I won money on a work trip to Vegas – do I have to donate it to my employer?

A reader writes:

I work for a medium-sized national nonprofit. Recently, I attended and presented at a conference in Las Vegas on behalf of my organization, during which, on an off evening, I tried my hand at black jack and ended up winning $2,500. I mentioned this excitedly to one of my colleagues back in the office and we had a good laugh about it. Well, my manager overheard and asked for a meeting, during which she said that the right thing to do would be to donate my winnings back to the organization, since I was in Vegas on my work’s dime.

I was taken aback and didn’t really know what to say — I ended up saying “Oh, I hadn’t thought of that. Thanks for mentioning.” But didn’t actually say yes or no.

So is there some unspoken rule here? Yes, I was traveling on my organization’s dime, but I gambled with my personal money. I feel really put off by her request — and in a way, I actually *did* donate back to the company, because instead of expensing a meal, I used some of my winnings to treat myself to a nice dinner that night. Am I obliged to make a donation?

No, absolutely not. Your manager is way off-base.

You were gambling with your money, not the organization’s, and the winnings are yours to keep. After all, if you’d lost money, you wouldn’t expect them to reimburse you because it happened on a work trip. It’s not reasonable to say that you bear all of the risk and none of the reward.

This was your own personal, off-hours activity. If you’d happened to win money in a private poker game with friends when you were traveling for work in Des Moines, I highly doubt your organization would feel entitled to that. What if you’d gone to a local fair and won a prize there? What if you’d entered a radio contest while traveling and won 100 bucks from that? These are all private, personal things done in your off-hours, and your employer has no claim on them.

It doesn’t matter that you were in Vegas because of work. Your activities there in your off-time are yours, as are any resulting winnings.

And yeah, nonprofits can be weird about money in a way that other employers aren’t, but none of the above changes just because you’re working at a nonprofit. It’s still not their money, and it’s not reasonable for them to feel any claim to it.

If your manager brings it up again, you can say something like, “It was just something I was doing on my own time, not as part of my job. But if the organization expects that in the future, we should let people know ahead of time. I don’t think many people would gamble on work trips if they knew they’d be responsible for the losses but wouldn’t get the winnings.”

Read an update to this letter here.

{ 342 comments… read them below }

  1. Roscoe*

    Stupid stuff like this is why I’m glad to be out of the non profit space. They feel entitled not only to more of your time, but your money as well.

    You should definitely tell her that she is extremely off base and it is inappropriate to even ask that

    1. Amber T*

      It would be nice of you to donate that back, just like it would be nice of you to donate your retirement saves, 10-50% of your salary, your kidney, your firstborn child…


      1. Specialk9*

        “I’m so glad you said that, boss! I had assumed that I was on the hook for gambling wins and losses on work trips if I used my own money. Great!!! You’re right that I won $2,500 on the Vegas trip, but for the February trip I gambled and actually went in the hole by nearly $30k. I am so excited that I get to expense that! I’ll go submit the expense report now for you to pay me back.”


        1. AKchic*

          That is actually a great way to handle it. The right amount of snarky in-your-face can-of-worms to show how off-base the manager is.
          If *that* manager wants to be a martyr and donate any winnings they may receive, that’s their decision. Requiring it of everyone is a no-go.

        2. FaintlyMacabre*

          I had a coworker who had accidentally been paid too much (direct deposit) right before a Vegas trip. He gambled and lost all his paycheck, plus the extra. When the error was discovered, my company decided to just let it go, figuring it was more effort than it was worth to recoup the money. So they did fund his losing Vegas trip!

          1. Audiophile*

            Oh god, I’m getting anxious just thinking about that. I can’t imagine gambling my whole paycheck. .

            I gambled on recently on a trip, won twice and then lost what I won. I smartly walked away after that. THAT was hard enough. I think I’d need to be picked up off the floor if I lost my entire paycheck through gambling.

            1. FaintlyMacabre*

              Yeah, unsurprisingly the dude was a bit of a train wreck. He just kept going to the atm, figuring it would cut him off when he was out of money, which is how he didn’t realize there was so much extra. Not how I roll, but whatevs!
              ( I went to Vegas, found 20 bucks on the floor of the Bellagio and wagered it all on blackjack. I got a 20, the dealer got 21 and I called it a day.)

              1. RJ the Newbie*

                We had a project manager who did this on a trip to Vegas. He not only cleaned out his bank account, but was about 20K in debt when he came back. On a side note, the expense report he wrote to cover some of his ‘losses’ could have won a Creative Fiction award. He tried to expense lap dances and what was clearly a call girl visit. Still shaking my head over it.

                1. pope suburban*

                  Normally, I’m a pretty hands-off, live-and-let-live person. I figure that everyone has their reasons and their story, and that’s not my business. But sometimes I hear about a person like this and I am just *consumed* with curiosity about how their mind works. Like…what is the mental landscape of a person who thinks that expensing call girls is acceptable practice? What is it like to be so bold, and/or divorced from anything like working norms?

                2. Disconnected*

                  @Pope Suburban, it’s not that they think it’s reasonable, rational or even vaguely appropriate. It falls under “Oh dear, I’m so far in the hole that I will panic and possibly ruin my source of income in an attempt to dig myself out from under a pile of debt.”

    2. GG Two shoes*

      And pay you less than market rate for the privilege. I work in a NPO adjacent field and I think about going back into non-profit work sometimes. It’s stuff like this that makes me not want to jump back in.

      1. Dan*

        I actually work for a very large non-profit… but we’re not in the “for a cause” business, so most days I go to work I forget we’re a 501(c)(3).

        The reminders I work for a non profit? Um, no profit sharing or bonuses. Holiday parties are on the minimal side. Along with that, no lavish social functions or other “company perks” outside of an otherwise very generous benefits package and competitive pay.

        This place is very much a “here’s your salaried paycheck, do your 9-5, go home” kind of place.

          1. CMart*

            Ha, mine too. “You’re the finance department, you’ve seen our cash flow” is the mantra any time an event rolls around and we’re informed that they went through the trouble to set it up but it’ll be $X to participate and food/drinks are on you.

        1. Emily K*

          Yes. A large, well-established, national nonprofit headquartered in DC and focused on lobbying/public education is a world apart from a small, local nonprofit focused on direct service provision. The former can often be a lot more like working for a for-profit company just, as you said, with somewhat fewer perks and bonuses. The latter can be a lot more like working for a start-up, where there’s a lot of professional opportunity, but the culture will ask you to sacrifice everything and there’s often one person who’s really running the show with a very informal management style.

          1. Jesca*

            That is exactly right, I think.

            Also, I have been going back to school for a Business Management Degree, and many programs and even classes are geared towards those wishing to start non-profits. Sort of like teaching them how not to fall into these traps.

          2. De Minimis*

            Mine is medium sized, and we’re closer to a for-profit as far as travel and parties.

            The most austere work situation I’ve ever been in was my time with the federal government.

        2. General Ginger*

          Dan, you’re living the dream :) Minimal holiday rigamarole/social functions, good benefits, go home at 5 — that sounds amazing.

        3. GG Two shoes*

          It sounds very much like we are in the same field, but we aren’t a 501c3. We are a different 501c.

    3. Hills to Die on*

      Yes, she’s an ass. Keep your money and don’t entertain this nonsense for another second.

    4. Amelia*

      I don’t miss working in a non profit, even though I thought the work we did was good. Non profit managers often have their own special brand of “out of touch with reality.”

    5. Kathleen_A*

      I work for a non-profit and this is just ridiculous. The reaction of people here if a staff member wins money on a work trip to Vegas may be “Congratulations!” or it may be “Gambling is silly” or it may be “Can you lend me some money?” (kidding!), but it would never ever be “You owe us that money.”

      (And I am speaking from direct experience here since I had a coworker, now retired, who often had extraordinarily good luck in these things and won money with some regularity, including at least once when it was *several* thousand dollars – a lot more money than the OP mentions.)

      I mean, if you bought a raffle ticket from a coworker, would you owe the organization a share of your quilt or whatever it was too?

      1. whingedrinking*

        I worked in film briefly, and there it’s fairly common for the crew to do five-dollar Friday. It’s open to everyone, but one time when I was on location the director won, and he chose to donate the cash to charity. This was a savvy move on his part – as the best-paid person on the shoot, he might have rankled some people if he’d kept it – but from there it became an expectation that you’d donate the prize. At which point I stopped playing. I already give to charity, and on a production assistant’s wages, those five bucks were part of my entertainment budget.

        1. Roscoe*

          See, for something like that, I feel like you should have just not let him play if people would get mad that he won. I understand its hard to say that, but it just seems petty to all chip in, but decide he can’t be a winner.

          1. Screenwriter*

            I think he made the decision himself, and VERY wisely. Directors can millions of dollars, whereas the crew–especially production assistants–are sometimes earning barely above minimum wage. He/she joined the fun, to be part of the group, for cameraderie, and then of COURSE donated when they won. The only other option for him or her might have been to treat everyone to a great dinner somewhere, or order in a special cake or something like that (depending on how much it was). The ridiculous thing is then whoever spoiled the whole thing by expecting the CREW not to enjoy their winnings.

          2. TootsNYC*

            I can see him wanting to play for the camaraderie, and to boost the pot by $5.

            But I also think he should have said something about other people NOT donating it, once that became a thing.

            Or, if he’d been able to foresee that, he could have instead used the money to buy everyone pizza or something, so that it’s not so much donating, but spending on you guys.

        2. Justme, The OG*

          That happened with my mom too. She happened to win the raffle, and as a VP who was paid better than the rest of the staff she donated it to charity. And I think maybe brought breakfast for the staff.

        3. Alli525*

          At my last job, we did an NCAA basketball tourney pool and Super Bowl Squares. If a “regular” employee won, good for them, they kept all of the winnings (like ~$400 max I think). If a senior-level person won, it was essentially expected that they would buy pizza for the office or something along those lines… which was something they were expected to do every now and then anyway, like after they finished a big all-hands project. It was never an official policy, just “what’s done,” but it always worked out in the four years I was there. (The year my college team won, and I subsequently won the pool, was the best year ever. Spent my earnings on a massage at the Four Seasons.)

