Join the Trail

A personal letter every Sunday morning on money, meaning, and the courage to build a life that finally feels like your own.

Not a broadcast. Not a funnel. A letter — written by someone in the middle of the same transition many readers are navigating themselves.

A new essay each Tuesday, and a Sunday reflection that builds on it. Some weeks deep on the math — bucket strategies, sequence-of-returns risk, the real numbers behind FINE. Other weeks deep on the meaning — identity, purpose, what to do when the spreadsheet says you're free but something underneath still isn't.

Each letter ends with a question or two worth sitting with — the kind of prompts that follow you into the week, not the kind you answer in thirty seconds. Occasionally a behind-the-scenes note: a short video from a trail, an early look at an upcoming guest post, what I'm working on next. And if you've ever missed a post on the blog, the Sunday letter is the easiest way to stay close to the writing without having to remember to come back.

This is for people who are successful on paper and restless underneath. Readers who have done the hard work of building a career and a life and are now asking the harder question — what's the second half actually for?

Thanks for being here at the beginning.

The trail is better with good company.

🌵 Desert FI