updates: the shady investor, the needy boss, and more

Here are three updates from past letter-writers.

1. Should I work with this investor or run for the hills?

My letter was actually published the same day I was leaving for a vacation. While I was away, I had some time to really reflect on your response and think through my next steps. What stood out to me the most in your response was when you said that this investor seemed cavalier about my protection; after reflecting on my interactions with him, I think this statement hits the nail on the head. I am also incredibly grateful to the commenters for sharing words of wisdom. Nearly everyone was urging me to not pursue this opportunity. Several people had even expressed that they were in similar situations that didn’t pan out the way they had hoped. I knew in my gut that something wasn’t right, and I think I just needed some validation.

I came back from vacation knowing I would not be taking part in this opportunity and interestingly enough, I never heard from the investor again. This pretty much confirmed exactly what I was thinking in the beginning, which was that he was perhaps viewing me as a means to an end. To be fair, I did not bother to reach back out either. We essentially both ended up ghosting each other. I am glad I did not spend any of my time giving him my ideas or knowledge; my husband recently started his own business, so instead, I’ve been pouring my free time into helping him grow it. It’s been extremely fulfilling, and I am able to get that “entrepreneur bug” out of my system!

I sincerely wish this investor the best in his business endeavors, but I’m happy I didn’t take him up on this offer.

2. My new boss needs constant reassurance

The good news is two-fold: Jim has had some wins in his area of work that seem to have calmed his anxiety at least to the point he’s not fretting at me constantly about his own work. He’s definitely an anxious person though — I hear from him at least once a week about how much he’s worried that generative AI is going to take over his job. That’s easier for me to ignore than a stream of anxieties in our one-on-ones though. The other part of the good(ish) news is that due to some big miscommunications with him, I implemented shared note-taking for our one-on-ones and that has turned out to also help give our meetings better structure. We have a shared running document where we add notes about the current meeting at the top and save all the previous ones below. We both add agenda items to this document. It’s definitely helping keep our weekly one-on-ones on track and gets me around the issue that I don’t want his advice on anything I’m working on because I can think more carefully ahead of time about what to discuss (oddly, he’s constantly suggesting I use generative AI on my work tasks, even though he’s super anxious about this technology — I ignore that advice too).

The bad news is that his anxiety is the least of his problems. He works incredibly fast on projects that really need thoughtful work, says yes to everything with no prioritization for our team which has resulted in us being signed up for work that is nowhere near what we should be doing, and makes a lot of mistakes. After more than a year in this job, he still doesn’t understand the fundamentals of our technical field. I spend a lot of time correcting his misconceptions, although I’ve realized it doesn’t really do much good so I’m trying to pull back on doing that too. My grandboss, Jim’s boss and my former manager, is highly uninvolved in our team’s work to the point I doubt he is seeing the majority of Jim’s mistakes. All this to say, I am pretty sure I’m not long for this job, which is disappointing because it used to be a great position. I have hired a summer intern so am planning to stay through the summer since there’s no one else to mentor them, but am thinking of giving notice at the end of the summer and working as a freelancer/contractor for a while. Very excited to be my own boss! Thank you again for your great advice.

3. I deliberately over-claimed a tuition reimbursement (#3 at the link)

Shortly after I emailed you, I actually got offered a much higher-paying job at a company in California and decided to take it, so I ended up just paying everything back in full and it feels like a weight off my shoulders. I’m much happier at my new job too and have a lot less stress. I wanted to say thank you again for your advice – it was very much appreciated.

{ 30 comments… read them below }

  1. Zombeyonce*

    I’m really glad that #1 didn’t continue to put time into working with that investor. LW said they were a “successful entrepreneur and investor” but didn’t want to share any info about their existing companies, so I really wondered how successful they really were, especially since LW couldn’t even be sure they were legitimate. It had the reek of a scam to me. I wouldn’t have been surprised if they were not only asked to work for free, but to start contributing their own money “for the business to succeed” or “to show their commitment” after a while.

    1. Jinni*

      The last “successful” investor/entrepreneur I met who wanted my input…didn’t really have a business that functioned. He had a website that didn’t work despite having claimed that he had been a web developer for 20 years. He had a partner who did coaching and taught exercise classes and meditation (that wasn’t the business). After asking a LOT of questions, what he said was that he had a *million dollar idea*

    2. dogmom*

      Yeah, it sounds like an MLM, but I’m sure LW1 would have mentioned if it was Amway or Primerica or something.