        4. Thursday Next*

          It’s like the 30 Rock episode when Liz Lemon wins the pool, then ends up in a backfiring series of acts of “donating” the winnings back to the crew through picking up bar tabs, hosting ice cream socials, and giving away a watch her grandfather stole.

          Yeah, bosses just shouldn’t participate in some things.

        5. GH in SOCal*

          I’ve mostly seen producers/directors participate by putting their $5 in and writing someone else’s name on the stub so they can’t win. Anytime an above-the-line won they would do something like order an ice cream truck for crew lunch. I’ve never seen it turn into an expectation that below-the-line crew would do the same — it’s unfortunate that happened on your set.

          1. Screenwriter*

            Yes, exactly. Ice cream truck, In n’ Out truck, something fun. No one would expect below-the-line to do the same; how ridiculous!

    6. Canadian Teapots*

      My first reaction, in all honesty, was to wonder if the manager had sticky fingers and was trying to figure out a way to get their hands on some of that money.

    1. Fake old Converse shoes (not in the US)*

      Yes, especially considering salaries in non-profits.

    2. Princess Consuela Banana Hammock*

      Absolutely. If OP bought a lotto ticket on their own dime at a gas station while traveling for work, would the nonprofit be entitled to that? How about OP’s first-born child?

      The manager is out of line and being coercive. It’s shitty behavior.

      1. Inspector Spacetime*

        The company would only be entitled to OP’s child if conceived on a work trip.

  2. Technical_Kitty*

    If they push you can tell them they need to pay you for every single hour of every work trip and do the same for every other employee.

    1. The Foreign Octopus*

      Ooo, I like this. Hours sleeping and simply breathing on the trip count as work, so there you go.

  3. The Foreign Octopus*

    It honestly baffles me how a person, who I assume has a brain, can think that that is a normal request to make. I’ve never worked non profit and from what I’ve learned here, it’s a weird ballgame, but still. This is so far away from normal that it is 100% worth pushing back on, and if your manager keeps coming back on it, ignore the entire thing.

    1. Vesty McVestPants*

      I’m often surprised at how people- complete strangers- have no problem telling me I should donate my long hair. They’ll just walk up to me on the street and often respond defensively when I say that’s not something I’ll be doing. Who are you to tell me what I should do with my own things- be it hair, money or anything else that is mine?

      1. Hey-eh*

        This used to happen to me as well! “Your hair is so long, have you thought about donating it?” was usually the phrasing. I actually had donated my hair once, then grew it out again and a few years later I donated it again after getting married. So at least I was able to say, “Yes I have in fact!” But it doesn’t change the fact that it’s a super weird thing to say.

      2. Annie Moose*

        Ugh, that’s so weird. No, I don’t want to donate my hair… I have it long because I like it long. Grow your own hair out if donating hair is so important to you.

          1. Kathlynn*

            This is the only time I have said that. Though there are several reasons a person might not be able to donate their hair. (like dyeing your hair)

        1. General Ginger*

          Wow. I’ve never had long hair, so haven’t experienced this myself, but I’m just baffled that anyone thinks this is an OK thing to do.

          1. SarcasticFringehead*

            The other big one is people telling you that you should never cut off your hair, which starts out annoying but can end up creepy if, say, you’re 12 years old and the substitute school bus driver is really insistent about it. Hypothetically.

      3. Kathleen_A*

        Oh, my goodness – back when I had long hair, I used to hear that too, Vesty! I mean, what in the world?

      4. Jadelyn*

        I’ve gotten that one from time to time and it always weirds me right the hell out. Bad enough talking about how you should donate your money, but my hair is a literal part of my body so…??? What part of your brain thought you should get a say on what I do with it?

        And it’s always completely out of the blue, not like I mention maybe cutting my hair and them going “oh if you do you should donate it”, but as Hey-eh said, “Your hair is so long, have you thought about donating it?” I usually give them a baffled look and reply with “No, why would I?” That usually gets them kind of fumbling for a response and I genuinely enjoy “returning the awkward to sender” in these instances.

        1. AKchic*

          “Have you thought of donating your brain, it appears that you’re not using it.”

          I’m mean, though.

        2. Lehigh*

          The thing that really bothers me about this is that nobody suggests that people with short hair should grow their hair out to donate it. But if you grew it out, you obviously have some obligation to cut it to donate (and then, presumably, grow it back out to have it the way you like it). It strikes me as a double standard.
          On top of being invasive, of course.

          1. Lindsay J*

            Nono, you have the obligation to cut it to donate, and then grow it back out, so you can *donate it again* the next time a random person tells you you should do so.

      5. Oxford Coma*

        Tell them to donate a kidney. If they act confused, say “Oh, I thought we were telling other people what to do with their body parts.”

      6. Narise*

        And my response would be..’You should don’t your brain to science. Like immediately. Don’t wait.’

        To be fair though I worked with one lady and she took her hair from down to her but to her chin one weekend. I did ask her if she had donated it because I couldn’t imagine any other reason to make such a drastic change. Fingers cross I didn’t offend her when I asked but she seemed OK with it.

        1. Marillenbaum*

          A friend of mine did that once in high school–she went from having waist-length hair to a chin-length bob overnight! We were all amazed, until her hair was waist-length again the next day and we learned it was all a prank to freak out her mother. Well played, Kimberly, well played.

        2. Jadelyn*

          Eh, I mean if they’ve already done the deed, then you’re asking about something that’s already happened, not offering a random stranger your unsolicited suggestion for how and why they should go and alter their personal appearance.

      7. EddieSherbert*

        My favorite is when they specifically say “donate it to X” (with X being a well-known but not that legitimate organization you can give your hair to), and then I can go into a tangent about how X actually throws away 90% of the hair they get and then sells the wigs (they are not donated).

        People usually try to escape and walk away rather quickly at that point, full of regret for ever speaking to me…

        1. stitchinthyme*

          Heh, I have done this as well, usually when someone mentions donating hair to X. I’ll generally point to some sites that have data about them, and suggest (another organization that accepts hair donations and has a much better reputation) instead.

        2. aNon*

          I wish someone had warned impressionable high school me about X. I’m still really sad that I got the worst haircut of my life (I could not handle short hair back then) and my hair likely didn’t benefit anyone the way I thought it would.

      8. It's MY hair!*

        OMG, I thought I was the only one!!!! My hair is down to my waist, all the way around. If I had a penny (not even a nickel!) for every person I don’t know who walked up to me and told me I should donate my hair because there are kids with cancer who would love to have hair like mine….I could have retired ten years ago.

        I actually considered it once, but then found out that one of the big hair charities doesn’t donate the wigs that are made so that took care of that.

        1. Rusty Shackelford*

          Yep. Most of the people who insist that you donate to That Certain Charity don’t realize that (a) the wigs are intended for people with alopecia, not cancer, (b) they are not all free; recipients are charged on a sliding scale, and (c) a lot of hair is discarded because it’s unusable, and some is sold.

          1. Callie*

            Yep. They don’t want gray hair, or colored hair, or a lot of other things, so that rules me out. Not that I’m inclined to donate to them anyway, given their shadiness.

            1. Jadelyn*

              There’s that, too – I’ve been coloring my hair for years, they wouldn’t want mine even if I tried to give it to them.

              1. LaurenB*

                Have you thought about not dying your hair so you can donate it?

                *ducks and runs*

        2. Nonprofiteer*

          I worked for an organization that provided a variety of services to kids with cancer and other illnesses, and we regularly received boxes of hair in the mail. We absolutely weren’t in the wig business, and I felt so bad for the receptionist who had to deal with it.

      9. Jules the Third*

        So, yeah, remember Hal, earlier today, saying “women don’t face the same expectation in every one of their personal decisions”?

        Read this thread Hal, read this thread.

      10. smoke tree*

        I used to get this as well, when I had long hair. I was already planning to donate it and I went to a hairdresser that would automatically ask if you wanted to donate if you were cutting enough hair at a time. It’s a bit baffling that so many people apparently assume that no one with long hair is aware of this precious opportunity. Another factor is that most places won’t accept hair that’s been chemically treated or dyed, so it’s not like it’s a possibility for everyone.

      11. Allison*

        I can’t remember if anyone came up to me on the street and said that, but at one point my friends were hell-bent on getting me to donate my long hair, and they made me feel selfish for refusing. I did eventually end up cutting my hair short, but not all at once, and I did not donate, which I think some people found upsetting.

        1. Jadelyn*

          That’s really crappy of them, I’m sorry to hear they pulled that. I don’t understand how some people feel so entitled to other people’s decisions like that.

          1. Live and Learn*

            I once had a friend who frequently told me how envious she was of my long, thick hair and would routinely ask me if she got sick (she wasn’t sick) if I would cut off my hair so she could have it made into a wig. She was extremely serious. When much of my hair fell out last year due to health issues I couldn’t help but notice she did not offer hers…

            1. Kate 2*

              Right? It’s always them telling other people what they should do for charity, mysteriously they are always too busy bossing other people around to do it themselves.

      12. Tuxedo Cat*

        It happens to me, too. I’ve also had people get on my case for not donating blood. This sounds like a humblebrag, but I really don’t weigh enough to be able to do so.

        1. Pebbles*

          I’ve had this happen to me. I wouldn’t mind donating blood except that I’m anemic and they won’t take my blood anyhow, so why bother? And I don’t care to listen to these people telling that me I should take iron supplements so that I can then donate. (Yes, there are also health benefits to not being anemic, but funny how these people don’t seem to mention that…)

        2. Me2*

          I’ve had hepatitis so can’t donate. It’s no one else’s business though, so when I decline people look at me like I’m a monster. I’d love to donate, I can’t, and it’s none of your business why. Sheesh, I’m feeling curmudgeonly today.

        3. Keep Your Eyes On The Prize*

          I can’t give blood because I’m anemic which is too bad because I’m a prolific bleeder.

        4. WS*

          I have the same problem: I had a kind of cancer that means I can’t ever donate blood or organs, but people who really should know better get on my case by saying “You spent so much time in hospital, you must know how valuable blood donation is!” Sure, but you don’t want my blood!

