Into the Wind

Last summer, I had a chance to go sailing on a four-person boat. I have a thing for saltwater. I’ve always dreamed about having a teeny Sunfish and a teeny house on a teeny inlet, maybe near the Puget Sound. So when I learned I’d be sailing with two people from marketing and a professional skipper, I was stoked out of my mind.

We had lunch outside. I could barely eat for all the excitement. Once we got on board, the skipper asked us to captain the boat. I volunteered early, hoping to just steer her out of the harbor and let a friend take over. I wiggled her around in between the shallows, getting more and more terrified.

The wind was fierce. I was cold with two coats on. The Bay seemed to be telling us to stay on dry land and retreat quietly to the machines. I thought we would sit down and learn some basics before getting on the boat. After all, I didn’t know the stern from the bow. But no matter—it turns out that you can learn to sail in the water without too much trouble.

Pick something on the horizon, focus on it, and steer into the wind. The boat will tilt onto its side, secured by a lead keel. You can’t see it, but it’s important to remember. Your friends and your stomach will revolt. Never mind all the spraying and shouting. Head windward. Hold steady. It’s okay. You’re doing great. Go go go.


I’m in California this week. I keep looking at the water on the way to work, remembering how much it scared me that day. Exhilarating fear and tired relief. I haven’t felt that kind of rush again until now.

I’ve decided to work on personal projects and come back to freelancing. Next Friday is my last day at Facebook. This wasn’t an easy decision for me. I’m leaving a stable job for wilder winds, but with everything I have planned for this year, it feels like the right thing to do.

The water seems calm now. The sun outlines its surface with a white sheen. I’m shuttling south with a few bittersweet feels. The wind is picking up along the highway.

Onward. Ignore the shouting. Keep going. You’ve got this.

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