my employees won the lottery and quit, but now they want their jobs back

A reader writes:

I’m a divisional manager. I manage several smaller teams and report to the manager of our entire department. Several years ago (before I worked here), one of the teams won the lottery as a group. The entire team played except for Mary. Mary was invited to play but chose not to. After the win, everyone quit, including the manager.

In the years since the win, Mary has moved up to team manager. The lottery money has been a problem for her former team members and manager. One died from an overdose and another is in prison.

Our department is expanding, and some of Mary’s former team have applied to work here, citing financial issues and the need for an income. The departmental manager, Jon, has said he wants all of them to work on Mary’s team. Mary and I both think this is a bad idea. Mary thinks her old team will be bitter about having to come back to work and to have her as manager (when they left, she was entry-level and the most junior person on the team). A few of them have publicly expressed bitterness and regret about spending all the money and needing to work again. There are spots on other teams they would be qualified for, but the spots on all the teams are entry-level only. Jon said he doesn’t think that Mary managing some of her old team members will cause conflict, but Mary and I both disagree. Do you have any idea how I can approach Jon with these concerns?

I answer this question — and four others — over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

Other questions I’m answering there today include:

  • Client asked me to disclose the salary of someone I recommended
  • New coworker dresses much more nicely than me
  • My employee communicates terribly
  • Should I tell my new boss about a personal problem that’s affecting my work?

{ 326 comments… read them below }

    1. Atlantic Beach Pie*

      There is a British show called “The Syndicate;” it’s 3 seasons and each one follows a different group of lottery winners from a workplace lottery pool (syndicate is the British term for a group of people that play the lottery together). The second season has a similar plotline to this letter.

      1. chewingle*

        SOLD. I had heard of the show but didn’t know what it was about.

        Also, I hope OP updates about this.

          1. Elizabeth West*

            Trust me, some of the updates Alison gets are from REALLY old letters. So you never know.

        1. The Rural Juror*

          I’ve watched an American documentary or docuseries about lottery winners. Wish I could remember the name…it’s been a while ago now. It was pretty interesting! Several of the people featured in the show had been murdered 0_0

          1. AGD*

            I remember watching a documentary called Lucky about a decade ago, though it may be totally distinct as I don’t think it had any murders in it!

      2. pancakes*

        There’s also a play about Viv Nicholson, based on her autobiography, both titled Spend, Spend, Spend.

      3. Lady of the Lake*

        The 4th season is currently being broadcast at the moment in the UK! (although frankly I feel it’s gone off the rails a bit this season.. still enjoyable though!)

    2. Quinalla*

      Likely, but it is also very common for lottery winners to have a hard time after winning – overspending, getting caught up in drugs, etc., so this sounds completely believable honestly.

      1. Marzipan Shepherdess*

        So, LW1, your former employees now want to return to jobs they’ll resent having to do because they’ve blown all their lottery winnings and you’re wondering about re-hiring them? Let’s see…you’ll be getting bitter, resentful people who don’t want to work but HAVE to because their spectacularly poor planning has left them broke. Sounds to me like a recipe for disaster (or the plot of a sitcom, as has been suggested) but NOT like anything you want to have going on in your company.

        There are thousands of people who would love to have a job, really WANT to work and would bring a good work ethic and a positive attitude to your firm. Why on earth would you even consider hiring people who fit none of these descriptions?!

        1. Artemesia*

          This. I would lean toward not hiring any of these people who come bitter and snarling. And if you do re-hire any certainly don’t put them on a team for Mary to manage and stick her with their bitterness and resentment of her.

          Why would you want these people back? The competent efficient ones presumably managed their wealth and don’t want their jobs back, so the ones begging are the ones who have poor personal management skills and quit in glee. Certainly don’t bring them back at entry level if they are more skilled. And certainly don’t put them on Mary to manage when she doesn’t want to deal with that.

          I’d be inclined to not hire any of them.

          1. GammaGirl1908*

            This. You don’t owe them their jobs back, even if they are qualified. If they can’t adjust their attitudes, they have no business working there. Further, it’s not the company’s fault that they had no idea how to manage their money and couldn’t be bothered to learn. I’d like to think that if I won enough money to quit my job (so, at least $5m after taxes), after 10 years I’d still have money.

            This reminded me of this Slate / Dear Prudence letter, titled “My Husband and I Blew Through $3 Million. Now We’re Broke”:


          2. Vichyssuave*

            This seems overly harsh to me. I completely understand the reservations LW has, Alison has pointed out, and the commenters have brought up, but that’s something entirely other than refusing to hire people because they have “poor personal management skills”.

            Screen for bitterness and resentment about needing to work at all. Screen for how they might handle working for the same employer and especially for Mary. Heck, screen for just being upset they all up and quit and left the company in the lurch if you so choose. But unless the job is something like financial planning, let’s not deprive people of jobs because they have made financial missteps.

            1. Artemesia*

              I am not saying no one should hire them — just that THIS company should not hire them and put them on a team with Mary who does NOT want to manage them. This is asking for trouble. An unforced hiring error.

              1. Fran Fine (formerly Diahann Carroll)*

                I agree with you. And way for this company to cut Mary’s legs out from under her as a manager by overriding her desire to pass on hiring these people back.

              2. Vichyssuave*

                I think you missed what I took issue with, which what felt like value/character judgement.

                There are lots of reasons for OP’s company not to hire them back. I just think we need to be careful throwing around words and phrases like competency and personal management skills when it comes to the financial situation of potential hires.

                1. Joan Rivers*

                  You’re being very generous, but in this case these are people who already worked there and then left and we know what their choices were, and it goes beyond just having a few overdrafts. It’s not different from someone who happily quits because she thinks she found her dream job, or her dream husband — and then comes back to you saying it was a terrible mistake. It wasn’t just a bad match, it was major drama.

                  She may have a tale of woe, but it was her choice. And she may or may not fit in if she returns. Sometimes it’s better to start fresh. Better for her as well as the company.

                2. ErinWV*

                  Replying to Joan: your hypothetical is equally inappropriate. It would be callous to refuse to consider someone for hire because they previously exhibited behavior that you thought was kind of stupid.

          3. Amethystmoon*

            I would not hire them. They may need the money because of poor financial decisions on their end, but they don’t need to have their old jobs. Certainly not their exact same old jobs. It probably would be best if they split up and went to other companies. If their jobs at all involved managing budgets, for sure that’s a case where they should not get hired.

          4. tamarack and fireweed*

            Well, they’re likely to be not to be a homogeneous blob.

            The priority of the employer regarding the whole group should be to keep developing Mary and NOT have her working conditions in any way negatively impacted by any of their former co-workers, should they return. And while it sounds like most of them would turn out problematic at the current state, I’d take it on a one-by-one basis.

            (It would also not be exceedingly fair to not consider a former co-worker who *would* work well, and maybe hasn’t even had any particularly negative experiences related to their winnings – maybe the money went to pay for kids’ education and parents’ nursing home care, and they always wanted to come back later…)

        2. MCMonkeybean*

          I think “don’t really want to work but have to because they need money” would describe an awful lot of perfectly good employees. I think they are right to be concerned about whether they would adjust poorly to reporting to Mary specifically if she used to be junior to them, but I don’t think “only here because they need money” is a particularly good reason not to hire someone…

          1. Not So NewReader*

            While most of us don’t want to work but do need the money, we don’t say these things out loud where cohorts can hear us.

            I go in a tiny bit different direction. I assume that most people don’t want to work and as a bit of respect toward them, I try not to mention stuff about wanting/not wanting to work. Why dwell on it and make it worse? Try to make the best of things. Most of us are in the same boat.

            I do think that not wanting to work stands on its own as a red flag. How many random people could interview at this company saying this and still be hired? Probably none. The next hurdle is can they maintain a cooperative attitude, be approachable, and be willing to get along with others? It really does not sound like it from what I see here.

            Just as an aside, I do know how money can just fly away. And a person doesn’t even have to spend in a crazy manner. A person can do sensible things with their money and a decent pocket of change can be GONE. Maybe it is just me, but if I came into a couple million, I would probably keep working because it would fill up my time and help me NOT to spend the nest egg. Having too much unscheduled time can encourage spending. In some ways I feel bad that these people lost their money. But I don’t think it’s up to the company to fix that problem.

            1. Joan Rivers*

              “If you love what you do you’ll never work a day in your life.” That may not be possible for many, or happen every day, but I think it’s worth thinking about. Some people in “menial” jobs find joy anyway, and those in creative ones often do.

        3. Niii-i*

          The thing IS, they might not Be such a homogenious group as they seem. There might Be people on that bunch, who are not bitter, who understand their cause of action and are genuine about looking for Work.

          That’s why Alison’s suggestion is good. Meet these people imdividually and see If they can offer something your company needs.

    3. Lora*

      This actually happened near me when I lived in the Midwest – a car dealership abruptly closed its doors as employees had won a pretty good size lottery pool.

      That said, managing that kind of money usually is not easy at all if you’ve never done it. Had an aunt and uncle who got a large settlement from an insurance company after one of their children was killed in an accident. They had both been very working poor prior to that. Money was gone in about 10 years and they both had to go back to work: they bought a huge house for their extended family to stay, extended family ran up all kinds of bills and needed legal snafu bail-outs. They said the hardest thing was really lots of people asking them for money and figuring out how to say no, especially to their adult children, and understanding that while yes TECHNICALLY you have the money for something that doesn’t mean you have to do it.

      To be honest I know a lot of people like this. They find out the hard way when they’re trying to retire on what looks to them like a lot of 401k. They realize that if they live to be 90, they will be flat broke by age 75, and heaven forfend they need any specialized medical care.

      1. MusicWithRocksIn*

        Those huge houses can be such a money suck. You have to think about taxes and heating and cooling costs and upkeep and groundskeeping. That stuff only works if you’ve invested enough money to have a solid income just based off investments that surpasses the upkeep of the house. I grew up in an old money town – no one passes the family mansion off to their kids anymore, they sell it off and move down south.

        1. SeanT*

          People hit the lottery and buy a huge house, fancy cars, a boat…..
          Forgetting that all that stuff has a lot of ongoing costs involved in it beyond the purchase price.

          1. Liz*

            Yes! I always say if I won big in the lottery, like hundreds of millions, never have to worry about money ever again amount, I’d take care of ME first, then everyone else. I have no problem helping out friends and family, but I won’t do it at the cost of my financial security. I have a plan on what to do, and how to do it, and it does include investing enough so that I can live VERY comfortably off of the interest.

      2. Captain dddd-cccc-ddWdd (ENTP)*

        … And this type of thing is why lottery syndicates are banned at a lot of companies!

        1. Sleepless*

          That’s kind of what I was thinking. The problem here has been compounded by a group of people going in together. I’m mistrustful of any kind of partial ownership of a valuable asset anyway, so I’m a bit biased.

        2. Cmdrshpard*

          A lot of people spend money on things they literally piss down the toilet, beer, wine, spirits can be expensive and recurring. But it does not make it a waste if they enjoy it.

      3. TiffIf*

        My dad is an engineer and a meticulous planner. His way of indulging “if I were rich fantasies” was budgeting out the lottery win and finding the exact make and model of sound system he would want to buy, writing out the specifications of how large a home he wanted, etc. He has literally never played the lottery in his life. The only thing he ever entered was the Publisher’s Clearinghouse Sweepstakes.

        I thought he was a complete nerd when I was a kid, but as an adult I actually think that if I ever did come into a large amount of money I would do exactly what he did–budget it out and plan it. He also always said never take the lump sum, take the yearly distributions option.

        Though I still think my dad is a complete nerd. It’s where I get it from.

        1. Bryce*

          My lottery fantasy is to sit on it for a year or so, fins out what my budget looks like when I’m not trying to splurge but not worrying about money either (imagine getting my car maintenance done when the manual actually recommends it!), and then figuring out from there what I want to donate and spend on luxuries and such.

