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Personal growth

I spent the holiday weekend with friends in a cabin in upstate New York. We tore down an old shed, cooked meals together, watched movies, and thoroughly enjoyed one another’s company. I went to bed with the sun and woke up to the sound of birds chirping and water flowing. I rarely checked my computer, and when I did it was brief and with purpose. It was easily one of the most enjoyable and memorable experiences I’ve had in a long time.

Since shutting down my company, I’ve pondered how I want to spend the next few years. What I want to learn, what I want to accomplish, and where I want to be.

As I said at the end of my XOXO Festival talk (18:36 for those who can’t bear to hear me drone), “learn all the things” has been my North Star in life. While 4chan hasn’t been financially rewarding, I’ve accumulated enough experiences, opportunities, and relationships to last a lifetime. My startup, while objectively a failure, was similarly rewarding. I wouldn’t trade either experience for anything.

That said, I can’t help but to feel that I spent the past four years neglecting myself. I took the “always be working” mantra to heart and spent many sleepless nights trying to figure out how to grow—not myself, but the company. That meant agonizing over daily App Annie e-mails and Google Analytics dashboards.

As the company wound down, I felt like I was drowning. For the first time in years, I was free to spend my time however I saw fit. I hated the thought of it—it felt like going from running 100 miles an hour to a dead halt. And so I did what any drowning person would: I grasped desperately at anything that might keep me afloat. That meant scheduling meetings back-to-back and exploring any and all employment opportunities. I quickly became busier than I was running a company, and burnt out within weeks.

It took a close friend to slap me back into reality and view the absence of a full-time job as a blessing and not a curse. To embrace it as an opportunity to recharge and make calculated decisions about my future instead of spontaneous ones. To focus on myself for the first time in nearly four years.

Another, much older friend challenged me to think about myself at 50. What would I be excited to tell my younger self about the life I’d led? I haven’t come up with a great answer, but I do know that it doesn’t involve wealth or material possessions—something I find incredibly liberating. I just want to be comfortable and happy.

To that end, I plan to spend the foreseeable future investing in and learning more about myself. I hope to spend more time away from the computer and doing activities I already enjoy like cycling and cooking, and learning new ones like dance and gardening. As someone who can be stubborn and stiff, I want to place myself in situations that force me outside of my comfort zone. I want to spend time with people different from myself, learn from them, and build strong relationships.

That said, I find doing great work to be extremely gratifying, and hope that when I return from this sabbatical of sorts that I’ll have a clearer sense of how to spend my time going forward. Everything is on the table, including and especially things not related to what has traditionally been my wheelhouse—the Web.

Every day, I’m reminded that there are important problems that can’t be solved with just 0s and 1s—so-called “hard” problems. I’m not qualified to solve them now, but that’s precisely the point of taking time to acquire new skills and learn more about the world I don’t already know. Or maybe I’ll just become a pilot, volunteer worker, or trail guide—who knows.

That’s what excites me the most: I don’t quite know what I’m looking for, but I can’t wait to find out.

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