Weekly Insight
Greg Downs is more than 800 days sober. After we talked, the number I kept coming back to was a smaller one: how long a hard moment actually lasts.
For most of his life, a bad feeling meant reaching for something within minutes. I know that pattern from my own drinking. The feelings I didn’t want to feel got handled with alcohol.
Greg told me that when his thoughts get loud now, he remembers a phrase from the rooms, HOPE: hang on, pain ends. Then he walks, calls a friend, writes in a journal, or goes to the gym. Early on, those moments were especially brutal for me too. Today they come less often, and I meet the hard feelings with compassion, the way Greg does.
That is what a count of days is made of. Each day holds a few uncomfortable minutes you got through without changing how you feel by force. Those minutes are the work.
This week, the next time a feeling gets heavy, set a timer for 20 minutes and do one thing from Greg’s list. When it goes off, notice where the feeling is now. Then tell one person what happened.
Hard moments are temporary.
Podcast
For 14 years, Greg Downs managed money for ultra-wealthy families in Palm Beach, at one point overseeing $4 billion. He grew up on a dirt road in central Florida, never felt like he belonged in those rooms, and drank until he was funny enough to fit in. On August 5, 2024, he was arrested in his own driveway. That day became his sobriety date. In jail, he found his first AA meeting.
On Thursday we talked about what he noticed once he got sober: he had been spending money for the same reasons he drank, to change how he felt and avoid something he didn’t want to look at. That led him to adapt the 12 steps for money. He now coaches people through it with ClearPath Financial Coaching, writes the newsletter Financial Sobriety, and runs The Sober Money Club, a weekly peer-led group. His book, 12 Steps to Financial Sobriety, comes out in February.
We also got into fake shopping sites that let you fill a cart and hit buy without ever spending a dollar, which Greg calls non-alcoholic money. He told me about his 10-day silent meditation retreat, how writing became his creative outlet, and the day his ankle monitor came off, which was also the day he picked up his one-year chip.
“Shame thrives off of secrecy.”
You can listen on Spotify and Apple Podcasts as well.
My guest this week is Parker Gates on Thursday, October 22 at 11:00A ET
Parker got sober more than 23 years ago and has been building his life one slow piece at a time ever since.
At six months sober, Parker told his sponsor he wanted to skip ahead to eight years. His sponsor laughed and said, “You can’t handle eight years.”
Since then, Parker has co-founded companies, taught at Stanford’s d.school, and become an executive coach who has worked with hundreds of founders and senior leaders. He writes The Practice, a newsletter on leadership, inner work, and building a life worth living, and his first book is on the way.
We’ll get into asking for help, being a beginner, and why the things that last are the things that grow slowly.
Who I’m Celebrating
Anna Noelle Rockwell joined us for October’s Clear Hour, and she sent me photos of what she was working on during the hour.
The piece is called Dying Queen of the Night, a working title. It’s 16x20, graphite and watercolor on panel, and the subject is a night blooming cereus, a flower that opens after dark and is gone by morning. In the photos you can see the pencil lines still loose, with red watercolor washes running through them. It’s in progress, and I’m grateful she shared it anyway.
Thank you, Anna, for the time you spent with us and for showing the work before it’s finished. I’m looking forward to next month’s session.
Join us for November’s Clear Hour
A guided practice to settle in, then an hour to make something.
No experience needed.