        2. Cmdrshpard*

          You are almost always better off taking a lump sum, and investing it versus taking the yearly payout. The interest earned will almost assuredly be more than the additional money from yearly distribution.

          1. TiffIf*

            Interesting point–I’ve always heard the opposite because the lump sum will incur a higher tax rate than the annual.

            1. Anonomatopoeia*

              Eh, maybe it will, but if it’s a very large lump sum to begin with, there’s a decent chance the annual amounts will be taxed a lot anyway. Well, and, maybe in the intervening years we will putt our heads out of our asses in the US and institute a motherlover of a high tax rate on big incomes, because obviously we really should. But so, you win $200 million dollars or something, and the tax burden is 60% for high incomes but — then you only get $80M to play with … like, okay? You should be able to live on the interest/income from that pretty handily in most places without ever putting much of a dent in the principle anyway. (Assume say a 2.5% return, which is $25K a year per million in income, which is an amount somewhat less than I think most endowments assume for their budgeting purposes. That’d be $2M a year; I think endowments usually budget for about a full percentage point higher, so now you’re at 2.8M a year). If you instead get the total paid out over 25 years, that’s 8M a year which probably is in about the same bracket anyway, and you’re looking at 3.2M a year of which you need to save a bunch in order to not be broke in 25 years. So…eh.

              Also, depending on the lottery, you might or might not be able to assign the years beyond the end of your life to an heir. So if you are in your forties, sure, you certainly hope you will live to be 70, but if not, if you get hit by a bus in 2 years and your kids are teenagers now, do you want to risk them struggling with college debt or just, you know, have your estate put the principle in trust and create a scenario where they can draw from that trust for education, just in case.

              (on the other hand, if my kid, a young adult who has shown fairly poor self-control for spending money what he ain’t got, were to win a jackpot, I would probably advise him to consider annual payouts so that he can only be broke for several months at a time and hopefully would have time to learn from his mistakes)

              Not that I have a fairly comprehensive idea about things I would or would not do should I win a large lottery jackpot or anything, mind.

              1. Self Employed*

                Point of information here: if we’re talking about US taxes, tax rates here are marginal. That is, you don’t pay the highest tax rate on the whole amount of income. You just pay it on the amount of income that falls into that bracket. It is complicated to explain and to calculate, but right now with higher income taxes being under discussion I want to make sure people KNOW that if the top bracket rate goes up, it doesn’t mean the government is going to take that percentage of the whole income.

            2. TrainerGirl*

              It all evens out in the end. You pay the taxes whether it’s at one time or over a number of years. The only reason to take the installments is if you simply can’t trust yourself to budget and you want to ensure a payment coming in. A lot of people go broke with the annual payments too. A friend of mine was dating a guy who won about $4 million, and even though they’d been together for a couple of years, he broke up with her because he claimed she only wanted him for his money. He’s been broke for years, using the annual payment to pay off debts.

          2. Pennyworth*

            That may be the case if the lump sum is invested, but I suspect most people who take the lump sum spend it on houses, cars and holidays.

          3. RebelwithMouseyHair*

            I think that for people who don’t know how to invest and manage money, the yearly distribution is safer. Those employees needing to go back to work would have benefitted from it.
            I’d do that simply because I can’t be bothered to manage my money. I’m pretty frugal, and I really don’t care about having extra money unless I don’t have to think about it too much. Very few people have any kind of talent at managing investments, they don’t know how it works and don’t want to take the time to learn.

            1. PotatoEngineer*

              You can get loans based on that yearly payment, and end up just as broke as taking the lump sum. If the act of applying for a loan will make you stop and think twice, then it can save you from making bad decisions. But loans and credit cards are so easy to get…

              My understanding is that the lump sum is better because those annual payments are based on really conservative investments, and you can afford to be more aggressive with (most of) your lump sum, and thus make more money…. IF you invest it.

          4. I Wrote This in the Bathroom*

            I was also thinking “take it and invest”. In addition to your argument, I am the kind of person that would’ve failed the marshmallow experiment as a kid, i.e., I don’t trust whoever would be in charge of my yearly distribution payments not to disappear with half of my money a few years down the road.

        3. FreakInTheExcelSheets*

          I haven’t gone to this level of planning, but my family does have a “when I win the lottery” list (and yes, we named it when, not if, because of course it will happen /sarcasm/). Generally speaking, it’s a couple fun things we would want, assuming there’s money after paying off mortgages/cars/etc., but my mom has actually brought it up with her financial advisor out of curiosity. The current plan is to dump the money in a trust where it’s hard to access the principal and basically take the earnings as winnings.

        4. TardyTardis*

          I have actually worked out a spreadsheet on various types of lottery wins and how much would be left after taxes (including the Medicare Extra Tax For Rich People), how much I would be likely to get with a relatively low yield for investment income, how much of *that* is left out of taxes, and how much net per month that would turn out to. Hey, this is how accountants dream…

      1. Anonymous Badger*

        It is a plot that happened on The Office, but it has happened a few times in real life. There was a recent case in Ontario where a bunch of the workers quit after winning the lottery in 2019, for example.

        So unlikely? Maybe. But it could’ve happened.

        1. Wendy*

          My father always participated in the office lottery pool, despite being the business owner, because he figured if they happened to win then everyone would quit and he’d want to be able to quit too instead of having to completely re-staff his office from scratch :-P

          1. No Name Today*

            This is exactly what OP and Mary are facing from the departmental manager.
            Good news, we are expanding.
            Downside, we have to quickly fill positions to keep momentum.
            I know! We will hire a bunch of employees who worked here before.
            Problem solved.
            Yes. If the problem is filling positions with people who are familiar with the company and have some institutional knowledge that is less than an decade old, then whoo hoo.
            If the problem is choosing from the best candidates the one who doesn’t have a prickly history with the company in general and Mary in particular, well, you can’t just tap someone.
            Departmental manager want to help ex-employees. Bully for him. That’s great. But help Mary first.

            1. Nea*

              “But help Mary first.”

              That’s so important! Mary is the one who stayed and put in the work. She needs to be supported and listened to now.

          2. turquoisecow*

            Yeah I’ve participated in a few lottery groups in the office and the rationale from a lot of people is that if everyone wins they don’t want to be the last person in the office scrambling to do all the work. It’s usually only a dollar or two so I’ll throw in also but I don’t expect to win.

            1. somanyquestions*

              Yes, exactly, lol! The thought of Doug having millions while I am still stuck here is enough for me to keep buying into the lottery pool.

          3. Gray Lady*

            My husband did that too once even though he doesn’t like gambling, for exactly the same reason. He did not want to be the only one left in his department in the very unlikely scenario that they won.

      2. Clewgarnet*

        I worked for a business where the marketing department won the lottery. Most of them didn’t quit (it wasn’t THAT much) but the ones who stayed very clearly didn’t care about their jobs any more and were just coasting.

        The business folded after 18 months or so.

      3. A tester, not a developer*

        We had it happen with a small team in my company. They all left, but a couple wanted to come back after 3-4 years because they got caught up in the excitement of having “F-you money” and didn’t think about that fact that unlike their co-workers they weren’t close to retirement age/still had kids to put through university/mortgage payments, etc.

        They were not pleased that they were no longer considered experts – the admin system they had used had been replaced, and the clients they had dealt with had new contact people they were happy with. I don’t know if they took jobs in other departments, but I know their original home didn’t take them back – they were too “Well, the way we used to do it is the PROPER way” in their interviews.

        1. No Name Today*

          I was commenting and stumbled into that as I typed. People who left my department a year ago wouldn’t recognize the system. And five years ago? Even I don’t remember the ins and outs because WE DON’T DO THAT ANYMORE.

        2. Sharrbe*

          I was on a hiring committee where the interviewee had some knowledge about our department because he worked for the same entity just in a different role. Throughout the interview, he kept discussing how he hoped to carry on the good work that the person who last held this position performed, and how much he would like to be able to rely on that person as an example of how the job should be done. He was clearly trying to present himself as this person’s successor. Well, that wasn’t a great a great strategy on his part. I worked with that former employee for a long time. To put it mildly we had a very…….difficult working relationship. In addition, the position that he was now applying for was now drastically different than the one held by this former employee. Every time he brought up this person’s name, I cringed inside. All I kept thinking was “Stop talking. Stop talking. Stop mentioning that name.” and “Don’t hold this against him. Don’t hold this against him.” Well……it was hard not to hold it against him.

          Moral of the story, do not go into an interview with assumptions about the position you’re applying for.
          Technology becomes outdated, positions are restructured, and aligning yourself with a particular current or former employee right out of the gate is REALLY risky.

      4. Kelly L.*

        Yeah, it kind of reads like a fable or a cautionary tale–it’s not that it doesn’t *make* a good point, but it seems too on-the-nose.

    1. Lilo*

      It is based on truth though. Something like 70% of lottery winners end up bankrupt. They get targeted for scams a lot.

      1. Charlotte Lucas*

        Yes, combined with the fact that people who play the lottery tend to be risk-takers & not savers, financially.

        Your first phone call if you win the lottery should be to a lawyer.

        1. NerdyKris*

          There was a great Reddit post about that years ago. Detailing what income level you should be living at, how to safely invest money, setting up trusts for people instead of just handing them a lump sum, etc.

          There’s also studies that show the more money you have, the more you feel the need to increase it, leading to risky behaviors instead of stable investments.

        2. TiffIf*

          Additionally, only 7 states allow winners to maintain anonymity. Six states allow winners to form a trust to claim winnings anonymously and California forbids winners from remaining anonymous.

          If you are in a state where you can claim anonymously, consider doing that.

          1. Pennyworth*

            Where I live I get to decide if my winnings are anonymous, and financial advice is always offered with big winnings (as in ”you really need to discuss what to do with this windfall with a financial planner “). If I ever had a big win I think I would keep quiet about it and make a plan that would provide financial security until I die, but I’m not interested fancy cars and houses.

          2. somanyquestions*

            If I could keep it anonymous, unless it was something huge I might not even tell my family. I have a lot of cousins.

        3. Artemesia*

          yeah the secret to hanging on to a windfall is to tie it up; get an investment manager with an established bank or whatever and invest the money so that when relatives crawl out of the woodwork you can say ‘oh the money is all tied up in investments and real estate — I don’t have any lying around.’

      2. Lucious*

        True, but there’s a family/ community element as well. People who come into money quickly aren’t usually the problem- their friends and family are where the wheels come off. How many of us who came from poor backgrounds can look our brothers, sisters, mothers and fathers in the face and say “no”- even if it’s for the better?

        Say yes to everyone and your moneys gone. Say no to someone (or everyone ) and watch the accusations and lawsuits fly. Stir in your family becoming profitable extortion , kidnapping and fraud targets , and it’s little wonder most people who win the Lotto end up miserable and broke.

        1. Fran Fine (formerly Diahann Carroll)*

          How many of us who came from poor backgrounds can look our brothers, sisters, mothers and fathers in the face and say “no”- even if it’s for the better?

          *raises hand* I do it all the time. Then again, I’m incredibly ruthless (and possibly inherited some of my father’s sociopathic tendencies), so that helps.

          1. FreakInTheExcelSheets*

            Same here! Luckily I’ve never had to do it with financial stuff, but those of us with sociopathic tendencies need to stick together. I would have no problem telling people that I’ve never met or haven’t seen in over a decade “we have zero actual relationship so no I’m not giving you anything”. For direct family (which is quite small), I do have some practice with “no, this is mine” – yes I was taught to share but also that other people are not entitled to your things.

            1. Fran Fine (formerly Diahann Carroll)*

              yes I was taught to share but also that other people are not entitled to your things

              All of this. People know better than to ask me for anything monetary at this point, lol. The answer will always be a quick and resounding, “Hells no!!”

        2. Wendy*

          Yep – and it’s not really even a “fault” thing. Rich people tend to be related to other rich people: not only is having money the best way to make more, but the safety net factor is HUGE. It’s the difference between having a safety net for unexpected expenses and you BEING the safety net for other people’s.

