Field Notes

When I start working with a client, usually in the first session, I tell them something that can be confusing at first: "I care where you end up, and I don't care where you end up." What I mean is that I care about them and the life they're building. I believe in their inherent goodness and potential. I want their choices to reflect what matters to them and where they are in their life. That includes the work they do, the people they surround themselves with, and what they have the energy and

During an early morning bike ride several weeks ago, a song came on that made me pull over. I looked at the title, saved it to a playlist, and hit replay. I can't stop listening to it. "the old story," by Trevor Hall, with his wife, the poet Emory Hall, on vocals. It's about the old stories we carry about ourselves, and how they keep shaping our lives. We all have them. Some we're conscious of and know so well that we don't even stop to question them. Others are running underneath the sur

On Monday afternon I wrapped up a coaching relationship with a long-term client I've loved supporting. For these completion sessions, I typically create a detailed artifact that captures the arc of our work together, including milestones, learnings, and quotes. I shared my screen and we read it together, scrolling slowly so he could see his transformation reflected back at him. About halfway through the document, he stopped me. "Damn, I've said no to a lot of stuff." In our very first session

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

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