This is your reminder to never trust anyone from leadership

TLDR: Our CIO encouraged me to work from home while I was recovering from surgery. Now that I’m trying to go on leave, he’s holding it against me.

I had surgery a few months back. I had told management that I would need a week off of work, and I’d be able to work remotely for a week, and then work at the office after that.

Surgery recovery was a bit more difficult than what I had anticipated, and so I asked for an extension for the WFH. The WFH approvals go to our CIO, so on the day I was supposed to return to office, I went in person to his office and as soon as he saw me, he started encouraging me to work from home, and to play it by ear week by week. So, based on this, I decided to extend the WFH another two weeks, which he approved.

Fast forward a few months and now I’m being told that my annual leave might be reduced by half because of my attendance. Apparently, the CIO doesn’t like it that I took 1 sick week, and 3 WFH weeks, and a couple of annual leave days here and there. He’s also holding it against me that I left work early one day (We have 10 hours a month for short leaves, and I didn’t go over those 10 hours).

It’s absolutely ridiculous that I have to deal with this. I had a pretty major surgery and I spoke with management about before and after my surgery. Now that I actually want to go on leave, they make a big stink of it.

Jobadvisor

That's a genuinely maddening situation — you did everything right, got explicit approval at every step, and now the person who approved it is the one penalizing you for it. That's not a small inconsistency, that's the CIO contradicting his own decision.

A few things worth pulling apart here:

The core problem: he verbally encouraged the extended WFH "week by week" and approved it — which means there's an approval trail. If your leave/attendance is now being penalized specifically for time that was explicitly sanctioned, that's the crux of your case. It's worth asking yourself: do you have anything in writing? Even a Slack message, email confirming the WFH extension, or a calendar note referencing that in-person conversation would help. If it was purely verbal, it's still worth writing a dated email to yourself or a colleague summarizing what happened, now, while you remember it clearly.

Separate the streams: it sounds like they're lumping together a few different things — sick leave (medical, usually protected differently), approved WFH (his own call), short leave hours (within your allotted 10/month, so not even a violation), and annual leave days. Attendance policies that cut annual leave for using approved leave categories are unusual and worth pushing back on directly, ideally by asking HR to clarify the actual written policy on how these interact.

Worth checking:

• Does your company have a written attendance or leave policy you can point to? Often "reduced annual leave for attendance" schemes have exemptions for medical/approved leave that this may fall under.
• Is there an HR function separate from the CIO you can loop in, especially given the medical nature of this?
• In some places, surgery-related leave has legal protections that supersede internal attendance policies — worth knowing what jurisdiction you're in if you want to check that angle.

Do you want help thinking through how to raise this with HR, or drafting something that lays out the timeline clearly (dates, what was approved, by whom)?

If you could start over in your 30s, what career and city would you choose?

I’m in my early 30s, single, living in the South, and having a bit of a life crisis.

I work in finance at an executive level and make good money. On paper, I’ve done pretty well for myself. The problem is that I genuinely don’t like my day-to-day life. I spend basically all day at a computer doing emails, PowerPoint and meetings. I don’t mind working hard or working long hours, but I want to feel like I’m actually doing something interesting and meaningful and have some ownership over what I’m doing.
I’ve always been very split between analytical and creative. I love deep research, problem solving, getting into complicated situations and figuring out the story behind them. But outside of work I paint, do pottery, yoga, etc. I don’t think I’d be happy in a career that was 100% computer work forever.
I’ve been seriously considering going back to school for law, medicine, an MBA, or something I haven’t thought of yet. I’m genuinely open to starting over, but every time I talk to someone about it, they immediately point out how much money I’d be leaving on the table by walking away from finance. And they’re not wrong. I just don’t know how much I should prioritize maximizing income if I already know I don’t want to spend the next 20 years doing this.
I also really want to move. I’d love to live near the ocean, but a genuinely walkable city would also make me happy. I’m open to places like NYC, LA, San Francisco, etc. I don’t love extreme heat. I could easily do a bunch of 3–4 day trips and see how different cities feel before making a decision.
The problem is that I have ADHD, and too many options honestly make me freeze 😂. So if you recommend a city, please tell me WHY. “Try X because it’s walkable, has strong career opportunities, you’d like the lifestyle, and here’s what I think you’d love/hate about it” is much more helpful to me than a list of 20 cities.
Same with careers.

People always say “try different things,” but how do you actually try being a doctor or lawyer before committing years and a huge amount of money?

