Staying where you aren’t happy.

It is rare these days that loyalty and seniority are rewarded how it was depicted in popular media. These days the best way to make more money is to leave and find a new job.

Never let anyone make you work hard, work hard for you and for your goals.

In my 20s I didn’t realize how much more valuable my time was compared to the money I was being paid to give it up. The most valuable thing you have is the rest of your life, you’re being paid to give someone else your life for a time.

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I regret staying in my first job too long thinking I’d advance internally.

Your health comes first.

I’m happy that I switched from electrical engineering to software engineering. I feel like the prospects are better and still feel that way even though things are rough right now.

I regret being scared during my first 5 years as a software engineer. I’ve stayed in jobs too long. Going forward, once I get that feeling that I’ve outgrown a role I know its time to start looking for the next thing. No more lingering for that extra year. I’m in my mid 30s and so am feeling the age pressure to make my next couple big moves soon before I’m looked at as too old to be an “IC with a bright future” haha.

I have too many…I’ll pick my favorite lessons as they’re all kind of related

Don’t stay at a job too long. Eventually, you’ll be training a new hire that makes more than you and they’ll probably be your replacement.

It only takes a couple promotions before your career development stagnates usually because you’ll always be seen as the person you were when you started. Get a new job elsewhere with a title higher than the place you left and that becomes your new baseline. Repeat every few years.

If you want to earn more money, get a new job. Bonuses magically dry up. And your yearly performance increase won’t ever keep up with inflation. Even lateral moves at a different company can mean decent salary inceease as market rate changes over time. (This doesn’t always work with a lateral move so shoot for a higher position).

Don’t sweat the specifics for job requirements in postings. They’re not expecting someone that hits every bullet point. That would be dream candidate that doesn’t exist. If you’re at least familiar with what they’re asking for and can pick it up, then you’re good. Most of the time you’re trained on the job anyway. Just demonstrate you’re competent.

(Oops didn’t realize this was a CS / programming community. Hopefully some of this still applies)

There’s one thing that I regret to this day - going fulltime right after school.

I studied gamedev, and we had a game going on pretty strong, which we were determined to finish in our free time. We were working on it with my roommate and a classmate, who is in general a pretty creative person - he writes LARPs for one group, is leading a amateur theater group, leads our game development team, masters RPGs, etc. He also works as a programmer, just like me.

When we finished school, he decided to stay working part-time, two days a week, and continue living in the student’s appartment with our 3 more friends. Keeping his expenses as he had before during school, and focusing on his creative projects in the free time. Because as someone without a car, family, and i a shared household, on a programmers salary, you can get by pretty comfortably.

I, on the other hand, decided to go full-time. And boy does it sucks to get energy for hobby projects after you’ve spent 40 hours a week of working. Sure, I had more money - but the fact that after paying all my necessary expenses (which I was able to do even part-time), I was left with 3-4 times as much money didn’t really help me at all. Sure, I had financial security, I could buy whatever I wanted and didn’t need to pay any mind to my spendings, but was it worth it? I’m more and more conviced that it wasnt. I had to start forcing myself to work on my hobby projects that I’ve loved before. I started postpoing it, and was stressed by trying to shove that much work into so little time.

The money didn’t help it at all, especially since I didn’t really need them.

He’s still working on plethora of projects I’d love to join in, but my contribution is getting less and less reliable, and more and more stressful for me, because the 8 hours of job work per day will just suck all energy out of you, especially since the projects are usually also programming related.

If I could change it, I’d never start working more hours than I need to comfortably get by, even with a little bit of frugal lifestyle. It’s not worth it, and the stress caused by trying to overwork myself with the hobby projects, missing deadlines with both work and said projects, has taken a great toll on my mental health in the past 4 years we’ve finished school. In fact, I didn’t even manage to finish my diploma thesis, after postponing it for three years, so I don’t even have the Masters even though I did finish the state exam.

So, if you can, limit your work hours as much as you can to get by, and work on your own projects in the meantime (if that’s what you want). The money are not worth it.