        3. Sans Serif*

          I got very lucky. My immediate family inherited a lot of money from a relative. We split it evenly among us, and although it’s more money than I ever thought I’d have, it’s not an insane amount where you need bodyguards or something. Since we all were given the same amount, there’s no one bugging each other or envious. And we haven’t told anyone else.

  1. ATRM*

    This letter is definitely one written based on The Office! Which we all watched wayyyy too much of during our plaque year.

      1. Phony Genius*

        Depends if you’re talking about plaque on your teeth, or a wall-mounted award plaque.

        1. Charlotte Lucas*

          I have been to the dentist in over a year – definitely a plaque year.

          I have an appointment exactly 2 weeks after my second vaccine shot.

      2. Mallory Janis Ian*

        Well I was employee of the month for thirteen months in a row. That’s right — I won so many times they gave me an extra plaque in lieu of a pay raise!

  2. JC*

    Letter writer 3- I was always told dress for the job you want, not the job you have- so she may perceive that management will take notice of her, although she may just be getting used to the norms of your company. Perhaps her old company valued a stricter dress code, and she just is in that mindset, or perhaps she just prefers it. I honestly wouldn’t give it a second thought, she can dress how she wants.

    Letter writer 4- is this person brand new to working, or very young? I was exactly like this in my first job- I asked questions about things I was doing, assuming my management would know the minutiae of the role and tasks I was performing. I didn’t understand that management are dealing with a multitude of issues, or simply can’t recall every single detail. Just continue giving feedback around being more specific, and help your employee realise her place in the wider team/ company- once she understands how it all fits together, I’m sure she will understand the importance of communication.

    1. jen*

      That’s a really good point about letter writer 4 – your boss has their own work and may not be tuned into your tasks. This is something I learned in my first few jobs as well. My present boss is awesome about this when I come to her with questions. She’ll just say, remind me really quick which project this was?

      1. Sparrow*

        I do think it makes sense to point out that, while it’s front and center in employee’s mind, that’s not also true for OP. It might be worth suggesting to the employee that she think about from the other perspective – if a coworker asks her about an invoice she hasn’t been actively working on, what information would she need to understand the context/identify the specific invoice?

    2. ArtsyGirl*

      I figured there are three possible explanations. This could also reflect previous job expectations. If her last position required business attire, it might take her a while to adjust to a different corporate culture. It might also be an indication she is still feeling a bit insecure and dressing professionally gives her the “fake it ’till you make it” confidence. Or it could be personal preference and she loves business attire and high heels.

      1. Kimmy Schmidt*

        While I don’t wear clothes like this everyday, I’m definitely the person in my office who overdresses. I like pencil skirts! I like heels! I like blazers and dresses and shiny jewelry! None of my coworkers have ever seemed to notice or care because it doesn’t affect them.

        1. ArtsyGirl*

          Me to Kimmy. I am a graduate student and dress professionally because I like looking polished (and I find it gives me some instant authority over my students) and because unlike most of my peers, I worked outside academia for nine years before going back to get my PhD so my wardrobe leans towards business casual.

        2. RabbitRabbit*

          I work in an administrative department in a hospital, and one of the nurses in the department (management level, does not work with patients now) used to work in the ICU before moving into desk work. She frequently rocks huge heels and dangling, jangling jewelry such that you can hear her coming. She’s said she appreciates the chance to dress up now.

        3. Miss Muffet*

          me too! I dress nicer than a lot of my colleagues (well, in the before times anyway) because i just like looking put together. My colleagues only ever noticed to say how cute my shoes were or what a nice dress. No one ever cared otherwise. It was just chalked up to my personal style!

        4. tangerineRose*

          Yeah, I like wearing jeans and t-shirts myself, and in a previous job, that was the norm, but some people liked to dress up, and as far as I know, we all accepted it.

        5. Keymaster of Gozer*

          I confess I’m more comfortable in a formal suit at work, which puts me as a major outlying position in my field (IT). However, most firms accept it as my own personal quirk.

          Admittedly it’s easier when I rock up in medieval style gowns. I alternate a lot.

        6. MCMonkeybean*

          Same. I recently have gotten more casual but for many years I was usually wearing dresses and heels just because *I* like them. I would get comments sometimes–usually positive, but occasionally something like “man, how can you be comfortable in that?” and I’d be like “man, how can you be comfortable in your long jeans when it is 80 degrees outside I assure you I am plenty comfortable in this dress.”

          Honestly it seems extremely rude and passive aggressive to have said to her that “another colleague” dressed more formally and that it was weird. I can guarantee she did not feel that was as “casually mentioned” as OP claims. That is literally just saying “hey, you dressing up is weird” but trying unsuccessfully to be subtle about it and there’s no way she didn’t know that was what they meant! If someone higher up in the office has an issue with it for some reason then they can bring it up, but otherwise MYOB.

      2. Richard Hershberger*

        Mostly, I am amused at how the casual dressers are as obsessed with the topic as the formal attire crowd was, back in the day. Back then the casual dressers made the argument that wearing a suit doesn’t make you more productive. Flip and script and they turn out to be just as kneejerk judgmental about meaningless trivia.

        1. tangerineRose*

          I think many of us casual dressers are afraid that we’ll have to dress up more if too many people wear formal attire.

          1. Fran Fine (formerly Diahann Carroll)*

            That’s never happened in any workplace I’ve ever been in (and I’m the overdresser everywhere I work because I love fashion), so while there’s a chance it could happen, I think it’s minuscule. Usually uber casual environments like the one OP mentions working in is that way because people at the executive level want it to be that way – those people are less likely to change the entire corporate culture based on one (or a couple) lower level employees who choose to dress up.

      3. CoffeeIsMyFriend*

        I think I fall into the insecure camp a bit – I often dress slightly more formally than many of my colleagues because if I don’t I look really, really young. Granted, after a year in my position, I am more likely to dress casual if I am working with people I know, but if I am working with colleagues I know less or outside people I don’t dress casually (though I am still in line with our overall culture). It’s about MY comfort, and honestly I rarely think about how my colleagues are dressed.

      4. GothicBee*

        Yeah, regarding #3, dressier clothes have always been the bane of my existence (it’s impossible to find stuff that fits me properly no matter what size I am), but some people just really love dressing up every day. I remember some people back in high school (!!!) who would come in every day wearing business casual and heels at a minimum.

        I just wish we could get to a point where everyone could wear what they’re most comfortable in and quit worrying about whether someone looks too professional or not professional enough. But that’s mostly cause I want to wear t-shirts and jeans everyday. I will never understand the need to police what people wear if they’re just gonna sit at a desk 8 hours a day.

        1. Charlotte Lucas*

          I work for a government agency, & everyone pretty much just dresses to their preference. If there are meetings with external people, they usually dress up more, but it’s definitely a “dress how you like” kind of place.

        2. MCMonkeybean*

          Fit-issues is actually one of the main reasons that I wore dresses pretty much every day for years and often looked overdressed as a result. My butt is two sizes bigger than my waist so if I go for a fit-and-flare dress then I only need to accommodate one of them lol.

          1. Fran Fine (formerly Diahann Carroll)*

            This! I have chicken legs that don’t go with the rest of my developed body (especially my broad shoulders), and fit and flare dresses have really saved me from looking crazy, lol – I actually look proportional when I wear them.

    3. Skeezix*

      LW 3
      I find myself in a similar position. For the 1st 4 years I worked at my company it was “business attire”. There would be occasional Jeans Day (clean, no rips, but your top and shoes still had to be ‘business’).

      Then Jan 2020, they changed to business casual and jeans were allowed every day (but no sneakers)! I had just spent the previous year investing in good quality dresses, skirts, and owned 1 pair of jeans that I usually wore once a week on Saturdays. When we return to the office, I plan to go back to wearing my dresses & skirts. I spent good money on them and to not wear them would feel like a waste.

      I can see how the new employee might occasionally wear a pants suit in to work. If she had to spend $150 on this professional outfit, why should she be forced to relegate it to the back of the closet because New Company allows jeans??

      1. NotRealAnonForThis*

        That was my thought as well.

        We relaxed the dress code a bit (we’re back in the office about 90%, but we are not allowed vendor visits or outside appointments, so dressing as though we may have an impromptu business-formal-required meeting isn’t exactly necessary), but when it was pointed out to me, I thanked them for the reminder, but I don’t *own* much that fits the current bill of “dress code” though I own plenty that worked under the more formal one, and honestly, I’m not wearing jeans and a button up in August in the midwest. I’ll stick with a long dress and blazer. I can ditch the blazer at the front door and not be miserably hot and sticky.

      2. Malarkey01*

        I’m doing a lot of “business attire on top/ready for bed on the bottom” dressing right now. I actually do feel like I personally am more professional when dressed better just as a personal quirk, but I have fully embraced the yoga pant comfort.

      3. Where’s the Orchestra?*

        I’m in this boat – my last job was a lot more formal, so my work wardrobe is also more formal than the norm. I’m slowly investing in more casual clothes, but I’m not getting rid of the clothes that I have and fit just because the new place is less dressy than the old.

      4. CupcakeCounter*

        Yup. At old job, my new boss came in wearing business attire and we were a jeans and flannel trucking company. She simply didn’t have much in the way of jeans or flannel and didn’t feel like shopping for a whole new wardrobe when she had spent good money on quality slacks and had then tailored to fit her properly? She did move to booties and sweaters (from heels and jackets) with those pants very quickly but I don’t think she wore jeans for a solid few months and even then it was limited to Fridays.

      5. CTT*

        Yup. And even if she does want to update her wardrobe to match this new environment, casual clothes cost money too. Switching up an entire wardrobe is hard!

    4. TWW*

      I can think of lots of reasons why someone might want to dress up more than required.

      As a young mix-race person, I wore a dress shirt and tie when traveling for work, even though my in-office attire was much more casual. I felt better treated in airports and planes when I looked more professional. It might have been all in my head, or it might have been real, but it doesn’t really matter.

        1. Fran Fine (formerly Diahann Carroll)*

          Yup. I’m a black woman who gets phenomenal treatment based on the fact that I stay dressed to the nines everywhere I go (people have told me I look like money) – I distinctly remember the difference in treatment I received in public when I was poor and dressed like it. It wasn’t nearly as nice or accommodating then.

      1. RebelwithMouseyHair*

        My Chinese/Malay friend said the exact same thing. He had to travel for business once and discovered that he was actually treated with respect. He then started always wearing a suit to travel, even for holidays. Even got upgraded to first class once.

    5. RC Rascal*

      It’s possible her former employer required that kind of wardrobe, it’s what she owns and can’t afford to go out and buy casual clothes. We had that happen; hired a man from a bank who had a stay at home wife and 2 young children. He kept wearing his banker clothes because that’s what he owned.

      A separate coworker wore a shirt and tie every day. He was younger, but liked wearing the shirt and tie. It made him feel professional, he collected them and had some funky ties. When the office dress code switched to jeans he wore the jeans and kept the shirts and ties.

    6. CommanderBanana*

      Or, she may have come from an office that had more formal standards of dress, and hasn’t yet/doesn’t want to replace her wardrobe.

    7. Momma Bear*

      Or she may have that wardrobe from a previous job. A couple of my coworkers dress better than most of us. I just look at it as that’s what they are comfortable with and as long as I am dressed the way I need to be for my role, no need to worry about it, though I might be inspired to wear something different now and then.

  3. Dust Bunny*

    Not enough words: Does my mother secretly work for you? She can deliver entire monologues that use no actual nouns (and always has; it’s not new/we have no concerns about her cognition) and then gets annoyed when my dad has no idea what she’s talking about. I am absurdly good at keeping track of all this–I can drag up conversations we had weeks ago based on a half-sentence with no specific information.

    But it’s exhausting. I’ve finally started pushing back a little and insisting she use real words instead of just empty pronouns.