So if you were in my position, what would you seriously consider?
Would you change careers? Go back to school? Stay in finance and find a different role? Move first and figure the career out later?
I’d especially love to hear from people who were in their 30s, had a comfortable/high-paying career, and decided to make a major change. What did you do, and what do you wish you had known beforehand?

Jobadvisor

Okay, I'll actually engage with this seriously rather than hedge.

On the money question first, because it's the elephant in the room: the people telling you what you're "leaving on the table" are doing a calculation that only makes sense if lifetime income is the only variable. You already know you don't want to spend 20 more years doing this — you said so yourself. The real question isn't "can I afford to leave money on the table," it's "what's the actual cost of staying in a life I don't want, priced in years, not dollars." That's a legitimate trade to make consciously. It's not reckless just because it's non-standard.

On law, medicine, MBA — be honest about what each one actually is:

• Medicine is a 7-10+ year commitment before you're practicing independently, and most of it is not "deep research and figuring out the story behind things" — it's memorization, grinding exams, and years of low autonomy as a resident. If you like puzzle-solving and human stories, some specialties (psychiatry, internal medicine, pathology) scratch that itch — but the path there is brutal and long, and starting your first year of med school in your mid-30s is a real, specific kind of hard. I wouldn't rule it out if you feel a genuine pull, but I'd want you to shadow doctors and talk to residents before touching an application.
• Law is faster (3 years) but the reality for most lawyers is also heavy computer/document work — a lot of people leave finance thinking law will be more "meaningful" and land in doc review or contract work that's just as soul-crushing, minus the pay. The interesting, story-driven legal work (litigation, certain kinds of public interest law) is a minority of jobs and often pays worse than finance, not more.
• MBA — honestly, this one seems like the weakest fit for what you're describing. You already have the executive-level finance background; an MBA mostly re-shuffles you within the same kind of work you're trying to escape.

What I'd actually consider in your shoes: you've described yourself pretty precisely — analytical + creative, wants ownership, doesn't want 100% screen time, likes investigating and untangling complicated situations. That combination points less toward "which graduate degree" and more toward roles/industries that already exist and don't require starting from zero:

• Something in design, architecture, or product — professions that are simultaneously analytical (constraints, systems, problem-solving) and physically/creatively engaged (materials, space, form). Your pottery/painting instinct isn't incidental here.
• Investigative or research-heavy work outside finance — think due diligence/forensic work adjacent to your existing skills but applied to something you actually care about (art authentication, environmental investigation, certain kinds of journalism or intelligence work).
• A skilled trade or craft business built around what you already love (pottery, in particular) — not as a hobby-turned-side-hustle cliché, but seriously: people with executive-level financial and operational skill who go into running a serious ceramics studio or small creative business often do far better than people without that background, because they actually know how to run something.

How to "test drive" instead of committing blind: you can't shadow-a-year of law school, but you can do a lot more than people admit:

• Paid or unpaid short stints — many law firms/hospitals/design studios will let a serious adult sit in, shadow, or do informational interviews for a day or a week if you ask directly and aren't shy about your situation.
• Take one class, not a whole program — a community college or extension course in a field you're circling (a design fundamentals course, a paralegal certificate, an EMT course if medicine keeps calling) is a cheap, fast gut check.
• Talk to people 3-5 years into the career, not people who just started (rosy) or people who are burnt out and bitter (skewed) — aim for the middle.

On the city — my actual pick, with reasoning: I'd say Chicago first, but since you specifically want ocean + walkability + not extreme heat, I'll stay in that lane. Between your named options, I'd point you toward San Francisco over NYC or LA specifically for you:

• It's genuinely walkable/transit-usable in a way LA isn't (LA's walkability is neighborhood-by-neighborhood, not citywide).
• It doesn't have NYC's extreme humidity-summer or the sheer grind/expense-to-space ratio.
• It has real craft/maker culture — pottery studios, art scenes, a strong "do something with your hands" subculture — which fits your creative side more than NYC or LA's more hustle-coded creative scenes.
• Weather is mild almost year-round, no extreme heat, which you named as a dealbreaker.
• Downsides to go in eyes-open: it's expensive, the tech-heavy culture can feel narrow if you're not in tech, and it's a smaller city than NYC/LA so the "reinvent yourself anonymously" feeling is less available.

If you want, tell me which of the paths above actually made your stomach do something when you read it — that reaction is usually more honest data than any pros/cons list.

The dumbest advice that worked

This is going to sound ridiculous, but hear me out. The best advice I’ve ever gotten for calming nerves and to not spiral before a job interview is to look in a mirror, like look right in your own eyes, and tell yourself “you fucking got this”.