        5. Marion Ravenwood*

          I’ve had this a few times. I’m O-, but have really small veins which means my previous donations have been too slow to get enough blood out, and I’m on my second strike (basically I get one more failed donation and they take me off the register). If I could magically make my veins bigger and my blood flow faster then I would donate as much as possible, but I’d rather not risk that third ‘no’.

        6. Bad Blood*

          I tried 3 times, the first 2 I had low iron and was refused. The last time they sent me a letter that said not to donate anymore. I believe it was because I had recurring mono when I was younger.

          The good news is I can say I tried and they don’t want it!

        7. Temperance*

          I don’t donate blood for many different reasons, including political ones and the fact that last time I did donate was really horrible and traumatic. For my office’s last drive, I counted 6 different requests from one person for me to donate before I shut her down.

        1. Lissa*

          I know a lot of long haired dudes…now I need to poll them and see… How strange and inappropriate, though, that someone’s first thought on seeing somebody else with something nice is “you should give it to someone who deserves/needs it more.” Why just with hair, going down that route? Oh, your old wedding dress? You should give it to a poor bride! Hey homeowner – you should donate your home to refugees in need! Car owner? You know, there are single moms really struggling to get to work. Oh, your old wedding dress? You should give it to a poor bride! etc etc.

          It really bothers me that there’s a certain element in society of trying to get those who have 3 pieces of candy to give one to someone with none, as opposed to going to the candy factory. But I have seen a weird amount of this on social media too.

          1. Chameleon*

            “It really bothers me that there’s a certain element in society of trying to get those who have 3 pieces of candy to give one to someone with none, as opposed to going to the candy factory. ”

            I love this phrase and plan to pull it out anytime my mother-in-law pulls the “why don’t you just donate your house to the poor then” as a reason why she should not pay taxes on her multi-million dollar mansion.

            1. Lara*

              She probably sees herself as the person with three pieces of candy and perceives taxes as being forced to share.

          2. Lara*

            I get what you mean – no-one should tell you what to do with your own posessions or life. But I dislike the implication that helping the needy is inherently bad. If one of your kids had three pieces of candy and the other had none, you’d tell them to share. And I feel like there’s a galaxy of difference between ‘have you considered giving your wedding dress away rather than leaving it in a box in the attic’ vs ‘sacrifice your only means of transport to a single mom’.

            1. Kate 2*

              See, I don’t think the wedding dress thing is appropriate either. It is none of our business to tell other people what to do with their belongings. And to use the factory analogy, why isn’t that person asking wedding dress companies to donate?? It would be amazing PR for them, they could probably get a spread in Vogue or another magazine for it. And did the person in question donate THEIR wedding dress? Maybe that person with the boxed up wedding dress plans to give it to the next woman born/married into the family. Or maybe they just want to keep their OWN wedding dress and look at it when they are old and remember.

              Having money to burn, figuratively or literally, like the stereotypical rich person who gives their dog a diamond collar, is different than going around asking ordinary people to give away their belongings because you THINK they aren’t using them.

              1. Lara*

                But by that token, all charitable solicitation is suspect. Individuals – say Cathy from the office – pressuring you to give up personal belongings is a very different thing from Oxfam pointing out that hey, if you donate your wedding dress, a poor child gets fed and a poor woman gets a nice dress.

                And I’m sorry, but no, Brides4Us are not going to get a Vogue spread out of donating a dress to a singular poor woman. It’s why we have charity shops etc, because getting that kind of donation requires personal charity or an extremely skilled fundraiser.

            2. Lindsay J*

              I mean, if one of my kids earned the pieces of candy in a school contest or something I probably would not make him share with the other kid. Sometimes people get to have things that you don’t have, and that’s okay. The world is not always fair. And sometimes fair isn’t always being exactly equal.

              (But, I am not a parent, and for good reason, so I might be off-base here.)

              If grandma gave one kid 3 pieces of candy and the other none because she likes the one kid and not the other, then I am redistributing the candy (or buying the kid without candy some candy) and grandma and I are going to have a talk and some distance before she sees the kids again.

              1. Lara*

                Eh, I don’t have kids either. I think that’s a matter of opinion rather than there being one objective answer :)

        2. MicroManagered*

          I’ve had several (male) exes with long hair and I myself (female) used to have long hair. It’s not as common to approach a male with long hair and suggest donating it? It’s more common to ask if he’s growing his hair TO donate it. And, since I’ve had several male friends do that–grow their hair for the express purpose of cutting it off to donate–I suppose that’s not off-base. But you’re correct that there’s a disparity between how women are approached about donating their hair and how men are (that I’ve seen/experienced).

      13. MicroManagered*

        Things I don’t miss about having long hair! The unsolicited “you should donate your hair” + offense when you don’t congratulate them for such a noble and original idea thing is so common.

      14. SpaceNovice*

        I just realized how many times I got that when I had long hair. Ugh. I’m sorry you have to deal with that as well.

      15. doll hair*

        I started telling people “I’m keeping it so I can use it to make a porcelain doll rooted with my hair!” and it creeps most people out enough to back off, OR they find it interesting enough to ask questions, which I enjoy fielding.

  4. Lily Rowan*

    I really like Alison’s point about how they wouldn’t pay you back if you had lost money!

    And off-topic, but wow and congrats! I must be too timid of a gambler, because I’ve never won more than about $400.

    1. Not An Admin*

      I really like that part, too. It helps point out how crazy the request is.

      It would be one thing if she were chastised for gambling while on the work trip, but even then, that’s a slippery slope, especially when the employee isn’t dressed in company uniform or wearing the conference badge. (And I’ve seen those at the tables in Vegas before.)

      LW, congrats on your win! That’s some great luck there.

    2. Magenta Sky*

      “But if you’d like to back with a stake me for my next trip, I’m sure we can work out a deal.”

    3. many bells down*

      We got married in Vegas and we were leaving the casino so my new husband put the rest of his gambling stake into a penny slot machine … and won $800. We kept the suite for the rest of our stay with it!

    4. Steve*

      “Oh you must have miss-heard the conversation. I actually LOST $2500! I’ll submit the expense report for reimbursement before I leave today.”

  5. Nox*

    There’s a line from the movie G.I Jane that first popped into my head as I read this………..


  6. Mike C.*

    If you boss presses, then make sure to account for every lost hand and deduct from the winnings as Alison points out. I’m don’t think it’s likely that you won all that on a single hand after all. Then tell them to get lost anyway.

    Why would a non-profit even begin to think this was appropriate?

    1. Friday*

      I’d be tempted to tell my boss that while I won 2.5K, overall I gambled away 3K so would the company be reimbursing me $500 for this.

    2. Princess Consuela Banana Hammock*

      Why would a non-profit even begin to think this was appropriate?

      Because the manager is a loon. I’ve heard some nonprofits say things like this to their staff, but it comes from a misguided sense of “full dedication” to the job. These are often the same groups who try to force employees to donate to the organization.

      1. Jadelyn*

        I’m not even all that sure this is the sort of thing that would necessarily happen only at nonprofits, either. There’s a lower threshold for loony BS in the name of Dedication To The Cause, but there’s no shortage of bizarrely entitled managers in the for-profit world, either.

        1. earl grey aficionado*

          Yeah, I’ve been surprised at the nonprofit bashing in this thread because I’ve absolutely seen similar entitlement in the for-profit sector. I get that the “all in” attitude can be more endemic in nonprofits, but this is definitely a bad/naive boss issue and not an “all nonprofits” one.

          Anyway, congrats, OP!

            1. earl grey aficionado*

              I should have specified, sorry! I meant that there’s a lot of negativity towards nonprofit employers happening in the comments of this particular post in general (not in this thread started by you, Mike C.).

              My intention was to affirm Princess Consuela and Jadelyn’s points that while there are systemic issues in nonprofits, OP’s problem seems to be an overreaching boss, which can happen in any sector.

            2. Jadelyn*

              …Oh, come on. Really? Literally the first comment in the entire comments section for this post, is a generalization about nonprofits being entitled and doing stupid stuff because of it.

    3. AKchic*

      I don’t think it’s the non-profit in general, but a lone manager who overheard the discussion and seems to think it’s appropriate to not only butt into the conversation, but try to act as if it *is* appropriate to dictate where the money goes.
      For all we know, the actual c-suite and board would be appalled by the very idea of requiring staff members to donate gambling winnings to the organization and this is just a rogue manager with a gumption idea (I know the last non-profit I worked at would have absolutely been appalled and outright refused to do such a thing).

      1. Jadelyn*

        I agree, I think it’s almost certainly just this manager on a power-trip or having misguided sensibilities around boundaries and work travel.

      2. bonkerballs*

        Yeah, the my previous non-profit actually used petty cash to buy us all lottery tickets when the pot got absurdly high one time. None of our tickets won, but we had fun buying and checking them.

    4. Free Meerkats*

      You should look into how the IRS handles gambling accounting. Especially since you won enough to meet the reporting threshold. It could pencil out that you (at least on paper) lost money on the trip. If that’s the case, give that info to your manager and ask for reimbursement. I’m sure he’ll see the error in his ways.

    5. MicroManagered*

      If you boss presses, then make sure to account for every lost hand and deduct from the winnings as Alison points out.

      I feel like engaging with this ludicrous request to this extent gives it too much validity. If it were me, I would use a script like Alison’s to point out the error in logic, but then the conversation stops after that (or escalates to grandboss or something if they REALLY keep pressing).

  7. The Photographer's Husband*

    I’m just going to record here via text what I would (allegedly) do if I were in such a position:
    Manager: You should donate your winnings
    Me: BAHAHAHAHAHAHAHA /chokes a little, clears throat, composes self
    Me: Heh, no.

    1. Irene Adler*


      “You should donate your winnings.”

      Me: You bet! Right into my back account.

      Course, if it was me, the dough would have been spent by the time I returned from the trip.

      1. Crystal*

        Yeah, Vegas gets ya there. The most I’ve ever won is around $800 on one roulette spin (I felt like I was having an out of body experience) and yes, I spent it all there. Ate some amazing food, got a cabana at the pool, etc. etc. It was really worth it!!

