The Crossroads of Should and Must

This is a story about two roads — Should and Must. It’s a pep talk for anyone who’s chosen Should for far too long — months, years, maybe a lifetime — and feels like it’s…

Don’t Fuck Up the Culture

On Monday, October 21, 2013, I sent this letter to our entire team at Airbnb. I have decided to publish this in…

Real Artists Have Day Jobs

Your job is just your side gig. 

Pair Designing Our Relationship

How we applied UX principles for knowing each other better

Here’s How It Feels to Cliff-Dive With a Paralyzing Fear of Heights

I’ve had a phobia of heights for…

Invest in Life Experiences

Why you need to buy less shit to be happy in life.

Who Am I?

The things one writes in those moments of existential crisis.

The Lure of the Abyss

What’s so fascinating about the dark?

Raise Good Human Beings into Billionaires: Response to Charles Tips

If you’re asking how to run a…

Do Something Random

Every week, do something completely off the cuff