The Archive

Every post I've written, in reverse chronological order:

The Retirement Line Item Nobody Budgets For: Adult Kids · October 20, 2026 · At seven, my son planned to build a nest in the Japanese maple out front and raise ten kids there, as long as he could plug in his Wii. Now he’s a college senior dreaming of a ski town. Parents who support adult kids spend 2.4 times more on them than on their own retirement. Three conversations to have before you leave full-time work: with yourself, your partner, and your kid.

7 Questions to Ask in Building Your Downshift or Retirement Budget · October 13, 2026 · Floating on an inner tube into a jungle cave in Belize, I heard the lead guide say one word in Spanish: culebras. Snakes. Nobody else caught it. A good guide watches for what you can’t see, and a good retirement budget should too. Seven questions I’m working through, from post-exit health insurance to the Roth conversion window that closes at 63.

Five Financial Decisions That Made My Downshift Possible · October 6, 2026 · I was fourteen, shivering in a borrowed tent on the Appalachian Trail, too proud to ask my dad for the gear that was sitting in our basement. Thirty years later, five financial decisions that made my downshift possible: dual Roth IRAs funded with bonus money we wanted to spend, a brokerage account jumpstarted by a rental sale, a paid-off house that cut our base burn rate, the 1% AUM fee I never paid, and a donor-advised fund that changed how we think about giving.

The Weekday World I Never Saw · September 29, 2026 · A 10am gym visit on an ordinary Tuesday was supposed to confirm how empty my future weekdays would be once the paycheck stopped. Instead I found a packed parking lot and a life already running in plain sight. Why testing pieces of retirement before you actually retire matters as much as the number itself, and what the spreadsheet can't tell you.

Already Gone, Not Yet Gone: The Psychology of the Final Stretch · September 22, 2026 · A BB gun was supposed to be the whole gift. Then my dad said there was one more thing. A backyard trampoline, built behind my back while I played cards at a table, is a picture of what the final stretch before a downshift or retirement actually feels like: still clocking in, still cashing the paycheck, while the life your savings rate bought gets quietly assembled somewhere you can't yet see.

She Could Have Asked Me to Keep Working · September 15, 2026 · A Slurpee flavor told me something at nineteen. Thirty years later, my wife told me something far more important when I brought her the biggest financial decision of our married life. Her three fears, only one about money, and what we actually agreed to.

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 · A March drive through the Valley of the Sun, windows down, street tacos under the palm trees, and a phone call home: this was the change we needed. Then came learning the desert’s rules, from white cars to monsoon season. The shift from accumulation to distribution requires the same. 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 · Days after wading five miles up a red-rock canyon in a national park with the people I love most, I was at 31,000 feet over Kansas, flying away from them for a client meeting. 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 · In late 2025, I started blocking out mornings for a fountain pen and a journal. The plan was to hang on until 55 or 59½ and live smaller. Then two words lit up like dry kindling meeting a spark: Financial Independence, Next Endeavor. The post that introduced FINE to one of the most established audiences in the FI space.

The Seven Signs You're Ready for a Next Endeavor · August 11, 2026 · Alone at a desert trailhead one Saturday morning in 2018, I put in my AirPods and heard a language I didn’t yet speak: Roth conversions, savings rates, something called FIRE. Years later, a $1 million milestone taught me that crossing a number isn’t the same as funding the life. Seven signs you’re ready, from the financial threshold to the moment the accolades stop working.

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 · Over coffee in the good china, hands wringing, my parents finally told me: for fifty years my father had written every check, until a shoulder injury from shoveling snow meant he’d written his last. They were in their eighties. Why waiting that long has a cost, and five levels of financial community to help you find your people before you need them.

Taste It Before You Can Afford It · July 21, 2026 · Twenty-five years later, I can still smell the bread. We were twenty-six, in Paris in March on flights earned by volunteering to get bumped, eating baguettes and cheese on the steps above the city. Why the dream isn’t the reward but the strategy, what my ideal Tuesday looks like, and how a taste of the life tells you whether it’s the one you want.

