Essays

Imagine You Break Up With Someone You Love and They Will Not Stop Visiting You

After reading my first website traffic report today, I learned that breaking up no longer means disappearing from someone's life.

After a Long Marriage, What Is It Like to Date Again After 50?

I didn't join Hinge. I joined a rock-climbing gym.

How Long Do You Wait to Date After a Breakup?

Are we asking the right question?

What Do You Do When Everyone Says It Can't Be Done?

How Do You Trust Again?

A founder asked me how he could trust anyone again. I had lived that question for twenty-five years.

Read the Room

Anything Is Possible

My son came to me with an idea and I recognized the look in his eyes.

Learning to Hear “No” the First Time

Turns out “no” isn't always the beginning of the challenge. Sometimes it's the last word.

15 Questions I Probably Shouldn't Answer

Everything people have asked me since the book came out.

Does a Founder Ever Really Come Home?

Running a startup teaches you how to live under pressure. Nobody teaches you how to stop living under it when you come home.

Time Travel Is Easy

Four people came back into my life in the same month. Meditation had already taught me what memory does to the past, and it was strange to watch them try to visit a version of me that no longer exists.