I started my engineering career as the second hire on a small team at a healthcare software company. Nobody was organizing the work. Nobody was setting priorities. We were just… building stuff and hoping it mattered.
Two years out of school, I started doing it myself — not because anyone asked me to, but because someone had to. That decision changed everything. Within a few years, I was CTO, the team had grown to 40+ engineers, and we were acquired. It was a great ride. But I made a lot of mistakes along the way that I’d do differently now.
Here’s what I’d tell my younger self — and what I’d tell any developer just getting started.
Don’t get trapped in your current stack
It’s easy to get comfortable with the tools your employer uses. You get good at them, you become the go-to person, and then five years pass, and you realize you haven’t learned anything new. That’s a problem.
Look at job listings — not necessarily because you want those jobs, but because they tell you where the industry is going. If you’ve been heads-down in relational databases, spin up a Redis instance. If you’ve been building in one cloud provider, poke around in another. When I joined GitLab, I didn’t know Ruby on Rails. I took a Udemy course. Turned out routes are everywhere once you start looking.
Learning something low-stakes and new regularly is the best thing you can do for your career anxiety later. When you actually need to job hunt, it feels like muscle memory instead of a crisis.
Don’t stay somewhere that’s making you miserable
I did this. After an early-career acquisition, the cultures were incompatible with how I liked to work. I knew it after the first year. I stayed two more anyway because I believed in the team and the product. By the time both of those things had eroded, I’d spent three years being pretty unhappy.
Life’s too short for that. If you’re miserable and nothing’s improving, start looking. That’s not disloyal — it’s honest.
Always be interviewing, even when you’re happy.
Not necessarily applying everywhere, but staying warm. Look at listings. Talk to people who’ve left companies you’re curious about. Ask them what they’d do differently. LinkedIn is useful here — not just for applying, but for maintaining real relationships with people who can give you a straight answer about what working somewhere is actually like.
That’s how I actually found GitLab. I was a customer. One of our internal teams loved the product — and this team liked almost nothing — so I paid attention. I didn’t join for a while after that, but I was watching. When the opportunity came up, I already knew why I wanted to be there.
Ask better questions when you’re interviewing.
Most candidates either don’t ask enough questions or ask safe ones. Ask hard ones instead. What’s the voluntary attrition rate? What are you actively working to improve about your culture? What does a bad quarter look like here, and what happens? If someone gets uncomfortable with those questions, that’s useful data.
And if the answers are too polished — if they sound rehearsed — that’s worth noticing, too. The best answer I’ve ever gotten to a hard question was an honest one, even when it wasn’t great news. That tells you a lot.
Customize your cover email, not your resume
Nobody has all six things on a job description. The company probably won’t find someone who does. What a short cover email does is show you actually read the listing, you understand what you have, what you’d need to learn, and why you want to work there specifically. A paragraph. That’s it. Most candidates skip it entirely, which means doing it at all already separates you.
Where you work matters beyond the paycheck
I talked to someone once who had higher-paying offers elsewhere but chose a company working in solar power because he believed in what they were building. He didn’t regret it. There’s no formula for this, but you spend a huge amount of your life at work. The mission matters. The team matters. Whether the people around you are learning and growing matters.
Don’t optimize purely for comp, especially early on. Optimize for learning, for people you respect, and for work you can get behind.
One last thing
The interview process goes both ways. You’re evaluating them as much as they’re evaluating you. Companies that can’t handle honest questions, or that penalize you for having four of their six requirements instead of all six — those probably aren’t places you’d have wanted to work anyway.
The best companies know that hiring is a two-way conversation. Find those ones.
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