Field Notes

On Thursday, I was on my bike before dawn, cruising along the Ashokan Reservoir. The sun was rising, turning the sky pink and purple. Great clouds moved slowly across the open sky. I looked out at the water and saw the sky reflected back at me. Then they appeared: Canada geese in a giant V, crossing overhead, heading south. "On August twentieth?" I wondered out loud. I squeezed the brakes, screeched to a halt, and watched them disappear over the ridge line. I hopped back onto my bike, moved

I’m working with a CEO who keeps saying yes to opportunities that drain him. He knew his last company wasn’t the right fit months before he left, and after it went public, he took significant time off and swore he wouldn’t do it again. A year later, he was pulled back in by an even bigger, more prestigious opportunity. He came to me wanting to understand how he could see the pattern so clearly, move all the way through a transition, and still end up in the same place. Almost everyone I work wi

Last winter, one of my Substack readers wrote me with a question that comes up all the time with my coaching clients. She asked how I rebuilt my community after I got sober and transitioned careers. Was I still in touch with the people who loved the old me? Did I still travel with those friends? She'd been struggling with it for several years. Here's what I told her. Nearly all of my close relationships ended after I left venture capital in 2017. I had invested so heavily in my career that alm

In late 2017, just months after I left RRE Ventures and was navigating the liminal space between careers, I sat in an empty Starbucks in suburban Boston with Jim Rosen, a founder turned executive coach in the second half of his career. I wanted to hear everything about his path: what called him to the profession, how he got started, what trainings he attended, and how he built his practice. This was the very beginning of my own journey to becoming a coach. I was in the parking lot at the trail