The Crazy Woman Speaks

On a Sunday transcontinental flight , I was stuck in a middle seat next to a woman reading a book filled with crazy conspiracy theories.

I minded my own business, thinking of a friend at Berkeley who once saw members of a cult walking down the street toward his house. Though heterosexual, he took off all his clothes, clasped the hand of his roommate and, when the missionaries knocked, invited them in for a religious debate. I imagined the argument I would have with my seat-mate in a situation like that, sipping tea naked on a couch, atomizing her world view.

While I was busy with that, the woman opened her laptop to view some paintings of flowers. Almost involuntarily, I mumbled something about how pretty they were. She mentioned that these powerful, emotional works had been painted by people with autism and dementia. She had dedicated her life, she said, to helping them paint.

Tears didn’t actually come to my eyes until a few minutes later, when I saw the pictures of the artists next to their paintings, smiling for what seemed like the first time in a long time, oblivious of the bleak institutional setting in the background. What prompted my seat-mate to help folks whom almost everyone else had given up on?

It was another reminder that people whom I disagree with are good people, and that they are as likely to be right as I am. This has been the essential humbling experience of life in my 30s, especially of my life running a startup. You see how many surprising shapes and sizes good people come in, and occasionally get zinged with how fallible you are.

Whereas my imaginary argument with my seat-mate had made me feel smug but still bad, my actual experience of her made me feel good. It’s an experience I’m lucky to have had, not just on the plane, but over and over again at work.

The reason most people have fixed opinions is that they get tired of never seeing them enacted, but I get to see my ideas in action every month at Redfin. We try out beloved website features & make hiring decisions, and discover they sometimes don’t work out. The rubber meets the road. The crazy woman speaks.

In this way, a startup turns you into both the lab rat struggling desperately to survive and the lab scientist standing back and measuring his performance. It gives you less patience with the ideologues telling you what the rat should have done.

If more people could see that the measurable, indisputable outcome of getting your way was sometimes disconcertingly bad — if reality could surprise you more with how often people you wrote off turn out to be your savior — we might stop listening to the smug partisans on talk radio, the outlandish political candidates in both parties, the outraged voices in our own heads.

And, stuck in the middle, we might get more out of our crowded, lonely flight across America.