it markets itself, is that HR could be gearing up to implement some kind of productivity monitoring for remote workers. It’s no secret that the C suite doesn’t think much of remote work, and would bring us all back 5 days a week if they thought they could (they did try after covid, but enough people left as a result that they had to compromise on a hybrid setup), even when jobs can be done remotely.

    To be honest, I’m already making plans to exit since this is the last straw for me, but we’ll see how that goes.

    1. Keymaster of Gozer*

      Not in the US but do work IT and I can say that in theory we could watch everything you do on a work computer.

      In practice however, those kind of ‘constantly reporting back’ productivity systems and ‘listening in on calls’ stuff don’t get used much past the first few weeks once the management realise how much data they have to now comb through (who has the time to listen to recordings of all the staff!) and when IT blow a gasket over the server space/bandwidth it’s eating.

      We can watch everything but there are limits on what we can *do* with that infomation. You can log into your personal email on a machine and we’d see it but we’re not permitted to store or access your passwords.

  37. AnneSurely*

    Um, so I was today years old when I realized that a former boss might have been illegally taking advantage of me (and some others) by classifying me as a 1099 employee when I shouldn’t have been based on the type of work I was doing and the way the position and working relationship was structured. (That is, I was a regular employee, but he gave some of us job titles with “consultant” in them.) It’s been a long time, and that working relationship ended badly enough that I have no wish to revisit it, even if it were for a justifiable “gotcha” moment. (Not surprising that he was not the best manager or communicator. It took over a decade of feeling intense shame about that experience to realize that I didn’t need to carry that with me anymore, and probably never should have felt that way in the first place. Feelings validated when I looked up the company on GlassDoor and saw more recent reviews of leadership there. I was young and made some errors, but the biggest one was assuming that I was at fault for not thriving in my first professional position despite poor management.)

  38. Shandra*

    OP 3, is it possible your colleagues are hostile because they wanted someone else in your job, and/or the company didn’t consider internal candidates first?

    At a past employer, someone who initially came in as a temp filled a permanent position that opened up because of an internal transfer. Several employees questioned management why internal candidates hadn’t been given a chance first.

    1. Jane*

      That might be possible, but I nevertheless wonder about people who take out their anger on the person who got the role. It’s cowardly, pure and simple, and all bullies are cowards.

  39. Le Anon*

    LW1. Babes. Squirrelfriend. This is me sending you my best dead-eyed Scorpio energy. She would have been dead to me at “flipping out when I left after nonpayment.” By the end of your tale she was well into “suspicious fires and cut brake lines” territory. (That’s a joke but I would absolutely go well out of my way set her reputation alight, if she has any left at this point.) Get thee to therapy and exorcise her tentacles from your too-kind heart. And in the meantime make sure all communication is going through a lawyer.

    1. merida*

      yes yes yes

      Also, maybe this is terrible but I laughed at the “suspicious fires” wording – a friend of mine had a sometimes-non-paying and all around dysfunctional boss too. My friend has since quit, and now (unrelated) criminal charges are official filed against the ex-boss, and there’s a lot of unofficial gossip too. Word on the street is that there was quite literally a suspicious fire…… I so wish I was making this up but I am not.

  40. Ann O'Nemity*

    OP #1, “tax fraud” is an eye catching headline, but don’t let it make you feel bad about advocating for yourself.

    You believe that you’ve been misclassified as an independent contractor when you should have been an employee. The first step is to talk to your employer, which you have done with unsuccessful results. The next step is to ask the IRS to determine your employment status for tax purposes. If the IRS agrees that you should be classified as an employee, you will have a lower tax bill and your employer will have a higher one. It is very unlikely the boss will face some sort of criminal “tax fraud” charges; they’re just going to owe more money – and there is even a Voluntary Classification Settlement Program (VCSP) that will help them through the process.