  2. Sloanicota*

    #3 controversial opinion, but I’m really struck by how these tuition-reimbursement plans are being implemented. The original program had enough restrictions that OP was still stuck paying for what were for her significant expenses (which is why she had the temptation not to split out the different costs and get more reimbursement) *and* she had to repay in full because she left her job. I’m getting some real “company store” vibes. Congrats OP for resolving your moral dilemma honestly and on the new job.

    1. Radioactive Cyborg Llama*

      I don’t think it’s unreasonable for a company to only want to pay for tuition if it is going to benefit the company.

    2. GreenShoes*

      Tuition reimbursement payback if leaving the company within X time is pretty common along with not being reimbursed for fees.

      I mean, I don’t think it’s unreasonable for a company not to want to pay for things like student health services, university recreation, campus radio, etc. Most will pay for things like lab fees and books.

      1. Sloanicota*

        Ok, I admit I don’t know a lot about this, but why is the company offering tuition reimbursement specifically, rather than more money (which could be used to pay off loans)? Is it so the program can be targeted at younger / more entry level employees? Or is there a government or tax incentive to this type of program that makes it more advantageous to offer than cash?

        1. Insert Clever Name Here*

          It’s usually for something directly required for the job or for advancement at the company and that you are working on while you’re employed with the company. So as a supply chain professional my BA in History is not something that my company would reimburse me for, but they may reimburse a portion of an MBA because ostensibly the things that I will learn in that course will directly benefit the company. If the company gives me more money in my paycheck I might decide to put that towards a new patio rather than getting my MBA.

          1. Insert Clever Name Here*

            And since you specifically asked about targeting younger/less experienced employees, fwiw I’m in my late 30s and while not in management am in as senior a position as I can be in my department without going into management. If I wanted to make myself more competitive for management positions, I could go for my MBA and my company would reimburse it (but I don’t happen to want either of those things).

        2. GreenShoes*

          It’s advantageous for both employer and employee to keep it as a specific benefit. Anything up to $5250 is tax free for the employee and tax deductible for the employer.

          Plus, it’s way to control the use of the dollars. There’s no recourse if a company offers that money as salary to an employee to study Accounting only to find out the employee actually is studying Zoology, or just taking the money and not studying at all.

        3. Fluffy Fish*

          realistically because cash/putting the money towards student loans would cost them more. theres more employees already with a degree than employees pursing a degree. typically theres also stipulations on grades required, what degree programs are eligible, caps on how much they’ll pay and even caps on how many people they’ll cover a term (first come first served)

        4. Warrior Princess Xena*

          My firm offers reimbursement for the funds used for our professional exams + preparatory materials, which can be pretty hefty. And it’s mostly because the company is saying “we want people with X set of skills and are willing to reimburse some or all of the money involved in getting X set of skills”.

        5. MassMatt*

          In many fields, you need to keep learning to keep skills up to date and stay abreast of change. Science, finance, technical fields all have tons of licenses, certifications, etc. The world is changing, faster than ever, and if you don’t continue learning you risk getting left behind.

          I got several licenses and a major certification (maybe roughly like a CPA) on my former employer’s dime. These gave me a big leg up earlier in my career. Jobs further up the ladder place more and more emphasis on them until they outright require them.

          I get that not every career needs more education, and not everyone has the time and energy to do it. But IMO failing to take advantage of tuition reimbursement is leaving money on the table, akin to not taking advantage of retirement plan matching contributions.

      2. Sandi*

        I think it depends on the context, as always. I have taken college courses on coding that were more useful and much cheaper than intensive week-long ones offered by companies, so I expected my workplace to pay for all the related fees. In that case they wanted me to learn a new topic.

        I agree that paying back the tuition within X time is very reasonable, provided it is clearly stated and ideally it’s a sliding scale (pay back 75% after 6 months, 50% after 9 months, etc).

      3. Ginger Cat Lady*

        I mean, a lot of STUDENTS don’t want to pay fees for all that stuff, but they’re stuck with them. I did a masters as a *distance student* and never set foot on campus, and still had to pay fees every semester for the health center, the rec center, computer lab fee, and they even tried to force me into a meal plan.
        If I could have just paid tuition & books, I would have been a lot happier, too.

    3. DisneyChannelThis*

      Yeah I know several people who didn’t go back to school even though company had tuition reimbursement because they didn’t want to lock themselves into working for that company for that long. There’s a real fear too, that once company knows you can’t leave without paying back tuition (20k-60k) that they are going to mistreat you.

