If you could start your career all over again, what would you change?

Not making more decisions. The things one regrets are the things not done. Should have changed companies/jobs more often. At the start it was great being part of a company/team for a long time, after that you realize that in the end it is a job (even it it's also a passion) and it's good to be exposed to different things.

Also wished I'd taken a bigger interest in somewhat core things sooner, e.g. static-typed functional languages and distributed systems. Basically seeking out challenges rather than performing well in my comfort zone. Still exploring less technical, soft areas with unknown outcome as yet.

I started a job and within the first 2 days saw a red flag with the CEO. I should have listened to my gut and walked right back out of that job. I spent years in a job I should never have started because the CEO had an odd mix of compassion and abusiveness that kept me on the fence for years, and I'm just recently realizing exactly how damaging that job was both personally and professionally.

If you have a bad feeling about a job shortly after you start, trust your gut and go.

I would love to be a professional chess player. I have been playing chess since I was 10. I have always been good at problem solving and maths. I didn't took chess seriously as I didn't see anyone playing it to earn a living, I didn't even know something like that exists.

Later in college, I won back to back chess tournament and with just a few days of practice. That's when I realized I might had a chance have I taken chess seriously since my early days in school.

I'm sorry you only asked for a single decision. I'd change multiple things.

1. Bet on myself sooner. Start a business SOONER.

2. Learn how to sell.

3. Study more material that'd help with improving programming skills, rather than business acumen.

4. Skip college.

5. Just START, rather than waiting for the perfect storm.

Stayed in a toxic team long enough to injure my health. There are some things doctors can't fix. Definitely not worth it.

I didn't take any more CS classes in college because during the first course I took my freshman year, there was a lecture and lab component. During the lab, you would code on a computer in an IDE and submit the projects/assignments. During the lecture you'd learn and then take written exams, which involved coding Java by hand. I had no issues with the labs and really enjoyed them, but I greatly struggled with syntax, etc, when writing the code by hand. I was 18, too stubborn, and butted heads with the Professor about it - I kept trying to argue why my lab performance should have demonstrated more of a competency in the subject than writing by hand, but the rubric was final and the exams were a large portion of the grade, and my grade suffered because of it.

After that experience, I declared my major to something non STEM and never took another CS course again, and ended up working for the first 4-5 years of my career in non engineering roles.

However I still ended up being pulled into coding as a passion all those years later, in which I self taught the CS coursework I needed online by taking Computer Science MOOCs and reading textbooks, etc, and now work as a software engineer.

I can't help feeling like if I was a little less brash when a freshman in college, I probably would have loved the CS major and my career could have been very different. I can't complain about where my life/career has ended up though, so perhaps it was all for the best.

I'm not sure I regret the job choices I've made, but if I knew how healthcare laws would have changed over the last decade or so I would not had the same priority for finding a job and probably would have spent more time trying to make it as a writer. I have a pre-existing condition so in 2008 it was very valuable for me to obtain employer-based health coverage before I aged out of being covered under my parent's plan.

If I knew that the age until which you are covered by your parent's health plan was going to be extended to 26, I would not have focused on getting a stable, nice benefits job. I would probably have tried making it as a writer, and unless I had some big break I would have probably considered grad school (which I was planning on for my first couple years after college until I found I preferred working on real world projects to research more or less).

Not 100% sure how that would have worked out. I probably would not have gotten married until I had a stable position somewhere, so I'd be starting my family much later (if at all, if my writing career took off I might be more focused on that), almost certainly wouldn't have ended up with my wife, since the circumstances that brought us together would be very different, odd to think about...

Probably would be more ambitious but with less happiness than I am now, but it's very hard to say. So I don't regret the path I went down, but it's strange to think that so much of my life was based on an assumption (that I needed to secure employer-based heathcare ASAP) that ended up being wrong.

Working for a company and thinking of work in terms of "career". If i could start all over again, i would be trying to do something on my own.

Ship more often, launch more often, learn to validate ideas sooner, have fun along the way.

