a client sent me a thank-you check as a way to avoid paying my boss

A reader writes:

I am hoping you can guide me in the right direction with a predicament I have recently stumbled into.

I have been working for the past two years in the construction field, building luxury homes for wealthy clients. One of the clients we have, Gilbert, has been our client for the past few years and the business relationship between him and my boss has been so fruitful for both parties, that we have built four houses for Gilbert already since I have been here. My boss, Adam, also happens to be a close family member.

Gilbert will occasionally give me a list of items that need fixing or attention (usually items an inspector noticed during a visit) and my job is to handle those items and make sure the home is ready to be shown by realtors. Gilbert has become a great friend of my boss, and will frequently join us during holidays with his wife. So handling these items has always been the norm and I enjoy doing them since Gilbert and his wife are nice people.

A few days ago however, Gilbert and Adam had a falling out, and when Adam found out I had been doing these tasks for Gilbert, he was very upset and told me not to do anything for him again without his approval. I was not in trouble because as I mentioned above, this is how it always was. That afternoon when I returned to the office, I heard Adam and Gilbert arguing over money. The line “If you want to have her (meaning me) doing tasks for you then you need to pay me (my boss)” was used by my boss. I guess the problem was that Gilbert has been told before he needs to hire a real maintenance person for oversee these homes, but does not want to spend the money.

Fast forward to this morning, I grab the mail from my box and head to my desk. I received a letter from Gilbert saying how happy he was that I was helping and how thankful he was to have me helping him so consistently over the years. The last line in the letter was “Enjoy this gift.” His “gift” was a very large check, one that would really help the horrible financial situation I’ve been in the past year. It’s very obvious why he gave me the check, I assume to spite my boss and make a point.

My question is, what do I do? My financial situation has been so horrible this past year that I occasionally have to go without meals to pay rent. This is not something my boss (or the rest of my family) knows. However, I almost feel as though that money should go to my boss since they were arguing about money, or that at the very least, I should disclose that I received this gift from Gilbert. I am just afraid that disclosing this will mean I miss out on the thousands of dollars hes offered me. Not disclosing it leaves me vulnerable to a bad situation if Gilbert ever tells my boss that he gave me money. I feel like I am being used as a pawn in their game of toxic masculinity.

P.S. My boss and his family, as well as Gilbert, are very, very well off. So I don’t feel bad about taking the money since I know a check of this amount is expendable to them both. I am just worried about the ramifications of not disclosing this and my boss finding out that I had essentially been keeping a pretty big secret.

I would love to tell you that you can keep this money without mentioning it to your boss. But unfortunately, I don’t think you can, at least not ethically.

You need to disclose it, because (a) that’s money that you’re getting from a client, which makes it your employer’s business, and (b) it’s money as a thank-you for work that you’ve done in the course of your job for your employer. Like, you wouldn’t have been doing all that work for Gilbert if you didn’t have your current job, right? It was part of your work responsibilities. And (c) it could potentially impact your employer’s business dealings — if they’re trying to tell Gilbert that he needs to pay for the work you’ve been doing for him, it’s going to complicate things if he now says, “Well, I just gave her a large check to cover it.” And it’s really going to complicate things if he tries to argue that that makes that work a separate arrangement between you and him, rather than services your company was providing.

On its face, it certainly doesn’t seem unreasonable that your boss wants Gilbert to pay for these extra services — and it makes sense that he would direct Gilbert to pay the company (as opposed to you directly) since that’s how this works. It sounds like Gilbert was trying to score a snarky point by deciding, “Sure, I’ll pay … but it’s not going to Adam.” But it’s not really his prerogative to decide that — his business relationship is with your company, not you directly, and you were acting as an agent of your company when you did that work.

So I do think your boss needs to know about this. And for now at least, you’re better off not looking at the money as “money I was given that may now be taken away from me,” but rather as “a weird check making me a pawn in a business dispute.” I’m sorry!

Read the first update to this letter here, the second here, and the third here, and the final one here.

{ 232 comments… read them below }

  1. Goya de la Mancha*

    “I feel like I am being used as a pawn in their game of toxic masculinity.”

    And it was really shitty of Gilbert to put you in that type of situation.

    1. Hills to Die on*

      Yeah, Gilbert isn’t being nice about the position he is putting you in. I just really, really, really hope that you get the keep the check when this is all said and done. Please give us an update!

    2. boo bot*

      Worst. Games night. Ever.

      A thought that might (or might not) make you feel better, OP: that check only works to Gilbert’s advantage if Adam finds out about it, which means he will make sure Adam finds out about it. If you keep it, the question is not if you’ll be screwed, but when.

      1. Hills to Die on*

        Yes, I have no doubt that it was intended as a slap to Adam. Gilbert’s ego need Adam to know he’s been slapped. It was done deliberately.

      2. Countess Boochie Flagrante*

        This. OP, I totally get how tempting it is to just take the money and run (and in the larger context here, the run part might be a valid choice; this whole situation sounds kind of shady), it is probably the worst thing you could do here.

        1. Artemesia*

          If it were a small amount or a bottle of champagne or something you might skate but as a major check, it is clearly payment for work rendered by Adam’s company and you WILL be royally hosed if you keep it or don’t immediately disclose it to Adam.

        2. AnnaBananna*

          Yep. And the fact that Adam is a family member on top of this complication? Oy. Gilbert is such a turd.

          OP: quickly tell Adam and then forget that you were even offered the money – it will make your life easier in the long run. Although if/when Gilbert and Adam get over their tiff, you might think about having a ‘not cool, man!’ chat with Gilbert.

      3. Lady Blerd*

        Very true. Gilbert is shitty for putting you in that situation and would still be shitty if you didn’t have financial issues. Don’t be a pawn in their fight.

      4. Aveline*


        OP – This is not a gift. It’s a bribe to get you on his side.

        If you think of it that way, your choices become a lot clearer.

      5. Genny*

        This is such a good point. Gilbert has shown you he’s not a particularly honorable party, so I wouldn’t trust him to keep his mouth shut (in fact, I can almost guarantee it’s only a matter of time until he spills the beans). I’m sorry they put you in this crummy situation, LW.

      6. marmalade*

        Yep – Gilbert is going to make sure Adam knows about the cheque. You’re already caught in the crossfire, but not telling your boss will definitely make the situation worse.

    3. Gingerblue*

      This, exactly. Gilbert is being horribly manipulative here, and I would treat him with caution going forwards. Assume he’s more interested in spiting your boss than your wellbeing.

    4. RUKiddingMe*

      O it is absolutely douchebag behavior. Gilbert will definitely make sure Adam knows about it, one way or another. If OP keeps it she will lose her job.

      I’d also like to address OP’s statement about not eating in order to be able to afford rent. Doesn’t sound like Adam is paying very well. Maybe taking advantage because OP is family so of course she will work for below market pay?

      IDK of course, just speculating, but I’d suggest OP look at what else might be out there with an eye to finding better, not family involved, not toxic masculinity soaked, game playing type work.

    5. chickaletta*

      Totally. These aren’t the nice people you think they are. Nice people don’t use large amounts of money to play games with innocent people. This is good information for you to have going forward.

      1. Else*

        Seriously. Especially as from what we’ve heard here, Adam is absolutely the reasonable party in this situation. It’s weird that this has gone on so long without any apparent quibble – how did you manage to do these things during work hours without his approval? Or were you expected to do them outside of work hours? Did you have to use company resources and contracts to do them? This is confusing. I’m SO sorry that the stress of having something that you need show up in your inbox as a bleep manipulative poison pill. :( And don’t trust Gilbert – he may be generally pleasant enough, but he’s clearly a thoughtless person who likes to play games when feeling affronted.

    6. AKchic*

      And look at it this way – if Gilbert had been paying Adam for your services in the first place, perhaps Adam’s business could have been affording to pay you better wages so you wouldn’t have been skipping meals to pay your bills?

      Gilbert purposely cultivated a friendly relationship with you because you were useful to him. He used his friendship with Adam to get free services. Adam rightfully called him out on it. Now he’s using you to punish Adam for making him pay for the free services he’s been getting (and keeping your wages stagnant/low). This one-time payout is keeping your monthly wages low.

      Tell Adam. And renegotiate your salary. You’re worth more, and making Gilbert actually pay for the services you provide will help you earn and collect that higher wage.

  2. Amber Rose*

    I’m so sorry LW. I know what it’s like to stare at unethical money from the side of poverty. But I think if you just quietly take the money, you’ll be setting yourself up for much worse suffering down the road. You have to look at the long term here. Is it enough money to offset possibly losing your job, losing your relationship with your boss, and maybe facing legal conflicts? (IANAL, of course, but money and legal conflicts are best friends.)

    1. Foreign Octopus*

      I agree.

      When you’re being dragged down by poverty and you’re hungry and you can’t see a way out, any sort of money looks tempting enough. God knows I considered some pretty skeevy things when I was scraping at the bottom of the barrel but, OP, please don’t do this. It will seriously cause you more problems down the line.

      I know you didn’t write in for financial help and so I’ll only suggest speaking to a financial advisor. They might be able to help you here.

      Good luck and just remember that this poverty won’t last forever. The winds will change in your favour soon.

      1. AnnaBananna*

        Also, since Adam is quite successful, it might be time to have a chat about getting a raise to help with that financial situation. There’s no need for poverty if you’re effectively supporting a successful company. Make sure Adam knows that!

