The Archive
Every post I've written, in reverse chronological order:
Landing the Plane, Part 2: Timing Your Exit and Maximizing Your Final Working Year · September 8, 2026 · The golden handcuffs are designed to make it hard to leave. There is always one more bonus, one more vesting date, one more reason this particular moment is not quite right. Here is what the final working year actually looks like: when to leave, what to protect, and how to set up the life you have been building toward.
Landing the Plane, Part 1: Building Your Drawdown Framework · September 1, 2026 · Moving to Arizona required learning a completely different set of rules. So does the shift from accumulation to distribution. We explore the drawdown framework behind the bond ladder, the December 15 evaluation, and the five-year reserve that lets you leave on your own terms.
How to Find Your Next Endeavor · August 25, 2026 · Five paths to meaningful work on your own terms, a pressure test for each, and the income modeling reality most FINE content skips. Start here before you leave full-time work.
The Sequence That Determines Whether Your Retirement Lasts (And How to Sleep Through the Chaos) · August 18, 2026 · Jim and Karen followed every rule and still ended the decade with $594,400. James and Keisha followed the same rules and ended with $3,053,000. Same starting portfolio. Different decade. Here is the math behind why, and the three protections that let you sleep through the chaos.
FINE: The Middle Path Between FI and FIRE That Most People Are Actually Searching For · August 17, 2026 · Guest post at ESI Money · The post that introduced FINE to one of the most established audiences in the FI space. The middle path between traditional retirement and FIRE, for people who still have something to give.
The Seven Signs You're Ready for a Next Endeavor· August 11, 2026 · From the financial threshold to the moment the accolades stop working and something shifts. Seven signs that tell you whether FINE is the right path for you right now.
Why $20K a Year Changes the Retirement Math More Than You Think · August 4, 2026 · A mechanic whose body gave out, a compliance director who didn't plan to leave, and a corporate couple buying time. Three households show why a modest income ramp during the most vulnerable decade changes everything.
The Financial Conversations Most People Avoid · July 28, 2026 · The financial conversation my parents avoided for decades finally happened in their eighties. Here's why you shouldn't wait that long.
Taste It Before You Can Afford It · July 21, 2026 · How a sample of the life you dream about tells you whether it’s the life you want.
You Can Look Wealthy or Build Wealth. Pick One. · July 14, 2026 · To be wealthy, you have to resist the gravitational pull of other people’s opinions.
The First Tastes of Freedom on the FI Journey · July 7, 2026 · The days are long but the years are quick. A retrospective of the patience and principles that got me to the freedom I experience today.
Not the Lattes. Here’s What Actually Retires You Early. · June 30, 2026 · The choices you don’t think matter and how they affect when you become FI.
Six Things I Wish My 45-Year-Old Self Had Known · June 23, 2026 · What I would send back to the guy standing on a glacier at 45, with a job he loved, a life mostly right, and a few things still missing.
The 10-Year Window Most People Miss · June 16, 2026 · A Paris café at dawn, a fountain pen, and the question that wouldn't let go. Why the decade between 45 and 55 is the most strategically leveraged window of your financial life and what most people do instead.
The Four Types of Work — And the One Most People Never Reach · June 9, 2026 · A mountain overlook, a career-defining decision, and why most people never reach the one type of work that makes everything else worth it.
I'm Not Leaving Yet — And Here's Why You Might Not Want to Either · June 2, 2026 · The difference between one more year syndrome, inertia, and actually being ready.
The Three Paths Out of Midlife Stagnation · May 26, 2026 · A teenager runs 650 miles across a continent on overnight trains for a ten-pack of tacos. And somehow that may explain exactly where you are right now in your financial independence journey.
Reclaiming the Part of Me I Thought I’d Lost · May 19, 2026 · The strange thing about losing yourself to a career is that it usually happens while you're winning. This is a story about reclaiming and capturing some of the truest parts of ourselves while on the FI journey.
The Five Questions Every FI Journey Eventually Forces You to Answer· May 12, 2026 · Five questions the spreadsheet can't answer, but your FI journey eventually will.
The Stop I Almost Slept Through · May 5, 2026 · The invisible cost of staying where you are too long.
Joy in the Most Unexpected Places · April 28, 2026 · A bartender, a secret off-menu dessert, and a lesson about what happens when you stop trying to win the room.
The Gilded Cage · April 21, 2026 · What it actually feels like when the math says you're free but the engine keeps running.
Three Versions of Enough · April 14, 2026 · Financial independence is one kind of enough. But there are two others, and most people never name or even consider them.
Cutting the Ankle Weights: How I Finally Reclaimed My Life · April 7, 2026 · How it feels to cut loose the things that look like success but feel like an anchor.
From the River to the Corner Office — And Back Again · March 31, 2026 · The seasons of your career and what I wish someone had told me about each one.
Fresh Tracks: What a Glacier Taught Me About the Second Half of Life · March 24, 2026 · The avalanche control crew triggers the release on their own terms, before the mountain decides for them. So should you on your FI journey.
The Harder Trail: Why FINE is the Adventure Worth Taking · March 17, 2026 · A mathematical deep dive into the Financial Independence Next Endeavor (FINE) framework, and why the trail that looks harder from the bottom but is more enjoyable and leads somewhere better.
How FI Led Me to FINE: A New Way to Think About the Second Half of Life · March 10, 2026 · The story of how I became a believer in FINE: retiring younger, making a meaningful contribution, and having a smoother transition into retirement.
Your Financial Road Map: 10 Signposts to a Rich, Meaningful Life · March 3, 2026 · What does 'enough' actually look like and how do you build toward it deliberately instead of just hoping you arrive?
7 Principles That Can Help You Build a Rich, Balanced Life · February 24, 2026 · Seven ideas that quietly reframe how you think about building a life, not just a portfolio.
The Moment I Realized the Life I Built Wasn’t the Life I Wanted · February 18, 2026 · Scraping ice off my car thousands of miles from the life I missed, I knew something had to change.