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.


  • Asher Bearman

    This is simply a fantastic post. Concise, relevant and poignant – makes a great point. Thanks for sharing.

    • GlennKelman

      Thanks Asher, always appreciate the commentary and support.

  • Loren Feldman


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    Similarly, I am learning to open my mind to these humbling experiences as I stumble through my 30s. I make an effort to open my mind to everyone with whom I share a significant few minutes or few hours. There is always something positive that we can take away. Thanks for the excellent perspective!

  • Fred Schoeneman

    This is some good writing, Glenn.

  • Brian Wilson

    Thanks for your candor on this. I think it can start by ending this current trend of calling other people “crazy” because they have a different worldview when it comes politics, religion, conspiracies, whatever. I am not saying that everything is equally right, it's not. However, it is a special type arrogance to think that our worldview is the only one that is reasonable and sane.

  • Jorgeleo

    You know the saying “fast, cheap, durable. Pick two”?
    Well there is also “right or happy, pick one”. We tend to make our minds, and be emotionally invested, on being right. But that will not makes happy in the long run.
    Same thing with people, we make our opinions about them, and for all of our observations, we might be occasionally right about our evaluation. But that will not make happier or better relationships.
    The only way to get happier is to create more relationships regardless of how wrong we might think they are.
    It is a difficult lesson to learn in this American culture that highly value pride and money. Both concepts push one to individualism, as opposed to relations.
    I would like to know what would it take to revert this trend, because I believe that there is a brighter future in rejecting pride and righteousness.

  • alexlod

    This post calls to mind a quote I read in Dale Carnegie's “How to Win Friends & Influence People.” The quote is semi-relevant, but still worth sharing. And by the way, great post, Glenn! I recall a time when Goyer and I both agreed we wish we could write as eloquently as you. Anyway, here's the quote:

    I shall pass this way but once; any good, therefore, that I can do or any kindness that I can show to any human being, let me do it now. Let me not defer nor neglect it, for I shall not pass this way again.

  • Will

    The older I get (yikes, I'm almost 50), the more I try to revert to the mind of a child. Thankfully, I have a wonderful 11 year old boy at home whose world is not jaded or petty, but open to the wonders each day brings.

  • Nils Gilman

    I resemble that remark….

  • Angela Distefano

    I had been clicking around redfin with my morning coffee when I stumbled on this post. I was momentarily disoriented, wondering if I was still on a real estate blog, when I started reading. I can't tell you how much I appreciate this post, especially the fact that I have encountered it on a real estate blog, but you have made my day, possibly my week. Thank you!

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    This is some good writing, Glenn.