You Can Look Wealthy or Build Wealth. Pick One. · July 14, 2026 · At sixteen, I revved the V-8 of my $500 Gran Torino at stoplights while Buffy pulled away in the white BMW convertible her parents bought her. Nobody noticed. Two junior colleagues whose paths split on a single question, the gated community that nearly swept us up, and why being wealthy means resisting the gravitational pull of other people’s opinions.

The First Tastes of Freedom on the FI Journey · July 7, 2026 · As a kid, I smuggled bottle rockets home from South of the Border, hidden near the spare tire. Years later, freedom sounded like a bathroom fan with a loose bearing, humming while we paid off $90,000 in student loans one colored square at a time. What quiet freedom actually looks like, from a $25 hat to a two-week vacation, and why you shouldn’t quit today.

Not the Lattes. Here’s What Actually Retires You Early. · June 30, 2026 · A long-haired, Harley-riding youth pastor taught me to rappel on the cliffs above the Potomac. Years later, on our first date, my future wife leaned back over the edge on a rope I was managing. The big rocks that actually build your exit, starting with a $770 car payment that could compound to $624,000, and why at some point you have to trust the gear.

Six Things I Wish My 45-Year-Old Self Had Known · June 23, 2026 · Dog sledding on an Alaska glacier, a bear tour with no bears, and a family tradition born from terrible puns. I was 45, with a job I loved and a life mostly right. Six things I’d send back to that guy, from the boulder that eventually rolls downhill to why contentment is a skill, not a personality type.

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. Then two weeks in Europe with my family, the most time I’d taken off in twenty-five years. Why the decade between 45 and 55 is the most leveraged window of your financial life, and what most people do with it instead..

The Four Types of Work, and the One Most People Never Reach · June 9, 2026 · Four hours on a Blue Ridge overlook, wrestling with a decision. My nonprofit work hit three circles: I loved it, I was good at it, and the world needed it. But at $40,000 a year with a baby on the way, the fourth circle couldn’t carry a family. Job, Career, Calling, and Next Endeavor, and what changes when the fourth circle only needs to contribute.

I'm Not Leaving Yet, And Here's Why You Might Not Want to Either · June 2, 2026 · On Lake Geneva, the mail is still delivered by a college student who leaps from a moving boat to the dock and back before it passes. Leave too early and you land wet. Leave too late and you miss the ride home. The difference between one more year syndrome, inertia, and intention, plus what a well-timed jump actually requires.

The Three Paths Out of Midlife Stagnation · May 26, 2026 · A teenager runs 650 miles across Europe on overnight trains for a ten-pack of tacos. And somehow that may explain exactly where you are right now. When midlife stagnation hits, most people Double Down, Burn It Down, or Turn Around. Only one of them works best when you start before you have to.

Reclaiming the Part of Me I Thought I’d Lost · May 19, 2026 · Arizona woke up parts of me I didn’t know I’d lost: the Eagle Scout who felt most alive on a trail, the kid who journaled and read for pleasure. Losing yourself to a career usually happens while you’re winning. Three identities that fell away, from a forum handle I chose to retire to a 4:30 AM phone call in Sedona that changed what it means to be a son.

The Five Questions Every FI Journey Eventually Forces You to Answer· May 12, 2026 · A cool May morning, first on the trail, past teddy bear cholla that look soft from a distance but can stop you cold. Weeks earlier I’d run 2,000 Monte Carlo scenarios, but no model can answer these five: what you’ll really spend, whether you’ve tested the scary scenarios, what you actually want, whether your spouse is fully aligned, and whether you believe the plan.

The Stop I Almost Slept Through · May 5, 2026 · At nineteen, backpacking Europe on a Eurail pass, I fell asleep on an overnight train to Munich and woke up hours past my stop, headed for Prague. It took thirty years to get back. Missing your stop while you sleep happens more than once in a life. The cost of staying too long that almost nobody calculates, and why FI is ultimately a courage question, not a math one.

