How I became (and stayed) a successful programmer

3 strategies that have been crucial to the longevity of my programming career

For a while now, interest in programming has been skyrocketing. So there are a lot of beginners out there starting their careers — and that’s a wonderful thing!

If you’re one of those beginners, eventually you may start thinking about the long-term prospects of your new skills: How do I take a new skill like programming, grow it, shape it, and tune it over time so I can achieve longevity in the industry?

I asked myself that same question early on in my career. Now, a mere 15 years into it, I’m hoping I can give you some answers.

Below are a few general strategies that have helped me become (and stay) a successful programmer over the long haul.


1. I surround myself with programmers who are way better than me

Over the course of my career, I’ve always tried to pick work where the people I’d be working with are exceptionally talented. To put it more bluntly, I put myself in the company of programmers who were way better than me.

This is crucial, because the best way to improve (at anything) is to learn from people better than you. It might be a nice ego boost if you know more than everyone around you, but you’re otherwise just flat lining your actual progress.

When I’m around these talented programmers, I constantly keep my eyes and ears open for nuggets of wisdom. I watch how my fellow programmers carry themselves, how they breakdown a problem, how they talk to each other. I look at their code for patterns and style choices that I can mimic. I remind myself to talk less and to listen more.

Unless you’re the Michael Jordan (or dare I say the LeBron) of your respective field, there should always be someone better than you — this is a good thing!

You have nothing to lose and everything to gain in such a situation. Take advantage of it. 🚀


2. I occasionally leave my comfort zone

I’ve found it beneficial to leave my programming comfort zone once in a while. It helps me think differently by challenging a bunch of established ideas I already have.

For sure, you don’t want to do this constantly because it can be hard to get into a rhythm with your normal area of work. But in moderation it can really open your mind to new ways of thinking.

For example, my comfort zone is Java and Android. But over the last year, I’ve taken on stuff well outside that zone:

  • I helped build an open-source framework. Turbolinks Android was the first time I’d ever worked seriously with Turbolinks (new tech to me), it was my first open-source project ever (new process for me), and it was a cornerstone for Basecamp 3 for Android (a new product for the company). It was one of the hardest projects of my career!
  • I started writing Kotlin instead of Java. I’d been writing Java for over a decade, so picking up a new langauge was no trivial task. Not to mention I’d never written a single line of Kotlin previously! But before I knew it I jumped in head first and am now writing Kotlin most of the time. (Incidentally, I’m completely in love with the language!)
  • I’m learning the underpinnings of our open source rich text editor. By learning the ins and outs of Trix, our Android team will be able to better utilize its capabilities now and in the future. But as someone who isn’t totally up to speed on advanced Coffeescript and DOM manipulation, this has more or less melted my brain. But I shall prevail!

Here’s what’s important to remember — none of this stuff was particularly easy or comfortable for me. In fact much of it was downright uncomfortable, nerve-wracking, and filled with doubt. At times I literally felt like I had no idea what I was doing.

But as challenging as they were, I did them anyway because I knew how valuable those experiences would be . They gave me the opportunity to work with a variety of the programmers, let me reacquaint myself with technologies I’d fallen behind with, and let me learn brand new stuff that few others in the company got to. All of that made me a better programmer.

So find a programming task that takes you out of your comfort zone and make it your next project. Then watch it pay off in spades. 💰


3. I value being independent

When you’re just starting out, you’re going to have a lot of questions. That’s OK!

What’s most important is how you choose to find the answers to your questions.

One philosophy that’s always served me well is to be independent. Usually this means that I’ll try to do most things myself first, and only when I really get stuck, I’ll ask for help.

Being independent has tons of benefits, but to name just a few…

  • You learn how to be resourceful. Finding answers may just be one Google result away, or it might take a dozen different queries. You might have to patch together 5 different solutions that you’ve found to work together. Who knows. Finding the answers you need on your own is a skill that’ll serve you well for years.
  • You earn respect by being courteous of other people’s time and work. When you prioritize your independence, working with other programmers is easier. They’ll appreciate that you’ve done a lot on your own and have taken it as far as you can before asking for help. By respecting other people’s time and work, you’ll earn respect back. And mutual respect is the cornerstone for trust and solid teamwork.
  • You start developing your creativity. When you need to come up with answers, you’ll find yourself coming up with creative solutions you hadn’t considered. You’ll try things that seem crazy and out of the realm of possibility. Some will work and some won’t, but you’ll begin to develop a palette of creative solutions that you can draw from many times down the road.

The next time you have a burning question, see if you can answer it yourself, even if it takes a little longer than asking someone. It’ll be worth it.🔥❓✔️


Becoming a successful programmer is, like anything worthwhile, hard work. But these strategies have always served me well in the long run — after all, I ended up getting my dream job working at Basecamp. I hope they can help you get to where you want to be, too. 😀

I hope this article was helpful to you! If so, please do hit the heart button below and let me know on Twitter.

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