@iamtimhoover

My Favorite Day

Timothy Hoover
Lessons Learned
3 min readJan 7, 2013

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Saturday was my favorite day since I moved to New York. I didn’t explore the MOMA (although I love it), I didn’t ponder my life on a bench in Central Park (I’ve actually never been there, shh), and I didn’t swing on a swing at Ann Hamilton’s show at the Armory (but I heard that you should). I worked for 12 hours.

Jess, Eric, and I met up to work at a little apartment in Brooklyn. We stocked up on snacks, spread out on a freshly-assembled desk, plugged in, and got to work. It felt like grad school again—it was perfect. We were happy to be there, working in a window-less room on a beautiful Saturday. For 12 hours we each did what we do best. Eric drew pixel-perfect icons and spun the records. Jess crafted organic negative spaces and typographic hierarchies to a level of completion I don’t even consider. And I sent out a MailChimp campaign with a blatant spelling error in the header, and then tried to argue that perfection is stupid. We ate too many tacos, and drank a few Modelo tall-boys.

I couldn’t help but get fired up about life. Not only was the day warmly nostalgic and crazy productive, but we were all doing what we’ve been created to do. We’re building things, and we’re taking risks. And we were doing it together. It wasn’t all exciting, it was hard and tedious work. But we made decisions, we made mistakes, and we progress.

Sunday wasn’t as productive. But as I laid around reading, I thought a lot about what made Saturday feel so special. Why was it so great? Because none of us know what is going to happen next, and we’re all scared. Eric just left a great job at a great firm to pursue freelance and a personal project. Jess and I are putting the final touches on a book that we’ve been working on for over a year. One that we’re getting ready to release into the world to be judged, and hopefully enjoyed. And we’re all trying to sell a beautifully crafted product that lost its popularity 30 years ago. It is scary, and it is exciting. We could easily fail. But, it’s that possibility of failure that makes me so certain we’re on the right path.

We’re chasing something that might not work out, or pay off, or be successful. The chase forces us to become vulnerable. And that vulnerability is what allows us to connect. And that connection allows us to trust one another. Jess and Eric trusted me to take initiative and send out our MailChimp campaign. When I failed, Eric and I laughed. Jess laughed a little less, but we all moved on because we agree that none of us know what we’re doing.

I’ve heard you’re not supposed to start businesses with good friends. Because money complicates friendships, or because you’re supposed to keep life and work separate, or because of some other stupid reason. Well, I’ve started three with good friends and I couldn’t be more thrilled about walking a tight-rope of failure with all of them. From Ryan and Ryan, to Jess and Eric—I’m lucky to have friends that want to work hard on Saturdays, and that want to chase things. You should work with your friends, and you should let them get mad at you when you spell things wrong.

When’s the last time you did something where the outcome wasn’t guaranteed? Or where the possibility of failure, surprise, and success were equally present? Were you doing what you were created to do, with people who will allow you to fail? I hope so.

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Timothy Hoover
Lessons Learned

An opportunity maker, Head of Product at Canary (www.canary.is), and Cofounder of Kern and Burn (www.kernandburn.com)