How to Leave a Tech Job
Two years ago I left my job as Head of Design Studio at Airbnb, in search of something new. Not a retirement, but a transition. I left a great job and a great team. Yes, I was worried about how stupid this idea sounded.
I’ve spent the last few years working through the transition, and occasionally connecting with others curious about doing the same. Recently, though, I’ve noticed a steady uptick in people reaching out. Hardly a week goes by when I don’t get a message like:
Hey Judd! I’m thinking of getting out of tech, finding a new career, and I wonder if you’d share your experience with me.
The increase might not be hard to explain. On top of the regular clown-show-dumpster-fire of many tech jobs there are, you know, a few anxiety-producing things going on in the world right now. One or two, at least. You can’t really blame people if they’re looking for something different and better for themselves.
So when I get messages like the above, I say yes. We meet, I ask questions, I lend some support, and I share my experience. Really the same four ideas, I realized. Why not write them down, a colleague said? Ok.
And now for the necessary caveats. This is just my experience. YMMV. I don’t know if these observations apply outside of tech, but I suspect they do.
I’m well aware of the incredible privilege inherent to all of this, and that there are many, many people who don’t have the luxury to make these choices. So you might just say — boo hoo, cry me a river. But the fact is that this is my life, it might be similar to yours, and we shouldn’t devalue our own realities either.
And none of this has been a panacea for me. The most important truth I wish I’d heard when I was thinking about bailing out of tech is this:
Leaving tech is hard because tech demands a piece of your identity. Struggling with the transition is normal. The world is large, and there’s lots for you out there. Give yourself the time to find it.
Here are four guiding lights that have helped me get there.
Rewire Satisfaction
A tech career carries a specific definition of success and productivity. Getting past those definitions was the single biggest challenge when I left full-time tech.
Certainly it’s the number of hours, even if you’re not on the Elon Musk “hardcore” crazy train. But it’s not just the hours, it’s the always on culture, which the pandemic only made worse. From endless emails and Slack messages to late night “got a minute?” pings from the boss, tech trains you that the work is never done and your shift is never over.
Tech’s definitions of success also get their claws into you. At this company we have impact, people. We drive metrics! We crush OKRs, and ship the roadmap on time at all costs. We’re asked to judge ourselves and our worth by these measures.
And the calendar. Oh my god the calendar. I worked hard to find a healthier relationship with meetings over the years. But up until the end, most of my days were mostly full with meetings. If I wanted to know how useful and productive my day had been, I only had to count them. (right?)
And then it all stopped.
When I left tech, I thought I’d feel relieved. Free. But I’ve struggled to reconstruct my sense of satisfaction without the signals I was so accustomed to. My hours were my own. No OKRs, no goals except the ones I set for myself. No meetings I didn’t want to take.
After almost 15 years, I didn’t know how to rewire it. Certainly not quickly. I underestimated how much those definitions of useful, productive, and satisfied had become a part of me. Even recognizing how unhealthy they were, it was hard as hell to push them out.
I wish someone would have told me that I might feel agitated at the end of a perfectly good day, for seemingly no reason at all, unable to feel fully satisfied without the markers that tech had driven into me. And that I might feel guilty about that too. What the hell is wrong with me? This transition is a privilege and a gift. Why can’t I just feel happy?
I don’t have the magic bullet (although see below) — I only have this advice. Be aware that this may be a challenge for you. Mixed into the relief, the joy, the freedom to build a new career might be the anxiety of your hours being your own, your goals being in progress, and your calendar being (relatively) empty.
This is normal. Maybe even healthy. You’re going through withdrawal. It’s detox. If you feel that same anxiety I did (do), maybe now you can put your finger on the cause. You’re not doing a thing wrong. A change is underway. And the anxiety means it’s working.
Find Anchors
If you’re thinking of leaving a tech career and you know exactly what’s next for you… congrats! As far as I can tell, most people are deeply not in that place. Most people are like I was — they have a sense of what their next career might look like, but need to work through it.
