Leaving Airbnb

I wrote this in early 2013, but it was too raw for me to post at the time. I guess I needed 18 months of self-reflection and a whirlwind startup experience to come back and make this post public! This is largely unedited to preserve what I felt at the time, even though my thinking has changed a lot since then. I would love your opinions and thoughts.

I felt like I just ran a marathon, but it was only the first day.

I had put in notice at Airbnb and was slowly starting to tell friends, family and colleagues. People were uniformly shocked.

“Why?! Didn’t you say Airbnb was amazing?”

“Did something go wrong? Did you get let go?”

“Are you an idiot?”

(That last one gets a chuckle out of me every time!)

I don’t blame them. Who leaves a hyper-growth company known for amazing culture, in a senior role, with a seriously-awesome team?

I mean, put it that way, and it does sound pretty stupid to leave.

I had a good thing going. I loved my Online Marketing Group (affectionately known internally as OMG), and my boss was amazing—he was collaborative and he gave me enough rope to do my own thing. Better still, Airbnb is a travel company (awesome) that solves problems using startup gumption and innovation (awesomer).

Really, what the hell was I thinking?

Let me explain. At some point in our lives, we reach a stage where we start losing touch with the very things that got us there.

I started my career as an engineer. I worked at Shopzilla, a comparison shopping engine, as an associate software engineer straight out of college. I didn’t really join a “team” so much as worked on a bunch of projects with some guidance from other engineers when they could make time for me. I broke into software engineering the hard way: making tons of mistakes; developing, refactoring, and re-refactoring my code over and over again as I learned new things; grinding away at improving my skills on nights and weekends (sometimes out of necessity due to the nature of having operational ownership of my product).

I landed in the Consumer Acquisition team, which meant that I was the lead on building a number of very cool products, including a bidding algorithm, a publisher placement optimization tool, data management systems, reporting interfaces, and all manner of crawlers, API interaction code, etc. I also worked myself to the bone because when you’re spending millions of dollars via a barely-held-together prototype built by a couple of scientists and a 22-year-old greenhorn engineer, EVERY MINUTE I WAS NOT CODING THE COMPANY WAS NOT MAKING MONEY! and EVERY SECOND THE SYSTEM IS BROKEN WE ARE LOSING THOUSANDS OF DOLLARS A SECOND!

Not gonna lie—it was incredibly stressful, and I couldn’t help but somewhat resent my “business overlords” who didn’t have to come into the office at 2am on a Sunday because some data processing script failed to run upstream (which in turn, stalled my own scripts) or stay up all night fixing a production issue because I needed to rectify a last-minute change to a bidding algorithm that I was coerced into pushing live Friday night (those were the early days, when we had no testing infrastructure to speak of and I was too junior and naive to push back on demands).

After a few years of high-pressure development hell, I wanted out. I asked to be moved into a product management role, and enjoyed it. I continued to move more and more toward the “business side”, eventually landing a role at another startup managing a search marketing P&L, but being hired to run both business and engineering teams due to my background. I was much, much happier and stayed on this path for a while.

By the time I joined Expedia, I was a VP with a team of 45 and a calendar full of meetings.

I had meetings.

Lots of meetings.

So many meetings, in fact, that I’d literally be in back-to-backs from 7am (calls with my London team) to 8pm (calls with my APAC teams) with maybe a 30-minute window to grab a quick lunch. I would try to block out an hour here and there just so that I could catch up on emails or try get started on real, actual work.

I loved working for my boss and I also enjoyed leading a high-performance team (some of my reports were seriously amazing individuals), but I would often feel like something was missing. I had built valuable relationships, a fantastic team based in five offices around the world, and got heavy exposure to senior management, but it wasn’t enough. I wasn’t totally fulfilled. I needed something more, but I couldn’t place it. After some challenging professional incidents and a lot of personal reflection, I made the decision to leave Expedia and then moved my then-eight-months-pregnant wife from Seattle to San Francisco to join Airbnb.

Airbnb was a refreshing change of pace. My team was small, nimble, and each person was truly fantastic at what he/she did (and we all got along great socially). When I had interviewed at the company, I knew that the company was in the middle of a new organizational expansion centered around international growth. I was nervous about this given my recent experience, but the leaders at the company convinced me it would be different. Things were fine at first, but as Airbnb continued to grow like a rocket ship and added hundreds of new people each quarter, I started seeing some of the same trends I saw at Expedia, where large-company dynamics made getting work done rather challenging.

Don’t get me wrong. Working and collaborating with people is a passion of mine, and solving organizational problems also delivers a great emotional payoff. I just realized that, at this point in my career, I wanted to get back into building products—improving the lives of customers, as opposed to stakeholders.

I wavered. I thought that maybe this was what happens to people as they take on more senior roles. Maybe this is my fate?

I kept telling myself:

I shouldn’t complain. I am truly lucky to have a job at Airbnb and live in the most amazing city in the world for people who love technology and startup culture.

I soldiered on.

What really changed the game for me was the birth of my daughter. She was born two months into my tenure at Airbnb. Hindsight is 20/20, but I didn’t know how much she would rewire my brain, and upend the structure of my life.

The transition to fatherhood for me was hard, but in the beginning my daughter just slept, ate, and pooped all day, so there wasn’t much to it. I thought I could easily manage both being at an intense place like Airbnb and being a great dad. However, as she got older, I missed big milestones or witnessed them through a smartphone screen, after the fact. I’d come home late after a work event and walk straight into our dining room, firing up the laptop to begin furiously working on a presentation, with her looking up at me and wondering what the hell I was doing while she sat next to me.

Sitting turned to crawling. Crawling turned to walking—and there I was, still on my computer, working through another iteration of my strategic plan.

I enjoyed the work. I absolutely loved my team and company. I was proud to be a part of something truly amazing and meaningful to so many people around the world. But I was also ignoring my duties at home. More importantly, I knew that it would be too easy to continue down this path, and I’d be none the wiser, until it was too late. Weeks would pass into months, months would pass into years, and my daughter would grow up as a perfect stranger, right beside me.

I get sucked into my work. I’m a bit of a workaholic, and my sense of loyalty was transforming into a persistent sense of guilt. I was already feeling like I wasn’t giving enough to the company if I left early for bath time or skipped out on a happy hour to spend more time with my family. I would feel the opposite every time I made a decision to stay late, go out with colleagues or travel abroad for meetings.

I decided that both continuing at Airbnb and being available for my family wasn’t sustainable. There was still too much work to be done at the company before I could even consider stepping off the gas. I would feel guilty about all the compromises I was making, which would keep the vicious cycle moving in an ever-accelerating negative feedback loop. The team depended on me as a manager and leader, and I was already starting to feel less effective.

I needed a situation that gave me enough flexibility to spend more time at home. Not “two hours more a week” time, but true flexibility. If my wife was having a bad day, I’d leave the office early and then put in a few extra hours after we put our daughter down for bed. If we decided to go to the zoo on Saturday, I could enjoy my time there and not be zombie-walking two steps behind everyone, glued to my iPhone.

I don’t mind investing a ton of time and energy into something I believe in, but as a new father, I now had to do it on my terms, for the sake of my family. If I was going to put in crazy hours, so be it—I have no problem with that—but having control of when and where I put in those hours was key.

It was tough, but I put in my notice in early January—with a heavy heart but believing I was doing it for the right reasons. I wasn’t sure exactly what my future would look like, and I knew that I was jumping out of a once-in-a-lifetime-unicorn-rocketship, but I also knew that things would work themselves out in the end.