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 almost every friendship was through work. My professional and personal lives had essentially become one.
The unraveling was gradual at first: I stopped seeing certain friends and colleagues, skipped meetups and dinners, and dropped off group texts. Then, COVID forced a lockdown and the process accelerated.
Few of these friendships ended with a conversation or a clean break. Most just faded as I built a new career and moved deeper into parenthood.
I struggled with this early on. In the deepest stretches of the messy middle, I became resentful. It stung when close friends didn't reply to a text, told me they had too much going on, or would cancel lunch the night before, and it stung even more when a few would mockingly call me "coach."
The truth is I was pulling away too. I no longer wanted to spend time with some of these friends and engage like I used to because it didn't feel right anymore, but I thought something was wrong with me for it. Eventually, the texts and invites stopped coming.
The grief came later, when it dawned on me that I couldn't keep all of these friendships. My values and interests were changing, and one by one, some relationships lost the thing we had in common. I realized I'm not who I used to be, and that became okay.
I'm still loosely in touch with many of the people who knew the old me, and with a few, the friendship remained intact, though with more distance. I have a lot of love and respect for them, and I'll text or email an old friend or colleague when I'm thinking of them, just to say hi, without expecting anything in return. I genuinely miss them and those days.
Earlier this year, I was meeting a client for lunch in the West Village. I was returning to the table from the bathroom, and I passed two old friends, both VCs I'd spent years co-investing with. They immediately said hi and waved me over.
Two things rose at once: appreciation for that chapter of my life and my friendship with these guys, and gratitude that I chose a different path, even though it cost me some very close friends.
We talked for a few minutes, said we should grab dinner soon, and never did. The moment felt complete just as it was.
I don't travel and vacation with the old crew anymore, but I do with new friends.
Some of them came through work. As I went deeper into coaching and healing, I built relationships with other practitioners, and they became my community, online and IRL. We have coffee, hop on Zooms, trade voice memos and group texts, and support each other in a way I hadn't experienced before.
The rest came through place. When we left the city for the Hudson Valley, we chose a community that values nature, art, and diversity of thought. A place like that self-selects a very different mix than Tribeca did. The people we've met through school and town are the ones we want to build a life alongside. We've been there full-time for three years, and there's nowhere else we'd rather live.
All told, rebuilding my community took the better part of five years, and no shortcut would have gotten me here.
I’ve come to see that these friendships completed rather than failed. A season of life ran its course, the way seasons do, and the people who filled it were exactly right for their time. I’m grateful for every one of them.