        1. Antilles*

          At least you made it off the casino floor with your money. I have no actual stats for this, but I’d guess the overwhelming majority of people who win a few hundred bucks on a single lucky hand/spin/dice end up giving that money right back to the casino trying to chase their “hot streak”.

          1. I Like Pie*

            I did exactly this, I was playing video poker with my friends and was on a streak winning “double down.” I was up a couple hundred off of a $10 bet and my friend’s husband said, after I asked, “I wouldn’t push it…” and I thought, “but I’m on a hot streak! Look how many in a row I got!” The three of us, plus the bartender had some serious debates. In the end, I hit “Double Down” and whammy. Lost it all. That was 13 years ago, I don’t miss the money, but I love that I have the story to share. And a lesson learned.

      2. The Cosmic Avenger*

        “Sorry, boss, I already donated my winnings to The Human Fund….”

  8. CatCat*

    I’m shocked your manager said that to you, let alone set up a meeting for the purpose of doing so.

    1. Parenthetically*

      THIS was what got me about this situation. Not just, “Oh, you should donate your winnings” off the cuff, stupidly, but a MEETING, before which she presumably had time to contemplate what she was going to say and decide she really, really meant it.


      1. PB*

        Yeah, it reminds me of the letter where the manager called a meeting to tell their report to have their tonsils removed. The manager called a meeting to ask something ridiculous and invasive, had time to think and realize it was ridiculous, and then went ahead with the meeting as if it were NBD.

    2. Environmental Compliance*

      Oh my gawd, I missed the meeting part. I was so flabbergasted by the request itself I skipped right over that the manager considered such an appropriate request that she set a meeting specifically (I assume) just for it. My brain hurts from considering what thought process (or lack thereof) the manager had to go through to get to that conclusion….that was apparently important enough to set a meeting up for.

      1. Lil Fidget*

        I was thinking maybe the manager thought OP had won the money through something associated with the event, like won the raffle at the conference – that is the only way I can justify this request in my head. And even then, it’d still be a marginal case (and not something to schedule a meeting over). If I were OP I might just assume the manager was confused and say, “oh no, this was with my own money on my own time, so of course it wouldn’t go back to the organization!”

        1. Environmental Compliance*

          Even then, I won like $75 at a work conference once in gas cards and my boss was excited for me because she knew I had a long road trip coming up. I think we had even agreed to switch if she won gas cards and I won restaurant gift cards. I can *kind of* understand it a bit more than not-conference-related-winnings in a roundabout way, and I could *kind of* understand it being a one-off statement that was supposed to be dry humor…..but to set a meeting up for it just…..bwwaaaaahhhhh?

    3. Jadelyn*

      Holy carp, I missed that part. I caught “meeting” but thought OP had just made offhand mention of their winnings at an existing meeting and the manager jumped on it right then. That gives this a whole new dimension of WTF.

  9. AnotherAlison*

    I assumed this was going to be something you won at a raffle or a fake conference-sponsored casino night or similar. I wouldn’t agree, but I could almost see the point in asking you to donate back those types of things. Not real winnings from real gambling, though. That’s silly.

    1. LQ*

      I was totally expecting this to be a conference raffle kind of thing. (Which, I think there might be a case there maybe…?) But just you’re a person out in the world. Do they think that people who work in Vegas and occasionally gamble after work are entitled to those winnings because there job requires them be in Vegas? No. Your time. Your money. Your loss. Your win.

  10. aes_sidhe*

    Tell the manager you lost X dollars at another table/slot machines/etc. and to reimburse you for the loss.

    1. Crystal*

      Yep. I’d say “that was right before I’d just lost 2,500 coincidentally so we’re even!”

    2. Hibiscus*

      Gambling winnings are reported to the IRS as taxable income, so how exactly is the employee supposed to clear that up if it’s the non-profit organization’s? I assume they can’t report it using the org’s tax exemption certificate.

    3. AvonLady Barksdale*

      I was gonna say… makes me wish I’d asked my company to reimburse the 10 bucks I lost playing Princess Bride slots at the Encore a few years ago.

  11. Environmental Compliance*

    I like Alison’s wording – “I don’t think many people would gamble on work trips if they knew they’d be responsible for the losses but wouldn’t get the winnings.” Because that’s exactly right – sucks to be you if you lose, I sincerely doubt they’d ever even consider to cover that, but apparently your manager has the balls to assume that they’d have any fingers in the pot with a win.

    I think I’d laugh and tell them if they wanted to give me specific money to gamble with, I’d try to win them something next time, but there’s no guarantees. Otherwise, I’ll continue to use my own money to win *my own* money.

    1. Luna*

      Yeah Alison’s wording is spot on.

      I’m also impressed that LW responded in such a good way, I don’t think I would have had the composure to do that!

      1. Environmental Compliance*

        Right? It was a really professional way to respond without committing one way or another.

  12. Ladylike*

    We are definitely going to need an update from this OP to see if the crazy manager ever came to her senses, or if she continued to push the issue.

  13. Llama Grooming Coordinator*

    This might be a dark horse December candidate…IF she’s actually serious about this. Which, since she called a meeting to say this, I think she might be.

    But is she normally sarcastic? Does she have a deadpan sense of humor? Because the only way this is even remotely acceptable, in my opinion, is if she’s just joking around. And even in that case, she’s off base – because she caused you to take her seriously.

    (Again, I’m not saying that it’s okay if this is just some messed up prank. It’s just that a messed up prank would be marginally less inappropriate than actually demanding your employee’s gambling winnings.)

    1. McWhadden*

      I can be pretty deadpan but I wouldn’t set up a one-on-one meeting for the purpose of making a deadpan joke.

      1. Llama Grooming Coordinator*

        True. But I was trying to think of ways that LW’s boss Fergusina might not automatically be a candidate for worst boss of the year.

        (I mean, she won’t win because of Jill from last week, at the very least. But she’s definitely a contender.)

    2. Crystal*

      It’s a non-profit. As someone who worked in non-profit development for many years trust me, she’s dead serious.

      1. sange*

        Absolutely. Fellow nonprofit dev lady here – we recently had a meeting about our life insurance policy at work, which included a helpful reminder that donating a portion of your life insurance is a wonderful way to continue a legacy at a cause that is important to you!

        1. drove my chevy to the levee*

          I think this was an episode of Law & Order, only they were bumping off the employees to get the payout.

        2. Jadelyn*

          …wait WHAT?

          I’m so glad I work at a (relatively) sane nonprofit. There’s some nonsense about justifying our low salaries with Dedication To The Cause, but nothing on this kind of scale. Justifying giving me less money, okay, irritating but I accepted that when I came to work here. Asking for some of that money BACK? Hahaha no.

        3. Llama Grooming Coordinator*

          See, I’d just be tempted to give money to everyone BUT the organization if they pulled that.

          Do they also want a cut of your retirement benefits?

          1. Lily Rowan*

            Yeah, I have former non-profit employers as contingent beneficiaries on my life insurance (I mean, I worked there because I liked the cause), but it literally never occurred to me to put my current employer!

          1. sange*

            I think it was like 60% a joke, 20% practice for one of my colleagues in trying to practice her elevator speech about planned giving, and 20% straight up serious. And yes, we did have one person do it!

        4. Lau (UK)*

          Sorry… WHAT? Also in dev, used to run legacy giving. At no point did it occur to me to ask our staff to make us a contingent life insurance beneficiary…

      2. BRR*

        I work in development and I know somebody had the “great” idea to see this as a source of income. I bet this person also loves employee giving campaigns.

      3. Llama Grooming Coordinator*

        This makes me glad that as messed up as my own nonprofit can be at times, I haven’t had to deal with that yet! The worst we’ve ever had was an ad about our Amazon Smile campaign, from what I remember.

        But I’m low on the pole.

        1. Observer*

          Well, Amazon Smile makes sense. If you’re shopping on Amazon anyway, it takes all of a few seconds to set it up.

          1. that lady*

            the leaving a non profit as a beneficiary of life insurance (or Certificates of Deposit) is a legitimate strategy employed to raise donations that “costs” zero dollars. I’ve seen it at work as a former banker and life insurance sales-person.

            1. Observer*

              Sure. But asking your employees to do so is utterly inappropriate.

              The only time it’s an appropriate ask is when it would otherwise be appropriate to talk about other types of bequests. And it’s pretty much NEVER appropriate to ask your employee for a bequest.

      4. Barbara*

        I was laid off from a Top 25 university last fall. Every year they made a serious push to convince us employees to donate to the capital campaign. And they’d include testimonials from other employees, saying how rewarding it was.

        It’s like “Dude, I have 3 educational institutions that are pushing for contributions. I spend over 200 hours here for low pay. Leave me alone.”

    3. Marlene*

      She can be as serious as she wants to be but I’d still keep her cold prying fingers off my money.

  14. BRR*

    Not only is the concept ridiculous, for most organizations and people $2,500 is a very sizeable donation. I would probably just ignore it.

  15. MLB*

    I know this is work, but I would be an asshole about it, in the nicest way possible, by explaining exactly what Alison mentioned. “While I may have been on a company paid trip to Vegas, I was gambling in my free time with my own money, so I don’t think it’s fair to assume any money I win is being donated to the company. If that was your expectation, it should have been made prior to the trip. I certainly wouldn’t expect the company to reimburse me for any money I lost while gambling.”

    1. Lil Fidget*

      This is a really nice script. Especially if OP can say it in the right tone of being patient and matter of fact rather than super hostile, I think this would go over very well.

      1. EddieSherbert*

        +1 I both like this script AND think the tone will be crucial if you use it (I would probably come across hostile, despite my best efforts – but could probably handle Alison’s without sounding too bad).

  16. Crystal*

    Yeah, this is not surprising to me at all. Guess I’ve worked at non-profits too long. This is also why I’ve never in my life told anyone from work when I win money in Vegas, no matter the circumstance.

  17. McWhadden*

    Good advice. But I’d offer an alternative script if she brings it up again.

