When I left TripAdvisor a year and a half ago, I wasn’t expecting to return. I’d had a great time over the preceding six and a half years, learned a lot, made an impact, and climbed the ladder. I’d worked on a dozen different teams across the Core Product department, finished up with a helping of Operations, and honestly couldn’t see where my next personal S-curve was going to come from if I stayed. Time to close that chapter of my life and move on to new and exciting things.

I’ve written a bit about startup life, but one thing I haven’t really discussed is how it gave me a new perspective on my time at TripAdvisor. Somehow, living through the rocket ship years of 2008-2015 hadn’t seemed particularly remarkable from the inside. Of course revenue was going up 30% per year, every year. Of course our market share was monotonically increasing. Of course our competitors were unable to catch up, and eventually fell away. Of course the stock went from 7 when I joined to a high of 110 (ok, ok, down to 80 when I left, but still). It’s not that it was easy – but the wind was at our back, and hard work paid off so consistently that it seemed like a natural law.

It was a wild ride, and I was tremendously lucky to have stumbled into it. It was only when I left that I realized just how unusual it had been. I had an amazing time at HelloShopper, and learned many things I wouldn’t have by staying at Trip. I learned about new technologies and modern development approaches, startup operational challenges, effective use of AWS, how to build a great, diverse team from a very small base, and so on. I learned a lot about the Boston startup scene, met some great angels and VCs, and learned a little more about how The System works. But I also learned how hard it is to find product-market fit. How frustrating it is to work, and work, and not be able to get users to do the thing they came to the site to do. To see time slip away, and the runway shorten, and not know how to succeed. Everything that had seemed so natural at Trip sullenly refused to fall into place. I’d known this once, but forgotten: success, it turns out, is hard.

And so HelloShopper closed down. I looked around for a while, which is a story in itself, had a number of opportunities, and ultimately chose to go back to TripAdvisor. Given the above reasons for leaving, a lot of people have quite reasonably been asking me why.

When I was initially thinking of leaving TripAdvisor, I was very upfront about it with my boss. We’d had discussions about other positions within the company, and he knew that I was talking to a number of different groups to evaluate their opportunities. At the same time, I was also very transparent with him about the fact that I was looking outside the company. When I left, it was on extremely good terms – I still kept in touch with many of my friends, still had the occasional get-together at my house, still heard some of the gossip. And the story I heard was of a company in transition.

One of the things I’ve always respected about TripAdvisor has been its willingness to retire old strategies that were still working, but clearly not viable over the long-term – for instance, when they moved from pop-ups (which brought in crazy revenue) to meta price displays (which were a far better user experience, but harder to monetize). Taking the long view like this isn’t easy – you’re foregoing easy money on a bet that it’s the right time to abandon a proven strategy, and intentionally hurting short-term profits in favor of the future. Most companies don’t have the conviction or discipline to catch this falling knife, and end up getting eaten from below. Trip had been transitioning to a new model since before I left, and it looked like they were figuring things out.

At the same time, a role had opened up on Commerce – a team I’d always been interested in. The Commerce team has a combination of analytics, reporting, feature, platform, and operational responsibilities, is tightly integrated with key business functions, and has a front-row seat to the surprisingly intricate way in which money is made. This would be an incredible education. The old manager had recently moved to another team, and they were looking for someone to replace him.

Lastly, Trip was getting ready to start a long-overdue overhaul of the code base. This was tremendously exciting – the opportunity to be involved in a re-architecture at this scale is a pretty rare opportunity, and certainly not something I’d expect to find elsewhere. Working with people I knew well, liked a lot, and respected the hell out of to get the technology into shape for the next decade – all while avoiding the rewriting-from-scratch anti-pattern – was a pretty big deal (details to follow in future posts). In the end, it was a pretty easy sell.

Joining a new company is exciting for all sorts of reasons. New people, new challenges, new technology, firehoses from which to delicately sip, terminology to puzzle over, politics to divine. Going back to Trip allowed me to skip a lot of the accidental complexity and get right to the good stuff. It isn’t the same as before – the company is different, the business environment is different, the challenges are different, the role is different, I’m different. There are new headwinds, opportunities, and subtle complexities to work within. Do I regret the fifteen months I was gone? Not at all. But now’s a great time to be at Trip, with the business and technology both poised for their next big S-curves. It’s great to be back!

* The above image of an owl is © Daniel2005, CC Attribution 2.0 Generic. The image has been cropped and resized to fit the space, and has had color removed.