How Long Can I (Should I) Keep This Job If They’ll Keep Me?

Four years ago, I joined a much smaller company in a role that didn’t have a job description. The total expected compensation was more than I had ever made and I threw myself head first into the excitement of the new opportunity. The energy at the company was great then. Some people were clearly not top performers, but everyone joked a lot together and got along. It wasn’t a well-oiled machine yet in my department, but it was getting there.

A few months later a number of those fun, joking people were shown the door and others who joked in the corporate-appropriate way were let in to take their seats. I managed to come in with the new wave, despite not fitting with the rest of the group, and I flailed through the following years putting out a few good projects and being pregnant, twice (my best projects of all), enabling me to somehow still be gainfully employed to this day, despite plenty of reasons for me not to be.

Covid turned everything upside down and I also owe my current employment to the pandemic. Being able to work remote, heads down, and hide my awkwardness much more efficiently helped a lot. So here I am. Just months away from achieving my initial goal of surviving through my first vesting cycle. It’s a huge win. My net worth growth in the past 4 years has been strong due both to my existing investments and my stock in this company that has proven itself a rocketship.

So now the question is — when do I leave? If I have that choice, anyway. My ego is tore up all sides of Sunday (is that a saying? If it’s not it should be) but maybe that’s fine. I’m not getting any raises or stock refreshes or promotions — EVER — at this company — but does that matter? So what if they’re showing me the door. I can say “see the door, not going to go through it yet, you’re going to have to shove me through it.” And maybe they won’t shove me. Maybe they don’t care enough to do so, especially if I’m getting my basic work done and not causing anyone harm.

Looking ahead to next year, assuming I manage to last at least through April 1, when I plan to likely be heading out that door… I can stick around another year and it would be pretty darn lucrative and probably a decent situation for me as long as I don’t have to go back to the office. Going back to the office is likely a requirement if I want to have any sort of career growth in this company but as I’ve already covered that’s not really possible anyway so the best I can do is focus on getting my projects done, communicating effectively, and hiding as much as possible.

What I don’t want to do is get fired. And it’s hard to not get fired when I’m this bitter. When I see where I thought I’d be and where I feel I have things to contribute being handed to my peer (who happens to be a friend now but still.) A peer who was supposed to report to me when I went out on maternity leave, who was hired to fill in for me when I was having a baby, then who went on to surpass me in so many ways. These things happen but it still hurts. It hurts that he is the go-to trusted ear for my former boss, who I respect a lot, and she prefers to have nothing to do with me these days. I get it, I understand it, but it sucks nonetheless.

My new-ish boss, well things are awkward with him. I’m sure they got more awkward the second he saw how much I’m making. It was weird going from peer to report knowing he likely was making – a lot – less and then having him see how much I was taking home just – well it didn’t really set up our new relationship for success. He hasn’t been an asshole about it but I’m sure he would fire me in heartbeat if I slip up. Luckily I have a few high visibility projects no one else wants that I’ve historically managed well so I keep doing that and maybe… I’m ok? As long as I want to be.

I’m committed to. seriously applying come February. If I can get a better job that pays >$250k with base >$200 I think I need to leave. But it’s all sorts of questionable if I can do that. I’ve had 5 quick rejections from roles I applied to last month, so it’s surely going to be an uphill battle to find anything that is a fit. I might be stuck anyway. So perhaps I ought to try to focus on liking this job and doing my best and all that.

I just wish this job had any legs. Where do I really go from here? Any comparable role requires technical skills I do not have, nor can I gain these technical skills without going back to school and spending a lot of time becoming an expert to be competitive at my level. I’ve been specifically kept out of the projects that actually make sense in the broader industry and am allowed to work on projects that are pretty company specific with no results other than surviving them. So it’s a challenge in building up a story for what’s next, without an opportunity to do anything worthwhile.

Maybe for even $260k that doesn’t matter. Or does it? I have no career. I have no future. All I have is the next two years. It’s not enough to retire on. I still need to figure out what’s next… and how I get there.

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4 thoughts on “How Long Can I (Should I) Keep This Job If They’ll Keep Me?”

  1. Can I ask what the percentage jump from your prior role to your current role is? I’m fielding out a couple of job opportunities recently and they all seem to be ridiculously high (some are like.. triple what I’m currently getting paid, so I’m obviously not going to get it).

    How did you sell yourself during the job interview process? I would feel so nervous selling myself for a job that’s 2.5 – 3x what I’m currently making, compensation wise.
    David @ Filled With Money recently posted..What is a Pay Cut and Should You Ever Do It?

    1. Well it was kind of a weird case because the head of the department recruited me directly, and I also went from pre-IPO companies where a part of my compensation was in worthless ISO (but that was considered as part of the total compensation package) to RSU where the stock actually would be paid out. I was making $190 base with no bonus and a chunk of worthless stock. I probably had a higher OTE at the startup with whatever the stock was supposed to be worth at the time. My base at my current job started at $165k, but then I had a 20% bonus on top of that and another $60k in RSU give or take, which made it a lot more of “real” money (though bonus and RSU also variable.) So it didn’t feel like that big of a leap. The bigger leap was from $170k to $190k — the only time I negotiated for more when I took a new job. $190k was so hard to ask for but I felt baller at the time and went for it.

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