    4. Fluffy Fish*

      I think your quibble is with the cost of education more than the company.

      Tuition reimbursement benefits both the employer and the employee. The employer gets an employee with upgraded knowledge/skills and the employee gets a discount that will (potentially) increase their salary through their career and that they can eventually take with them.

      It would be bad business for an employer to invest $$$ in an employee without asking for some kind of return on their investment.

      That said I have seen some CRAZY requirements. Like 5 years for every semester.

      1. Nobby Nobbs*

        5 years for every semester?! At that point it’s just indentured servitude!

        1. Fluffy Fish*

          i suspect the goal was to say the “offered” a benefit but not actually want anyone to use it.

    5. Ellis Bell*

      It struck me as a bit dodge that it wasn’t made clear to the OP what bills they would be stuck with before embarking on the course. I don’t know if that’s the employer’s fault, or the educational facility or what but I don’t think it’s an okay situation to leave someone in.

      1. Zephy*

        Eh, the original letter mentioned that the school’s billing structure was a little weird – like, they charged almost half the cost of a given course as a “fee” rather than “tuition,” so it’s possible that whatever their bursar is doing is so unconventional that no reasonable person would have even thought to ask. Or maybe OP should have spoken with the school’s financial aid or bursar’s office before enrolling, hard to say without knowing all the details. But the company has the right to follow their policy as written. I’m glad it worked out for OP in the end.

    6. Tesuji*

      Eh, the restriction she ran into was that the company covered tuition but not all fees, which seems reasonable to me.

      I would imagine the scenario the company is thinking of is one in which someone buys a computer/software or runs up expenses for a field trip the class is going on, which the college is happy to include on their bill.

      We don’t know enough about the situation, but there is actually an ongoing issue these days of colleges trying to hide tuition increases by adding more and more required fees on students.

      I could easily see a scenario where HR gets a bill that shows fees for campus childcare, fitness facilities, or just “health and wellness” (all of which are things that some colleges have as mandatory fees rather than part of tuition) and have the reaction that those aren’t the kind of things the company reimburses for.

      1. Ginger Cat Lady*

        Universities absolutely pull crap like this. My daughter got a “full tuition” scholarship and committed to the school thinking she would not pay tuition. But it turned out that was only “full tuition” for the base university tuition. They also charged “differential tuition” that was for the college the classes were in at the university.
        And the “differential tuition” was not included in the scholarship. And it was 60% of the overall tuition. If you count mandatory fees for everything they could think of a fee for, it was only about 35-40% of the cost of attending that school. She was pissed. And she tells them that every time they call her for more money, right after asking AGAIN to be removed from their call and email lists.

    7. Captain Swan*

      This type of benefit program is incredibly common in my field. I have had previous employers pay for my PMP prep class and exam fees as well as roughly two-thirds of my MBA. Every time I put in a request for funds, part of the form was an acknowledgement that if I didn’t stay with the company for a specified period of time after the funds had been paid out I had to pay back the remainder. That didn’t apply if the company laid me off. it’s a (usually) good deal to enhance your credentials.

  3. Devo Forevo*

    #2, all my sympathies with your anxious boss. The only thing AI has helped me with in the workplace is building Excel formulas without having to learn more about Excel :)

  4. Captain dddd-cccc-ddWdd*

    Update 2:

    > The bad news is that his anxiety is the least of his problems. He works incredibly fast on projects that really need thoughtful work, says yes to everything with no prioritization for our team which has resulted in us being signed up for work that is nowhere near what we should be doing, and makes a lot of mistakes.

    All of these issues could be linked to anxiety — I think untreated/undertreated anxiety could be the root of most of his problems. Rushing through projects rather than give them deeper thought – potentially he gets anxious that they are “undone” and have deadlines looming. Says yes to everything – anxiety over implications of pushing back against the person making the request, etc.

    I can understand the fear around Chat GPT etc making humans redundant, and he certainly isn’t alone (based on what I see around LinkedIn etc) in worrying about the implications of those AI models.

    As an anxiety patient (now well controlled with medication) I recognise some of this, not the specific details but the pattern. I think it is common to “fixate” on something and then something else and so on. Once the anxiety inducing thing is resolved or goes away by itself, it’s like there’s a nemesis “vacuum” to be filled. It’s worse having undifferentiated anxious feelings than having something to attach them to, make it concrete.

    I hope he is able to get help with this someday.

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