    1. BRR*

      I would love if it was possible for the LW to treat the manager’s comment as a joke and just act confused. “Oh, I thought you were joking.” “Why would I donate my personal gambling winnings?”

  18. Steve*

    Ironically, that’s sort of how the IRS treats gambling: winnings are taxable, but losses may not be tax-deductible.

    Specifically, wins are always taxable income. Losses are miscellaneous itemized deductions, but only up to the amount you won, and of course only if you itemize (which only 30% of people do, and it’s sure to be less with the recent tax law changes).

    P.S. I am not an accountant.

    1. Princess Consuela Banana Hammock*

      That’s not really analogous, though. And as you noted, losses are itemized deductions—people just fail to do them. That’s different from your boss requiring you to absorb your losses and donate your winnings to your employer.

    2. Y*

      That’s almost as crazy as citizenship-based, rather than residence-based, income tax.

      Good thing the only places that do that are Eritrea and some other tinpot country I can’t quite recall at the moment…

  19. Ray Gillette*

    To use a far simpler example, you spent money and received a good (albeit, that good was more money).

    If you spent $20 and bought a sweatshirt, that’s not the company’s sweatshirt.

  20. StressedButOkay*

    This is – really gross. I work in a nonprofit, too, and I would be furious if they tried that. If I was the OP, and the manager presses, my response would be ‘Thank you for your suggestion but where I donate money to is a personal decision especially since I used my own funds during my downtime on a work trip.’

  21. FormerHoosier*

    I worked at a non profit where there was a significant amount of travel. One time my colleague was traveling with the executive director and their flights were oversold and they were offered free tickets. The exeuctive director told her she had to donate to the non profit her free flight but that he could keep his because he was the ED.

  22. Sleepy baby*

    A very small, very petty part of me would feel inclined to see if I could retroactively expense that dinner you treated yourself to on your own dime…

    1. Princess Consuela Banana Hammock*

      And bill for all your time spent gambling, since it’s apparently “company time.”

  23. Valegro*

    I attended an event hosted by a large corporation for people in my industry, including some students. They did a free raffle for gift certificates good for a pricey piece of apparel ($600-1000). A student won one, but had no use for it. The corporate sponsor offered to auction it to the room and the student accepted. An older gentleman bought it for more than face value to support the student which was really kind of him.
    One of my coworkers who is very wealthy by marriage threw a fit that the money should have been donated to charity! She was grumbling how rude the whole thing was. I told her that was a huge amount of money for someone in school, or even me being several years out and deeply in debt. She continued to sulk and grumble about it for days.

  24. Brett*

    So… who is paying the $625 federal gambling winnings tax?
    You do not get to deduct charitable donations (or any other deduction) out of gambling winnings; it is just an up-front flat 25% tax.

    1. Rusty Shackelford*

      You mean that $10 winning lottery ticket in my purse is really only netting me $7.50? Dang it.

      1. Brett*

        It is only taxed as regular income if you are professional gambler (at least for federal), otherwise it is taxed at a special flat rate (as well as withheld at that rate).

          1. Brett*

            Had one good win in Vegas once. It was when I was in the 15% bracket so I had to pay _more_ in taxes than my regular income.

            1. AnonymousMom*

              The reason you paid a higher percentage is because your total income was higher because of your substantial win, not because gambling income is taxed at a special higher rate. The winnings just moved you to a higher tax bracket.

        1. Steve*

          Do you have a reference for that? I’m fairly sure Mike is right, that it’s withheld at 25%, but when you file your taxes the following April you will pay your regular rate on it.

    2. OlympiasEpiriot*

      No?! But, if it is classified as income and one donates the winnings, surely that amount comes out as a charitable deduction from one’s total income, no?

      1. Brett*

        Only if you itemize, and then you only come out even or ahead if your are the 25% or higher tax bracket and your itemized deductions were larger than your standard deductions without the donation.
        (If you don’t itemize, since the casino withholds 25% off the top, then you are out the $625 out of pocket with no tax benefit if the employer takes a $2500 donation.)

  25. memyselfandi*

    If I won money (whether traveling for work or not) I would be quiet about it at work. People can react in funny ways to others’ good fortune.

    1. A Nickname for AAM*

      Especially in the nonprofit sector! I’m nonprofit but my husband is paid well, the only time I’ll let anyone have a whiff of that is if people are concerned about financial struggling, like “Rents are going up so much in this city, you must be starving to death!” or “Oh no your car is in the shop, can you afford to fix your car?” or “You need a root canal and we don’t get dental insurance!” Then I’ll say, “Oh my husband has a decent job, we have some savings for stuff like this, we’ll be OK” and leave it at that.

      No new cars. No nice purses. No vacation photos. No nice clothes.

  26. Tasslehoff Burrfoot*

    This is one of those where I’m just amazed at how other peoples’ minds work. I would never think to tell my employee she had to donate the winnings (other than jokingly, of course). I don’t understand how your brain arrives at this conclusion. It’s so far past what’s appropriate that it just confuses me as I struggle to understand that thought process and how it must have gone.
    OP, definitely don’t donate your winnings – they’re yours and your org. has no claim on them whatsoever. If she brings it up again you might consider just staring at her as if she’s some heretofore unseen species and you’re genuinely baffled by what your seeing and hearing. Then just turn and walk away shaking your head in bewilderment.

  27. pleaset*

    ‘I was taken aback and didn’t really know what to say — I ended up saying “Oh, I hadn’t thought of that. Thanks for mentioning.” But didn’t actually say yes or no.’

    Good answer – avoiding saying “yes” just because you were surprised.

  28. Triple Anon*

    This is silly. You can gamble almost anywhere. There is some kind of casino or race track or other place where gambling is legal within driving distance of most places in the US. What about lottery tickets? What if you bought one on your lunch break and won?

    So apparently this organization thinks there’s something special about Vegas and different rules apply there. So if you gambled there and lost money, would they reimburse you? That seems to follow their logic.

  29. mf*

    “if you’d lost money, you wouldn’t expect them to reimburse you because it happened on a work trip. ” –> Point this out to your manager. Bet she’ll change her mind on this immediately!

  30. UKDancer*

    The manager is totally off. In my field we have to declare gifts and that includes things we win when we’re at llama herding conferences or trade fairs, as a lot of them have prize draws. Anything above a certain amount has to be surrendered (so I never bother entering raffles with high value prizes). That’s to avoid us being potentially influenced to engage in unethical activity by any of our llama feed suppliers.

    That said what you do in your own time with your own money is your business. The manager has no right to say she should be entitled to the money the OP has won. I go to social dances while I’m on business in different cities and sometimes there’s a tombola or a raffle at the dance. If I win anything it’s my prize and not the organisation’s. Although when I won a nice box of chocolates I did share them with my colleagues because I couldn’t eat all of them.

  31. Where's My Coffee?*

    After years of reading these I am convinced you are doomed to a terrible work life if you have more than two of the following factors:
    -woman who feels cold, is young-looking and/or has food/scent allergies,
    -at a non-profit
    -working in a male-dominated industry doing the work of 6 people,
    -in a field so niche that all global participants know one another,
    -has coworkers incapable of having direct conversations unless they involved very specific ritualistic coffee and/or tea demands.

    I’m always cold, but I look old and my industry is large and not male-dominated, so I’m safe FOR NOW. Get out now, OP, while you still can.

    1. NaoNao*

      Oooh I can guess where you spend the non AAM time. Perhaps a certain snark forum? :P

    2. whingedrinking*

      I’d like to add anything where you work in the private sector, but your job involves caring for or educating others (what do you mean you want more money, isn’t helping others reward enough?!).

    3. GG Two shoes*

      Well I hit the cold, young woman at a npo, in a niche field so… should I run? lol

    4. Where's My Coffee?*

      Eek sorry was actually trying to be more silly than snarky. Just noticing some of the same trends seem to repeat lately (not necessarily just in the letters, but also in the comments), and was just teasing a bit :)

  32. AKchic*

    You do not owe your employer your winnings, regardless of their non-profit status.

    I have to wonder if the manager is going rogue and this is a gumption idea to drum up donations, or if the c-suite and board members are actually on-board with this idea.

    For now, ignore this ridiculous idea. Document it, just in case, but do nothing else. Don’t donate your winnings. Do whatever you want with them. Should the manager bring it up again, you have options. You can go to HR (if you have one), or the manager’s boss; or you can flat out ask if the company will be paying you for the time you spent gambling, since they feel entitled to the winnings, and if you will be reimbursed for the losses you sustained previously, and if this is standard protocol and why it isn’t in the P&Ps, and since it isn’t, when will it get into the P&Ps and the employee handbook for traveling employees. You would also like to know if they will be reimbursing you for the taxes you will be paying on your winnings, because “donating”… er, sorry, forfeiting, the money to the company does not negate the tax liability on your taxes at the end of the year. Act very wide-eyed, innocent and open about your questions, not smart-alecky about it. See what happens. Bet they will back down.

  33. Leave it to Beaver*

    I’ve worked for a few established non-profits and there is definitely a culture wherein employees are expected to not only support the cause professionally, but personally as well. No matter how much one believes in the cause, I don’t believe I owe more to it simply because I work for an organization. Nonprofits statistically pay less than for profit companies, so technically they’re getting my professional expertise at a discounted rate — I consider that my donation to the cause. The only time I have donated back to my organization is if a friend was doing a benefit (walk/run/bake-off) in support of them. (I tend to do that generally, support organizations that impact those I know and love)

    1. Pollygrammer*

      Lots of nonprofits ask their employees to donate, which is just totally absurd. I may believe in my org’s cause but do they really think there can’t possibly be a cause I don’t believe in more? Or that I think has a wider reach? Or greater need?

      1. A Nickname for AAM*

        I just got an email, “Ask your friends and family to donate! This is part of your job description.”

        And…it is.

  34. Bee Eye LL*

    This reminds me of stories I have heard here in the South about preachers showing up at people’s houses demanding tithe to the church after hearing of people winning at the local casinos.

    1. AKchic*

      I’ve heard of instances like this too. A few where the local pastor came a’callin’ to neighborhood folks who didn’t even attend their church, but because they lived in the neighborhood, they needed to do not only their neighborly duty, civic duty but also their religious duty and donate/tithe to the neighborhood church (!!!).