  41. KatieP*

    LW1, you sound like a very loyal friend, and your former boss was lucky to have you. She has been so disloyal to you, and it probably hurts to realize it, that you owe her nothing. Take care of you. She needs to figure her own way out of the mess she made.

  42. merida*

    OP1 – For what it’s worth, it’s possible that this isn’t the only criminal and unethical thing she’s done… (And even if she’s a model citizen outside of this tax fraud incident, she still is responsible for her twisted actions in this situation!)

    A friend of mine had a (somewhat) similar boss situation – on several occasions, my friend’s paycheck bounced when she tried to deposit it. She didn’t even work there very long. But her boss was such a nice person, a pillar of the community, etc. so my friend kept giving her grace. She’d eventually get paid but the boss had to be reminded multiple times, and one time it took months. The boss always had excuses. My friend felt guilty when she eventually put in her notice (didn’t want to let her boss down) and I reminded her that none of the dysfunction was her responsibility to fix. Fast forward to now, when my friend is happily in a new job. She’s heard the town gossip that the ex-boss isn’t paying her employees and other stories of financial woes. Recently the news broke of multiple criminal charges of large-scale monetary fraud (totally unrelated to her not paying employees). More and more stories are coming to light. Turns out ex-boss is not a “good person” after all but a calculated criminal! Very shocking at first, but it’s all starting to make sense.

    All of that is to say, I’m SO sorry all this is happening to you OP, and while I don’t wish a job loss on anyone, I am glad you got out when you did! Maybe you dodged (even more) bullets. There are better things out there for you.

  43. J*

    OP #1 – do we have the same former boss?! I worked for a woman who owned her own interior design business and had almost an identical experience…we got along great, became close and I was truly a great employee for her. Then she went through a rough time personally and financially and suddenly wasn’t able to pay me. She freaked out when I said I had to stop working for her since she couldn’t pay me anymore and came up with the money to continue paying me, but tried to make me feel really bad for requiring a paycheck when she was “going through extenuating circumstances.” I was so stressed out during that time, I couldn’t sleep. I should have quit then but didn’t – lesson learned. She then inappropriately re-classified me as a 1099 instead of a W2 employee because it would save her money on taxes and she wouldn’t have to give me benefits, but thankfully I did know to withhold my own taxes each paycheck and got benefits through my husband’s employer anyway (otherwise I would’ve been in a precarious situation). She did so under the guise of giving me a raise since I was now “costing her less money,” but of course that raise never came. I resigned 3-4 months later when it became even more clear that her business was in trouble and she was continuing to take advantage of me in several ways out of financial fear. She freaked out again when I resigned and called me a bad person and said many unkind things. When I listed back to her all the things she had done in the previous 8-9 months, she seemed genuinely surprised that any of it was a problem and said that she thought I understood that she was going through a difficult time. I didn’t report her but looking back now I wish I had because I know she has since treated others poorly. Some people are so self-absorbed that they truly can’t understand the impact their actions have on other people. I’m so sorry this is happening to you and you should do the right thing and not feel guilty!

    1. J*

      I’ll add – I didn’t really understand that classifying me as a 1099 was actually unethical and illegal at the time, otherwise I would have reported her and asked to be reclassified by the IRS.

  44. LW1*

    Thank you to Alison and all the commenters for your feedback! I think some of you were right that there may have been some trauma bonding going on there. I’m definitely going to examine how I show up for people who wouldn’t do the same for me. A former coworker and I are getting together to file the right paperwork with the IRS and our state’s DOL, and I followed my state’s rules for requesting my final paycheck. Thank you for making me feel more secure in standing up for myself! I will update when the taxes get straightened out :)

  45. Retired Vulcan Raises 1 Grey Eyebrow*

    Excellent update that you are sorting this out properly with the IRS.

    Even if your boss had kept paying you in full and being sweet as pie, you would still need to officially sort out your taxes, regardless of whether that gets her in trouble.

    Some things are too risky to tolerate / cover up for even the best friendship – which this certainly never was.

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