    1. Sola Lingua Bona Lingua Mortua Est*

      My spouse does this. I printed several red cards for “abuse of pronouns” to counter it.

      1. Dust Bunny*

        OMG Mom would [figuratively] kill me! But we’ve spoiled her all these years. She has no idea how much mental energy I put into keeping track of this stuff.

      2. Corporate Lawyer*

        LOL, I love the red card solution!

        I once said to a coworker, “I’m putting you on a pronoun diet.”

      3. JanetM*

        Heh. When I’m aghast about something someone has done, I am likely to explain to explain to my husband, “I can do nothing but recite pronouns. He… she… it… they… THINGY!” and wave my hands about.

        I do not do this at work. Just to be clear :-).

        On the other hand, my husband is as likely as not to start conversations with me by asking, “Did you hear the news?” To which all I can say is, “I have heard some news; what in particular were you thinking about?”

        1. Jack Russell Terrier*

          My mum: can you get me the thingamig – it’s in the whatdoyoucallit.
          Blank stare from me:
          Mum, shooting daggers, tone at the end of her tether: you know what I mean
          Me: ….

          1. Deejay*

            My mother does that all the time. And one time, she really took it as far as possible.

            Talking to my sister, turned to me. Said one word “Bring”, then turned back to my sister and continued.

      4. So they all rolled over and one fell out*

        It’s only vaguely related, but my spouse knows (friends and/or coworkers) at least four people (nick)named Brie (various spellings but pronounced the same) and two or three Lisas. She very frequently uses their names in a sentence without telling me which one she is talking about, which makes it hard to follow. For instance the two Lisas are very different people, so if she says one is thinking about changing jobs, that’s either very surprising or very not (one of the Lisas is always saying she’s thinking about changing jobs, but she rarely does). Or it matters which Brie she is talking, especially when it’s about school – our own kids are in the same school as two (half) of the Bries’, but one of the two works in the dirstrict and so has inside info that’s relevant to our family.

        1. RebelwithMouseyHair*

          My partner does this too. He has three brothers and three sisters, and will say “my brother did X and my sister asked him Y” and expect me to know who he’s talking about. Then he has several friends with the same name too. We’ve had to give them all nicknames: Eric beard, because he’s always had one, and Eric Moscow because when I met him he was just about to go to Moscow, Eric Harvard because he studied there and Eric shoes because he owns a shoe-shop. My partner will still tell me something about Eric and when I ask, which one, he’ll say “Eric!”

      5. Canadian Yankee*

        My spouse does this as well! We’ll be walking through the dense urban neighborhood where we live and we’ll have a “conversation” that goes like this:
        Him: “Wow! Look at that!” [note: no pointing or anything]
        Me: “Look at what?”
        Him: “That!!”
        Me: “I don’t know what you want me to look at.”
        Him: “You don’t see the building? It’s right in front of you.”
        Me: “…We’re in the middle of downtown. There are dozens and dozens of buildings in front of me.”
        Him: “I guess we can’t communicate with each other. Fine. I was just making small talk.”

        1. hodie-hi*

          Oh, Canadian Yankee… My spouse does this same thing ALL THE TIME, with the same ending! Plus due to injury/age/laziness he uses the wrong words to refer to things and gets frustrated when I don’t immediately understand. He gets frustrated with how dense I am, multiple times a day. It’s so exhausting and feels so unfair to be cast as the difficult one.

        2. adk*

          My husband will do this then accuse me of being unobservant. No, it’s not that I’m unobservant, I’m just not observing the same things as you. I was reading bumper stickers on that Jeep that just drove by while you’re looking at buildings. I’m not seeing the same things you’re seeing.

        3. Not So NewReader*

          My husband would actually point. If he wanted to show me something in a position 2 o’clock from us he would point in a direction of 11 or 12 o’clock. And then not understand why I wasn’t looking over toward the 2 o’clock area. I have never seen anyone point so badly.

          I tried telling myself that it’s the difference in where we were standing. This might be a believable explanation except for the fact that it happened all. the. time.

          If I showed him where he was pointing in relationship to what he wanted me to see, he would vehemently deny that he was so far off the mark.

    2. Threeve*

      I use vagueness tactically sometimes. My brother is horribly indecisive, and sometimes if I know he’s going to take forever to make a simple decision, I refer to something very vaguely implying that he already has made the decision and just needs to provide it. “Right, we were going to order lunch from that place you thought sounded good before, remind me the name?”

      1. Dust Bunny*

        It would be less frustrating if Mom weren’t convinced she is always very direct and concise. The reality is that she has no middle ground between “bites your head off” and “hopelessly vague”.

    3. 3DogNight*

      I personally have this issue. It’s aphasia caused by a migraine medication I took for a couple of years (and is worse when I have a migraine). For me, I do try to figure out the words, and I do a LOT of practice for what I will say when I have to ask someone for something, or tell someone something. In my case, a medical issue, it’s just as frustrating for me as it is for everyone else. Thank GOD my husband usually knows where I’m trying to go with what I say.
      HOWEVER, I do not expect people to fill in my blanks. I do so much better when I can type out what I need, versus saying it.

          1. anony mous*

            Same thing happened to me. It got better once I stopped taking it, but I don’t think my brain has ever been the same as it was before.

            1. Sled dog mama*

              That’s what caused this?! I was on that too for a bit (I went through so many combinations that I can no longer remember what I was on when) but the time I was on that does seem to line up with with the aphasia getting worse.

              You are welcome for the entertainment couple in Walmart who had to listen to me remind my husband we needed a new shower curtain while unable to remember the words “shower” or “curtain”. I believe the description came out something like one of the things that keeps the water from getting on the floor when you stand inside the thing where you get wet and soapy.

              1. Merpaderp*

                As a professional interpreter, let me just say that was a *great* interpretation for “shower curtain”!

      1. NerdyPrettyThings*

        I have the same issues sometimes when I’m battling brain fog. I wonder if more people will have this issue post-Covid. I’ve heard the brain fog can hang on for months. It definitely helps to communicate in writing when possible, and when people can help me from context (although I certainly don’t expect it).

    4. Sleepless*

      My MIL started most of her stories in the middle. She did use people’s names, but they were people I didn’t know, like her coworkers and friends. If you asked her who somebody was, the answer was so convoluted you ended up even more confused. I got to where I just nodded and smiled a lot. I can just imagine doing this with a coworker, when I actually needed to know what they meant.

      1. GT*

        My MIL does this, too. Is this person a friend, relative, neighbor, former neighbor? Luckily, she doesn’t care if I don’t know who these people are.

      2. Absurda*

        My mom will have a conversation with my brother but forget it was with him. She’ll then restart or reference that conversation with me and get frustrated that I have no idea what she’s talking about.

    5. Nicki Name*

      That letter can’t be about your mom, that’s clearly MY mom. She has a habit of vocalizing a thought about something she’s thinking about and not realizing that other people don’t have the context of her other thoughts to realize what she’s talking about. Or switching context in the middle of a conversation, not realizing again that she needs to catch people up on the new thing she’s mentioning.

      After a sibling was diagnosed with autism, the whole family realized that our parents are probably autistic too, which may have something to do with this trouble. Then again, my dad and my sibling don’t have this problem, so whatever’s going on isn’t insurmountable.

      1. pagooey*

        Dust Bunny and Nicki Name, my long-lost siblings! My (…our?) mom is a LEGEND of “you know that place by the thing where we went that time?” constructions and has been for years; I read L4 and just assumed she’d returned to the workforce on the sly.

        Her most famous example, ever: “You know the guy on that show ‘Frasier,’ not the prissy brother and not the old man, but the other guy?”

        1. Peter Piper Picked a Peck of Pickled Peppers*

          But it’s perfectly clear who that is, LOL

          I sometimes struggle to communicate clearly and concisely. I ramble, switch thoughts halfway through a sentence, struggle with word-finding. But I quickly become aware that I’m communicating badly and try to get back on track. If I think through what I need to say ahead of time, I can usually make sense.

          With written communication, I often rewrite and edit a lot before I feel that I’ve made my point well.

          And I’m also neuro-atypical. So perhaps there a link there.

        2. Noncompliance Officer*

          My MIL does this when giving directions. “You’re going to turn left at that place that used to be that restaurant before it burned down. It’s right before that store that used to sell those things we bought when had that problem in the house.”

          1. Corporate Lawyer*

            Is your MIL from New England, by any chance? We New Englanders are (in)famous for giving directions by where things used to be. “You take a left where the gas station used to be, keep going past where the Star Market used to be, and then take another left at the Dunkin’ Donuts.” (That last one is particularly unhelpful: here in the Boston area there are at least three Dunkins per square mile.)

              1. RebelwithMouseyHair*

                Our house is in the street just past the pink bakery (that was painted a dull brown at least ten years ago, but the hot pink was just priceless!)

          2. Absurda*

            Hahahaha, my family used to do this in our hometown, but not so much anymore. “it’s right before the street where the big tree used to be…” or “it’s on the same street as Todd’s house”.

    6. Sled dog mama*

      This could also be my husband. I have taken the “Mr.Bennet” approach, when he pauses for my input (which doesn’t always happen) I say “I have not the pleasure of understanding you, of what are you speaking?”

    7. Sleeping Late Every Day*

      I had the worst vague-speak problem with staff researchers of the PhD persuasion – they’d start the conversations in their heads while in their offices, then by the time they’d get to my office, I’d get the last sentence and be expected to know what the hell they were nattering about. Or they’d (very vaguely, of course) reference something from long before I worked there and expect me to remember it, then say, “Oh, I’m sure you’ll figure it out!” Grrr. Nice people, but they drove me bonkers.

      1. Djuna*

        I’ve had the same thing with non-academic people too, they start the conversation in their head and are at least two-thirds through before they (in the before times) pop up at my desk. I usually gently pause them and ask for more context. For repeat offenders, I’ve been known to remind them that I am not inside their head and so they need to start at the actual start.
        Communicating over Slack this past year and change has made all of that so much easier. For most people, when they’re typing something out, they spot the gaps better.

    8. KRM*

      An old colleague once turned to me and said “Did you remember to put the thing in the thing???”. I had to ask him to say it again but use at least one more noun, so I could help him.

    9. Clemgo3165*

      Being of a certain age, I can attest to the fact that nouns are the first thing to go. Sometimes you just can’t remember what the name of that thingy is, or when that invoice came in, or the name of the company it was for right off the top of your head. So you end up substituting hoping that the person you’re talking with will help you fill in.

      But’s that’s the beauty of 2021. These data holders we call computers that can keep track of all those details for us. I’d suggest cutting a bit of slack and asking the employee to come to you with a fully formed question, including details. They may be asking off the cuff, getting themselves into trouble making themselves clear. I’d also be sure that I was allowing time or a means for asking such questions.

    10. WritingIsHard*

      I have a very writing-heavy job (as you might imagine) and sometimes I literally struggle to find words at the end of the day. My partner has gotten very good at interpreting what, “You know the thing?” means. That doesn’t work when you don’t have a close personal relationship with someone, though. I usually try to slow down and take a moment to think about what I’m trying to communicate first. In the case of the OP, it sounds like it might be a bad habit rather than a fundamental communication flaw.

      1. Djuna*

        Same here, and on Friday I am generally out of useable words by lunchtime.
        If people need words on Friday afternoon, I can produce them, they just take waaaaaaaay longer to shape into anything publishable.
        Luckily my co-workers are tolerant sorts who just joke about me needing my weekly reboot to clear my cache.

      2. Workerbee*

        I will wholeheartedly embrace this rationale for why I have trouble finding words sometimes. I both write at work and am an author, plus sometimes I’m immersed in the feelings of a scene, and that perfectly crisp word or phrase to describe it all can get gummed up in the works. Ordinary people conversation after that can be wretched.

    11. Glenn*

      I have a friend who is infamous among our friend group for speaking in weird riddles. In his case, the problem is apparently _severe_ ADHD, and he is much more comprehensible when he’s medicated. Otherwise, his mouth is just permanently 5-10 steps ahead of his brain.

