What's that one thing you would do, if you got to rewind your career?

This is a great question. I spent the last ~10 years hopping around jobs, working at both FAANG and small startups, but I never stayed anywhere more than 1-2 years. I also moved around a lot. My biggest mistake was focusing too much on salary, job title, technologies and self-development, and not enough on forming deep relationships with others. That was true even in college where I got good grades, but I rarely went to lectures, study groups or parties.

Now I'm here with a relatively broad network but few deep connections. I don't have anyone I can ask for career advice, have beers with, chat with about work, or discuss for new opportunities. Looking at my resume you'd think I'm "successful" - but it's the opposite. It feels kind of lonely and at times I'm sad.

No matter what you do in life, in the end it's all about people. Don't waste your opportunities to get to know your fellow coworkers/classmates/bosses. Make some friends.

Also, don't burn your bridges. There were times in my career when I sacrificed relationships so that I could move on. For example, leaving a co-founder behind when I no longer believed in the company. Looking back, I was kind of an asshole and too immature to realize it. I wasn't capable to fully empathize with the people around me. I truly regret that now.

If I could rewind my career I would do these things.

* Stay longer at my first company. It was an old school tech company most of the developers were 40+ years old. It had cubicles and outdated technologies. After 2 years, I grew bored and I left because I wanted to work with exciting tech,make more money, and work with younger people. Over the years, I realized it was the perfect company for my personality. Stable, low key, and quiet, they allowed people to grow into a real engineer. I took it for granted.

Eat healthier. You might think this is unrelated, but as I have improved my health, my clarity and speed of thought has improved exponentially. Had I done this a couple decades sooner, I would have likely done even better in my career and had better interactions with others.

Never work for other people. Never work a 9-5. I would have started selling my own things or working for myself before leaving my parents house.

At 32 and finally working for myself, I can’t believe I spent almost 10 years building someone else’s dream.

Having lived in NYC for most of my life, and surrounded by friends in finance and finance tech, I thought working as a developer in one of the Wall Street firms (investment banks, hedge funds, etc.) was the pinnacle of a technology career. Man was I blind.

Needless to say, on the other side of the continent (and in NYC itself, to a lesser degree) was the Silicon Valley tech industry.

So while I pludged around doing LoB .NET, others were grinding leetcode to get into these tech companies that not only offered stupendously superior compensation but also work and lifestyle perks that put working as a technologist in finance to shame.

If I could rewind my career back ten years, I'd do everything I could to get my foot into the SV tech industry whether here in NY or moving to California. That said, I'm still trying.

I recall back in 2011 or 2012 a Google recruiter even reached out to me and I just ignored her thinking a job at an investment bank was far superior to a job at Google (whether or not I would have passed the Google interview is another story of course...). If I could travel back in time, I'd kick my earlier self in the mouth.

I'd find a mentor. Heck, I didn't even know what that word was or how important it was until I was a good 10 years into my career.

Ask for more money/set salary expectations higher.

Yeah, I know what you're thinking. Sounds a bit like a cliched answer, right?

And yes, it does. But I'm the only person in my peer group who went in the tech industry, and I had absolutely no idea what the market rate was for software engineers or web developers in said industry. As a result, I ended up seriously underpaid overall, especially given I was the one who was asked what my salary expectations were.

Alteratively, I guess it'd be focusing more on networking and connecting with people. I never realised the importance of thing growing up, so I never ended up with a network at all, or anyone to rely on for anything.

Make time to speak more with my manager about the role I wanted that didn’t seem to be available, rather than accepting that role at a less stable company and then getting laid off from it due to cash flow problems a month after my former manager had hired someone else into the role I’d wanted.