On top of that, most people need a fucking break. Weeks or months of valuable time spent decompressing, reconnecting with friends and family, and exorcizing demons (again, a massive privilege, I realize).
But once you’re done with that, my advice is — you need an anchor.
An anchor is a thing you can use to structure your life as you work through the transition. Emphasis on structure. It might not take up a lot of time in aggregate, but an anchor creates a rhythm around which you can build.
It’s probably not hitting the gym, reading a lot, or spending time with your kids. Those things are essential and wonderful, of course. But I think the best anchors are work-like. They create a regular obligation. Someone’s expecting you to show up and do something, and you’re excited about doing it.
For me, my anchor is teaching. I am a lowly lecturer at UC Berkeley. I teach one class a semester. I love doing it. It’s not the main thing I do with my time, but the cadence of preparing for class, teaching, and meeting with students grounds me.
The rest of my days are full of coaching, consulting, advising. All wonderful work that I’m thrilled to do. But all fundamentally unstructured, flexible, and open-ended. Without teaching, I think I’d feel unmoored.
Anchors are different for everyone, of course. It might be taking classes, a part-time job, or volunteer work. Before I started teaching, my anchor was pilot training. I never finished my license, but the regular cadence of studying and flights gave me the structure I needed at that time.
One of the best things about anchors is that they help you rewire satisfaction. The cadence of doing something useful, something you love to do helps your brain and your heart get rid of all the unhealthy expectations that tech drove into you.
Seek Community
The best thing about every tech job I ever had wasn’t the tech or the job, it was the people. Colleagues, mentors, friends. My professional community inspired and educated me, often without even trying. I’m fairly sure it was only because of these people that I was able to put up with the rest of it for very long.
I have more time for my personal community than I’ve had a in a long time — and that’s invaluable (and a big chunk of the point of leaving). But now that I don’t have a community built into my job, I’ve found it absolutely essential that I seek it out. I need it to inspire me, humble me, and set my brain on fire.
But, of course, now I have to be intentional about it.
So I cultivate the community of students and faculty at Berkeley. I have my wonderful clients. And of course I stay connected to the amazing research, design, and product communities that sustained me for so long. We have email lists and Slack channels. I attend dinners and events, and go to conferences. In some ways I’m more deeply connected now than I was when I was working full-time in tech.
It would be much easier to avoid these things — to rely on only the community that comes to me. But two years of this transition has confirmed how essential a community that shares my professional interests and goals is to my well being it. Seeking it out is like going to the pharmacy, and it’s definitely a drug I can’t live without.
Have Patience
Shortly after I left Airbnb I met with a colleague who suggested it takes 2–5 years to settle into your next career. Yikes, I thought, that’s a long time. But most people can’t skip ahead. The work you need to do is usually impossible while you’re still wrapped up in a tech job.
So my final, and in some ways most important piece of advice is — be patient. Easy to say, hard as hell to do. Not least because, well, we’ve got to make a living. Patience can be hard when the bills come due.
But this is also an incredibly transitory moment. Exciting, wonderful, difficult, scary all at the same time. It will probably be full of all the highs and lows that your tech career was.
So take work that you need to take. But also give yourself the grace and time to figure out the plan. You sort of can’t rush it. You may find that the very next thing you try is a hit, and you shoot off like a rocket. Or, like me, you may end up going through several iterations before you settle into a path that feels good.
Either way, be confident you’ll get there in the end. Sure, you could go back to that sweet, loving embrace of another tech job. There’s no shame in that. But if you can be patient, the same things that made you successful in a tech job will make you successful in an independent one. Just keep going.
I’m an executive coach — feel free to reach out. Send me an email at judd@juddantin.com. I write about leadership, product, design, and management. Check out my newsletter One Big Thought. Sign up to get email updates here. And Remember that No One Has Any Idea What They’re Doing.