    12. Sandman*

      My husband does this, too. Sixteen years we’ve been having this conversation. NOUNS. I JUST NEED SOME NOUNS, PLEASE. Anyway, good luck OP, but I don’t think you’re going to fix your coworker!

    13. Single Noun*

      My old boss used to do the opposite- she’d come in my office and say a noun, and I’d have to ask questions until I could figure out the rest of the sentence.

      “TPS Reports!”
      “Yes…? What about them?”
      “Did you run them?”
      “Yes, is there a problem with them?”
      “Where are they?”
      “In the folder where they go…?”

  4. TWW*

    I skeptical of this letter, but in the spirit of taking OP at their word, I think it’s possible that OP doesn’t know the whole story, and some of the info OP does have seems to have come to them second-hand.

    With that in mind, it is baffling that these people are “citing financial issues” in applying for their old jobs (or any jobs for that matter). That’s so unprofessional that I think their applications can be rejected for that reason alone.

    1. Evan Þ.*

      I’m a bit skeptical too, but that part actually makes sense. They previously quit because they’d won the lottery, so now that they’re applying for a job there again, it makes sense they’d explain “the lottery money ran out, and it turns out we need an income after all.”

    2. ahhh*

      I was thinking while they won the lottery it might be a smaller amount than the millions that we often wish for. Maybe $200k-ish. That’s a few years of not having to work, a couple spending sprees and that money would be gone. However for some that $200k might be a life changer and the lottery winners might have thought “I’m set for an easy life if I’m careful”. Everyone’s financial situation is different.

      I agree OP might not know the whole story, he said he started after the lottery win, but as a divisional manager I would think his manager would have filled him in. I agree that that Mary needs to have more input and influence in this decision than anyone else. I feel like there will be some bad blood with former coworkers now having to report to their former trainee, not to mention having to come back with their tail between their legs.

      While I think the former coworkers should be interviewed, they do after all qualify, I think this situation needs to be looked at fulfilling the needs of the company, not helping out an old friend.

      1. Richard Hershberger*

        I know a guy who won $250,000. He made the observation that this is enough money to get you into trouble, but not enough to get you out of it. Fortunately he had his head on straight. His wife really should have retired already, due to medical issues. The money let her finally do that.

        1. EmmaPoet*

          That is an excellent way to put it. That could cover a house, car, and a few shopping sprees, but it’s not “retire immediately and live off the interest from the interest” money.

          1. Elenna*

            And even then it depends on COL – a one-bedroom condo where I live is generally 500k or more.

            1. EmmaPoet*

              Oh, sure, where I am it’s the same thing.
              If I won a big lottery, I’d move back to my home state where it’s cheaper and I could get a nice house for around $100,000, but $250,000 isn’t enough to tempt me to quit.

          2. The Original K.*

            Yeah, that’s not “never work again” money, to me. I’m not that old, living another 50 years is very possible for me. That’s “pay a few bills, take a fancy vacation, and sock away/invest the rest” money.

            Really, if I have another 50 years on the clock, the “never work again starting now” number is pretty big. 50 years is a long time. If I netted a million today and wanted to live on it for the rest of my life, that would mean I’d live on $20K a year. I can’t live on that (and I don’t have dependents). I could retire on a million at 65+, not in my 30s.

            1. Richard Hershberger*

              I feel pretty much the same way about the stimulus checks. Order out a nice dinner, then the rest go into the kids’ college fund.

            2. Pescadero*

              ” If I netted a million today and wanted to live on it for the rest of my life, that would mean I’d live on $20K a year.”

              Only if you bury it in a coffee can in the back yard.

              You can easily make $30K-$40K per year in interest/dividend income on $1 million.

              1. Not So NewReader*

                Yeah, I read the link above with the couple and the $3M. I was thinking to myself invest it and that income stream is $100k per year. Just 100k extra per year can be a lot of fun, keep working and retire early.

            3. Seeking Second Childhood*

              A friend and I warned our old manager that if we won the lottery, we would be applying to job share. The manager said if we win the lottery, you can take that up with my manager… I’m in the pool too and I’m one year from retirement.

        2. Absurda*

          Yeah, and a lot of lottery winners don’t take into account things like taxes which can take a significant chunk out of the winnings

      2. Skeezix*

        We also don’t know HOW the old team quit. Did the give proper notice and participate in a transitional plan? Or did they walk in en masse, empty theirs desks, and strut out yelling “Peace out losers!” the day after the drawing?

        1. Rusty Shackelford*

          In the original post, the LW said they quit without notice. And given that, I would only consider hiring them back if people were eligible for rehire under those circumstances even if they hadn’t won the lottery.

          1. Skeezix*

            Yeah….. If they quit without notice, what is the company policy on rehiring people who do this?

            I would also have concerns about them taking on entry-level positions and having behavior issues due to thinking they should be in a higher position. And totally see “Mary”s concerns about having them now report to her.

      3. LKW*

        Sadly, even if it was a couple of million, people who don’t have good money management skills could easily blow through that quickly. Purchasing a house with a cash offer, buying new cars outright, a few grand trips and private schools for kids can easily turn a large next egg into something rather small. I’ve seen it happen. A relative inherited several million and within a few years they had spent most of it.

        It’s really easy to drain large accounts if you are spending the capital, not the earned income.

      4. GT*

        I think some people just see “large amount of money” but don’t really get how long it will last. I had a co-worker whose in-laws retired and sold everything to travel the US in an RV. They ran out of money within 6 months.

        I agree that the people wanting to return should be treated similarly to anyone else who might be applying to the company.

      5. ahhh*

        I probably should have added to my post but I didn’t explain my reasoning. The $200k is more that if they won a prize in the millions, split by a department might only be a coup hundred thousand dollars.

    3. Colette*

      I could see addressing the financial issues if you previously quit your job at the same company because you didn’t need the money.

      It’s actually really common for people to win the lottery and spend/lose all of the money – but, of course, no one thinks it will happen to them.

    4. Captain dddd-cccc-ddWdd (ENTP)*

      it is baffling that these people are “citing financial issues” in applying for their old jobs (or any jobs for that matter).

      What do you suggest they should say when asked about the ‘gap’ in their employment history (i.e. that they haven’t worked for the last 3 years or however long it is)? Some variant of “I didn’t need a job, but now I do” seems acceptable to me as a reason.

      1. TWW*

        Whatever you say when applying for a job, when asked why you want the job, it shouldn’t be, “I’m in financial trouble.” Hearing that as a hiring manager would give me real pause.

        It’s hard to say exactly what I find off-putting about that answer, except that if I have a choice between two similar candidates one of whom wants the job because they’re desperate for money, and the other who wants the job because they’re genuinely interested in working for my company or in my industry, I know who I’d favor.

        1. Not So NewReader*

          How about, “I came into some money, I took a break and enjoyed it. I also helped some family members, too. It was great. Now I am refreshed and ready to return to the workforce.”

    5. Elle*

      > With that in mind, it is baffling that these people are “citing financial issues” in applying for their old jobs (or any jobs for that matter). That’s so unprofessional that I think their applications can be rejected for that reason alone.

      I don’t know, I would think it was odd normally, but in a situation where they are applying for jobs when everyone knew they’d won the lottery, and people presumably know them a bit, I don’t think it’s that odd. They didn’t necessarily stick it on their application, but it’s not a totally weird answer if someone you used to work with asks ‘hey, why are you wanting to come back? I thought you won a tonne of money?’

  5. Heffalump*

    I can relate to #4. My mother would constantly refer to things as “the thing,” “the whosis,” or (worst of all) “the you-know.” If I were LW #4, I probably would have snapped at the employee by now.

    1. BubbleTea*

      I get frustrated by myself when I do this – in my case it’s a form of aphasia connected to a long-term health condition that is mostly resolved but pops its little head up from time to time, and losing my words is one of the early signs. But there are definitely people for whom this is just a normal way to communicate, and it does seem very inefficient. Maybe it feels great when someone does know what they’re talking about, like maybe they’ve connected on some higher plane where nouns are not required? But for the rest of us in the real world, we do tend to need more details. Even if sometimes I have to describe an object because its name has disappeared, or because it’s been replaced by something similar but not quite the same (e.g. “I need to vacuum the lawn”).

      1. Chris*

        Something like this was my thought when I read the letter. I agree with Alison’s advice, but the LW should keep in mind the possibility that this may end up being a medical issue rather than just an “odd habit”.

    2. Sola Lingua Bona Lingua Mortua Est*

      My dominant strategy is to not just guess wrong, but guess so horribly wrong that it triggers panic or disgust.

      “I want the thingy for dinner.”
      “Reindeer Goatcheese Meatloaf?”
      “No! Ew! Green Bean Cassarole.”
      “Potáto, Potàto…”

      “Bring me the whatchamacallit so I can cut my hair.”
      “Rusty chainsaw?”
      “Here you go.”

      “We’re getting a visit from you-know-who from Star Trek…”
      “Jar-Jar Binks?”

      “Did you do that thing I wanted you to do?”
      *flips coin*
      “Whatever heads means.”

      My philosophy is to never take it more seriously than I can prove the requester has.

        1. Mallory Janis Ian*

          Same with me and my husband:

          Me: Hey, it’s that one guy from that one show!
          Him: Oh, yeah, ol’ what’s-his-name!

          And we both know that we know what each other means, but neither one of us can think of the actor or the show name.

          1. Absurda*

            My parents do this, too. “Where do we know that actor from?”

            I will often think this but won’t say it out loud, IMdB is a godsend.

        2. EvilQueenRegina*

          My grandad: “Hey, it’s him, he’s been in things, what’s his name, it’s him with the face!”

      1. Not So NewReader*

        “My philosophy is to never take it more seriously than I can prove the requester has.”


        I agree, I can’t be the only one bringing my brain to the table. And no my brain is not for rent or for leaching off of.

    3. Sara without an H*

      Ah, yes. My parents both talked like that. The scary part was that the understood each other.

      But then, they’d been married for 60 years.

      1. Elenna*

        My sister and I absolutely talk that way to each other, but we also understand (most of the time). We definitely wouldn’t do that with anyone else.

      2. Checkmate*

        Actual conversation my late husband and I had

        Him : “Do you know where the thing is?”
        Me : “Did you check over with the stuff?”

        And we were able to understand what we were saying.

      3. Marillenbaum*

        My sister and I can do that, though not as well as we did when we were kids. Once, in a game of “Animal, Vegetable, Mineral”, she guessed correctly after a single, fairly general question, and everyone else said “These two can’t be on the same team again”.

        1. Julia*

          My best friend and I (met in college, not as kids) do that sometimes at karaoke. “I wanna sing that song!” and the other one pulls it up.

    4. MassMatt*

      I’ve worked with people like this, and it drives me nuts. The worst thing is when they repeat the same vague prompt more emphatically, as in “the report. You know, the REPORT! The REPOOOOORT!” Saying vague info more loudly isn’t being more clear. That one was eventually solved by simply grabbing the first thing at hand that fit the vague criteria. “Hmm, weather report from 2 years ago–here you go!”

      Second worst is where they start asking a question and… don’t say anything? Ask me when you HAVE a question, not before. This is work, I don’t want to play charades.

      1. JillianNicola*

        Oh my GOD my boyfriend does a version of this where if he’s explaining something and I don’t understand, he just repeats the explanation with the same words but in a slightly more agitated tone and it drives me innsssaannnneee. If I didn’t understand the meaning of the words in that order the first time saying them again a bit louder/more aggressive isn’t going to magically flip the switch! USE DIFFERENT WORDS. Which is essentially Allison’s advice to OP 4, just in a much nicer way lol.

        1. RebelwithMouseyHair*

          My partner will say something and I’ll hear “mumble mumble in the mumble down by the river”, I’ll say “sorry what was that about the river?” and he’ll say “down by the river”. He seems to have a talent for repeating the only part I actually heard.