        1. Kaaaaren*


          Use this weirdo situation as the jumping off point to discuss a raise, or at least… some kind of very generous bonus?

        2. it's-a-me*

          But! Don’t phrase it as ‘I need money because poverty’ but rather ‘I hope you’ve been more than satisfied with my work and I believe that even our customers are recognising that, so I would like to request a raise based on those merits’

          (Sorry if this is obvious, it’s part of my job to assume that NOTHING is obvious)

          1. P*

            I think it might depend a little on why the poverty; I mean if Adam is just not paying a living wage, I think that’s a valid thing to bring up. I don’t know the particulars but if this is some kind of family business thing (maybe I misread the letter) OP SHOULD let her boss/family know if they are essentially taking advantage of her and put a stop to it.
            Now if it something more like OP is getting a normal industry standard wage that a lot of people live fine on, but OP has a lot of debt or something, then yes, probably best not to bring up private details and focus on usual professional reasons to ask for a raise.

            1. P*

              Nevermind, OP elaborated below; the issue isn’t that their wages are below standards.
              OP, you should disclose this check and ask your boss what to do about it.

  3. AnotherKate*

    Agreed with Alison on all counts. I would also mention that it seems important to approach your boss/relative and ask for a well-deserved raise–no one should be working full-time and still go hungry to make ends meet, but it feels especially egregious in a family business.

    1. MK*

      If the OP is underpaid or due for a raise, absolutely. But she only mentions that her financial situation is bad, which can happen even if you are fairly- or well-compensated for a number of reasons.

      1. caryatis*

        Agreed. The fact that someone is in a bad financial situation doesn’t show that they deserve a raise–we have no idea what got OP into problems.

    2. Anonymousaurus Rex*

      This is what I was thinking. Especially as the OP says that the money is a sum that wouldn’t be huge to either Gilbert or Adam, but that would be huge to her, it sounds to me that OP may be underpaid (unless there are some extenuating circumstances like sudden unexpected expenses this year).

    3. OP*

      I addressed this below:

      My financial situation isnt a result of poor payment on my bosses side. My significant others job went through alot of administrative changes and he went from matching what I make to minimum wage (which is a whole other letter). As I mentioned below, my boss is my uncle, so I make a little above what my position makes in my area and I have good benefits. I did ask for a raise a few days prior to this situation since I’ve been stagnant for the past 2 years.

      1. ACDC*

        I didn’t realize your boss was your uncle! Professionalism aside for a second, could you approach him about this as your uncle and explain the situation? He might be more sympathetic to letting you keep the money. Or not, who knows? I think it might be worth a shot.

      2. AnotherKate*

        Very glad to hear that it’s not a case of your family screwing you! That being said, if Adam is living large to the extent that this huge windfall check from Gilbert is a mere “drop in the bucket” to him…he can afford to pay you more.

        This isn’t to say he’s a jerk; this isn’t to say that maybe you and your spouse need to adjust what “living within your means” entails; obviously there’s a lot that goes into this. But given that he can afford it, that this check is a huge windfall to you, AND he’s family…I might come clean with him about your current financial situation when you fess up about Gilbert’s gift. It might be a little embarrassing to admit how much the money would mean to you, but if it were me, I’d probably tell Adam. He’s family, and probably not a monster, so I think the net gain would be likely in your favor–he might be more likely to say, “sure, keep the money, you need it. I will handle the business relationship with Gilbert separately” instead of asking you not to cash the check or taking a cut of it for the business.

        1. Kaaaaren*

          Agreed. I think the OP should level with her boss (esp since he’s family). There is a high probability he will let her keep the check.

  4. Amber T*

    It’s also unclear who the money really belongs to… does Gilbert legally owe Adam money, and could Adam try and claim it from you? Gilbert said it was a gift, but could it be construed as payment to your company overall?

    Agree with Goya above, it’s a really shitty thing of Gilbert to do, even if on the surface it seems nice. He’s trying to buy your loyalty from Adam.

    1. Roscoe*

      That is what I was trying to figure out. Like is this a “tip” for a job well done, or is this money that is actual payment for something that should rightly go to the company. I mean, she should probably let the boss know either way, but it does make a difference in my opinion a bit

    2. Princess Consuela Banana Hammock*

      I don’t think Adam can try to claim the money from OP, but I do think Gilbert might try to argue he paid OP directly (which then gets into a world of legal and work-politics problems). It’s a very shitty thing for Gilbert to have done, and it puts OP in a terrible position with her employer.

    3. Murphy*

      I think OP has been doing these tasks for Gilbert “for free,” as in they weren’t explicitly part of the agreement that Gilbert has with Adam/the company, and Adam got mad when he found out. And then Gilbert “paid” for it by giving OP the check.

      I agree Gilbert put OP in a shitty position.

      1. TootsNYC*

        Though it seems like the OP has a mix of assessments about this–some of her comments make it seem as though these are reasonable “punch list” things that any builder would need to do; other comments make it sound like these are “little extras” she was doing as a favor.

        Normally builders aren’t done w/ the job until the building inspector signs off.
        (1st bold below)

        But the last line makes it sound as though the OP actually regards those things as true favors, and not “the last little details of our responsibility”

        Gilbert will occasionally give me a list of items that need fixing or attention (usually items an inspector noticed during a visit) and my job is to handle those items and make sure the home is ready to be shown by realtors. Gilbert has become a great friend of my boss, and will frequently join us during holidays with his wife. So handling these items has always been the norm and I enjoy doing them since Gilbert and his wife are nice people.

        This below makes it more likely that these are extras beyond the simple build (and the “ready to be shown by realtors” above may mean stagings and other “beyond the build” things).

        I guess the problem was that Gilbert has been told before he needs to hire a real maintenance person for oversee these homes, but does not want to spend the money.

        I wonder if, since the OP could use the money, she can talk Adam into letting her moonlight to Gilbert in this way, and maybe give the boss a much smaller cut than he would get if the payment went directly to Adam. But then there’s the whole “how much time does it take, and does that take away from my work for Adam?” idea.

        1. NW Mossy*

          OP can perhaps clarify, but I read this as maintenance/punch list work not being part of the OP’s normal job duties but something she’s doing because Gilbert asked. Had he formally asked for the work to be done through the company, it could still be done, just by someone other than the OP.

          1. Alice*

            If I could get my contractor (a relative) to send someone from his team to finish the last little details for a project I would be absolutely thrilled. So frustrating – the little things are apparently too little for him to worry about but no other contracter wants to finish someone else’s project. If anyone did ever finish the punch list I’d be thrilled and give them a tip myself too.

    4. Luke*

      The situation may be more fraught then it seems. In the event this dispute escalates into legal action between Gilbert and OPs boss , the payment of money to the OP for services rendered can be used to argue Gilbert contracted with the OP for work performed instead of her employer – which could damage the OPs firm. I agree that the OP needs to return the funds and disclose this event to her boss , if only to protect herself from any potential legal risk down the road. Lawsuits suck.

      1. Just Employed Here*

        Also: taxes. OP didn’t just receive the money as a gift (even if the boss lets het keep it, after she tells him about it). Are gifts taxable where the OP is? They sure are where I am, but this check was written as a thank you for services rendered, which makes is not a gift.

    5. Aveline*

      Well, even if the money isn’t owed to Adam, it’s still problematic.

      Sometimes gifts aren’t gifts. They are bribes and weapons.

      Remember why Gilbert is giving you this money. Hint: It’s not really appreciation for your work.

      This isn’t a windfall. It’s a minefield.

      Are you willing to lose your job with Adam over this?

      1. sam*

        and ALSO, if this is money for work that was done, how is going to be accounted for, tax-wise? just to throw a whole OTHER wrench into things.

    1. Sherp*

      If Adam is a good guy, he will let OP keep the money and not make it part of the issue he is having with Gilbert. Or at least not penalize LW for their issues.

      1. Hills to Die on*

        I have been there and am really hoping for a version of this where OP gets to keep it. It should be an apology bonus for the poition Gilbery put her in. Fingers crossed for you OP!

      2. Lanon*

        I’d bet money on it that adam will take all of it and also be insulted by the insinuation of a raise. I’ve worked with these types.

    2. Socks*

      Though I think it would be worthwhile to make the case to Adam that, while Gilbert should certainly still pay him, if he wants to “waste” money gifting it to OP, then he should be allowed to do that via OP keeping the money. Because OP should totally be allowed to keep the money if there is no major legal issue with them doing so, since it is not their fault that Gilbert was trying to do something unethical, right? It’s Gilbert’s problem if his bribe didn’t work out the way he planned, and I’m sure Adam could be convinced to agree out of spite. But I don’t know if that would work out, legally, if Adam still wants to pursue payment from Gilbert. I am very much not a lawyer, I just think that barring any legal issues, OP could certainly make that argument to Adam on just a social level.

    3. JS*

      Actually OP can keep the money as Gilbert said it was a “gift” explicitly. Adam has no claims to it. I am SURE Gilbert gifted it to spite Adam. However legally Adam can still pursue Gilbert for payment if he is claiming he owes him for it. Whatever Gilbert gifts OP doesn’t have to do with Adam. I would tell Adam that Gilbert gave her a gift and leave it at that.

