What I’m Trying With All of This

In mid through late 2021 I experienced what I would call burnout, the concept that I truly had nothing left in the tank emotionally to strive at my job, even if the interest remained. I still remember the vague googling around “recovering from burn out” in late 2021. It was… so disheartening. Looking back as someone who's found quite a bit of happiness and contentment with their job, I decided to write the article that might've helped me feel less alone and confused at that time.

Most of the advice revolved around “rest and recovery” and “taking a break”. I think it all stems from the popular conception of burn out, that you burn out if you work too hard for too long.

But I’d be worked 80+ hour weeks to get a launch out, and then feel “burn out” only to take a small break, get some good sleep again and feel ready to go. No, this was something else. Those sessions felt more like doing a really challenging workout and needing recovery than burnout, which felt more like an injury.

And around the same time, Adam Grant popularized the term “languishing” for the sense of aimlessness that knowledge workers felt during the pandemic. The loss of direct community and direction. But this wasn’t that, I had re-found a community of purpose at Guild that I was interested in, and I had specific goals I would like to achieve.

Finally, I knew what I was going through wasn’t depression because the desire was there. It wasn’t that I didn’t want to push hard or do good work, it was that when I started pushing, waves of emotional exhaustion would hit.

Having been through severe anxiety before, it was possible to differentiate between what felt like a serious mental health condition, and honestly, in retrospect what felt like an emotional work injury.

A Dall-E Representation of: the internal experience of burnout represented as a cave painting

How it Started

In late 2018 I left my first job as a software engineer to join a small startup named Pana that was trying something compelling in the business travel industry. They were a company focused on “Guest Travel”, or travel that was still for a company but was being done by someone who wasn’t a full-time employee at that company, like an intern or an interviewee. There were a number of r interesting technical and product challenges that they were trying to manage, and I just vibed with the group of people doing the work.

And in early 2020 I felt like an important part of that company. I could see not only the impact I was making, but vividly imagine a future where I could grow my career with the company and the people who worked there. We were on the cusp of signing some massive clients which could have fundamentally changed the scale we were working at.

At the time, I was working really hard with my team to deliver what felt like essential features.

And then the pandemic hit…

Within a few weeks, we went from being on the cusp of success to being on the brink of failure. We went through layoffs, pay decreases, and a remote working situation that made communication feel impossible. (Many of the tools and practices that we now take for granted really didn’t exist)

But, as a community, we pivoted. We found a new direction (within the travel space) to move as a company, and we started developing features to get there. It was weirdly a bit like summer camp for the final half of 2020. While we were developing features, there weren’t any users to test them, so there wasn’t that typical back and forth challenge of trying to prioritize maintaining existing code or shipping.

I even helped lead the architecture and launch one of the features I’m most proud of as an engineer. The beginnings of a financial matching and reconciliation system.

You might notice these are heavily rose-tinted lenses I’m looking back with. And… they absolutely are. I want to avoid papering over what were really challenging times or the arguments and back and forth that happened. But… the rose-tinting is important to frame my feelings. It was hard, but it felt purposeful.

And then… in early 2021 it happened. We got bought.

Joining Coupa

The funniest trope in acquisitions is how you’re still following “the same mission” but with “increased scope and resources”. It’s a silly statement, and I get why it gets said, but the reality is that new owners will have new and different opinions about what they would like to see. That’s… the point of an acquisition. It gets said because the alternative would be pretty crappy, “we’re going to change what you were working on and cared about, and you'll need to deal with it”.

The alternative, in an ideal world, also just isn’t entirely true. Ideally, both companies would like for there to be an on-ramp to that change. Maybe eventually your product changes, but there would be a slow wind down where your systems/tools/beliefs get absorbed into the larger org.

But getting acquired was a shell shock. Logically, I recognized trying to have maintained an independent small travel business through 2021 and 2022 would have been absolute madness. But emotionally, I was completely invested in the problem we were trying to solve and the way we were attempting to solve it.

In that sense, it was shattering. It wasn’t just that an external source had taken away something I (and my close coworkers) had been striving for. It wasn’t just that it felt so fundamentally out of the blue. It was that it felt like we had gotten so many of the things about working together as an org, about problem-solving, about communicating really right. The thought I kept coming back to was “oh, we got about as close as you could to getting it right, and we still were absolutely meaningless in the face of all of that”.

Trying to manage through those emotions while being promoted to engineering manager (a personal goal I’d had for many years in my career) while adjusting to a new company, culture, and responsibilities, was honestly just too much. I was actually burnt out. The dichotomy of getting the thing I had wanted (becoming a manager) while also having the identity I had attached it to ripped away (Pana Guest Travel) was a ton to process while also doing a job. So I left.

Joining Guild

In mid-2021 I left Coupa, took a 2-week break (where my wife and I roadtripped back to the West Coast) and joined Guild Education, a company that felt way closer to my heart. Guild had a mission of helping people I was fully bought in on, it aligned with a close personal interest of mine (education). I assumed that rediscovering that sort of emotional alignment, while working at a company that seemed to have an incredible employee experience, would, honestly, resolve my burnout. I had taken myself out of the fire.

And that’s when I realized I was completely and totally burnt out.

Usually when I start at a new company, I’m excited to jump in and start learning all the new things. Trying to get a better sense of what’s going on, how things work, and how I can start making a small but noticeable impact.

But at Guild, even though everyone was incredibly friendly, helpful, and patient, every time I tried to pick up new information I felt completely overwhelmed by the situation. I was confused by the terminology, by the flow of information, and by why everything that used to feel so natural felt so confusing. It was honestly completely disorienting.

So, I tried something new… I gave myself permission not to strive.

What Next

That’s all for this week! I wanted to focus on deep diving on the what and the why. Next week I’m going to dig into what recovery looked like, and why the Nike Running Club app became one of my go-to techniques.

This is continued in part 2 on recovering from burnout.