    5. Sleepless*

      I used to work with a veterinary technician who did that a lot, and I occasionally do it too! And there are a lot of “that thing” in an animal hospital. The funny part is that we always seemed to know what each other meant. I miss working with her.

    6. EvilQueenRegina*

      I can relate to that. My mother will talk about something, and then the next day will refer to “it” without any real context, by which time I’ve moved on in my head to thinking about other things and don’t always know what “it” was without some actual context.

    7. Mockingjay*

      Missed this letter yesterday, but wanted to say that I have family members who communicate exactly like this. One has a formal diagnosis (not going to mention what so as not to derail), but long story short, has to word associate to get to a point. Verbal communications can really frustrate them.

      It might be helpful to suggest submitting these questions by email, including the context and attributes Alison mentions. Maybe even create an email template (fill in the blanks) if there are routine questions or items to process.

  6. SunnyGirl*

    Those Lotto 6/49 commercials with everyone so excited to have won should always be followed with a cautionary tale like LW1.

    I really like Alison’s proposed solution: you interview and we’ll see. That is truly the most fair way of handling it.

    1. Grand Admiral Thrawn Will Always Be Blue*

      I actually did win a Lotto prize a few years back. The take home was quite nice but not huge, not enough to quit work. Maybe for a year. I used it to move back home from nine hours away. My experience…. for the average person, getting a big check from anywhere when you aren’t used to money can be tough to handle. It works on your fault lines, whatever they happen to be. And it caused my anxiety to jump track – before, I worried about how to pay for things. After, it switched gears to worrying about losing it, someone taking it from me. Sudden Lotto money is useful but has a dark side, don’t doubt that. And if you weren’t good with money before, it’s not magic, you won’t be good with it after either. ( I have told this to a few people but they never believe me).

      1. Richard Hershberger*

        My hobby interest is 19th century baseball history. You see the same sort of thing with the players, who were making good upper-middle class money. It is fascinating to see which ones saved and invested, and which ones needed to borrow train fare to report to their team in the spring. There was a class element to this. 19th century working class education did not include money management skills. But it was by no means that straightforward. It was about those fault lines in the personality.

        1. MassMatt*

          Pro sports unfortunately still has a terrible track record re: the players long-term solvency, it’s quite similar to lottery winners. The average length of many pro sport careers are surprisingly short, education for many of them has taken a back seat to athletics ( a whole ‘nother issue, many college athletes never even graduate) and the first thing many do when they start getting paid is spend big. Even if they got a signing bonus and a good salary, it doesn’t last long if you buy houses and cars for everyone in your family.

          1. The Original K.*

            There’s a fantastic 30 for 30 episode called “Broke” that lays out how pro athletes go broke. I found it fascinating (and kind of sad).

          2. Richard Hershberger*

            Some of the players’ unions have financial literacy programs, but it is hard to get the attention of a twenty-something kid who just struck it big.

        2. Heffalump*

          You would really enjoy Annotated Baseball Stories of Ring W. Lardner, 1914-1919, ISBN 978-0804729635. I enjoyed it, and I’m not much of a baseball fan.

      2. Anononon*

        I love playing the “what would you do if you won the lottery” game, but I would also be completely terrified, especially because my state doesn’t allow anonymous trusts to collect the funds.

        1. Anchee*

          I joke about this with my friends. I’m terrible at even daydreaming about a sudden windfall. My brain is wired to try and figure everything out. So, Oooooooh! I’ll travel so much! Turns into OMG what am I going to do with the dog!

    2. Archaeopteryx*

      Yes, not only did they blow through the money (which could be a failure of either luck, math, or self-control, or a combination thereof – sad but pretty common) – but some of them are publicly bitter about having to go back to work? Due to their own choices? These would be red flags for how they operate even if it wasn’t your own company they’d peaced out from. Proceed with caution.

  7. Dust Bunny*

    LW3: I mean . . . how do you want to handle it?

    If you want to keep up the polo-and-jeans look, go for it. If you want to polish up a little, go for that. I usually wear skirts or dresses because pants don’t like my thighs and I’m preserving the Last Pair Of Jeans On Earth That Fit Me for as long as I absolutely can. It has nothing to do with showing up my coworkers.

    1. MeTwoToo*

      Just want to say I feel the jeans thing so much. I went so far as to buy another exact pair from ebay. Same brand, size, shape, made in, number tag, everything. They did not fit.

      1. Dust Bunny*

        I bought a pair of Lee Riders in 2001 and one of these days I’ll put them on and breathe a little too hard and they’ll just disintegrate. I can also wear the Wranglers that are cut for women who actually ride–higher waist, relaxed legs–but I’m afraid they’ll stop making those, too.

      2. Rusty Shackelford*

        I went so far as to buy another exact pair from ebay. Same brand, size, shape, made in, number tag, everything. They did not fit.

        Been there, done that.

      3. Seashells*

        I bought a pair of work pants that I loved. So I bought an additional 3 pair- same as you I ordered the exact size, shape, made in, etc. and they all 4 fit differently! I was and still am disappointed. Because I assumed they would fit, I took off the tags and laundered them, so when they fit differently I had to eat the cost because I could not return them.

    2. Chinook*

      Exactly. I wear dresses because they fit better than jeans and dress pants. But, I have also learned that some people think that it makes me a snob or that I am wearing them at them when the reality is that I am just wearjng something that futs best and requires zero brain energy to coordinate.

      1. Dust Bunny*

        Also: I cannot make decisions that early in the morning. Dress = no coordinating anything because it’s all one piece.

        1. Hazel*

          Yes! to Chinook and Dust Bunny! I love wearing dresses because they’re easy, and they look better on me than pants or skirts, and I’m comfortable in them. I’m usually more dressed up than anyone else in any given situation, and I’m fine with that. I’m not trying to show up anyone else, and I doubt that the OP’s colleague is either. She may be just used to dressing this way.

      2. Mitzii*

        Dresses, A/K/A “onesies for adults”. I love dresses, especially in the summer since I won’t wear jeans between Memorial Day and October 1.

      3. Seeking Second Childhood*

        Even new pants do that. If you find a pair of pants that pissed at Walmart, you have to try on the one on the shelf next to it instead of just buying them both.

        1. Lawyer But Not That Kind of Lawyer*

          It’s because in most countries that purchase clothes from clothing factory productions there is a half an inch to 3 quarters of inch (depending on the clothing) allowance for something to qualify as meeting the size requirement. So unfortunately, you can try on 3 different size 8 pants and each of them fit slightly different.

    3. Personal Best In Consecutive Days Lived*

      I work in a very casual, jeans and T-shirt environment as well. One woman wore a nice dress every day. She looked professional and no one cares what you wear here (we don’t have a dress code).
      She did stand out for this, not negatively, it’s just that you would notice she was the only person dressed up.
      She was let go in her probationary period and I have no idea why. I thought her work was good but as her peer I didn’t have the complete picture.
      So about dressing nicer than your coworkers I’m of two minds. 1. It could be bad to be noticed for reasons not related to your work. 2. (I’m more inclined towards this one) People should wear whatever makes them feel good (within the bounds of a reasonable dress code if applicable dress code).

  8. Jellyfish*

    #4 – A former boss used to speak very vaguely and expect me to follow his thoughts without context. He’d come up to me and say something like, “Did you ask her about his project?”
    Eventually, I could respond with “too many pronouns” and he’d fill in the relevant details. It took many agonized conversations to get there though.

    1. irene adler*

      That’s my boss too!
      He starts talking to me as though he’s carried on a good portion of the conversation in his head. So I have to ask him for “more road signs please! I’m not following what you are saying!”
      It frustrates him too.

    2. BossCantThinkStraight*

      Okay, my boss does this in both writing (emails/IMs) and speaking. I’ve tried SO many things to get her to fill me in. Any suggestions? At this point, I’m having to say it multiple times a day, so it’s sounding really condescending–esp cause she’s my boss. It’d be way easier to handle if I were her boss. But alas… help!

      1. Jellyfish*

        I don’t know if I have any useful advice unfortunately! It helped when I’d explain, “hey, I’m in the middle of project X, so that’s where my mind is right now. You’ve gotta give me more context so my brain can switch tracks. Who is ‘her’? Which project are you talking about? I need nouns.”

        I guess framing it as a me-problem that I needed his help solving made it feel less condescending? I’m not sure that was the best possible approach either though. My boss also knew he had some communication issues, so he was a lot more open to suggestion on the topic. He still used too many pronouns, but it eventually was more of an amusement than a problem.

        1. Not So NewReader*

          I shortened it down to:
          He… WHO? or She… WHO?

          Other times I went with:
          Where am I?

          “Do you remember the thing?” got answered with “Not yet.”

          And then there’s:
          “I need a few more words.”
          “Does yes means do A, or does yes mean do B or does yes mean do A as well as do mutually exclusive B?”

          It’s tougher when you actually like the person and they drain the brain like this.

  9. foureyedlibrarian*

    For #3, don’t stress about it. She may come from a location or position that did require her to dress nicely, so that’s just the clothing she has in her closet. Some people dress nicer because it makes them feel better mentally. I wouldn’t do anything beyond complimenting her clothes if you find them cute. Also, you mentioned she’s a recent hire, so maybe her style will calm down as time passes. This isn’t an issue and I don’t think you should make it one. Like Allison said, your work should speak for itself.

    Personally, I dress nicer than my colleagues at one of the libraries I work at (I’m temporarily at two different libraries at our university) because 1. I came from a city where that was the norm, 2. I like fashion, 3. when I dress better, I feel better about myself and 4. the other library is more formal, so I figured it’s better to have one wardrobe than buying two separate ones.

    1. many bells down*

      In my case, I spent a decade as a SAHM and before that had a string of jobs that were very casual. I want to wear cute shoes and feel pretty now! I want to dress like a Real Adult! And sometimes I just want an excuse to wear this 50’s dress I made with a narwhal print.

    2. EmmaPoet*

      Yes, I tend to be dressier than my coworkers, but it’s because I like being dressy. I like dresses and jewelry and color. I don’t wear heels because I fall over with anything over an inch, but I have a small wardrobe of pretty comfortable sandals for summer and boots/walking shoes for winter. People tell me how nice I look, and these things suit me and are what I like to wear.

    3. Dust Bunny*

      When I started my first office job I had previously been a veterinary assistant, so I literally owned only grubby weekend clothes and scrubs. I started over completely with a wardrobe of secondhand officey clothes. They all came from the church thrift store in the fancy part of town so it was all designer pencil skirts and cashmere turtlenecks, bought for $2 apiece because in addition to not having any decent clothes, I didn’t have any money.

    4. SarahKay*

      Absolutely seconding the advise not to stress about it.
      When I started at my current company I moved from a retail manager job – skirt suits, etc – to an admin job in a casual dress (i.e. jeans every day if one wanted) section of the new company. I took a couple of months to really adjust and start wearing jeans or casual skirts every day.
      Then one Friday morning, about six months in, I woke up and just did not fancy wearing any of my casual stuff. I’d worn it non-stop for the last four months, after all. So I went with the full skirt-suit, smart blouse and heels… and spent the whole day assuring everyone that no, I didn’t have an interview, I just fancied a change. (I later discovered that my suit-on-Friday was particularly noticeable because even the sections of site that did require more formal dress had dress-down Friday and would usually wear jeans.)
      A couple of years later I moved roles to the main office which had the more formal dress-code and was actually very happy to have the excuse to use my suits again, and to have that clean line between work-wear and casual-wear. In fact, I liked the line so much that despite working from home for the last year I’ve still chosen to wear work-clothes on work days – although for the sake of my downstairs neighbour I skipped the heeled shoes!