      1. Genny*

        She might legally be able to keep the gift, but Adam could fire her for what appears to be a breach of ethics (depending on what the employee handbook says about accepting gifts, it could be more than just the appearance of a breach of ethics). The loss of income from this job, the tanked recommendation, and any potential difficulties in finding a new job likely aren’t worth whatever this check amounts to.

        1. Sunny*

          it might be a small enough company that there is no handbook but if its a 0 hour which it probably is that does not matter.

  5. Princess Consuela Banana Hammock*

    Wow, Gilbert is a class act.

    OP, unfortunately you have to disclose the “gift.” I would not cash the check or spend it. You definitely don’t want to end up in the situation Alison described where Gilbert starts to argue he had a separate business relationship with you by side-stepping Adam. You’re going to want some kind of paper trail to establish that this was more akin to a tip or bonus than it was to payment for wages.

    You don’t have to give the money to Adam, however, and you should keep track of the amount for tax purposes. Adam is going to need to work out the payment problems directly with Gilbert, but under no circumstances should you allow either of them to “recall” the check as if it were payment for your labor. Think of it as holding it in escrow until it’s clear that the money is safely yours.

    1. Aphrodite*

      I wouldn’t even hold it “in escrow.” Send it back to Gilbert immediately with a thank-you note indicating that while you really appreciate the thought you simply cannot accept a tip or bonus from a client directly. As for telling your boss, it’s probably best but I’ll let others address that.

      1. MK*

        I disagree with this. The OP doesn’t know how her boss will react; he may have cooled down and want to salvage the profitable relationship with Gilbert, so he may let her keep the money and let it go.

    2. JS*

      Gilbert can’t argue a side business relationship since he explicitly said “gift” and thanked OP for the help. You don’t “gift” and “help” someone in a business transaction. All this does is piss off Adam who if anything could tell OP to give it back in terms of accepting gifts from clients and the ethics behind that but can’t require OP to hand it over for services rendered given the note.

      1. Princess Consuela Banana Hammock*

        I understand, but Gilbert sounds sleazy, and it’s possible that he’ll try to muddy the waters after the fact. OP should keep the note that discusses it as a gift. As I noted, OP should not hand it over for services rendered, but she should disclose what happened to Adam and hold off on cashing the check until Adam has decided how he wants to proceed.

    3. Holly*

      Since Gilbert sounds cheap and/or sleazy, I also wouldn’t want OP to then hear “Oh! We’ve made up – I’m actually going to need you to give me that check back so I can pay the company for its services.” Or something else that would screw OP later.

  6. T*

    Just think of the check as a piece of paper. It’s not supposed to be yours.

    It’s REALLY hard to do that when you’re hard up for cash. What he is doing is trying to manipulate you. If you take the money, you will owe him. It’s not a gift. He’s trying to undermine your boss’ business and your professional obligation is to your boss.

    Then go ask him for a raise.

    1. What is legal is ethical here*

      Just think of the check as a piece of paper. It’s not supposed to be yours.

      I would respectfully disagree with this. Gilbert expressly said that the money was a gift, not a payment to the firm he engaged. The gift does not relieve him of the obligation to pay the firm. The money is OP’s.

      The potential for problems is more in terms of (1) does OP’s firm have a policy against accepting gifts? (2) would keeping it undermine the firm’s trust in OP?

  7. samiratou*

    I’m sorry, LW, that you’re in this situation. I hope that Adam realizes it’s not fair to penalize you for his dispute with Gilbert and lets you keep the check.

    1. TootsNYC*

      and that he realizes if his company deserves to get more money for the work you’re doing for Gilbert, YOU deserve to get more money for that work.

      (I’d love it if you could talk him into letting you take on a second job, doing this stuff for Gilbert and being paid directly by Gilbert)

  8. Icontroltherobots*

    Op – this is horrible. The fact that two wealthy people are playing games with someone is such dire financial straights as you, is repugnant.

    Here’s my perspective:
    You need to inform your boss, I would phrase it more as a “Gilbert has asked me to subcontract these services” and that you have received a “deposit”. I would ask him if providing these services is allowable under your business relationship or not. If he says no, and he probably will, you can return the deposit or not. Either way, you have to tell Gilbert that this is either 1) a business relationship with prices/fees or 2) not to be repeated because Adam said no sub-contracting.

    TBH if Adam isn’t paying you enough money to eat every day (!!) he shouldn’t feel entitled to all of your time and should get over Gilbert paying for these services.

    It’s also my understanding that competent employees in the construction industry are literal unicorns. Maybe consider job hunting?

    1. solar flare*

      I recommend against this because it’s… not… true. Gilbert has NOT, in fact, asked LW to subcontract these services.

      1. CM*

        +1. And I think it looks bad for LW to imply that she’s gone behind her boss’s back to solicit business.

      2. Icontroltherobots*

        I was trying to find a way for OP to keep the money and potentially start a business relationship with Gilbert. OP would need to be clear with Gilbert/Adam that this is as I mentioned, a deposit, all parties would need to agree to this new business relationship.

        Op need’s her boss’s buy in and Gilbert needs to know this is a new business relationship and that she does not accept “gifts”.

        1. JKP*

          I wouldn’t subcontract if I was the OP. On more than one occasion, I’ve witnessed a client try to end run around the business owner and hire the staff directly instead of the company. In those cases, the owner gave the staff permission to do so if they wanted, but warned them that if the client was trying to screw over the owner, they would eventually try to screw over the staff too. Sure enough, every single time eventually the subcontracting relationship blew up as the client tried to pull the same stuff with the staff.

          1. Em*

            And there’s a lot more to a business than just doing the work and getting paid. There are licences and insurance and regulations and taxes etc. Just a couple off the top of my head — OP is injured doing the work — does worker’s compensation cover her if she was doing it as a side business? Something major (and expensive) goes wrong with the work — does OP have commercial general liability insurance to cover it?

    2. TootsNYC*

      I wouldn’t present that as “something that has already happened without your approval,” because a boss would rightly be upset at the employee undercutting his opportunity to earn his own income from that service. Especially because the OP is (1) capitalizing on a business relationship not of her own making, but of the boss’s; (2) using the boss’s resources (phone, desk, office time).

      But it would be nice if the boss would allow it! Or, charge Gilbert but pass most of the money along to the OP.

      1. Icontroltherobots*

        I’m saying present it as a “Gilbert wants to start this relationship with me directly”, boss would need to be okay with this idea and Gilbert would need to informed his “gift” is a deposit and that they have a business relationship now, that boss is okay with.

        I’m trying to find a way for OP to legitimize the creepy check, turn the situation into something boss can be okay with and make it clear to Gilbert that “gifts” are going to be considered a business relationship.

        1. Princess Consuela Banana Hammock*

          Although I understand the impulse, I don’t think this will legitimate the creepy check—I think it will create new and deeper problems for OP. OP cannot and should not try to transform receiving the check into a business relationship.

          1. Clisby Williams*

            I agree. OP needs to go to her boss and say something along the lines of “I don’t know what’s going on with Gilbert, but this seems really weird. He’s sent me this check.” (Present check and note). “What do you think I should do about it?”

            1. RUKiddingMe*

              I think she should show him a photo copy of the check and note…keeping the originals safe at home until this all shakes out.

            2. davida*

              Your on the right track , tell the boss (uncle) about it all and get bosses advise it looks like a tip / gift but is it ?

          2. RUKiddingMe*

            Since the note said it was a ‘gift’ and a ‘thank you’ specifically using those words, legally can she keep it? Not should she, that’s a different question. I just want to know the legality of her keeping it.

            1. Lexie*

              Just because someone calls something “a gift” doesn’t mean it actually is one. This specific story doesn’t read like bribery, but how many bribes are ostensibly labeled as gifts?

              Legally the OP could probably keep it, but it would be incredibly foolish to do so, at least in my field. If were to do work for a client that my manager specifically said I wasn’t to do unless the client paid for it, it would be a very big deal if I did the work anyway. It would be a bigger one if it appeared that I was doing the work and being paid directly by the client. Up until the fight, the OP could claim ignorance that she thought she was supposed to do these things, but not anymore. I definitely wouldn’t try spinning it as a subcontract/deposit. That would make it look worse, not better.

              Maybe it’s different for her, but in my field, not disclosing honestly, completely, and without trying to benefit would result in an immediate firing plus a career-killing scandal. I can’t imagine someone getting hired anywhere if word got out.

              1. Agent of SHIELD*

                Bribery is defined as “the offering, giving, receiving, or soliciting of something of value for the purpose of influencing the action of an official in the discharge of his/her public or legal duties.”

                OP is not an official and is therefore not discharging public or legal duties. Therefore this is not bribery.

    3. WellRed*

      I would phrase it more as a “Gilbert has asked me to subcontract these services” and that you have received a “deposit”.
      Nooooo! That is not only untrue, and even if it were, that would be even worse. You can’t just subcontract on your own with your boss’s clients. Also, we don’t know that she isn’t being paid enough (although I suspect that’s the case).

      1. Icontroltherobots*

        The idea here is that when boss says no – OP returns the check to Gilbert – tells Gilbert that she cannot accept gifts and boss has not okay-ed a subcontracting relationship.

        Boss says it’s fine – OP goes to Gilbert and says, are we in business now? with rates/rules/no creepy checks- If Gilbert says yes – OP keeps the check and has a side business. Gilbert says no – OP gives back the check and says, I don’t accept “gifts”

      2. Shoes on My Cat*

        Agreed!!! And fwiw, OP just mentioned in a comment above that she is actually being paid a bit more than industry standard and had just started talking to her boss about a raise. Her financial situation is due to a separate issue.

