12 Month Hiatus

I took a year off.

Writing that feels weird, almost like confessing to a crime. After I left Fundera/Nerdwallet at the beginning of this year, I committed to taking 6-9 months of time with one rule: I couldn't make any decisions about what to do next. I had never taken an extended break before - I had always known what I was going to do next and let momentum carry me from one place to another. It generally has served me well, but I wanted to try something new in the hopes that a break would allow me to reset and give me more clarity and confidence.

Taking time off is most certainly a privilege. I did all the cliche things one does: travel, spend time with family, read, exercise, pickup old hobbies, spend time with friends, etc. All of that was absolutely wonderful. It was also genuinely shocking and borderline frightening how fast days would go by. But the downtime can also be extremely difficult. All I've known is forward motion and planning for what comes next, so this was unfamiliar territory (although, perhaps committing to clearing my head and making no decisions was preparing for what comes next).

I learned a lot about myself over the past year. I found that so much of my identity was tied up in what I did. Telling people "I'm taking a year off" was a really strange thing to do. It made me question who I was. My whole professional career I identified as a tech entrepreneur, and all of a sudden I was in between things.

I went deep on a series of ideas that could have easily turned into startups. One was around programmatically enabling any company to build a world-class SEO program, another was a "roll-up" of internet businesses that had indestructible product market fit around people's various passions, and another was on preventing heart disease (which I will publish some more thoughts on soon because I'd really like to help someone accomplish this). I came within inches of starting one of them, but it was within my "No Decisions" window and I'm glad I stuck to it. The easiest thing for me to do would have been to start another company. It's all I've really known, and it's the thing that I most identified with. Not starting something during this period was very difficult.

I did my best to go with the flow and embrace the idea of wu wei to see where it would take me. I'm very happy with the process and thrilled with where my journey concluded. Next month I'll be tackling something new for me with a group of people I've long admired and respected. I'm equal parts thrilled and nervous. It's an evolution of what I've been doing, and I am eager to step outside of my comfort zone and embark on a new adventure. I don't think this opportunity would have emerged had I not sat still for a bit. After ample time off exploring, I feel like I have boundless energy to deploy. I'm ready to go.

Reflecting on the experience, these are some of my most important takeaways:

  • Hobbies bring great joy. I rekindled my love with tennis, joined a club, and hit 1-2 days per week. I'm playing at a 4.5-5.0 level with ex-D1 players and I love being competitive again.

  • The world is big and beautiful and should be explored in a variety of different ways if you can. Traveling to new places by myself, with family, or with friends was wonderful. I'm committed to adventure.

  • There's nothing better than quality time with family. I got a lot of it over the past several years and had the opportunity to watch my kids grow.

  • While working from home had its benefits, I am very over it. I need to be in an office with people making things happen. There's no substitute for it for me. People have different styles. Mine is in person. I also find that being in the office during the day makes me more present when I am home.

  • It's easy to mentally atrophy if the break is too long. I recommend time off to anyone who can do it. But 12 months is too long for me. Somewhere between 3-6 likely would have done the trick.

I entered this hiatus with a great deal of uncertainty. And while there's more clarity about some things, there are still countless unknowns. I'm looking forward to continuing to explore them, whatever they may bring.

Collect this post to permanently own it.
Ride It to the Sky logo
Subscribe to Ride It to the Sky and never miss a post.