  10. Generic Name*

    #4 My son (who is autistic) does this, and it drives me bonkers as well. He’ll launch into some story, and I’ll have to stop him and say, “Dude, context”. Or I’ll say, “I can’t read your mind. You’ll have to use words to tell me what you are thinking”. Regardless of the reason why she does this, her behavior indicates that she actually doesn’t understand that your thoughts are separate from hers and she’ll have to put in some effort to explain things to you. I suggest sitting her down the way Allison suggests but add something like, “It really seems like you think I know what you are thinking, but I really don’t, so you’ll need to put the thoughts you have in your head into words and tell me out loud so I know what you are talking about.” This may seem harsh, but most people who have a tendency to forget to provide context sometimes (I’m constantly forgetting if I’ve told my husband something or I just thought it) realize it and will fill in the missing pieces when someone points it out. Your employee genuinely seems to not understand that you do not automatically know what she is thinking.

    1. Filosofickle*

      Good advice. My mind works fast and jumps around a lot, and I frequently change topics or start talking mid-stream. I honestly don’t realize people don’t know what I’m thinking — since I hear the voice in my head I kind of assume all that was verbalized. As an adult I’m pretty good at overcoming it but it’s a lifelong struggle to make sure I’m providing signposts as I talk. My childhood best friend and I worked out a system where I warned her with transition words like Tangent & Random so she knew I was about to say something confusing.

      1. NotRealAnonForThis*

        “Left Field”
        “Turn Signal!”

        Its been a lifelong struggle, ongoing, to get all of the thoughts and words out of my stream of conscious thought and into spoken (or written) word. Written’s a touch easier.

        1. Filosofickle*

          Writing saves me. I blurt it all out, cut 50% of the words, clarify what I’m actually trying to say, reorder it to get the important bit first, and voila I make sense.

    2. Not So NewReader*

      omg. I had a family member who was literally shocked to find out that people knew about things that she did not know about. This was a highly educated person and for the most part was actually very kind. But this became a tripping point… a big tripping point.

  11. Lifelong student*

    Re trainee with nice clothes- I was in your trainees position once. I actually may have posted this comment before on the same letter!
    I spent years working in a para-professional position where I dressed up both to make a good impression on clients and to promote being perceived as a professional by clients and co-workers. I later moved to another career where I was a certified professional- just when business casual became a thing.
    I had an extensive wardrobe of professional clothing- all classic things- which I continued to wear. Co-workers seemed to take umbrage at that.
    I was not willing to spend on a new wardrobe of sporty clothes when I had things I enjoyed wearing. Over the years, my wardrobe did change to some degree- but I still wore nice jewelry and other things I had acquired over the years. I found that comments were still made.
    I don’t dress for anyone else- I dress for me!
    Don’t judge others attire.

    1. Unkempt Flatware*

      Exactly! “Don’t judge others attire”. I dress the way I do so I don’t get treated like I’m the admin (no shade here I’m just not the admin) and asked repeatedly to make copies or something. I also dress the way I do so that my attire communicates, “don’t even think of sexually harassing me-I’m way too powerful” as I work in the construction industry and deal with BS too often. Let her do her thing.

  12. jen*

    This response may seem silly but maybe her previous job called for this dress code and now that she has a new job with a different dress code, she can’t afford to or doesn’t want to spend the money on more clothes. I was in a similar situation with my present job, it’s way more casual and I actually only had 2 pairs of jeans that I wore on the weekend. One pair was not appropriate for an office, even a casual one.

    1. pancakes*

      It doesn’t seem silly. It’s quite possible. It could also be the case that she simply likes the clothes she already owns and doesn’t want to buy a new, more casual wardrobe for this job just for the sake of blending in.

  13. Pay No Attention To The Man Behind The Curtain*

    #3 “it makes me feel a little uncomfortable and creates a lot of pressure for me to dress more formally…” I realize these are old letters and the OP is probably long gone, but they are insecure and need to work on themself, maybe in therapy, not decide that a coworker’s totally normal actions makes them “uncomfortable” and need to change. Management will definitely compare the two of you for future promotions — work ethic, professionalism, confidence, ability, etc. — previously you were the only one and felt secure, and now you will have to step up your game.

    1. jm*

      we’re simply socialized to be resentful of that sort of situation. i had a teammate who resented my promotion because she started a *month* before i did. never mind that she worked fewer shifts, so was not around when they needed someone in charge.

  14. Michelle Smith*

    Eh, while the first one might have been a creative writing exercise, it also could be real. In my last job, we played the Mega Millions every time the jackpot got pretty large. It would have been amazing had we won!

    These people’s biggest problem is they didn’t plan ahead for how to handle this influx of money. The first thing you do is call an attorney. There are some out there that specialize in representing people who come into large sums of money like this. You get the attorney to set up a trust and to represent you in the media/to family and friends that come out of the woodwork begging for cash gifts and charitable donations. Then you contact a financial advisor to make sure that you are set up in solid investments that will provide stable income over the long term. I have thought all of this stuff out and know who I would call for each piece of this and how the money would be spent. Plan ahead people! The last thing you want to do after getting a windfall is to lose your financial independence and be forced to return to work.

  15. Atlantic Beach Pie*

    For those asking if #1 is from a TV show: There is a British show called “The Syndicate;” it’s 3 seasons and each one follows a different group of lottery winners from a workplace lottery pool (syndicate is the British term for a group of people that play the lottery together). The second season has a similar plotline to this letter.

  16. Aggretsuko*

    You know, we make jokes about winning the lottery and quitting, but if you actually DO so, guess what, this happens. Most people have no idea how to deal with this stuff at all.

    1. EmmaPoet*

      Sad but true. So many lottery winners go broke, or worse. Google Jack Whittaker if you want a wild ride through the worst of winning the lottery- and he was a millionaire before he won!

    2. Archaeopteryx*

      A lot of people could either life simply off the winnings (small house, simple tastes) and not have to work, or keep working and have big splashy vacations and clothes and splurges… but too often they refuse to choose and try to do both. And end up with neither.

      1. ggg*

        I know someone who came into life changing money and did not appear to enjoy any of it at all. No travel, no fun extravagances, nothing. Just put it away and kept working and living their life as they always did.

        They died — at work. It was sad.

        1. Ice Bear*

          Wow, that is really taking it to the other extreme. Why did they even bother playing? I don’t play often, but when I do I like to dream about what I would do with it. Mostly buy my dream house, travel, and donate money to causes.

          1. Jenny20*

            “Came into” does not necessarily mean a lottery win. Based on the wording, I read that more as an inheritance windfall.

        2. Not So NewReader*

          Was the person sad?
          I can see if a person had been poor all their lives that just having the money in the bank could give them the sense of security they could not have any other way.

          I inherited some money from my father’s estate. It was not quite a year of my husband’s pay- but more than my annual pay. I spent some off the top on a decent car and some much needed air-conditioners. The rest I left in savings. Years later, my husband commented, “Every time I think what if one or both of us lose our jobs, I remember that money you set aside. And then I remember that we’d be okay for a bit while we looked for our next jobs.” The peace of mind was so very valuable.

          1. tangerineRose*

            I was thinking this, too. Also, maybe the person spent some of the money on stuff that wasn’t showy or stuff they didn’t talk about much. Maybe the person had some great vacations or bought stuff for their hobby or something.

        3. Marillenbaum*

          This reminds me of a great Kurt Vonnegut short story, “The Foster Portfolio”. The young investment advisor is taking on a new client, who appears outwardly to be a staid, respectable, lower-middle-class man. He has his full-time job and a part-time job at a diner, his wife reuses coffee grounds to stretch them, that sort of thing. It turns out, he comes into an absurdly large fortune, and refuses to touch it. He lets the investment advisor do whatever he wants, but he keeps his side job to pay for things like Christmas presents or a new TV. I won’t spoil it, but it was fascinating to find out why he refused to change anything about his life.

        4. Marillenbaum*

          This reminds me of a great Kurt Vonnegut short story, “The Foster Portfolio”. The young investment advisor is taking on a new client, who appears outwardly to be a staid, respectable, lower-middle-class man. He has his full-time job and a part-time job at a diner, his wife reuses coffee grounds to stretch them, that sort of thing. It turns out, he comes into an absurdly large fortune, and refuses to touch it. He lets the investment advisor do whatever he wants, but he keeps his side job to pay for things like Christmas presents or a new TV. I won’t spoil it, but it was fascinating to find out why he refused to change anything about his life.

  17. Emily*

    LW3: Your coworker choosing to dress somewhat out-of-place reflects on you less than you think. If the dress code is really informal, then no one is thinking “LW3 is sloppy”, they’re thinking “huh, that’s interesting that New Person is dressed up.” Maybe in a positive way, maybe in a negative way, who knows. But she’s not singlehandedly changing the norms around dress code in your organization — you’re still doing the normal thing, she’s still doing the atypical thing, you don’t look bad by comparison.

  18. Chantel*

    Oh, wow, easily one of the most definitive dilemmas on this blog ever, in my opinion. If I ever wanted an update, it’s on this. And the tragedies the OP mentions – overdose, prison – remind me of what I’ve read about the problems lottery winnings can cause.

    I hope things work out for the best, OP, and I’m sorry you and Mary are experiencing this.

  19. bubba*

    For #4, I used to get this complaint from a manager all the time. The reason I had what she called “a communication problem” is that she would often start yelling at me in the middle of meetings or cut me off for what I was “going to say.” If I was really, really, lucky, she would just tell me my idea was “stupid” and then walk all over the building shaking her head and saying “stupid, stupid, stupid.”

    She was stressed out by a number of different things, and I guess I was her punching bag. She would always forget what she had assigned me and when I would catch her to follow up, she wouldn’t remember what I was talking about. I would go to talk to her with a perfectly framed idea or situation, and as soon as I opened my mouth she would roll her eyes and glare at me and I would get flustered and start stammering because I didn’t know what she was going to pick on to start screaming at me about.

    I even went out and got professional communications coaching because of my “communication problem.” They gave me my money back and said I didn’t need it.

    1. Goldenrod*

      She wanted you to be a mind-reader. In other words, she was projecting her OWN communication problems onto you! Classic. I’m glad you got out of there!

      1. bubba*

        Thanks! The worst part about quitting was that I had a meeting with her at 2:00 where I was planning on telling her exactly why I was quitting before I walked out in a blaze of glory.

        Then she called a meeting at 1 and quit herself because her mother had died and she wanted more time with her family. I felt bad for her and ended up staying on for an extra month to help her with the transition.

        The therapist I saw for PTSD after I quit did keep my money.

    2. Myrin*

      That sounds like an incredibly frustrating and demoralising situation, but I don’t quite understand how it relates to this letter – are you suggesting that the OP is in fact the problem and behaving like your old manager did?

      1. bubba*

        I’m suggesting that maybe the OP is the problem, but maybe not! None of us are there so we can’t say for sure, but it’s something to consider.

    3. Not So NewReader*

      I always wonder how these people land later on in life. I mean this person you describe here sounds like she is falling a part. To my way of thinking, she has to either stop and collect herself up OR what happens next will not be good… at all.

  20. Tomalak*

    I worked for someone who spoke in half-sentences or less and it was a total nightmare. He clearly thought I was being a pedant, a difficult person, when I questioned him further. All I wanted was the rest of the sentence. You can do all kinds of amateur psychology about what was going on in his head but it was just awful.

    1. Not So NewReader*

      I had a prof who never completed his sentences in class. I gave up trying to take notes. It was the worst class ever.

    2. tangerineRose*

      I used to work with someone who would start a sentence and then stop partway through and kind of nod and give us a look like we knew the rest. I never, ever knew what the rest of it was. Fortunately, he usually was just chatting, not talking about work stuff when he did this, but it was still so frustrating.

  21. Goldenrod*

    For Letter Writer #3: I think it’s unfair to expect someone else to change how they dress because it makes YOUfeel uncomfortable! I work in a very casual office but I’m someone who prefers to dress up for work. It’s certainly not to make anyone else look bad or feel less-than! It’s because it makes ME feel more confident.

    Everyone can make their own decisions about how they want to dress at work. But expecting someone to dress down just to conform is unreasonable! (In my opinion….)