    4. MK*

      “Gilbert has asked me to subcontract these services”

      No, he hasn’t. He has sent the OP a gift as thanks for services she had rendered to him in the past, so putting it like that is inaccurate. Also, your script suggests that Gilbert is asking for an future ongoing arrangement with the OP, which might inflame the situation further.

      1. boo bot*

        Yeah, I would put this to the boss straight. He’s playing toxic masculinity checkers, too – he will recognize what Gilbert is doing.

    5. Princess Consuela Banana Hammock*

      Definitely don’t characterize it as a subcontract! It’s not a subcontract, and if OP represents it that way, there are all sorts of new legal headaches that attach.

      Tell Adam exactly what happened—show him the note if need be. If he’s reasonable, he’ll let OP keep the money and chew out Gilbert.

      1. Icontroltherobots*

        I guess I was reading too much into the part where she said Gilbert wanted the services to continue. I was looking for some silver lining. Turn the creepy check into a legitimate service and not a “gift”.

        Also this was before OP mentioned she is fairly paid and not starving because scrooge McDuck wanted to swim in a bigger pile of gold.

        1. Princess Consuela Banana Hammock*

          Totally fair. The tricky part about it becoming a subcontract—in addition to the interpersonal and legal concerns—is that it would also require OP to start withholding taxes at a higher rate than if this were subject to the Gift Tax.

          Ultimately, I think OP should get to keep the money, but I understand that this will be functionally difficult until Adam and Gilbert finish their war.

      1. Iain C*

        We don’t do that here. Please read the posting rules.

        I have been very tempted to be a pedant too, over the same mistake, and “here here”, but it’s only important that it’s understandable. These are posts on a comment area, not articles in a newspaper, and noone had engaged you (or me) as their editor.

  9. BRR*

    If you don’t disclose the money, it could also jeopardize your current job. Ugh I’m sorry they put you in this position and that you have to deal with this.

    1. Dust Bunny*

      Yeah, this. I cannot imagine there is any way your employer wouldn’t be angry about this, and if you’re in money trouble now, you’ll be in a lot more without a job.

      Although, if he’s a skinflint, you probably should be looking elsewhere, anyway.

      1. RUKiddingMe*

        Using her as a pawn sucks so bad…I can’t even describe how angry I am right now. The fact that she is in a bad financial situation (granted they don’t know that) just has me seething. “Here starving person, have a sandwich…wait…not so fast…” Ugh!!!!

  10. Bea*

    This reads like the tasks he’s given you are things he should do himself or pay someone for. Instead he’s calling you and having you take care of them? And you took care of them on company time?

    I’ve been there once. We rented a room to Dude who hustled hardware into his retirement years. He would have me make calls for him to alert him to come pick up after a delivery, etc. He was selling my boss hardware as well. He used to toss me a $50 every few months. And I just pocketed it without any worry. My boss didn’t care one way or another.

    Since your boss is on shakey ground with Gilbert, you should disclose. I can only hope he’s not horrible enough to ask for the money. Maybe he’ll have you bill out x hours and you can keep the overage. I don’t know since he didn’t bill him out of spite, I can imagine this still working in your favor.

    Is this a company check? He’s playing with fire dolling out big checks for personal favors…that’s not a business write off. Praying it’s a personal check.

    1. TootsNYC*

      but if those “favors” the OP are doing are related to the buildings Gilbert is going to sell, then that’s not a personal favor. Are businesses not allowed to deduct gifts or “tips,” or is there a limit on them? Is there not some accounting category that this could go in? (

      Plus, if Gilbert is the owner of his business, he gets to authorize expenditures, no? Or payouts from the profit side?

      This is raising some interesting things! This would be taxable income for the OP–but would it be subject to withholding, etc.?

      This was fun:

      1. Bea*

        If he cuts a check to a person or non incorporated entity, he needs a w9 on file to send them a 1099 for any monies paid over $600.

        You can only deduct 50% of a meal, so sure a tip is deductible in a way if we’re talking about tips for services in that fashion. It needs to be properly recorded with a receipt.

        He has no bill to tip on. That’s unacceptable for tax purposes. You have to have proof that you paid for a service.

        Right now this is a check for a service he was never invoiced for. No. You cannot give Nancy at Your Fave Vendor a check as a gift without a bill. If you buy her a gift basket, you can write off that because recordable expense.

        Businesses have to track expresses meticulously. Accounting isn’t kidding when they require receipts for a reimbursement.

      2. Bea*

        It’s taxable. She should get a 1099.

        That’s recorded as income and you get slapped with self employment taxes.

        Anything over $600 a year.

        My old boss had a side business who owned the building. He cut me a check every year for 599 got the “work” I did as a bonus. Just under the magic threshold.

        You can’t just spend and write off anything you want and classify it as a Business expense. Unless you’re cooking books.

  11. MK*

    OP, you definitely need to tell your boss about the check. However, I think you should absolutely not give the money to your boss (or the company), because you risk being made further use of; he might tell you to deposit the check in the company account as payment to him from Gilbert for your services and consider it a “win”, as he got the money he was asking. Put it like this “Gilbert has sent me a monetary gift as thanks for the services I have been doing that were not covered by your contract. Is it appropriate for me to accept or should I sent it back to him?”.

    1. Doug Judy*

      This. It was a gift to you, and while you have to disclose it, I wouldn’t say you are by no means obligated to give it to your boss as a from of payment for what Gilbert owes him. If your boss pushes the issue (hopefully he won’t) just say you are not comfortable being a payment intermediary.

    2. Hallowflame*

      This this this!!!
      This money was explicitly described as a GIFT by Gilbert in his letter. Keep that letter in case Gilbert or your boss tries to claim the money is some kind of payment.
      When you disclose the gift to your boss, do NOT give him the money or consent to any kind of arrangement that would allow him to benefit from it (working X hours unpaid, etc.). You’re either going to keep the money, or return it to Gilbert. Informing your boss is just a courtesy.
      Also, since the money is a gift in appreciation of past services, you are in no way obligated to Gilbert if you accept the money.

    3. Kaaaaren*

      Yes! OP has to disclose that she received the check, but she should not under any circumstances pass the money on to Adam. Either she gets to keep it (with Adam’s blessing) or she returns the check to Gilbert. Adam should not end up with the money.

  12. tallteapot*

    But why has Adam been paying you so poorly that you’ve had to SKIP MEALS to pay your bills? That is a potential sign of a bad work situation. I do agree with Alison, you have to tell Adam about the check, but have you ever looked into whether you’re being paid fairly?

    1. arjumand*

      This is what jumped out at me when I read it, and I’m kinda disappointed that Alison didn’t address it.

      Yes, by all means, let’s get bogged down in discussions about ethics and what’s the right thing to do, when the OP is going hungry to pay the rent in spite of having a job.

      Excuse me, but WTF?

    2. OP*

      My financial situation isnt a result of poor payment on my bosses side. My significant others job went through alot of administrative changes and he went from matching what I make to minimum wage (which is a whole other letter). As I mentioned below, my boss is my uncle, so I make a little above what my position makes in my area and I have good benefits. I did ask for a raise a few days prior to this situation since I’ve been stagnant for the past 2 years.

      1. Bea*

        This is a relief to hear. More proof your uncle is a reasonable man and I’m hoping he lets you keep the gift.

      2. Dust Bunny*

        Okay, that’s reassuring.

        Nevertheless, I think it would be better if this were all above-board. And now that you mention that your boss is your uncle, that goes double. I hope he’s OK with it but there probably needs to be an understanding about where the limits are in terms of when you do this and what you do that isn’t taking away from your main employment.

  13. Anon Asst*

    Tell your boss immediately about the check. You don’t want to be accused of stealing or embezzlement or anything criminal. You did this work while working for the company. It’s like a secretary accepting a vendor payment because she facilitated in the process. Don’t keep it. It also has tax consequences.

  14. your favorite person*

    UGH. I’m so sorry OP. It feel sick about the fact that you are struggling so much financially and this money is being dangled in front of you like this. While it’s not part of this situation, you seem to be pretty valuable to both parties. Perhaps it’s time to ask for a raise?

    1. OP*

      I actually asked for one just a few days prior with my supervisor! She had not gotten back to me but a little part of me is hoping this will really up those chances of something substantial.

  15. OP - Update*

    Hi all,

    I sent this letter last week so a few things have happened since then. Mainly, one of my coworkers saw the check before I had a chance to say something. At this point, I had already decided to say something to my boss, it just sped up the timeline significantly. It may have been unclear above, but Adam is MY family member. So I knew that if it somehow got out that I accepted this money, and said nothing, I would be getting reprimanded by my whole family for screwing over the family. I told Adam about the check the next day since he didnt return to the office the day I got the check.

    He was not happy and he currently has the check. He thanked me for letting him know and a war is currently going on between Gilbert and Adam in my emails about this. It has become so bad that one of the homes we were scheduled to start next week (which would be a multimillion dollar profit for us) Gilbert has pulled us from. Which is most likely going to lead to a lawsuit since we have already signed a contract. I am on vacation starting tomorrow and wont return til next tuesday. I know ill be fine professionally, but I’m not so sure about my uncles company. We do alot of work for numerous clients of Gilberts stature so losing him wouldnt be awful, except for the fact that the zip code i live and work is all word of mouth, and one person like Gilbert trashing your company can really tank a business (I’ve seen it happen). Time will tell. I appreciate all of the responses. Still welcoming suggestions of what to do from here!

