I've Quit Four Good Jobs

I’ve quit four good jobs throughout my career. One of them, Dwolla, got acquired yesterday. I don’t regret leaving.

I left John Deere for Dwolla and had a blast while making lifelong friends. After seven years, though, I could feel my learning rate leveling off. At some point, shipping one more payments API felt like turning a crank I’d turned hundreds of times.

Knowing when to leave a place you love is harder than knowing when to leave one you don’t.

I left Vertex Software for Brale to start a company from scratch, but I knew going in that it was the wrong industry for me.

The average U.S. worker spends 45 years working. That seems like a long time until you see it laid out in front of you in a Tim Urban-style image.

A grid of 45 working years, one week per box, colored by employer — 45 working years, one week per box.

In those jobs, I’d answered “No” too many days in a row to Steve Jobs’ question: “If today were the last day of my life, would I want to do what I am about to do today?”

At Clipboard, the answer remains “Hell yes.”