  22. Phony Genius*

    People in office lottery pools need to realize that rarely will the winnings be enough to quit your job on. Twenty people sharing $1 million is only $50,000 each, and that’s before taxes. It’s even less if an annuitzed jackpot is converted to a lump sum. And a million dollars can disappear very quickly. Employees who join a lottery pool should expect nothing more if they win than to be able to “upgrade” their life, but not run away and start a new one.

    (And what do you do when 23 people have to share a $2 prize? When it happened to us, it was not even enough to buy a bag of candy to share.)

      1. Frank Doyle*

        Yeah, you put it in the pot for the next time the jackpot is big enough that you guys buy in again. (Which is usually in three or so days, since they keep getting bigger until someone wins it.)

    1. Elenna*

      This. I figure I would need to win about $4 to $5 million just on my own, to get enough money to quit my job. And that’s not “multimillion lavish lifestyle”, that’s “buy a condo and then budget on an annual interest income of 50k a year or so after taxes”. (Not that I play the lottery, but it’s a thing to occasionally daydream about.) You really have to sit down and write out what everything will be spent on before spending any of it, something which is often not easy for people who have not been taught how to handle large sums of money.

    2. Noncompliance Officer*

      I advocate for a ring of weapons with the two dollars in the middle, Hunger Games-style.

  23. Sunflower*

    #1 I remember when the lottery letter first posted a few years ago. I wonder if there was ever an update. That is, if the letter was real.

    1. Rusty Shackelford*

      The LW responded in the comments at the time, but I’d love to get an update!

  24. BRR*

    #3 because it sounds like you’re in the same role, I’m having a hard time to think of a situation where it’s appropriate for you to say anything. Maybe, in a small number of situations like if you met with clients and your coworker’s attire was making clients uncomfortable, you would mention it to your manager. But in this specific letter I don’t really think you’re able to say anything because you’re worried her attire make you look like a worse employee.

  25. Grim*

    Commenting on work dress, I started a new job and for the 1st several weeks I wore my normal work attire: dockers, leather shoes button-down shirt. Since I was new, many people would come and introduce themselves to me, thinking I was a manager. As most of the people introducing themselves to me where my peers (engineering), I started dressing like them in T-shirts. jeans and tennis shoes and I fit right in.
    It was kind of a drag, because I had an extensive wardrobe of dockers of various colors and various long sleeve button-down shirts. My collection of T-shirts and jeans grew over time and felt comfortable wearing them at work.
    If I wanted to be a manager, I certainly would have kept wearing the dockers and button-down shirts and would have been a step in the right direction for being viewed as a manager.

  26. J.E.*

    #1, I’ve heard of the lottery curse. I think I even saw a documentary about lottery winners who let it go to their head and spent all the money then had nothing. Some lottery winners act like they’ll be getting paid the amount of their winnings every year for the rest of their lives, not that it’s a set amount and if they aren’t careful it will all be gone. They probably should take the option of getting their winnings dispersed in the form of a monthly allowance and have a financial adviser to protect and help grow the winnings.

    1. Beth*

      Yup, nailed it. The idea of winning the lottery is “I’ll have enough money to do everything I want for the rest of my life!” Well, no; there is no sum of money large enough that it can’t be overspent. Even the lottery winners that agree to take their winnings in annual installments frequently overspend the installments so badly that they end up having to sell their future stake in the pot, just to dig themselves out of the hole.

      The same thing happens to the suddenly hyper-rich (such as rock stars) — they start buying million-dollar toys that require millions in upkeep, and poof, they’re broke. In fact, they’re in debt, because those multi-million-dollar payouts come with a lot of expenses, including taxes.

      I remember reading about Johnny Depp suing his financial advisors, because they never invested any money for him. They never invested anything because he spent it faster than he made it, and ignored them when they suggested that he reduce his spending.

  27. IrishEm*

    Holy conflict of interest, Batman!

    LW, you and Mary are absolutely right with your instincts, and I say that as someone with no managerial experience whatsoever. Mary will not be able to manage these ppl, they will think they can walk all over her because she used to be on the bottom rung when they left.

  28. Good Wilhelmina Hunting*

    #4 sounds like the type of person I’ve come across that goes around accusing others of not having “common sense” because they’re not a thought reader and want things explained properly.

  29. Beth*

    LW #4 — I have known WAY too many people like this, who apparently expect ongoing telepathy from anyone they’re talking to. I’ve never had to supervise one, but I spend way too much time playing Twenty Thousand Questions with my co-workers.

    (Especially when they need help with IT. “My computer isn’t doing things right.” What things? “That program.” Which one? “The one, you know, we use all the time.” No, I don’t know. “Excel.” What’s the problem? “I got an error message.” What did it say? “I don’t know, I closed it. Then it happened again.” What were you doing when it happened? “I don’t remember.” And on and on and on . . . )

  30. LurkNoMore*

    This happened in the early 90s, a person who played the lottery every week called her boss and told him she had won the lottery and that she quit!!! Lottery winner wasn’t derogatory during the call but you could tell they were excited about not having to work again. Boss asks winner if they are sure about quitting and don’t they want to take some time to think about it? Nope – winner and her husband were on their way up to Sacramento to turn in their ticket and claim the prize.
    Another call comes in a few hours later (about half way to Sacramento), winner was mistaken about the ticket and the numbers didn’t match this week’s ticket….could she have her job back?
    This has been my go to cocktail story/wedding table ice breaker for years….

    1. Mallory Janis Ian*

      Wow, she tipped her hand before she had even verified the ticket!? I wonder if she learned any kind of lesson about keeping your mouth shut until things are for certain or if she just continued to act before thinking.

    2. Cedrus Libani*

      I heard a similar story, possible urban legend but still entertaining: the office had a tradition of buying scratch-off lottery tickets, and someone slipped one of those fake winning scratch-offs into the pile. The coworker who got it, believing themselves to be $250K richer, activated the “take this job and shove it” protocol. Midway through quitting in a blaze of glory, they realized the ticket was fake…but having just told everyone precisely what they thought of the boss, the job, etc…their resignation stood.

  31. Anonymous for this*

    I have a team mate like the one described by LW #4. A colleague called her an “information hoarder.” She uses pronouns instead of using the real words, can be very vague about things, and sometimes just plain doesn’t share. That is, doesn’t share until she gets into a meeting and can present herself as very knowledgeable. But then she will say she told us about it when we were talking last week and she spoke about “that thing” and, of course, no one pinned her down because we were all exhausted from trying to pry information out of her. She does it with our boss, too. I think it is a habit, rather than meanspirited. She has said some things that lead me to believe that she developed it as a defense mechanism against a very boundary-crossing family. I encourage the LW to do her best to get her employee to change her ways.

  32. ahhh*

    Was there ever an update to this post? I think the original post was from a few years ago. OP can you let us know how this turned out?

    1. NerdyKris*

      No update it seems. A month ago Alison had hired someone to go through all the old posts and adding a link to an update if there was one. It’s fun to pop back into an old post and suddenly realize there was an update I never knew about.

  33. ElleKay*

    So, Mary needs to speak up.
    If she’s not comfortable managing these people then she needs to say so before he overrules her.

  34. TimeTravlR*

    Re the clothing question (#2) at the link. I was taught to dress for the job you want, not the job you have. Perhaps new hire is thinking that way. For me, going from a very buttoned down culture to a much more casual environment was really hard! It took me a long time to accept that I could actually wear jeans to work all the time. She may relax over time. Give her a minute.

  35. Firecat*

    I do that terrible communication thing with my husband. Basically when I’m not polished and am potentially distracted I can communicate like that.

    At work I just don’t speak while I am in what I call “fracture state”. I’ll also make sure I have my thoughts in order before hopping into my bosses office with a question.

  36. SeanT*

    Rule #1 of Office Life, if there is a loto pool you play it.
    You don’t want to be “the one” who is left behind.

    And you know, drugs are bad, don’t spend your lotto money on them.

  37. Smitten By Juneau*

    For LW #4 I once had a colleague like that. She came from a business formal environment (admin in our business school) while we on the central IT help desk (all phone/chat email – no face-to-face contact) dressed way down. It turns out that her wardrobe was all business clothing, or work around the house on weekend casual, so it took her a while to build up a wardrobe that was less formal. I think it also took some time for her to wrap her mind around our manner of dress being “OK”, and she almost never dressed as casually as most of us. For that matter, I almost never wore jeans and t-shirts, and tended to stick to khakis and polos, sort of low-end business casual (but I also came from a corporate environment.)

  38. HiHello*

    LW #3 – there is no way I would wear a tshirt and jeans to work, even in the most casual work environment. Jeans and tshirt is something I may wear to go grocery shopping. It still would be a nicer tshirt, though. Normally, when I am at work or seeing my friends, going to movies, having dinner, drinks – I am ALWAYS dressed up. It’s because this is who I am as a person and I am not dressing down because someone finds me dressing up uncomfortable.

  39. Kate 2*

    I have only seen one other person mention this, so I’ll add my thoughts re 3. I inherited bad genes from both sides of the family, health genes and mental health genes, but the one thing I did get was the good aging genes! One side of the family perpetually looks 10+ years younger than they are. I am 31 and get mistaken for being under 18. Mostly it’s been annoying, I’ve been ignored, laughed at, and discounted for most of my life due to my perceived age, not to mention lost out on opportunities. I know as I get older I’ll appreciate it more, but mostly I just want to get taken seriously!

    So I’ve learned to bring my age up early when I meet people, ex “college was almost a decade ago” or “I was too old to watch that kid’s show”, as people mention things like their favorite show as a kid, etc. The other thing I do is dress up, much more than required. And sadly it has a huge effect on how people treat me, even after they have gotten to know me. I have a cringe reflex towards anything “youthful” looking, and aim for things that age me. Pearl necklace and earrings, older style analog watch, darker toned clothing, tailored cuts, matte lipsticks, etc. I stay far away from “cute” or trendy jewelry, shirts with writing, pastels or bright colors, bright lipsticks and bright or colorful eye makeup, ruffles, lace, etc.

    And as another commenter said having a big difference between work and home clothing reminds me to behave more professionally: no whining, gossiping, swearing, etc. Nothing really bad, just things like: I hate answering the phone!” or “Did you hear what Donald said to Maxine?”. That’s enough to get you fired at worst at some places I have worked, at others it would “just” ruin your reputation with the boss and your coworkers, even as they listened! So yeah, I’m that person who overdresses at work.

    1. Roja*

      Your first paragraph is exactly how I feel. I’m 30 and have only in the last year or two looked old enough that people take me seriously. It’s doubly frustrating because if I mention that it’s frustrating, people just say I should be happy about it. No, I’m not happy that I’m being treated like a teenager! I’ve been a professional adult for a decade!


      1. allathian*

        Sounds familiar. I was still getting carded at 30, and the drinking age here is 18. I just laughed it off. By the time I got to 40, the law changed and now cashiers are expected to card everyone they think looks under 30. Even then it happened once or twice. By that time, I could take it as a compliment!

        I get it from my mother, she smoked most of her adult life and at 75 she could pass for 60.

  40. singlemaltgirl*

    thanks :) i was soooo curious. doesn’t look like there was another update other than to comment that all the lottery winners spent their money but only a few applied to come back. they had all left with zero notice. mary seemed like a decent sort but was afraid (i think reasonably so) about the attitude of these returning employees and they only had entry level roles available.

    frankly, i hire for attitude as much as anything else. if your attitude is entitled or your embittered or whatever, that’s just a strike against you when, as someone earlier said, there are so many people out there with great attitudes that you can work with. you don’t burn bridges for a reason. i think these folks burned that bridge (based on the update) so i wouldn’t even be giving them interviews.

  41. X-Man*

    I’m sorry but “they’re bitter about having spent all the money” is kind of hilarious to me. Why would you feel ‘bitter’ about you’re own spending habits? Did they feel entitled to just receiving more free money for life and are somehow surprised that’s not what the lottery is?

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