    1. Aphrodite*

      Look for a new job. Not only is your low pay (from a family member!) outrageous but it sounds like it’s a possibility that the company might eventually be headed for the trash heap.

      1. Di*

        Ditto. Look for a new job. Whether or not you’re being paid fairly, it’s insane to have your whole family as leverage in your decisions.

      2. TootsNYC*

        Just to clarify–higher up int he thread, the OP says she is actually slightly OVERpaid for her job and region, because her boss is her uncle. And that the tight financial circumstances come from a loss of income from her partner.

    2. Observer*

      This sounds like a roller coaster.

      If you are right about the threat to the business, it’s a good thing you told your boss. You may be looking for a new job shortly, and you don’t want anyone to be able to gossip about YOU.

    3. arjumand*

      “I know ill be fine professionally, but I’m not so sure about my uncles company.”
      “My financial situation has been so horrible this past year that I occasionally have to go without meals to pay rent. ”

      I mean . . . what? Who cares about your uncle’s company? You just told Alison that you had to make a choice between eating and paying rent, and you’re expecting us to care about Uncle Scrooge and the fate of his counting house?
      Unless you’re blowing your entire salary (minus the rent money) on the ponies, and so feel like you deserve to go without meals (which you don’t, let’s make this clear), I don’t know what’s going on here.

      1. caryatis*

        We also don’t know what’s going on here, and have no reason to blame the employer for the employee’s financial problems. It seriously could be a gambling problem! Or any one of hundreds of ways people get themselves into financial trouble despite being fairly paid.

      2. Myrin*

        OP explained in a comment above that her dire financial situation in the last year is due to a change in her partner’s job/his income, not her own payment.

      3. Clisby Williams*

        The OP has explained that her uncle is paying her slightly MORE than market rate for the job she’s doing. The financial problems aren’t because of that.

        Given that her uncle IS fairly paying her, it would be strange if she had no concern about his company.

    4. Hey Karma, Over here.*

      Oh, I had it backward, see below about Adam and Gilbert being family. But I still think that there’s a chance this is how they communicate and you will come back from vacation and find that peace has fallen again over their relationship.
      Enjoy your trip. Oh, and ask for a raise.

    5. Det. Charles Boyle*

      I hope you get the chance to talk to Adam and try to get a raise. Although, now that the company may be going under, it might not be the best time. Maybe think about getting your resume polished up and sending it out?

    6. Bea*

      Your uncle built his business and he’s taking the risk fighting with a large client. Try not to shoulder that worry yourself, I don’t think this will cripple him but you’re right it’s got it’s consequences.

      I’ve seen business owners do this over the years and none of them have gone out of business.

      I’m really sad he kept the check though. I wish he’d play his power games while allowing you a nice financial cushion.

      1. Hills to Die on*

        He surely knows what happened with your husband’s job and should really keep the check. Have you asked him if you can keep it? I can understand wanting privacy, but if he knows how truly bad your financial situation is, maybe he will give it to you. Especially if you show him the letter where it’s a gift.

      2. Aurion*

        Cashing the cheque of a client you are quarrelling with would significantly weaken your argument. Gilbert gave the cheque to OP, but seeing as OP is an employee (and family member) of Adam, I’d say it’d still hurt Adam’s side if Gilbert’s cheque gets cashed by OP. As Adam’s employee, OP is a representative of the company.

        OP mentioned that if she asked, Adam would just give her (his own, I presume) money. While that would be fraught in its own way, I don’t think any good could come of using Gilbert’s money in this situation.

        1. Hills to Die on*

          I really wish we had Cheques and not Checks here in the US. That looks so much prettier.

        2. Bea*

          That’s fair. I’m wondering what they’re fighting about exactly. He didn’t turn around and bill Gilbert for the work OP did. So it sounds like Adam just killed doing any more work with Gilbert unless Gilbert makes the situation whole and stop acting like a brat throwing his weight around, doing things underhandedly and such.

          It’s so messy. I can only assume the worst thing would be if Gilbert is refusing to pay for actual billed work orders that are outstanding.

          I’ve seen most small business owners just tell these pissers to take a hike and write off the loss.

          1. OP*

            I’ve kind of wondered why it was escalated so far as well. I know there is some history that I dont know about, which im sure plays a big part. But I think its mostly pride and principal an Adams side. Gilbert is a billionnaire and while my uncle is well off, hes not near that. Gilbert has been a little difficult in the past when it comes to him picking and choosing what he spends the money on. For example, he has no problem spending millions of dollars on marble, but wont pay and extra thousand to finish tiling a pool. Its worth mentioning that the rich people we build for are all pretty shady, so I think my uncle is just very tired of games after 30 years in the business, let alone from someone that is supposed to be a friend. Its also very possible Adam decided to pull the plug on the idea of the new project, although it didnt really sound like that originally.

            1. Genny*

              On the plus side, if Gilbert is this much of a jerk to your uncle, he’s probably been this much of a jerk to other people in his circle. I wouldn’t be surprised if everyone in the zip code are all secretly rolling their eyes at another one of Gilbert’s tantrums.

              1. bunniferous*

                Actually this is pretty par for the course for people with a lot of money-at least the ones who make it in the housing industry. I am not saying all well off people are like this but the ones I have known have been….different.

        3. Princess Consuela Banana Hammock*

          I agree. It’s unfortunate that Adam is holding the check, but until this all gets sorted out, that check is like a poison pill.

    7. Katie*

      I’ve scanned and haven’t seen it yet — I’m glad you haven’t deposited because it could fall under the Gift Tax as it isn’t a strictly employment payment. Gift tax from one person to another is $15k, and it sounds like this could be above that threshold. If it is, the burden is on Gilbert to pay the feds, not you, but still something to be aware of. Good luck.

      1. fposte*

        The burden of reporting cash gifts lies on the giver; they have to report gifts of over $15k in a year, but they don’t have to pay taxes until they hit a lifetime ceiling of $5.6 million per individual. But it’s never on the recipient, so the OP wouldn’t owe the money.

        1. Just Employed Here*

          But can this really be construed as a gift? I know the giver claims it’s a gift, but he’s paying it because of services rendered in the course of OP doing her job.

          The tax authorities in my country wouldn’t give a damn about any letter in this case. If the OP accepted the money, I think both she and Gilbert would be breaking laws on income taxation if this happened here.

          1. fposte*

            That’s a separate question that I don’t know enough to answer; I’m just noting that gift tax isn’t a factor here for the OP, even if it is a gift.

            1. Just Employed Here*

              Sure, but it’s still something for the OP to keep in mind.

              Also, if the OP isn’t in the US, things may be different: here, gifts are taxable starting from 4,000 euros, and it is the recipient who is obliged to report and pay.

      2. A Tax NERD*

        I don’t wanna derail the ethical advise to OP but this check would very unlikely be considered a gift for tax purposes. Even though Gilbert is saying it’s a “gift”, he’s giving it as appreciation for OP’s services over the years and that’s income. Gifts have to be given without any expectations from the giver. I hope OP gets to keep the money but it’s something she’ll have to report on her tax returns.

    8. Nita*

      Wow. OP, I’m sorry you keep getting caught in this stupid fight of theirs. It sounds like your best bet is to look for a new job that’s far away from this dumpster fire and pays better. Hopefully Adam will be understanding about you needing a better salary, and gives you a good reference. It’s up for debate whether that check was yours to keep (probably yes, but it sounds like some of the work you were doing wasn’t officially in your scope of work, and that complicates things). I suspect keeping it could have cost you your job though, so you didn’t have much of a choice.

      And really? You’d have your whole family on your case if they found out that you took the check, when they presumably know that you’re barely keeping your head above water, and Adam is not hurting for money? They’re some family then. My sympathies.

      Hang in there. I hope your situation gets better soon.

      1. Genny*

        I don’t think we should malign LW’s family. They probably have no idea about LW’s financial situation. How many people are willing to tell their families when they hit financial crises?

    9. Close Bracket*

      Oh gosh. I’m sorry for all this. I hope your vacation is restful and that you can leave the emails behind while you are on it.

    10. LiterallyPapyrus*

      Hi, OP,
      What a terrible situation you’re in. I’m so sorry. I have absolutely no advice that others haven’t already given, but your line about skipping meals stood out to me. If you’re comfortable with this, PLEASE reach out to a local food bank or food pantry to get immediate help. Nobody should sacrifice food for rent, utilities, medicine, or anything else. You can find a food bank close to you here: https://www.feedingamerica.org/find-your-local-foodbank and they will have a list of food pantries or resources in your area to get help with food. I’m a food banker and hearing that people are sacrificing meals to pay their bills breaks my heart.
      I wish you all the best!

      1. TootsNYC*

        Ditto the food bank thing! Lots of them don’t really want to know all your financial details; they just don’t want you to be hungry.