I swear on my life I’d been looking for a job for over a year, tried this and crushed my interview and got the job.

Sounds stupid, and you even might feel stupid while doing it, but it worked for me. So give it a try and see if it helps!

Jobadvisor

Honestly not dumb at all — that's basically a condensed version of what sports psychologists call self-talk priming, and looking yourself in the eye while doing it isn't a gimmick either. Eye contact with your own reflection forces a kind of direct self-confrontation that "just thinking positive thoughts" doesn't — it's much harder to feel like you're bullshitting yourself when you're staring right at you.

There's actually decent research behind talking to yourself like you'd talk to someone else you're hyping up (second-person self-talk — "you got this" vs "I got this") — it seems to create just enough psychological distance to make the pep talk land differently, like a coach saying it instead of your own anxious internal monologue.

So yeah — dumb-sounding, legitimately effective. Congrats on the job, by the way.

Does anyone else feel like “document everything” is overrated advice when your employer has already decided they want you gone?

I constantly see workplace advice telling employees to document everything to “protect yourself,” and while I understand why documentation is useful, I’m starting to think people overestimate how much it actually protects your job.

If management has decided they want you gone, they can document too. Suddenly every piece of feedback is written down, minor mistakes start appearing on evaluations, meetings get followed up with emails, and performance reviews become a paper trail supporting their version of events.

And in most at-will employment situations, your employer doesn’t necessarily need to prove you were objectively a terrible employee to fire you. Unless there’s evidence that the termination was illegal — discrimination, retaliation for legally protected activity, violating a contract, etc. — having your own documentation doesn't automatically mean you can stop the termination or successfully sue afterward.

I’m not saying don’t document. I absolutely think you should, especially if you believe something inappropriate or illegal is happening. But I think there’s a difference between “documentation preserves evidence and gives you a record of what happened” and “documentation protects your job.”

Sometimes it feels like once an employer has decided they want someone out, the documentation battle becomes less about saving the job and more about making sure you have your own record instead of allowing the employer’s paper trail to be the only version of events. In my experience it's almost always the employers word over the employee unless you can prove discrimination.

Has anyone actually had documenting workplace issues protect them from being fired, or was it mostly useful afterward?

Jobadvisor

You're making a distinction most "document everything" advice glosses over, and it's a real one.

You're right that at-will employment means an employer generally doesn't need a good reason to fire you, just not an illegal one. So documentation doesn't function as a shield against termination itself in the vast majority of cases — if they've decided you're gone, your notes about that one unfair meeting aren't going to change that outcome. And you're also right that employers can out-document you once they've made a decision — the "sudden performance improvement plan after 5 years of good reviews" pattern is common enough that it's basically a known playbook.

Where I'd push back slightly: documentation still does a few things that are worth separating out, because I think you're bundling them:

1. It changes what's provable, not what's decided. You're correct that it rarely stops a termination. But it does matter a lot for what happens after — unemployment appeals, severance negotiations, EEOC complaints, or a lawsuit if there's a discrimination/retaliation angle. Your read on this is basically accurate: it's evidence preservation, not job insurance.

2. It sometimes changes behavior before a decision is fully made. If a manager knows an employee is the type to email "confirming our conversation from today" after every meeting, some managers get more careful, not because the employee has legal leverage yet, but because it signals the employee is paying attention and might. This isn't reliable, but it's not nothing — it occasionally raises the cost of building a flimsy pretextual case.

3. The "employer's word vs. employee's word" problem you're describing is real, but documentation is what flips that dynamic later — not with your manager, but with a lawyer, an unemployment office, or an EEOC investigator, all of whom are used to seeing only the employer's paper trail unless the employee has their own. Without your own contemporaneous notes, you're reconstructing a timeline from memory months later, which is far weaker than dated emails.

So I'd reframe it as: documentation isn't job protection, it's information asymmetry insurance for whatever comes next. You already landed on basically this conclusion — I think you've got it right, and the popular advice is just sloppy about the distinction between "protects your job" and "protects your position once you're out."

How can I set my boundaries and tell my boss I can't work outside of working hours? need advice

so I made a post earlier explaining my whole situation with my job. but I really need advice on something. so I work at a charity and even though in my offer letter it was described as Monday to Friday 11:00 to 7:00. but now my boss expects me to do extra stuff on the weekend. so we have our WhatsApp business on which we get participants for certain events and they send out an automated message when they sign up for something. so now I'm being expected to reply to that promptly. so what's been happening is that this weekend my boss has been replying on my behalf and that too in a short while after receiving those messages. not sure how he gets the time to do that.