      I absolutely refuse to tell people when I have money. I learned my lesson the hard way when my grandma overheard me discussing a settlement offer with my attorney and made sure to call all the relatives about my “good fortune”. What she hadn’t heard was the information that it was our opening offer, not the actual settlement, so she told family that I was actually getting this huge high 8 figure number (she overheard me on my cell phone when I’d stopped in to drop off groceries to her since she’s never had a license). Funny how I started getting phone calls from relatives who’ve never had my cell number before and relatives I barely know and have never spoken to outside of large gatherings when they ask me for napkins to “see how you’re doing” (gee, you didn’t care when I was first in my car accident or having neck surgeries…).

      Never again. As far as any and everyone is concerned – I am broke. I have no money. I work full time and my kids are expensive. I am the epitome of my generation’s terrible financial situation and I have absolutely no money whatsoever.

      1. Antilles*

        I absolutely refuse to tell people when I have money.
        This is my strategy too. Even better, if you have moderate tastes, you don’t even need to verbally refuse. I just pull up in my six-year old Civic and she tells the entire “no, I don’t have money to give away” story without one spoken word.

      2. Kuododi*

        DH has the same situation with his side of the family. Apparently because DH has chosen to further his education, hold steady employment for longer than twenty minutes, have paid off vehicles and own his house rather than rent some flea bag trailer, must mean he’s rolling in cash. They regularly call to hit him up for $$ to bail them out of one or another disaster. Usually they’ve gotten themselves in trouble not paying this or that bill and they wind up surprised that they’re facing eviction, repo, or some other nonsense. Fortunately, DH set the limits a long time ago and the answer is always no!!!!

        1. AKchic*

          Yep. My settlement was nowhere near what our opening offer was (oh, but how I wish it had been!). After paying the attorney, 90% when to paying off medical debts (because neck surgeries are expensive!). Because I was 25, twice divorced and had an “invisible injury” (no crutches, not in a wheelchair, I was ambulatory and not on disability) it was hard to prove anything when their paid doctor was claiming there was nothing wrong with me and they were happy to vilify my doctor as “just wanting to get paid” (I have the best doctor in the state).

          Its been 10 years and I’m still bitter. I happily trash-talk the company that hit me whenever I can. We aren’t doing bad financially, but we could be doing better. We’ll never own a house, but I think a lot of people my age in my state have that problem.

        2. Knotty Ferret*

          Good job to him on setting boundaries!
          I literally moved 1500 miles away because I realized I didn’t have the will to tell my family no when they had a self-inflicted “emergency” need for cash.

    2. Iris Eyes*

      And there are other churches where they wouldn’t accept the money at all if it came from gambling.

      People get so weird about money.

      1. AsItIs*

        And there are religious institutions that are against gambling but happy to take money from gambling, to “save the sinner” or to “cleanse” the money or some other BS. :/

    3. Marillenbaum*

      This was actually a plotline on Greenleaf in the second season! Jacob (the son of the family) joins a rival church across town and attempts to poach one of his father’s lottery-winning parishioners to score favor with his boss/his father’s enemy.

    4. DCGirl*

      I was working at a non-profit when I competed on Jeopardy! and won $26,002 in two days. It was close to a year’s salary for some positions there at the time (over 20+ years ago). I never heard the end of it about donating to the cause after that.

  35. it_guy*

    Did they pay you for your travel time? Were you on the ‘clock’ while you were gambling? Did they provide the money to gamble with? Did they instruct you to gamble?

    Should you give the money back?

    NO X 4!

    1. Mike*

      I actually hit a jackpot in a Casino a couple months ago, while on the clock playing with money my employer gave me for the purpose of gambling (ok, it was partially company money, the rest my own), with the entire purpose of the trip to gamble. It’s still entirely my money, unless it was clearly stated beforehand that the employer gets any jackpots.

        1. EddieSherbert*

          This comment literally made me laugh out.

          …. but seriously, Mike… what do you do?!

        2. The Smile on a Dog*

          Slot machine companies sometimes give their employees money to gamble with for research.

            1. redwitsch*

              I was thinking that you were mystery shopper, because we do this too to check standards of casino services. 8D

  36. Mephyle*

    This has all been mentioned above, but there are two simple tests that can tell you whether the organization is entitled to your winnings; I sum it up as follows:
    1. Did they provide the stakes? No.
    2. Would they refund if you had lost instead of won? No.

  37. Annoyed*

    OP keep your money.

    Yes you were there “on their dime.” Working. It’s not like they gave you a paid vacation. Even if they had, that’s a ludicrious request.

  38. Long Time Reader, First Time Poster*

    They have a lot of 50-50 raffles at my kids’ school (winner gets half of the cash proceeds, school gets the other half).

    I found out the hard way that the “accepted protocol” when winning is to cheerfully donate your share back to the school.

    We won once, and I was super happy — we got a couple of hundred bucks. Everybody gave us the stinkeye when we promptly pocketed the prize instead of giving it back — I only found out later that we weren’t “supposed” to keep it.

    Now I just make straight up donations and don’t enter the raffles…

    1. AKchic*

      Oh good grief. I’d be furious.

      The junior high my oldest two kids went to used to have an annual cake sale for the music program. Each cake donated (some by bakeries, some by parents, some by kids/home ec class) went for hundreds. I’m not talking low hundreds. I watched a few cakes go for over $3000 one year. Most cakes went for $900-1500 each. A title one school, where over half of the families are on food stamps, this school thought it was appropriate to let the more well-off parents have a field day doing this for the music program. It really soured the less well-off parents who had to sit through the auction (because of course they made it a mandatory concert for the kids, so parents pretty much had to be there).

      1. Long Time Reader, First Time Poster*

        OMG. That is so gross. Our school is similarly tone deaf (it’s inconceivable that someone might have *needed* that couple of hundred dollars raffle money!) but three thousand dollar cakes?? That people were bidding on (or NOT) publicly? Just… wow.

        1. AKchic*

          I hit the bake sale at the end of the concert, when they were just selling regular stuff at the table outside of the concert (not auction). I spent $250 and walked out with 8 cakes, 30 cupcakes, a couple of tarts and 2 dozen cookies. They were trying to get rid of everything because the other low-income parents were so discouraged that they didn’t even buy the regularly-priced items set up in the hallway (because nobody had advertised it).
          I ended up handing out cupcakes and cookies to the orchestra kids, sent a cake home with one of our friends, drove across town and dropped off a cake with my grandma, another cake with my uncle, another cake off at my mom’s and then brought the rest home (two came to work with me the next morning).

          I vowed never to go to another bake sale. My dentist would have a field day.

      2. Jules the Third*


        My kid’s school just ‘suggests’ a donation high enough to provide some ‘scholarships’ for lower income kids, and nobody ever knows who the scholarship kids are.

    2. Eye of Sauron*

      I never really understood that… didn’t they already get 1/2, like that’s the whole point of a 50/50. And you’ll have less participation if people think they won’t get to keep winnings, so the next time the 1/2 they do get is reduced.

      1. Long Time Reader, First Time Poster*

        My town is pretty affluent, and I think people like to look generous in front of everybody else. When they announce the winner, and then the recipient declines, everyone looks at them and applauds.

  39. ECx*

    Unless the money was won in the name of the charity or at a charity event, then you keep the money. It’s yours.

  40. Argh!*

    Does your boss think the hotel gives a discount rate to conference attendees just to be nice? Sheesh!

  41. HRM*

    When I worked at a nonprofit, if we ever won gift cards or cash on work trips, at conferences, at related events, etc. we were expected to donate the money back or use it to purchase something needed for the office. I don’t think they would’ve gone so far as to claim my gambling money, but it’s kind of a similar thing just on a cheaper scale. I remember one time I went to a vendor fair and I won a $50 Amazon gift card and was pressured into using it to buy a rolling cart/bin thing for when we went to recruiting events so we didn’t have to lug 50 pounds of stuff around with us (because apparently buying us a cart for $40 was out of the question until I won the gift card.)

    In general, working at a nonprofit can be expensive. I’ll never forget the year the accounting manager announced to a group of staff that they needed to contribute more to United Way because we received several grants from UW and if we wanted to keep receiving our salaries we should donate some back. As HR I quickly stepped in and assured everyone we weren’t about to go under if they didn’t donate to UW and that no one needed to feel pressured into donating. What a nightmare that place was sometimes. I’m making $22,500 more a year now than when I left a a year and a half ago and no one expects a tithe to the business.

    1. LQ*

      The at the conference thing seems a little muddier (at least if you have any hand in the relationships that those vendors are trying to solicit). It may be because I work for government but we’d have to declare any of that kind of stuff and some you can’t take at all.
      But even here we wouldn’t expect you to give back the casino winnings! (Ok I’m sure there’s a special case of if you work in that specific area, but then you likely aren’t allowed to play at all.)

    2. Jadelyn*

      I really don’t think that’s comparable, though. If you’re winning stuff *from* or *through* the work event, that gets murkier – I still think it’s dumb for the company to call dibs on that (and frankly, if you’re relying on your staff winning raffles so you can buy office supplies, you’ve got bigger problems than the raffle winnings can solve), but so be it, they have at least some nominal grounds for doing so. But if you’re gambling on your own, while off the clock, and the only thing related to work is that you’re gambling at a casino in the town where you went for work versus gambling at a casino in your home state, that’s a whole other beast.

      The UW thing, though, wow that’s gross of them. Glad you stepped in and nope’d that in the bud.

  42. Q without U*

    I agree that the manager is completely wrong in this, but to be generous, it’s possible that she’s just confused. My university has a fairly normal conflict of interest policy, which includes things like this: if you’re solicited to take a survey (because of your work role) and you fill it out (even on your own time) and you happen to win the, “You could win a gift card for participating!” raffle, you can’t keep the gift card. You have to turn it over to the university.

    It’s within the realm of possibility that the manager has been trained on things like the above and just got confused about what the rules cover. I don’t think it’s the likeliest explanation, but I could see it happening.

