I left my job as CTO at Rent the Runway back in mid-September. I tweeted about it and updated my LinkedIn, but never wrote a farewell blog post. I figure now, about 9 months later, it’s time for me to talk about what I’m up to these days.
I left RTR after almost 4 years. It was an amazing ride. I learned more in those 4 years about myself, building companies, building teams, and being a leader, than I ever dreamed I would learn. I burned the candle at both ends. Beyond running and building an engineering team, I started building my own public persona after years of being unable to talk about my work online. I began speaking at conferences, writing, making friends with people who live half a world away from me through the magic of the internet. And last but certainly not least, I finally got married to my long-time partner and had a darling baby who is now 3 years old.
Phew.
So, when I decided to leave RTR, I decided to do it with nothing lined up. Well, nothing but some speaking engagements. I had never in my adult life experienced time without the next job or clear career move waiting. I went from undergrad to work to grad school to work, with no major uncertainty. I am a fan of doing things that scare me, and leaving a great job without anything lined up was hugely terrifying.
Fast forward to January. I thought that I would take a job, but every time I thought about going back to startup engineering leadership, I felt uninspired. I want to grow in a different way. I want to try different things. I love to learn and challenge myself, and I knew that I needed to break out and switch up my work again to keep that going.
So instead of taking a job, I’ve been exploring ideas with the goal of starting a company. And I’ve been writing a book on engineering management. And writing a column for O’Reilly, Ask the CTO. I’m doing an experimental leadership program with my friend Kellan. And I’m still doing a bit of speaking because I love it and it occasionally pays some bills.
Some days I write a little code, or some words. Some days I write on post-it notes and try to figure out what the next tiny step towards action is. I still get sick sometimes (thanks, kid!) and I haven’t managed to use any of this time to get back in shape, but I am meditating every day even if it’s only for 5 minutes at a go. Trying to start your own thing is incredibly hard. Everything is murky. You’ve been told that it is hard, that it takes longer than you will ever expect, and yet it is harder and slower and every day there’s the question mark of how long are you gonna keep playing this game of chicken with yourself? That’s why I’m writing this. Because as they say, publicly telling people you’re doing something is powerful motivation to keep doing it.
The luxury of being able to step off the beaten path for a while is not lost on me. I feel lucky beyond words to have a supportive spouse, friends and colleagues who have opened interesting doors. I believe that I can build something great, and so if you are wondering what I’m doing, I’m trying to build a company. Wish me luck because I need it.