Right after my divorce, I lived in a rented room in New York City for three months. I worked on my tech clients during the day, and at night, I walked the streets taking photographs until my feet went numb.
One evening, I was early for a date at a nearly empty bar. A guy sitting a few seats away shouted, "Hey bro, what are you drinking?"
He was tall, in a suit, and about ten years younger than me. "Bro" energy isn't my thing, but I answered. He told me how he loved this bar for the "hot" waitresses and also told me, unsolicited, about his dating exploits, in somewhat graphic detail.
He eventually told me he was coming to Boston in a few weeks (for a date, surprise!) and asked if he could stay with me. I rolled my eyes, but said, "Sure. Knock yourself out."
Three weeks later, he actually messaged me. For whatever reason, I said yes.
He came to Boston and generously took me out for a nice dinner, but conversation was agonizing. He spent the whole time talking trash about women while I sat there with nothing to contribute. The next night, he came back drunk and started showing me pictures of girls from a dating site.
Then he told me about a Bostonian woman he knew that I should meet, and showed me her picture. I was thinking, I really don't want to meet anyone you know. But she was beautiful and seemed great and nothing like him, so I agreed.
We met, and she was brilliant. She saw some photos I had taken in India and thought I was a pro photographer. Later, she found out I wrote software. She asked if I wanted to teach a studio class at an innovation high school she co-founded. The pay was a quarter of what I was used to making, but I said yes.
It was one of the best experiences of my life. At the end of the class, they gave me a $500 bonus because, as they put it, "You're the coolest guy in the world."
From there, they asked me to build the learning management system for the school—a project that paid me well over the next four years. She and another guy I met working there are now my best friends in the world. The school even paid for me to go to India twice to teach.
If I had been trying to optimize my career, or protect my network, or follow a strategic plan, I would have walked out of that bar the second he called me "bro." I definitely wouldn't have let him sleep on my couch.
The best things in my life seem to show up when I stop managing outcomes and let the current take me.