After 20 years at Redfin, and 10 months of unemployment, I’ve co-founded a new company. My business partner and I will announce our plans after we’ve built our product, but in the meantime GeekWire asked me to explain what I learned in the transition between Redfin and this new venture.

Many of us are in transition because society is in transition, with AI hollowing out big companies and making it easier to start new companies.

In the past, my own transitions had been harrowing, because I ran out of money or lost my sense of purpose. Leaving Redfin, I thought “here we go again.” I felt self-conscious being in the grocery store at 11 a.m. on a weekday. I was ashamed when I couldn’t come up with an idea for a company. But I made it to the other side.

To do that, I had to convince myself that I was an intrepid explorer, even if what I was exploring wasn’t Mount Everest, but instead what I could be. I wanted to feel brave about encounters I otherwise would’ve found embarrassing. Over the last year, I met people about becoming a high school teacher, a Whistler bagel shopkeeper, a candidate for the state legislature, the founder of a tree-planting nonprofit, the CEO of a pre-IPO company and a project leader for Sound Transit.

The way to prepare yourself to do one thing for a long time is first to consider everything else.

At the beginning of my exploration, a CEO recruiter told me the startup scene in Seattle was “dead” and that, for all of Seattle’s talent, more companies were forming in New York and even LA.

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