Your health comes first.

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

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.

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.

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.)

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.

Spent pretty much my entire life working from 16 onward. Financially, I’m doing alright, I have enough money that I could pay off my student loans right now and not be on the brink of ruin.

I’m so burnt out that I’m pretty sure I’ll kill myself when the money runs out after I get fired. I do not have the emotional wherewithal to start looking for another job in the age of video recorded interviews and 50-question corporate ball-gargling quizzes. I don’t want to jump through hoops anymore just to be able to live, to the point that I would actually rather die than try to get another shitty day job. I sort of hope I don’t get fired, but at this point I’m too tired to care all that much.

Best decision I made was taking an internship. I wasn’t really looking for one, but through some connections, one basically fell in my lap. It was in old tech I messed with in high school, so I was reluctant, but getting real world programming experience was fantastic. The team was great and I helped solve some interesting problems on a small project of theirs. They kept me on as long as they could (>1 year). I think people can be way to idealistic, especially when starting out. Go get a year or two somewhere, anywhere. You’ll have a ton more marketability and control over where you end up with experience and professional references.

Biggest career regret was waiting around afterwards for a time to try to get hired on at that same place. Not a ton of programming jobs locally and I wanted to continue my work there, but the company went through semi-frequent growth/shrink phases, and my team wasn’t able to get me hired in, though they did try for a while. There were plenty of other good things happening in my life during the down-time after this job and before the next, so it’s not really something I regret, but I definitely won’t wait on a company like that again.

After university, I was a volunteer teacher in Africa for 3 years. Then I went and taught English in Japan, and after that started working as a software developer.

If I had stayed in Canada and gone straight into a typical chemical engineering job, I would certainly be a lot better off in financial terms, but the whole reason I didn’t go into it was because I found it soul crushing.

One of my engineering classmates went into theater production, another did a master’s in English, and a third went to medical school. Clearly I wasn’t the only one having misgivings.

Bad idea: Tempted by a silicon valley startup because that’s what all the cool kids were doing. They were style over substance.

Good idea: leaving my otherwise excellent first real job. I owe them ( slidebook.com ) a lot. I wouldn’t be half the developer i am now if they hadn’t given me the environment to approach software as a science. That said, leaving was the right call.

I regret not taking my suspicions that I had adhd more seriously.

Ie I suspected I had adhd when I was in my early 20s now that I’m in my mid-late 30s and getting sorted out, I can sometimes daydream about how different my career could have been if I’d been firing in all cylinders the whole time. I don’t day dream for very long though, I’ve got things to do.

A few years out of college I was making $X, and was simultaneously approached by two companies. The first was located just outside of Paris, for $X+n (small $n). The second was about 50 miles from where I lived in Oregon, but was $2*X. I chose the second, which led me on a career development path that worked out well for me financially.

I wish I’d taken the job in Paris. It would have set me back a few years, financially, but in retrospect, I’d have valued the experience more.

I’m glad I worked at a startup without benefits while I still had coverage from my parents. I’m also glad I realized I prefer medium-sized companies before I lost that coverage.

I regret the mentality that kept me at shitty jobs for five years. Being afraid the grass wouldn’t be greener left me in a cycle of getting mad enough to polish my resume and send it out, but then never really following through.