    11. Empty Sky*

      Yikes. Well, in case you haven’t figured it out yet (and it sounds like you have) the purpose of the gift was to send a message to Adam that Gilbert can use his resources to harm him – in this case by suborning those closest to him, i.e. employees and family. I would not be at all surprised if Gilbert had some inkling about your financial difficulties, and chose to take advantage of them in this way. All in all I think it’s time to reconsider your definition of him as a ‘nice person.’ I think you dodged a bullet by not accepting it, so congratulations on making the right call there. I wish you the best in resolving your financial difficulties on your own terms.

    12. CM*

      This striation sucks. There was no way for you to take that cheque without getting lawyers involved, but there’s also no way for your uncle to take that cheque without getting lawyers involved so, now that he has it, don’t cooperate with him if he tries to make you help him cash it. That’s my first piece of advice. Just say, “This sounds like a contract you have to work out with Gilbert. I gave you the cheque because I wanted to be honest about what happened, but, if he’s going to pay you, he needs to make a cheque out to you or the company.”

      My second piece of advice is to find a job that’s not at your uncle’s business, if you can. I know that’a lot easier said than done, but family makes things weird — and, I don’t know your exact work situation with your uncle, but it sounds messed up if he’s taking such lucrative projects and you’re literally starving while you work there.

    13. LGC*

      Oh man, OP. You made the right decision, but I’m so sorry that this is such a goat rodeo. And why are they CCing you on their drama emails? It’s a small thing, but if you’re not doing so already, filter them to a subfolder where you don’t get notified of new messages. (I’d say delete them, but…I’m on the fence, just in case anything legal comes up.)

      Also, as roundly noted, I’d start looking for similar positions outside of your uncle’s company just in case things go south, since you think Gilbert can easily tank Adam’s company if he so wishes.

    14. drpuma*

      Hey OP, if you enjoyed (or at least didn’t mind) the kind of coordinating you were doing for Gilbert on the side, maybe ask your uncle if you can figure out some sort of commission structure for you to do similar support work for other clients *through your uncle’s company*. That would bring in additional income for you, and also your uncle’s company, no shady stuff necessary!

    15. Rob*

      I really wish you hadn’t given the check to Adam. Disclose it, yes. Hand it over, no. Given how Gilbert specifically called it out as a gift to you, I believe you are in a position to claim it as yours.

      Now, I’m not a lawyer or an accountant. Perhaps there’s some legal nuance that makes this a payment instead of a gift due to the existing business relationship. But I would have rather seen you retain possession of the actual check until that’s determined, after consulting with a lawyer and/or accountant.

  16. Observer*

    “I feel like I am being used as a pawn in their game of toxic masculinity.”

    I think you are completely correct.

    But that doesn’t change the fact that you can’t keep that money. The fact that your boss is rich doesn’t change that – if Gilbert has not been paying for these services, this is not your money to keep. If this were a gift ON TOP of the bill he paid, that would be different.

    Also, there is another ethical problem here. This looks like an attempt to keep you doing this work for him while on company time. That’s totally out of line. Even working for him off the clock is a problem if this is work that he would otherwise be paying the company for.

  17. MissDisplaced*

    Agree on all counts. You cannot ethically accept this check or money and you need to tell your boss you receiced it. If it were really a “tip” for services you might be able to, but tips are not thousands of dollars!
    I’m sorry Gilbert put you in this position.

  18. Hey Karma, Over here.*

    Dear LW, please give this check to your boss and tell him that you don’t understand why Gilbert would send it to directly. Because you’ve been there two years. That means their relationship precedes you; their family connection excludes you so the dynamics of the situation eludes you. For all you know they could do this same song and dance every couple years. Hell, you could have been hired to replace the last person who got caught up in their ego war. Adam was “betrayed.” Gilbert “bribed his staff.” Just speculating with all that, but if you like your job, just be transparent and give the check to Adam. If you need your job, be transparent and give the check to Adam. If something looks too good to be true…

  19. Sharon*

    This is a kickback. It would be unethical to accept it. The financial status of the person writing you the check is not relevant.

    1. Teapot PR consultant*

      Yes, and calling it a gift is irrelevant.

      If it was a hamper, a bottle of wine or movie tickets, sure, in many industries it would be considered a lovely gesture.

      As a manager I’m happy to see my staff get this sort of thing from clients.

      But when it’s a large cheque? Treat it as if it was written to you personally by mistake and send it straight into the company bank account.

  20. caryatis*

    OP–remember your bad financial situation is not your boss’s fault, and not something that anyone else is responsible for fixing for you. I assume you have plans for pulling yourself into solvency, and it might make you feel better to focus on those rather than the work drama. And if you can–a second job is a great way to improve one’s mental health as well as bank account.

    1. OP*

      I agree! I have been applying to restaurants in the area and since we are about to hit season I have a few interniews when I get back from vacation next week.

      1. Hills to Die on*

        Hello to a fellow non-wealthy resident of a small, wealthy ski town! It’s a unique kind of atmosphere, isn’t it?

      2. Foreign Octopus*

        Good luck with that. I would caution one thing though, as someone who once had to work three jobs to make ends meet, be careful with how many shifts you agree to. Don’t underestimate your need for a day off – an entire day. I thought I’d be okay with working only one short shift on a Sunday in the afternoon but knowing that I had to work that day meant I couldn’t relax properly and my mental health took a sharp decline.

        I know it’s tempting to take all hours under the sun but your mental health is important too. Make sure you’re realistic about how much you can do.

        I’ve had to pull myself out of thousands of pounds worth of debt. It wasn’t fun; it was very hard, and I hated every moment of it but you can do it.

    2. Dragoning*

      Okay, I’m curious–how does a second job improve your mental health? I’ve never heard that before.

      1. Blue*

        Not to speak for caryatis, but I imagine having to stress less about money would help lower anxiety – in the short-term, anyway. That might change the longer you do it.

        1. Nita*

          Yes, as long as the new job is not horribly toxic. When my husband’s main job became a hot mess, he started taking side jobs – they paid peanuts and they were horribly boring, but he always came home with a spring in his step and some funny stories. And those peanuts added up after a while! It wasn’t much, but they did make a dent in our bills.

          1. TootsNYC*

            Thanks for this story. It’s a point I want to make to my kid. That side jobs, even if they’re small, can be good for your mental health.
            Sometimes they’re better for you that the bigger job, because they’ll often have clearly delineated tasks, and it’s easy to feel like you’ve done something.

      2. Foreign Octopus*

        I think it’s to do with having more things to distract you from your main job.

        I’ve found that if I’m in a toxic environment and I can’t get out of it for various reasons, having something else to fill my time at the weekends really helps me to keep things in perspective. Also, extra money is always nice so there’s that.

      3. Dance-y Reagan*

        Agreed. My time with two (or more) jobs was a miserable stress-fest that included frequent tears.

      4. nonymous*

        When I moonlighted the second job kept me occupied in a relatively healthy manner (no time for binge-watching TV or eating out too much or other excesses), plus I was physically tired all the time so I fell asleep faster (less anxiety). I think the key is to find a job that one is overqualified for and look for a workplace that is chill. It was really easy to keep management happy with my performance and since I had other opportunities, career-wise, second job politics just didn’t bother me.

      5. Bea*

        Yeah out saved me to work 3 jobs before but I was working to fill my time. The money was nice but all extra, I didn’t need to worry if the side jobs went sideways, I could just walk away at any time.

        But I wasn’t in a financial crunch. Having to work multiple jobs to make ends meet is exhausting and soul crushing.

      6. Else*

        My father-in-law’s definitely did – his main job was okay and paid okay, but he was coming off of a long period of laid-off and looked for a second one to rebuild resources. The second one would never have been enough to pay his living, but it was doing a thing he loves and he kept it for years, and has now retired from the other one but is keeping the side gig. Not everybody loves their second job, but it let him pay off worrying debt and help build up resources, and everyone likes that.

  21. Chatterby*

    I would approach Adam with this as “Gilbert was so happy with my performance, he gave me a sizable check as a tip. Does the company have a policy on accepting tips or gifts from clients, especially over a certain monetary value?” –because you should not have overheard their conversation about money, nor is managing their interpersonal or financial issues any of your business. You should proceed as if you hand’t heard it.
    Do keep in mind that there should ultimately be 2 outcomes after disclosing this check to your company and Adam clarifies with Gilbert that this does not obligate you to do any work for him, will be considered a no-strings gift, not payment for past services, and all payments for work done must go through the proper channels:
    1) You keep the money.
    2) The check is canceled.
    Under no circumstances does Adam or the company get the money. If they want the money, tell them Gilbert will need to cut a new check addressed to them. Do not sign it over to them, or cash it and hand the money over. Doing that could result in a giant mess, since it’ll look like you accepted a bunch of money you never paid taxes on.
    If Adam gets mad at Gilbert over any of this, let him, and stay out of it. Every time they try to suck you in, redirect them towards each other.
    So remember, they are grown ups, they can deal with each other without you, and you don’t want a temporary gift that will tank your long term employment.
    I do wonder, if there is no non-compete or similar, if the LW might be able to earn some extra money doing tasks for Gilbert in the off-hours or weekends, provided she stays above board with all parties.

  22. OP*

    I really want to address this again in the thread since it seems that everyone thinks im being paid poorly.

    My financial situation isnt a result of poor payment on my bosses side. My significant others job went through alot of administrative changes and he went from matching what I make to minimum wage (which is a whole other letter). As I mentioned below, my boss is my uncle, so I make a little above what my position makes in my area and I have good benefits. I did ask for a raise a few days prior to this situation since I’ve been stagnant for the past 2 years.