  43. Bookworm*

    I mean, I suppose if you wanted to be generous you could pitch in for a really nice dinner or something. Maybe make a small donation to the org. But agree with just about everyone else: it’s your money!

  44. Bea*

    My frozen grinch sized heart says “ef that nonsense”. You already work somewhere for less than you’d make in the private sector and work for the cause, you don’t owe them your winnings.

    But I’m a crabby capitalist who will never understand that kind of thing crossing someone’s mind let alone falling out of their mouth.

    1. Louise*

      Eh, I’m a crabby socialist who works at a non prof and I still can’t imagine those words coming out of someone’s mouth.

      1. Bea*

        I’ve seen non profit folks say there are grants that require people donate a portion of their salaries to the cause. So there are a lot of these people out there lurking.

        1. LQ*

          I’ve only seen those that require board to be donating (though $1 is enough, and the ones we got when I was a part of it always had waivers for the community people on your board). Though I never had to work with united way so it may be different.

          1. Lau (UK)*

            Might be a UK thing but I’ve never seen that. Thankfully… Just…. what?

            The biggest issue we have with funders are however around the fact that they won’t fund any back office costs… so apparently we all work for free, right?

  45. HR Recruiter*

    I worked for the state government with a state that had a very, very strict laws about what state employees were allowed to receive as gifts. Similar situation would come up often. Employees attended conferences frequently, if they won anything at the conference they had to turn it over to their employer. We would usually find a loop hole to give it back to them. But those were prizes won by attending the actual conference or after hours conference sponsored events. In this case OP was gambling with their own money, so we would never even think to ask for winnings. Keep your money!

    1. Eye of Sauron*

      I totally understand the work related prizes or gifts that’s common even in the private for-profit world because of ethics concerns.

      But you’re right on the personal gambling wins.

  46. WolfPack Inspirer*

    As I get older and my supply of f*cks given runs ever lower, I find myself getting a lot of mileage out of “That is an interesting perspective.”

    In a quiet, pensive tone, it gets me free of irritating relatives while they still think of me as ‘a good girl.’ In a slightly more incredulous tone, everyone except the person I’m talking to gets the ‘this person is batshit bananapants’ signal to run away. Give it a nice questioning inflection and watch your junior asskisser gleefully take ALLL the rope he needs to string himself up into a cats cradle of demonstrated incompetence. It really is handy.

    1. Daniela*

      Can I just say how much I love your “cats cradle of incompetence”? That just made my afternoon!

    2. Jadelyn*

      What a delightful mental image that makes. I’m going to have to keep that phrase handy.

  47. ZSD*

    Can we put this one on the update list? I’d definitely like to hear how this one turns out. Thanks!

  48. Sunshine on a Cloudy Day*

    This is so out there that I do not, in anyway, think this is related to the OP’s case. However it is the one (relatively rare, though not unheard of) situation where I can see donating the winnings back to the company…

    So if the gambling opportunity were derived from something the company paid for… Like if the company paid for the hotel room and the employee received some sort of voucher to use in the casino (ala “thanks for staying with us – enter your room number when you sign up for your Rewards Card and you’ll have $100 to use on slot machines added to your card”), then if you won a large jackpot while using that $100 worth of slot vouchers. I can see where that might be sticky or just feeling like there’s some sort of obligation.

    True story (though thankfully not business related) – I live a bus ride away from Atlantic City and have attended my share of birthday parties/bachlorette parties there. My friends and I learned that one of the bus companies gives out a small voucher that can be used at the slot machines of the casino that the bus drops you off at (usually $10-$20). The rules were that you couldn’t just cash the voucher out for the face value and you had to play it all in one sitting… But! You could cash out any winnings you made – on the machine it just showed a lump sum (your voucher value+any winnings so far), but if you cashed out periodically it would give you the chit redeemable for cash for whatever you won so far. I always made, at the very least, my bus fare in winnings, and one time I made $150 – which is not a crazy jackpot at all, but hey, $150 off of free money is awesome in my book.

    Anyway – I can see this being slightly debatable (similar to recent discussions on airline points/vouchers) if the company paid for the bus fare (from my personal example) and an employee collected winnings from that. Again, though, I don’t think this is related to the OP’s specific situation.

    1. Rusty Shackelford*

      I see your point, but I disagree. I think it would be like the company insisting that you bring back any unused wee soaps to put in the staff bathroom. If the voucher comes with the room, it is meant for the use of the person in that room.

    2. Just Employed Here*

      I’m in a country where any airline points you earn on business travel can’t legally be used for the travelling employee’s personal travel (or they would be considered salary, and have to be taxed as such).

      Even here, gambling done in one’s spare time, even with a voucher originating from the hotel room, would be a private matter and nothing to do with the employer.

  49. OP Here!*

    Hi all, OP here! Thanks for validating what I thought was true. After the little sit down with my boss (it wasn’t a full-on meeting, just a “request to meet” where the only topic was my winnings – it was probably less than 7 or 8 minutes, so not sure what that constitutes), I floated the idea of donating the money hypothetically to two trusted colleagues over lunch – in the context of “I know that when you win money at a charity-sponsored event, the expectation is the winner makes a donation of some kind back to the charity – is this like that situation? Should I be making a donation?” and they both LOLed and WTFed and said I was being ridiculous.

    I’m chalking this up to another example of how even though my manager is really effective in many ways, she is also totally out of step with the culture of the rest of the organization. Case in point: in advance of this trip, my other colleagues were shocked that my husband wasn’t joining me on the trip – because of the nature of our work, people travel a lot and bringing family along is very common, so much so that finance proactively outlines the procedures for expensing things when traveling with family (very sane policies, I might add – shared transportation and rooms yes, employee’s meals yes, partner’s meals and plane/train ticket no, etc.) However, my manager came down hard on another staff member for bringing his spouse to a conference – so much so and to such an extent that HR intervened and told my manager to basically back off, he’d followed all expensing rules correctly and it was clear his work/conference participation was not negatively impacted by his spouse’s presence.

    I’m glad Allison answered this so quickly – this whole situation occurred about 2 weeks ago, the manager in question was out of office all last week, and we have our first regular check in since the situation tomorrow morning. We each submit agenda items for our check in, and one of hers is “Las Vegas conference – recap, etc.”…I am anticipating that the “etc” is another discussion about my winnings. Eek! Thanks to those of you who provided thoughtful scripts/suggested responses – I’ll be memorizing some of them tonight in case this comes up!!

    1. OP Here!*

      *** Correction, conversation was only 4 or 5 minutes – sorry, was typing on my phone :-)

      1. Crystal*

        we look forward to the update! Glad the colleagues were also like “ummmm, no”

    2. Observer*

      Your manager sounds incredibly tone deaf as well as unreasonable. Which could make your meeting more than slightly uncomfortable.

      Another thing you might want to point out to her, if she really gives you a hard time is that this could present both a legal and pr problem. Does the organization REALLY want to have to disclose that it has gambling income? Depending on your status (exempt vs non-exempt) and salary, requiring you to pay this to the org could be a FLSA problem – and in this context, her pressure on you could be seen as “requiring” it. And, depending on your locale, there may be legal issues with requiring “donations” from employees, etc.

      If you have a handbook, you may want to find it so you can show it to her, and then go straight to HR if this keeps up.

      PS It sounds to me like HR needs to rein her in or she’s going to stop being very effective. Driving up turn-over and / or alienating good staff is not a good way to maintain effectiveness. And the behavior you describe is very likely to have that kind of effect.

    3. Llama Grooming Coordinator*

      Does she also tell you not to expense extra guacamole?

      But girlfriend. Like, I’m pretty naive if you look at my post history here, but this is actually…kind of a big thing. It sounds like your job involves a lot of travel, and she is pretty unreasonable (huge understatement) about business expenses. This isn’t even that much of an outlier for her, from what you’ve said! Her asking for you to donate your gambling winnings isn’t even the most insane thing she’s done. HR had to tell her to back off. I’m getting quite a few yellow flags from this.

      I’m sure she’s a lovely person when you’re in the office. And I’m sure she Gets Things Done. But she’s also in need of being reined in.

    4. Totally Minnie*

      If she brings it up again in your next meeting and doesn’t respond well when you tell her you will not be donating your winnings, do not pass GO, head directly from that meeting to the HR department. She’s already been reprimanded for trying to enforce travel policies that do not exist, so let HR know that she’s still at it. They need that information if they’re going to make wise choices for the organization.

    5. AKchic*

      I recommend bringing the Employee Handbook – Travel section and maybe the P&Ps with you just in case she tries to enforce this.
      Also, if she pushes this, ask for HR and her supervisor to be brought in to the meeting. You have that option. See how fast she backs down. And document the entire thing and have it placed in your HR file just in case she tries to write you up for *anything* spuriously in the coming weeks.

    6. paul*

      If HR intervened with them *already* maybe actually telling them about this is a good idea.

      Hell I’d be tempted to bring my spouse on a trip to tweak them if HR’s already told them to back down over going after someone else for it.

  50. Aphrodite*

    This is why I never, never, never give a lottery ticket as a gift to anyone. I wouldn’t want to resent someone, however unconsciously, for not sharing any winnings. So sorry, but no lottery tickets as stocking stuffers.

    1. FaintlyMacabre*

      I once had a manager give us lottery tickets, with the understanding that if we won above a thousand dollars, we would buy her a nice meal. Sadly for all involved, that never happened.

  51. PizzaSquared*

    Maybe for a future open thread, but as someone who has never worked in the nonprofit world, I’d love to hear from folks to who, why? Maybe my view is just biased by the fact that all of the nonprofit stories I hear are here on AAM, where people only write in if there’s a problem. But it sounds like nonprofits generally: pay worse; have disorganized management; have weird boundaries; and expect you to give even more than you’re aready giving by working for under market rate. Even if you care about the cause, wouldn’t it be better to get a job in industry where you’d be paid and treated better, and donate some of your surplus (money and/or time) to the cause you believe in? Maybe this is a cynical way to look at it, but life is short, and I can’t imagine putting myself through the kind of treatment I read about here when voluntarily, no matter how much I believe in the cause.

