Latest Posts
Thoughts on reinvention, clarity, work, money, and the quiet decisions that shape a life. New essays each week as we explore what it means to build a life with intention.
Don't Leave It in the Field: An Open Enrollment Guide for an Earlier Exit
In 2016, our 11-year-old picked a plastic skull mask that earned him respect at every door and turned into a sauna on a warm night across 800 homes. It looked great on the porch, but it wasn’t built for the night he was having. Benefits enrollment works the same way, so here’s how to choose the options that fit the life you’re living, whether you’re 10 years out, landing the plane, or already retired.
7 Questions to Ask in Building Your Downshift or Retirement Budget
On a cave tubing trip in Belize, I heard our guide tell another guide in Spanish to watch for snakes. Nobody else caught it. That’s what good guides do. Here are seven questions I’m working through as I build my retirement budget, and the culebras I’ve found beneath the surface.
Five Financial Decisions That Made My Downshift Possible
I was fourteen, shivering in a borrowed tent on the Appalachian Trail in a waterlogged cotton sleeping bag, too proud to ask my dad, a retired Marine, for the gear that was sitting in our basement. Thirty years later, here are the five financial decisions that made my downshift possible, and the lesson it took me a cold night on a mountain to learn.
Landing the Plane, Part 2: Timing Your Exit and Maximizing Your Final Working Year
You've done the math. You know your number. Now comes the part nobody talks about: actually leaving.
The Financial Conversations Most People Avoid
My parents sat me down in their formal living room, coffee in china cups, Scotch shortbread on the plate, more uncomfortable than I had ever seen them. What they had to say was smaller than I feared, and far more revealing. It was the moment I understood that the financial conversations most people avoid are not just nice to have. They are often the difference between knowing what to do and being caught completely unprepared. This post is about finding the people who will walk that trail with you.
You Can Look Wealthy or Build Wealth. Pick One.
At sixteen I drove a $500 Gran Torino and revved the engine at stoplights hoping someone would notice. Nobody did. Most of us are still doing a version of this today. The car is nicer. The stakes are higher. And the cost is bigger than we realize.