    My Boss (uncle) has taken great care of me in my career and if I told him that I was skipping meals he wouldve just handed me money. I do NOT want a higher salary just because I am a family member. I am a young female, in construction working under a family member; it should be needless to say many people dont take me seriously. I want to work and prove that I earned a raise, so I waited til my role expanded naturally. But I did ask for a raise a few days prior to this incident, so hopefully this will help me get that!

    1. TootsNYC*

      If your uncle’s company goes under, maybe you can become that maintenance person that Gilbert needs. Though, Uncle Adam may see that as a betrayal, which would create all kinds of family drama too!

      Good luck. I hope this blows over.

      1. Bea*

        You don’t want Gilbert for a boss. If he treats vendors like this, nope nope nope. Get away from that man child!

    2. MegPie*

      From a fellow (not so young) woman in the building industry I totally get people not taking you seriously. I agree with a lot of the advice above so I won’t go into it more but I just wanted to offer commiseration and good luck. =)

    3. Bea*

      As a woman in manufacturing since 19, anyone who doesn’t take you seriously and doesn’t sign your checks are unimportant jackholes. Look out for yourself and those who sign your paychecks, you’ll do just fine.

  23. LadyPhoenix*

    I assume the cash was to pay for a service and basn’t gone thrpugh things like… taxes or such.

    That is the problem with big money—it often comes with lots of strings attached to it.

  24. soon 2be former fed*

    OP I recommend returning the check, saying that is should be given to your boss. Always stay impeccable when it comes to money. I’m sorry about your financial difficulties, but that is never an excuse to be unethical. And please avail yourself of food banks when you are really short of money, no shame in that.

  25. Be Positive*

    You seem nice in this letter. Just going on that and the fact you wrote in to help you decide I don’t think you can live with yourself if you kept it when things improve financially later in life. That is if your boss never found out

    I would tell the boss to avoid burning the bridge. Reputation is more important

  26. Rainbow Roses*

    OP, I read your updates. Even if your boss is family, I still suggest you look for a new job while you still have a job. Working for family have a lot of advantages, but so does working for “outsiders.” Nothing personal to get in the way.
    You did the right thing by reporting the check. There are rules (laws?) regarding accepting gifts over a certain amount of money. You don’t want it to come back to bite you 5 years later.

  27. Quickbeam*

    When I was a probation officer I had a parent offer me 10K to write a favorable report on his kid. I had no food in the house and a car that had no brakes. I didn’t know how I was going to pay for gas the next day. But I said no. Now, 35 years later, I can live with myself. The long term really matters. Ethical slippery slopes never ever slide into your favor.

  28. John Rohan*

    Something is a little off here, and it sounds like there are significant problems other than the check. The OP claims she has been working for the past two years building luxury homes for wealthy clients, and the business with Gilbert has been “fruitful” so it sounds like business is good. Yet, the OP’s financial situation has been so horrible she has had to go without meals to pay rent?

    I would love to hear more of the story. Of course that could be any number of issues, from gambling debts, medical bills, alimony payments, etc but I think ultimately that’s a more serious problem.

    1. John Rohan*

      I now see where the OP has partially addressed that – for some reason, in the original letter, I imagined her as a much older person who was much further in her career.

  29. Greg NY*

    In this particular case, I would suggest that the LW not cash the check right away and instead speak to her uncle first, if only because it would mean less hassle and fewer family-related and job-related problems. But wouldn’t this kind of a check be considered a gift? As far as I know, you aren’t always obligated to check with your manager or organization to see if accepting a gift is OK, it is by default OK unless you are notified otherwise (usually when you’re hired). I have always assumed that I can accept a gift if I have not previously been given guidance to the contrary, and I just checked with a coworker (I am in the office today) to see whether they felt the same (they did).

    1. Pop*

      This may vary by industry – in all of the jobs I have been in, it is VERY out of line to accept a gift from a client. A former job of mine, as well as a former job of my partner’s (jobs were in different industries) expressly forbid it, and accepting cash from someone outside of the system would have been grounds for firing.

      1. Kuddel Daddeldu*

        My company’s policy is limiting the value if acceptable gifts to standard business courtesy like (non-luxury) pens, working lunches, wall calendars and such. Never money. Also there is a monthly limit of any gifts total of about $45 before it becomes taxable income (this is Germany, although I am currently on loan to the US).

    2. DaffyDuck*

      There are a lot of jobs where accepting gifts are problematical. All federal and state government jobs to start. Many large organizations have rules regarding this, especially if over a certain amount. There are regional differences also, in some public schools end-of-year gifts to teachers are not allowed or must be small but I have lived in school districts where expensive gifts (over one hundred dollars) were given by some parents.

    3. periwinkle*

      I work for a major corporation and would be fired instantly if it were discovered that I had accepted a substantial monetary “gift” from a customer. Hell, I’d be bounced out for a small gift. We have a strict code of ethics and a yearly company wide ethics refresher – no claiming ignorance of the guidelines.

      Then again, at another company, a customer was so grateful that I untangled a mess for him that he sent a heck of a gift basket. I got to keep it, yum.

      So know your company guidelines before accepting gifts. Or giving them.

    4. Bea*

      Lots of places have rules about gifts and if you can accept them. It leads to favoritism and conflicts of interest due to the power it gives a client over a vendor. It blurs the professional lines.

      I’ve been able to accept gifts but if it were huge, thousands of dollars in this case, yes it’s important to disclose due to the splitting of loyalties. It can be a mole situation and such.

    5. Aurion*

      Yeah, I’m in procurement, and kickbacks are a serious no. If I receive a gift due to doing my job, the gift is for thanking my company of which I am a representative. All gifts that can be communal (e.g. food) is shared. I have yet to be given anything that is extraordinarily expensive or cannot be communally shared, but if I ever do I am expected to notify my boss. And I am in a tiny, tiny company.

      Cash (or equivalent of), during a time where my boss is in a monetary dispute with the client in question? No.

    6. Madeleine Matilda*

      A co-worker may not know any more than you know about whether you can accept gifts. I would check with your supervisor, HR, or, if you have one, your ethics official for the rules of your work place. Most work places I’ve been in have rules about gifts.

  30. The_artist_formerly_known_as_Anon-2*

    … or maybe, just maybe, Gilbert might hire you at a higher salary? To do these essential things?

    1) return the check to Gilbert, informing him that, oh yeah, you could really use the money, but ethically you can’t accept it. That may let him know = YOU’RE AVAILABLE.

    2) tell your boss what happened – and – you’ve returned the check to Gilbert.

    3) wait and see.

    1. Decima Dewey*

      Don’t do this.

      Screwing over your employer (an employer who’s a family member) is not a good idea. And Gilbert probably knew he shouldn’t have been leaning on you to get these jobs done.

      Admittedly I’m saying this as a civil service employee explicitly forbidden to accept all but very small token gifts from the public, and who is explicitly forbidden to charge someone for services that are part of my civil service job description.

      1. The_artist_formerly_known_as_Anon-2*

        Yes, I retract that based on later postings from OP that she is being treated fairly by her manager/boss/relative.

        That changes the entire equation. When I made that post – I was reading the OP’s OP! And it implied that she had to skip meals because she didn’t have enough money – the implication that she was underpaid by a family member.

        The clarification that she made later – I don’t know if she made it before I posted this or later – changes everything. But I have seen family members treat others badly on payday. My father made a bold step and left the family business ( a retail store ) and went into education, not just for the satisfaction of teaching but also for a steady paycheck. For the record, the business had been running for many years and when my father left it, it went down.

        BUT – he had to take care of his wife and two kids as well. And realized it was the right thing to do, thank God.

      2. Alice*

        Why would it be screwing over her family to leave her current job and take a job running Gilbert’s properties? A job is not indentured servitude, even a family job.
        Working for Gilbert might be less stable or less rewarding or have fewer opportunities for advancement, but it wouldn’t be a betrayal unless she signed a loyalty oath when she started the current job.

        1. Decima Dewey*

          I’m saying that’s how the family would see it.

          Also, as others have said, don’t work for Gilbert. The first time you have a disagreement with him over anything (salary, parking, which team will win this year) he’ll do the same thing to you.

    2. OP*

      He might hire me, but I don’t think so. We’ve spoken to him before about hiring someone but he just does not want to part with the money it seems.

  31. Free Meerkats*

    “Gilbert will occasionally give me a list of items that need fixing or attention (usually items an inspector noticed during a visit) and my job is to handle those items and make sure the home is ready to be shown by realtors.”

    This is called a punchlist and it’s part of every construction job, and every phase of the job. It doesn’t matter how experienced and good the workers are, something will need to be corrected at the end of the job or phase before it’s ready, and that should be baked into the contract. And usually on a major job, the punchlist will generate another punchlist, PRN. It can be a problem with overly fastidious customers or overly sloppy or slow contractors and can drag on seemingly forever. I think when we had the Garage Mahal (maintenance building) here built, finishing the punchlists took almost a year.

    1. OP*

      I avoided using industry terms, since not everyone reading the letter works in construction. But yes, they are punchlists. The list had over 100 items, but most of them were changing lightbulbs and changing various filters sine the home has been on the market for almost 2 years. However, no, in our area punchlist items (after we’ve obtained a NOC) are never the GC’s responsibility. The houses are typically on the market for a very long time (average on 1-1.5 years, due to the size) and because the owners typically fastidious like you mentioned, we do not include those services in our contract for that reason. It would be unusual for that to be in a contract in our area, typically once we have a NOC the homeowner will hire a maintenance staff or a property manager or just add that home to the list of the property manager they already have. I mentioned in the letter that I was handling the punchlist items since I had previously helped out the owners as they have become family friends. I just was not aware my boss took away that service.