    1. SoCalHR*

      I think a lot of people want to help certain causes or feel like they are contributing to the greater good. But to you point – there is a book I recently read called “Doing Good Better” where one the examples is a British man wanted to go be a doctor somewhere in Africa because he felt the call of the humanitarian cause. But he did the math and figured out that it would actually be more efficient and effective to get a job as a doctor in the UK and donate a large portion of his income to medical causes in Africa. So your ‘cynical’ nature isn’t actually all that cynical.

    2. LQ*

      Plenty of orgs of all kinds have these problems. You hear about it most when it’s government, education, and nonprofits because people specifically call those out. Most letters you read are about for profits, but because they don’t say “I work for a for profit business” you miss that that exists in that letter. (Not You you, just the general us as readers you.) I’d guess 4 out of the 5 of the quick answers this morning were for profit (maybe 5 out of 5…not sure) but none of them specifically said (though we can assume the first one was for profit pretty clearly and they wanted 90 minute presentations!)

      Lots of organizations of all legal entity types have poor pay, disorganized management, weird boundaries, and expect you to do more with less. Not all nonprofits have those things. Not all for profits don’t have them. It’s not really a blanket all nonprofits kind of thing. (And I think size generally plays a bigger role than for or non profit status.)

      (That said there is something to be said for what you’re talking about, generally referred to as Effective Altruism.)

      1. OP Here!*

        Just have to second a lot of what LQ says. Over the past 15 years I’ve worked for 4 nonprofits, and while they’ve all had their issues, nothing has made me think “lordy, I should get out of this line of work and go back to the corporate world.” Generally speaking, I’ve always had a much more jovial and supportive atmosphere, a more flexible schedule, a much more manageable work week, and a generally happier attitude about my work than my spouse and close friends who work in the for-profit world (and than I did earlier in my career). Every work place has its issues, and perhaps they are more common at non-profits, but as with everything else in life, you give up something (sometimes higher pay, or a more smooth-running organization) to get something (more friendly and laid-back work environment – this instance aside, of course – mission-driven work, more manageable work/life balance).

    3. Jadelyn*

      Honestly, yes, your view is biased by the fact that this is, it seems, your main source for What Working At A Nonprofit Is Like. By definition, the stories here are about the awkward and hard and weird and frustrating situations, so that’s definitely coloring what you hear here.

      Nonprofit salaries tend to be a little lower than for-profit companies, but how much lower varies widely. Some are paying half market rate (which is shitty because it means you’re basically selecting for independently-wealthy employees or employees with high-earning spouses or families supporting them, and screening out most of your lower- and middle-income candidates), but some are paying at market rate or close to it. Frankly, one of the big reasons nonprofits tend to pay lower is less because of their actual desire to do so, and more because people have gotten the wrong idea about how to evaluate a “good” nonprofit vs a “bad” nonprofit when donating money, and people tend to lump all overhead expenses together as “wasted money” – so a nonprofit that pays well and staffs fully (vs underpaying and trying to make each employee do the jobs of several people) may be perceived by misguided donors as “wasteful” because their overhead costs are higher than the penny-pincher charities’ costs are, get a lower rating on those various charity rating sites, etc. Which then affects their ability to get further funding, and the cycle continues.

      The boundaries thing is a little more of a valid cultural note about nonprofits, but again, it’s not all nonprofits, and not always to the absurd degree you see talked about on here sometimes. And there are nonprofits that have excellent boundaries! It varies, just like it does for for-profit companies – I’m sure there are startups out there that are entirely sane and have good boundaries, but then, those aren’t the ones you hear about.

      As far as why I work in a nonprofit, I’ve worked in both environments, and I prefer nonprofits. I feel better about myself and my work, and have more pride in what I do when I know I’m doing it for a reason beyond just “make the shareholders more money”. I just personally don’t do well in profit-driven environments. It’s not even about supporting this specific cause, to me – I wouldn’t take a nonprofit job at a, for example, anti-abortion organization or something, nowhere that’s outright contrary to my own beliefs, but I’m not selecting nonprofits to work at based purely or even mainly on my own activism areas. I work at an economic justice organization. Is that a good cause, to me? Sure! Is it where my heart lives, activism-wise? Not really. But I like knowing that my work is helping people, rather than just making more money.

      I could see myself working at a…what are they called? Socially responsible business? The ones where it’s a for-profit company, but one whose product or service is inherently about doing good things for people or society or what have you. Because again, it comes back to the core motivation. If the core motivation of the organization is money, then it’s not going to be a healthy environment for me and I will be dissatisfied with my work. So I accept that I’ll have to navigate a little more carefully to screen out the loony workplaces with no boundaries, and that my own cashflow may never reach that of some of my peers, but in exchange, I get to go to work feeling good about what I do every day, and that’s worth a lot to me.

    4. AKchic*

      For me – I needed a job, they allowed me to advance my career without needing a college degree, I was allowed to be myself without stifling my creativity or uniqueness, I was allowed a lot of leeway with my personality and with some of my personal causes that ran in tandem with the company’s causes, I believe(d) in the cause (still do).

      I spent 8 years in the non-profit company I was last with. I loved them. Unfortunately, I needed more money and I was burning out. Part of it was the clients, but it was mostly a coworker and a supervisor. I knew things couldn’t change there, and a job fell in my lap that tripled my salary. I knew that with funding cuts coming, it was the perfect time to leave and allow them to replace me at a cheaper rate (I was getting paid more than many others because of my longevity) and would allow them to restructure a bit for the better and I could advocate as a non-employee, donate money and maybe get on the board at some point.

    5. Not a Mere Device*

      In my case, it was partly because they were the people who were hiring, and partly because, while the pay was lower than at a lot of private companies, the benefits were significantly better. In particular, the only Americans I knew who got as much vacation time as I did were also working at nonprofits (mostly coworkers, but also a few tenured professors).

    6. KayEss*

      I’ve worked at a couple universities, and I liked having students around, the environment of a campus and the rhythm of the academic year, and just helping to support a lot of people doing independent, interesting intellectual work. University employment has its own weird dynamics separate from “cause” nonprofits, like tension between faculty/academia vs. staff and town/gown relation politics, but I genuinely enjoyed a lot of other aspects.

      That being said, I worked at one large-ish, high-end university (think Ivy League competitor), and between research, expensive private tuition, and the massive endowment… I don’t think I was ever asked to give to the university in any way (though there was other stuff like a United Way campaign), and we received COL and merit increases even in the aftermath of the recession. Later I worked at a small, more locally-oriented university that had a lot of students receiving aid and less income, and not only was there a hiring freeze and no COL increases at a point when the economy had supposedly recovered, the requests for staff donations (including what was mentioned above regarding bequeathing life insurance benefits, etc.) were nonstop even as they jacked up tuition and cut our benefits. So kind of like how some for-profit workplaces are cutthroat revenue-generation competitions where every one of your coworkers would sell you to Satan in order to take over your commission and some are decent places to work, not all nonprofits are created equal.

    7. Marion Ravenwood*

      For me it was partly that people I knew who’d worked in non-profits had had good experiences (they do exist!), partly the idea of contributing to the greater good/doing something for the benefit of others and/or society, and partly the work-life balance. There are negatives, but for me they’re not quite enough to counteract the fact that I do actually like working here most of the time, and are not too dissimilar to PreviousJob, so part of me reckons that a lot of this stuff is universal. (I should add that I’m in the UK and have worked in the public sector and non-profits all my career, so I may not be the best person to comment…)

  52. bookartist*

    Between everything I have learned here about how nonprofits really operate, and several bad experiences in trying to get help from ones that are supposed to help families like mine, makes me want to create a world without nonprofits or charities anywhere.

    1. Jadelyn*

      I mean, if you want to throw the baby out with the bathwater based on some stories you’ve read on a site that is, quite literally, all about the questions people have for how to navigate various unpleasant situations at work…your call, I guess.

      1. Bookartist*

        How about putting the baby in a bathtub paid for by everyone and having the democratic process allocate financial resources instead of people having to depend on the capricious and degrading nature of charity!

    2. Lara*

      I think improvement and reform would be better. Surely it would be preferable for your family to get effective help, rather than there be no help at all?

  53. JenMid*

    OP could say she won one $2,500 round, but it took her $2,499 to get there. Then write them a check for $1.00.

  54. Jemima Bond*

    Imagine the scene:
    LW walks into the office the Monday after a work trip, leading an adorable piglet on a leash, with a balloon tied to its curly tail.
    “What do you think you’re doing, Jenkins?!” cries Mr Percival the boss.
    “Well sir, when I was on that conference in the Midwest last week, I stopped off on the way home at the Iowa State Fair and whaddaya know, my luck was in at the coconut why…so here’s Percy Junior! You did say winnings should be donated back to the company. He likes acorns and chin-scratches.”
    Mr Percival is left holding Percy Junior’s leash and looking nonplussed…

    1. Koala dreams*

      Oh, that would make a great movie! Are the names from any specific movie or book?

  55. Koala dreams*

    Congratulations to the winning! I’m impressed with your neutral answer, I guess I’d have made up something like “So sorry, I already used to money to pay off my students loan, no money left!”.
    It would already be very nice of you to donate part of the money, maybe 10 %, to a person or a charity of your choice, for your manager to tell you to donate money to work is just weird.
    Good luck with standing your ground!

  56. missMouse*

    I wrote for a publication run by a nonprofit many years ago. Sometimes, another publication would re-print my articles and send me a check for $200. Oh, how quickly our director snatched that check off my desk, telling me the tight thing to do was donate it back to the organization! (I was making $11/hour at the time).

    I learned my lesson and hid and kept subsequent reprint checks.

  57. GreenDoor*

    Gambling wins and losses also affect your personal income tax. So…for you to have to possibly pay taxes on winnings that you don’t even get to keep? Um no. Just no.

    Enjoy your winnings!

  58. Database Developer Dude*

    If a manager had come to tell me that, I’d be dead… because you can’t breathe when you’re laughing so hard…

  59. gina*

    I would ask the boss “If I lost money would the company compensate me because I was in Vegas because of work?” That should shut them up. LOL

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