Stories, observations, and lessons.

Life

I Quit a Book About Not Quitting. Then Liz and I Picked a Misogi.

I quit David Goggins' Can't Hurt Me halfway through. Going back to it, plus a lesson from Jesse Itzler, led Liz and me to pick our 2028 Misogi: walking the Camino in Spain.

September 21, 2026 · 4 min read

Let me tell you about Ray Calloway. Ray was 65 years old when the letter arrived. It had been forwarded from his old California address — the house he’d sold after his wife died, after the heart attack, after the doctors told him to slow down or else. $47,488.74. Tax year 2018. A year he…

March 31, 2026 · 2 min read

There’s a saying in emergency medicine that sounds obvious until you’re standing over someone who’s dying. “Treat what kills first.” Not what hurts most. Not what’s loudest. Not what the patient is asking you to fix. What kills first. I learned that in an ambulance. Eleven years of lights-and-sirens, crash scenes, cardiac arrests, and trauma…

March 25, 2026 · 2 min read

As I write this email I’m fighting one of the worst colds I’ve had in years. Something I caught in Puerto Rico. Still with me almost a week later. I came into the office today only to handle an IRS Appeals call. Then straight back home to rest. But I had to share this story…

March 23, 2026 · 3 min read

Last September I put this week on the calendar and locked it shut. No client calls. No strategy sessions. No notifications at midnight. Because my daughter Bella is a Coast Guard Academy cadet, her schedule belongs to the federal government now, and the windows to be together don’t appear on their own. You plan them…

March 11, 2026 · 1 min read

The 3½-hour battle that proves the IRS grace period is over I’m flying out to Boston in the morning and driving to New London, CT, to meet with my attorney Eric Green for a podcast. On Saturday, I’ll attend my daughter’s graduation from Swab Summer “bootcamp” at the US Coast Guard Academy. But I needed…

August 14, 2025 · 3 min read