On failure

Several years ago, I started publicly celebrating my career successes with cupcakes, in the tradition of Lara Hogan. I had started working at Etsy, had just signed the contract to write Effective Devops, and was feeling optimistic about the direction my career was going.

A lot has changed in the past few years, and it's been harder and harder to find things that feel worth celebrating at all, let alone publicly. Part of that has been situational and burnout-related. It's been a long time since I felt like I had even the opportunity to do work that felt meaningful or significant to me, and I know that taking a break from so much conference speaking and book writing was the right thing to do  - especially when I was also recovering from major surgery and moving to a different continent. But even so, every time I thought about the cupcakes (and thus my career), I felt like a failure.

Sonia Gupta started a great conversation on Twitter the other day about failure. While I was comfortable sharing my story about getting the three-armed sweater award or funny anecdotes about my first ops job, those don't feel like the kind of failures that I've been struggling with recently. There's a big difference between "I messed up but it was a temporary setback that I learned a lot from" and "oh god I peaked when I was 30 and I'm never going to accomplish anything meaningful again". There's a big difference between feeling like I did some things that were failures versus feeling that I myself am a failure. Rationally, I know I'm dealing with the former, but emotionally it feels much more like the latter.

In a lot of ways, the simple absence of visible career milestones has itself felt like a failure, especially when my earlier achievements felt so significant and meaningful. But maybe this is a case of "mid-career" progress just looking different from that of an "early" career. When I was earlier in my career, the next steps and milestones were a lot more clear: I wanted to become a senior engineer, I wanted to speak at big conferences, I wanted to stop getting paid half of what my male peers were making for the same work. But now, with over a decade of experience under my belt, future direction feels less clear. Do I want to write another book? Do I want to keep up as much conference speaking? Do I want to keep doing operations or change focus, do I want to be more of a specialist or a generalist? What do I want the next decade of my career to look like?

Progress isn't always linear. It doesn't always come in the form of big concrete achievements. Sometimes there is no feeling of "this achievement is capital-D Done, I can move on to the next thing". Sometimes, progress is a bunch of behind-the-scenes work, considering questions that I have to answer for myself or getting my life settled to a point where I can start thinking about what's next. Transitioning and moving to a new country weren't career progress, but in retrospect they were necessary for me to get in a place where I could focus on my career again.

I'm not recovered from my burnout now, but I'm at least in a place where I can start to imagine the end of it, and start to think about better ways to think about how the past couple years of my career have gone than "I'm a big pile of failure and sadness":

  • A lack of visible progress is not a lack of progress. A lack of concrete public achievements is not a failure. Experiencing failures does not make you a failure.

  • Not all progress looks the same, and not all goal-setting looks the same, especially depending on where you are in your career (or in life). When I found myself unable to answer the question "what do I want to achieve next", changing the question to focus on "what kind of life do I want to have" or "how do I want to feel about what I'm doing" really helped.

  • I found this post from Captain Awkward super helpful for finding ways to feel like I was still somewhat productive while also trying to let myself relax and recover. Specifically, having two reading lists and breaking "productive" reading up into small chunks of time has been useful.

  • Looking for ways to feel good about what you're doing, whatever that means to you, is important. For me right now, that means figuring out how to be okay with things not feeling "Done", and looking for ways to celebrate the progress I've made even when that isn't wrapped up in easy-to-cupcake achievements.

  • Talking about failures and struggles can be a good thing, and can help to normalize them. Having my accomplishments be so public was good in a way, but I also felt like I was disappointing people or letting them down when I stopped feeling like I had things to celebrate. Feeling like I couldn't talk openly about my struggles was isolating, and isolation is not good for burnout.

So for now, I'm retiring my celebratory cupcakes. I've spent the past couple years feeling like I couldn't live up to those past accomplishments and worrying that I was a failure. I want to change how I think about failure going forward, and that means changing how I think about success and progress as well. Focusing so much on discrete, publicly visible accomplishments made it harder for me to see the small, gradual pieces of progress that  matter more to me at this point in my career - and life. I started the cupcakes as a way to demonstrate what it meant to celebrate my successes, and I hope that sharing this will help other people see what it might look like to sit with and learn from failures as well.