I wish I knew how to recognize a bad manager, and what to do when you find yourself working for one. I was eager to prove myself in my first job out of college, typical overachiever. Naively believed that if someone was a manager it meant they were good at what they did and wanted the best for you too.

Didn't realize until I burned out what a loss of time and energy it was putting so much effort into trying to do a 'good job' for someone who lacked empathy and was just not suited for management. It took me years to unravel the damage from that experience. I went into new jobs with what I would describe as PTSD learned from that first job. It was a professional trauma, and I didn't realize how disordered that startup and management team was until I worked at other places. I learned a lot from it. But it set me back a few years.

That brings me to my next point. The exciting, glamorous startups with high profile executives and investors are often just a huge mess under all the flashy PR and social media personalities. I don't regret learning that the hard way, just wish I wasn't so naive and allured by brand names at the start of my career.

Getting into the habit of ‘always be interviewing’, stayed 4 years at my first job where there were limited pathways.

The decision I most regret was moving to a city without many tech jobs (Philadelphia). The difference in number of available jobs, salaries, working conditions, and even the intelligence of coworkers is kind of mind-blowing, now that I've moved back to a city with a lot of tech jobs (Seattle). The cost of living is higher here, but it's worth it.

Moving away from Seattle after college before I had another job lined up. I quit the job I had in college (it was software dev but in the university) and went on a long road trip across the country. It was the single worst decision I’ve made in my entire life. (Probably)

That said, I couldn’t have known that entry level jobs were going to be so incredibly difficult to get after college. Almost everyone and their mother thought I’d have no trouble cause he’s so smart, has job experience, went to good school, etc. But most of them were extremely privileged and never had issues finding jobs /or/ had completely irrelevant experience.

I’d highly suggest talking to peers who are just a year or two ahead of you. They might shine light. Sadly, I had none to go by. I was entirely alone and had no relatable peers.

I would swap the 4 fruitless years in postgraduate academia for 4 years of team experience in a large IT corporation. My startup was very successful, but could have grown faster/easier (than 60-odd people in 14 years) with more such experience (as solo founder).

choosing ME over CS simply because the college was way more prestigious. College rankings don't matter beyond your first job.

Taking a job knowing that the boss was incompetent, but he thinks he is t a top notch.

Not taking out a loan for a CS degree. It's gotten in my way so much, especially recently. The paper saying that you took some courses is way more important than a github profile with projects.

I started a business early and ran a few service businesses with some success. Cash flow was always a problem and working your ass off waiting for the big payout put a huge strain on my wife and kids.

It wasn't until both my wife and I were working full time that we started to accumulate wealth.

No commitments? Start a business early. Some commitments? A regular paycheck and saving as much as humanly possible makes it easier to take risks later.

Listening to people who say “sleep is for the weak” and “stop trying to understand things, just learn by doing.”, “stop trying to understand the universe”, and “just do the obvious thing.”

Different people are different. Personally, I find I am 5% as productive if I am working while utterly confused and running on 4 hours of sleep. It sucks to look back on my effort and see I made as much progress as Luigi Cadorna did on this 10th time trying to cross the Isonzo river.

Pursuing advancement of technical proficiency over leadership. I would completely change that to focus more on administrative and managerial performance much earlier in my career. In my defense, though, leadership is really weak in software so that would require more initiative from less examples/guidance.

Not staying an extra semester to finish CS as a second major (my college required a senior thesis, like a mini–dissertation, for every degree). Having a minor in CS was about as useful in the technology field, career wise, as having a binary coded birthmark.

My biggest regret was ever taking a job in the first place. I should have worked for myself, my own business, from day one. Working for someone else robbed me of so much potential. Easily one of the biggest opportunity costs I’ve ever paid.

I wish I'd looked for more opportunities to work with and learn from more experienced developers instead of being so overwhelmed by imposter syndrome that I was terrified to take a job where anyone who knew more than me could judge me.

Choosing the wrong career. Finally moved from programming to writing fiction.

I should have learned awk and sed when they told me to.