When to stay, when to go: On burnout and grief
A personal post on burnout and grief.
A lot of people in tech are carrying grief right now, and I don’t think we talk about it enough. The pace of change with AI is dizzying, and the uncertainty is real, because none of us can say with confidence which jobs will exist in five years. When the ground keeps shifting, it makes sense that so many people feel overwhelmed and burnt out, and find themselves quietly mourning a future they thought they had.
Burnout and grief are easy to confuse, and I think that’s part of why people stay stuck. Burnout tells you that you’re depleted, so you try to fix it with rest. Grief tells you that something you valued is gone or going, and no amount of rest gives that back. Many of us are experiencing both at once, and we keep treating the second as if it were the first.
I’ve written about burnout before and how recovering meant changing the way I worked. In my last role in tech, I also had to consider whether the work itself still fit.
I know something about this from the inside. I was a CPO, I was making great money, and I still went to my boss and asked him to eliminate my role. It was the worst job I had ever had. I wasn’t creatively challenged, and I had very limited authority in spite of the big title. On top of that, I was regularly minimized and disrespected. I was also completely burnt out, but from the outside it probably looked like I had everything I was supposed to want.
For nearly a year, I tried to fix it on the margins. I took weekends to decompress and went on vacations with and without my family. Every time I came back, I felt the same deflated way, because rest on the margins doesn’t fix what’s missing in the middle. I kept optimizing the edges of my life while the center stayed hollow.
The timing made it harder. In 2020, after I sold my company, I joined the acquiring company as a product executive, and less than two years later, the acquiring company was acquired. Two acquisitions in under two years were intense. I was exhausted, it was the pandemic, we were remodeling our home, and our sweet dog was dying. I was already trying to manage grief, and now there was more to carry. I wasn’t giving myself room to feel any of it. I was just getting through the day, and I think a lot of people are doing the same thing right now.
A mentor told me to visualize my life after my career in tech and to really feel it. That exercise changed something for me, because it was the first time I let myself imagine an ending without treating it as a failure. When I finally asked my boss to let me go, my friends and colleagues thanked me for my courage and honesty, and my boss apologized and thanked me too. There were other executives in the same position (side note: acquisitions are very hard), and they were also appreciative of how I was walking away. The conversation was much easier than the buildup in my head.
I think there’s a lesson in that for this moment. Some of our fear about AI is fear of the unknown. There’s also a strange mix of excitement about what AI makes possible and resignation about what might be lost. When we’re talking more to bots than to other people, this moment can feel even lonelier and scarier.
For me, talking with friends and advisors helped. Asking to leave was easier than I’d expected, even though figuring out what came next was still hard. Talking about change doesn’t make it any less real, but I think we make better decisions when we look at it directly than when we let it hover over us.
If you’re stuck and afraid right now, I want you to know that how you feel can change. Once I started an exit plan, a lightness crept in. An exit plan isn’t a resignation letter. Mine had three parts: when I would leave, how we would scale back expenses, and what our personal monthly burn rate would be. It wasn’t perfect, but it gave me peace of mind and kept me on track, even amid the volatility. Having a plan didn’t remove the uncertainty, but it gave me something solid to stand on while I moved through it.
People often ask me how I knew what was missing. Here is the process I used:
- Track what drains you and what lights you up, so you’re working from evidence instead of a vague mood.
- Pick your top three to five values, the things you won’t compromise on even when it’s inconvenient.
- Score how well your work honors each one, from 1 to 5, and be honest with yourself.
- Find the biggest gap, because that may help explain some of the exhaustion.
- Get specific about that gap, so that if it’s autonomy, you ask yourself: autonomy over what?
For me, the answer was autonomy over my time and my creativity. Once I could name that, I stopped asking whether I should stay or go in general terms and started asking what I needed more of.
This is also how I think about the question of what jobs will exist in the future. Titles and roles are going to keep changing, and some of them will disappear faster than we expect. Your values are more durable than your job description, and they tell you what to filter for, so that the next thing you choose actually fixes the problem instead of repeating it. They won’t tell you what to do next, but they will help you recognize the right answer when it shows up.
I’m nearly three years removed from my last job in tech. I’m lighter (both physically and mentally). I rarely work on Mondays or Fridays. I have a wonderful yoga practice and community. I read one or two books a week. I’m writing nearly every day. I’m studying. I’m growing a profitable company and still having fun building products. Most importantly, I’m deeply connected to those I love.
It hasn’t been the easiest path. The first year after I left my executive role was filled with doubt and uncertainty, but I wouldn’t change where I am now for any title or paycheck. If you’re feeling the weight of this moment, I’d love to hear what’s draining you and what’s lighting you up.