      Punchlists wouldn’t take that long to finish in these scenarios however, a year seems like a very long time to complete a punchlist for a home, regardless of size. Our subs mobilize pretty quickly though which im sure is not the case when it comes to commercial projects or smaller residential homes.

  32. JSPA*

    First, if it’s “many” thousands, I’d check the tax free gift limit in your country. (In the US, where I believe the current limit is $15,000, this would fall on Gilbert to report, and would only affect his estate upon his death. In other countries it’s often much lower–under a thousand euros?–and the burden is on the recipient.) (Standard disclaimer: IANAL nor an accountant.)

    As far as framing, I’d tell your boss that you received a large tip, and wanted to ask him what the appropriate response would be. Explain that you’re worried that it could be seen as a quid pro quo or barter transaction (in which case, the IRS or equivalent could get very, very interested if taxes are not paid). If your boss says to go ahead and take the money–or to take it and give him some–you should probably still clarify who will be paying the IRS their chunk. If he wants to rip it up, I’d actually probably play a bit of hardball; go ahead and explain that there are times when you’re on beans and rice for days, to make rent, and that while you want to make sure everything’s done right, you’re also pretty desperate for a raise, legally-agreed-upon side work, or some agreement that will see you end up holding a chunk of money.

    For all you know, your boss ripped into Gilbert for taking advantage of you, and told Gilbert that the services you’d been providing were not part of the business agreement, and straight out said that Gilbert owes you, big time! You did say that your boss does not want his firm to be in the maintenance business, so he may not actually want to be paid for the work Gilbert charmed out of you, by implying you owed him.

    In which case, you may still need to figure out how to deal with the money as a payment to you as an independent contractor. Though as you did the work with no contract (written or otherwise), no expectation of payment…and as Gilbert may not have intended to pay anyone for it…I suppose it’s possible that it actually could fall under the heading of a legitimate gift.

    1. OP*

      Oh, Thank you! I didn’t even think of this. It wasnt $15,000 – but I’ll still check on this to make sure.

      1. A Tax NERD*

        Hi OP, I commented above on this, but if you get to keep the check, it is most likely not a “gift” for tax purposes, it’s income. The advice above is incorrect (sorry JSPA).

  33. The_artist_formerly_known_as_Anon-2*

    … and, if your boss is a family member, and building custom homes, and is successful, but is paying you WAY TOO LOW where you have to skip meals —

    YOU’RE BEING TAKEN ADVANTAGE OF. He’ll probably try to lay a guilt trip on you if you leave or mention salary. Don’t fall for it.

    1. Rainbow Roses*

      The OP has updated several times regarding her finances. It’s not her salary that causing her financial situation. She works for her uncle and she already decided to ask for a raise.

      1. The_artist_formerly_known_as_Anon-2*

        Yes, I saw her clarification after the posting was underway. The initial post indicated she had to skip meals to pay her rent. We didn’t know WHY, but the initial implication was that she was being underpaid.

        OP clarified the situation.

  34. Lisa*

    OP, I saw above that you don’t want to let your boss/uncle know about your financial difficulties because you want to avoid being handed money and not taken seriously.

    Would it be possible, though, while disclosing the check to your boss, to say something like, “To be frank, this check would make some things a LOT easier for me financially” ?

    You’re not outright saying “I might not be able to eat dinner tonight if you don’t let me keep it” but you’re also signaling that the amount isn’t pocket change to you, like it might be to him.

    It’s possible he might say “You know what? Cash it. I’ll deal with Gilbert.”

    1. Bea*

      He knows thousands of dollars isn’t pocket change to anyone.

      Anyone who is working in construction knows a large chunk of money would help out anyone on the crew even though they’re paying them above the regular rates.

      It will sound ridiculous to approach him in that fashion and cause more of an issue.

  35. Kenneth*

    “Business gifts” can definitely be a problem, especially if you’re talking about something outside “nominal intrinsic value”, and in particular if they have the potential to influence your decision making or create conflict between you and your employer. This qualifies on the latter point, since your boss and the client, Gilbert, are not currently on good terms. And given you said the check would help resolve some significant financial issues, we’re also well outside the realm of “nominal intrinsic value”.

    So ethically you not only need to disclose it to your boss, you’ll also need to return the check to Gilbert.

  36. RedinSC*

    Hi LW, I’m sorry your finances are bad right now, and this might have already been said. But reach out to your area’s food bank. Get some food assistance for now, skipping meals and going hungry isn’t going to help you or your family. There is no shame in this, the food bank is there to help people who find themselves in a bind.

    You take care of yourself, and that means asking for help when you need it.

  37. Rookee*

    If she had not overheard the conversation, what would the question and answer then be? Assuming she had not over heard the conversation and received this “gift” without knowing about the measuring contest going on in the other room, I guess the advice would still be to tell her boss? I mean, though if it is listed as a gift, and has no strings like asking her not to tell, surely he knows she will tell right?

    1. LGC*

      As I understand it, she’d still have to tell – she’d just feel less dirty and used by receiving the gift. There’s three separate issues here:

      1) Gilbert gave a vendor a large gift (worth multiple thousands of dollars).
      2) Said gift was primarily to undermine Adam’s authority by not paying his company for services directly.
      3) Said vendor is also financially distressed, and the amount would be life-changing in the short term.

      Really, the question is only about point 1, and most companies require you to report gifts anyway if they have formal policies. If they don’t, it’s usually the ethical thing to do to say that a vendor gave you several thousand dollars out of the blue.

      Point 2 means that LW should owe Gilbert nothing as he’s doing this in bad faith, and point 3 means that the best outcome would be that LW gets the money eventually in some form.

  38. msroboto*

    I don’t know if the OP needs to say anything to her boss. She should give it back to Gilbert and then let them fight over it or drop it. That way she is ethically in the clear and she isn’t handing the check to the boss.

  39. Linnette*

    OP, if I were you, I would go to my boss and give him a hug and thank him for setting this up with Gilbert. When he asks setting up what? Show him the letter and the check.
    Tell him that you know that he had to have a hand in this because he knows about all the work you have been doing for Gilbert before they fell out and that you are glad they made up.
    If he denies knowing about it, then you ask Uncle, what does he think “we” should do with this check? Most likely Uncle will say keep the check. He might say it should go to Gilberts account. In that case ask for a receipt so that you don’t have to pay tax on it since it was written out to you.
    If he does the first “Yay!” If he does the second, make sure you have a record and proof of where the money went.
    Why do it this way? No guilt. Any other way, your boss will think that you were going behind his back some how. This way, you can be just a surprised as him.
    Think about it. If Gilbert were paying your boss and they were on good terms and Gilbert had given you a large tip, wouldn’t you show your boss who is also your uncle and Gilbert’s friend?

  40. Submerged Tenths*

    I would be SO tempted to take the check, quit the job, and wash my hands of the dysfunction!

    1. Oilpress*

      The problem is that there is a near 0% chance that the money will remain a secret. It is within the customer’s interest to ensure it becomes public knowledge so as to execute some sort of revenge over the OP’s boss.

  41. Lucille2*

    Late to the party, so my apologies if this has been brought up previously. OP, many large corporations specifically have policies against accepting cash gifts or gifts of monetary value from clients or prospective clients to avoid even the appearance of unethical dealings. Gilbert has put you in a very bad position, and that is on him. Don’t give him the upper hand. I’m really sorry about the financial position you’re in and I understand the temptation, but it’s really important that you do the right thing in this situation. I believe from your letter that you realize there is a right and wrong way to handle this, but need some outside validation to be certain.

  42. Stan Firebaugh*

    You can’t be loyal to two people with opposing views. If you worked for me, I would have to let you go if you said you would like to keep the check. Your boss has to have your unconditional
    loyalty on this matter or he can no longer trust you and with that , you must go. The other party is using you as a pawn , regardless of the window dressing he uses. Part of what the other party says is true; you have been a lot of help to him, and your boss has paid you for those services. He wants to reward you with a check, but he is smart enough to know there will be a blow up when your boss finds out.
    Maybe Gilbert wants to hire you and use you to get you fired. These are just my thoughts but it’s not my first rodeo.
    If it were my decision I would tear up the check and mail it back to Gilbert with a thanks but no thanks note and report it to my boss by saying Gilbert was trying to give the money to me instead of you. Good luck!

  43. Whaow*

    Disclose to Adam but Keep the money. It is yours, explicitly given to you for your actions by Gilbert. A tip, if anything.
    I would phrase as “by the way just as a heads up Gilbert tipped me recently.” Done.

    1. CanCan*

      That’s not really disclosure. “Tipped” sounds like a $20 tip. The OP would be not only not disclosing it, but pretty much lying to her boss. Don’t do that.

      The OP needs to tell the boss and go from there.

  44. Charles*

    If you did previous work for Gilbert unpaid and on your own time, you could be due payment of for all of that time at your company regular or overtime rate. You could present timesheets and make the case to your boss. If all the work was done on the clock, then all of the payment belongs to your boss.

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