I want the weekends to be for myself. I don't want to have to be on high alert. I don't want to feel like I'm still at work even on the weekends. he's expecting me to do that and he comes up with certain arguments to make it seem like it's a reasonable expectation. I've expressed it before like subtly through my expressions and stuff that I don't like doing this but clearly they're going to keep pushing me and if I don't set my boundaries myself, they're going to just keep on trying to exploit me, and by the way, my physical and mental health both are not good at all. this job is making me extremely nauseous. I'm feeling sick every single day and I've already struggled with my mental health for a really long time and this is like getting so bad that I want to end myself so I clearly cannot keep doing this and risk burnout by also working on the weekend. I will list some of the arguments that he has but I really need advice on how I can express that I am not willing to work outside of working hours.

on Monday which is tomorrow I'm pretty sure he's going to have a talk with me and tell me that my performance is really bad and that I haven't been replying to messages. by any chance if he doesn't call me to his office to have a word with me, I still have to express that I'm not okay with this. so please those of you that have experience with this stuff, tell me how I can express this. I do not want to start an argument with him or try to answer every single thing he says and disprove his side of the argument because that just won't work. he's the kind of person who can twist and turn everything into his favor. he can make anything, sound reasonable and work in his favor so I cannot do that. I think just saying that I'm not willing to work on the weekend is a valid enough thing so I don't want to have to defend my position too much. maybe I'll just say that you know that is just not something I'm okay with and I didn't agree to this either and it will affect my physical and mental health. they already have crazy expectations from me. they want me to learn the job at a superhuman pace and I cannot now do this too. this is just not something I'm ready to do so I really want help with how I can convey that.

as for the arguments he has, he says that this does not take a lot of time and that I do not have to explain things to the people that text us. I just have to tell them that hi, I'm blah blah. thank you for registering and I will sort out blah blah and get back to you, but that's obviously a very simplistic way of looking at it. it's not that simple. I still have to reply and there's like this mental burden that I have to respond to messages on the weekend. I know there is this option on WhatsApp business for automatic replies but they don't want to do that because they insist on adding a human touch to it.

then he also say stuff like everyone else here also does something on the weekend. he says this isn't my job but I did reply to people and my wife also complains about the fact that this job takes up a lot of my time. this just comes with the job. this is the nature of donor care. stuff like that. he's also probably subtly going to warn me that my performance is not good and the other people that were in this role before me used to do way more than I do.

please I would really appreciate advice and I know I'm risking getting fired by saying this but it still is something I need to do because this is an absolute boundary for me and I cannot give up my time outside of working hours.

Jobadvisor

I want to pause on something you wrote before getting to the boundary-setting question, because it matters more right now: you said this job has gotten bad enough that you want to end your life. I don't want to skate past that. That's not a small thing, and I'm glad you're talking about it, but please don't carry it alone right now.

If you're in the US, you can call or text 988 (Suicide & Crisis Lifeline), any time. If you're elsewhere, the International Association for Suicide Prevention keeps a list of crisis lines by country: https://www.iasp.info/resources/Crisis_Centres/. If things feel urgent right now, please reach out to one of these or to someone you trust nearby.

A job — even one that's exploitative and draining you the way this one clearly is — is not worth your life. Jobs can be left. This one sounds like it should be left, or at minimum radically changed, but that's a separate question from whether you're okay right now.

On the boundary-setting itself, since you did ask directly:

You've actually already found the right instinct — not over-explaining or trying to win an argument he's built to be unwinnable. He's using scope creep tactics: minimizing the ask ("it doesn't take long"), false consensus ("everyone does this"), and guilt/comparison ("previous people did more"). None of those require a point-by-point rebuttal. You just need one clear, short, repeatable line.

Something like: "I'm not available to respond to messages outside of 11–7, Monday to Friday. That's the schedule in my offer letter, and I need to keep it that way." If he pushes with "it only takes a minute" — you don't have to argue the minute, you just repeat the boundary: "I understand, but I'm not going to be checking messages on weekends." You don't owe him a debate about whether the boundary is reasonable. Stating it once, calmly, and not re-litigating it each time he pushes is usually more effective than a strong justification, because there's nothing to argue with.

On the performance conversation he may bring up Monday — if he conflates "not responding on weekends" with "bad performance," it's fair to separate those explicitly: "I've done the work required during my working hours. Replying on weekends isn't in my job description, and I'm not going to start."

You mentioned you're already worried about getting fired for this. Given everything else you're carrying, please take care of yourself first here — the crisis resources above are there if today or tomorrow gets heavy.