(I’m actually finally planning to go back to part-time, and take another Masters in game design this year, and probably stay at that, so I’ll see how it goes. But seeing the difference between my best friend and me, where our paths diverted exactly by this, he’s turned out a lot better than I did after those three years.)

I’m not 30+ yet but getting close and there’s a thing I already have so

I’ve stayed at one place for a bit too long, wasted time not learning new skills and now that I’m looking for a new job, my resume looks a bit sad and I’m not sure the company-specific PM skills I gained at one place are going to be useful enough in a different one

I never worked in my chosen field and fell into software development instead.

I wish I could say it made me happy but it’s quite the opposite. I feel out of my depth every day and I’ve never been promoted or such, and I’ve been with the company for almost ten years.

I’d go do something else but I don’t really have any skills worth mentioning so I guess I’m stuck here until I get fired or am eligible for a pension (not gonna happen btw, there will not be any pensions for gen y and on.

So I just feel inept and stupid every day. At least it keeps a roof over my head.

Regret:

• Not taking care of my health. Too much sitting in front of a computer, not enough walking around. Too much junk food.
• Not keeping track of people after leaving their immediate circle (team changes, company changes, leaving college, etc.). Literally every opportunity I’ve had has come from somebody I know, yet I’ve done a poor job of keeping a network socially. It’s not that hard to chat with people every few months, but I didn’t initially put enough effort into it.

Happy:

• For me specifically, staying at my first job for a long time was really good. It helped me grow, and the company was pretty good with salary increases.
• In contrast to my regret, I did a good job of making friends with teammates and getting along with people I work with the most.

Not walking out the door when I should have. That’s a tough call to make and the conventional wisdom is that you shouldn’t quit your job before you have another one lined up, for understandable reasons. You have bills to pay.

The worst job I ever had was as a manager for a large utility. One time, we got quite a bit of snow. I didn’t have 4 wheel drive so I asked my boss if I could take a company truck home. He said that was fine.

The next day, he called me into his office and told me I was in trouble for taking a company truck home. I was very confused and responded that I had asked him about it before I left and he said it was fine. Turned out that motherfucker had been asked by someone further up the ladder if he signed off on it and instead of just saying, “Yep, I told him it was fine.” He proceeded to lie his ass off and then pretend like we never had that conversation.

He showed me what kind of person he was and what kind of company I was working for. I should have immediately handed him my badge and walked out the door but I didn’t. I stayed there for a few years after that. That was the tip of the iceberg on top of a completely toxic shit hole. The worst I have ever seen.

Never let someone try to take your dignity away from you and don’t spend any longer in a toxic workplace than you absolutely have to.

Being loyal to a start up. As soon as I got those shares , should have cashed out and moved on asap.

Change jobs as soon as you can, easily blame it on being young and they never held it against me when I finally did learn that. And since you’re in your 20s, they will never let you retire there anyway. So why stay?

Not cultivating my network.

Staying in jobs that made me miserable for longer than I could have.

Regret:

• Not getting into web development sooner. I spent a good chunk of my 20s trying to be an animator. I should’ve seen that it wasn’t going to work out sooner, and I even had friends who offered me web dev gigs. I eventually got one, but I could’ve got one probably 10 years earlier.
• Like some others have said, being loyal to startups. They’re never going to be loyal to you, so why bother being loyal to them?
• Really, the two previous points could be combined into a somewhat related point: don’t keep white-knuckling through on some career path if it’s looking increasingly bad. The reason I used to keep white-knuckling is I believed perseverance in the face of adversity was the most important thing. While I agree perseverance is important, it’s even more important to find that line between pushing yourself for a good career, and pushing yourself for something that may no longer make sense. It’s not always easy to let go of something that you’ve already invested time and energy into, but sometimes its the best way forward.

Happy:

• I developed frugal spending habits, largely due to my pseudo-artist lifestyle. While that isn’t directly a career thing, I’d argue reducing my spending allowed me to last without income longer, which let me be more choosy about which job I got next.
• I tried anything that interested me. This included programming - which ultimately became my career.