Joy in the Most Unexpected Places · April 28, 2026 · After a high-stakes client dinner in a private Manhattan room, the bartender leaned in and offered to raid the reserve cellar. The pressure lifted, and one of the most joyful nights of my career followed. Add a whispered tip about a secret Disney cupcake, and you get a lesson about leading with generosity instead of agenda, plus the generosity number most FI math never calculates.

The Gilded Cage · April 21, 2026 · At twenty-nine, I parallel-parked on a jammed Williamsburg street and ran to my first business school interview in polished oxfords, cufflinks jangling. Two decades later, the engine is still running. A re-org, an Apple Health alert, and the one-more-year loop from the inside, plus why a Next Endeavor is my runaway truck ramp and how the cage door cracks open one decision at a time.

Three Versions of Enough · April 14, 2026 · The first time I took a mentor to a real steakhouse, I did the Outback math before I ordered, palms slightly damp. Fifteen years later, my mother-in-law ordered filet mignon from a menu whose prices she literally couldn’t see. Financial independence is one kind of enough. Lifestyle and identity are the other two, and most people never name them.

Cutting the Ankle Weights: How I Finally Reclaimed My Life · April 7, 2026 · When the wire hit my bank account after we sold our Arizona McMansion, I exhaled like someone had cut fifty pounds of ankle weights off my legs. The slow sunrise that got me there: eighteen months of weekly flights to Minnesota, a recovery year, my father-in-law’s death at 62, and a week at Disney World with our six-year-old. How to find your own ankle weights and cut them loose.

From the River to the Corner Office, and Back Again · March 31, 2026 · In my early twenties, I waded the rapids of the New River holding my books above my head, then sat on a flat rock studying while kayakers and inner tubers drifted past. I wanted to dive in. Your career has four seasons, and here’s what I wish someone had told me about each one, from a Great Recession layoff to the question Winter keeps asking: are you finally ready to jump in?

Fresh Tracks: What a Glacier Taught Me About the Second Half of Life · March 24, 2026 · Six in the morning at Whistler, coffee in hand, when the first avalanche control blast rolled across the glacier. The crew triggers the release on their own terms, before the mountain decides for them. A cliff at Killington in my twenties, a McMansion that fit one season but not the next, and why at some point following someone else’s tracks stops being wisdom and starts being avoidance.

The Harder Trail: Why FINE is the Adventure Worth Taking · March 17, 2026 · Midweek at a client conference, I had planned a safe 75-minute desert loop. Then I saw a steep trail shooting up the ridge and remembered a snowy college night in the Blue Ridge Mountains. Two and a half hours later, legs shaking, something clicked. The math behind Traditional vs. FIRE vs. FINE, and three people, including my dad, who took the harder trail.

How FI Led Me to FINE: A New Way to Think About the Second Half of Life · March 10, 2026 · Driving solo to a desert trailhead on a Saturday morning, I heard a podcast host spend a couple of sentences on something called a Next Endeavor. I turned off the podcast and drove the rest of the way in silence. The story behind FINE, what the math showed me, where FIRE stops short, and a regional VP who found his most meaningful work mentoring young leaders outside the office.

Your Financial Road Map: 10 Signposts to a Rich, Meaningful Life · March 3, 2026 · Past the marked trails, on a narrow path with no recent footprints, I rounded a bend and found a second mountain hidden behind the one everyone sees. Money works the same way. Ten milestones from my own path, starting with $90,000 in student loans and a chart on the fridge, plus three versions of enough: survive, enjoy, and delight.

7 Principles That Can Help You Build a Rich, Balanced Life · February 24, 2026 · For years I chose the aisle seat so I could sprint off the plane. Now I take the window, and on a flight to Seattle I watched the Grand Canyon glow at sunrise while almost everyone around me stared at a screen. Seven principles for rebuilding a balanced life, from protecting your mornings and silencing notifications to building strength, investing in deep community, and designing rest on purpose.

The Moment I Realized the Life I Built Wasn’t the Life I Wanted · February 18, 2026 · Negative twenty degrees in a Minnesota parking lot, scraping ice off the car I kept there during the week, thousands of miles from the life I missed. By every external measure, I had made it. Then came a recovery year, a sunrise flight over the Grand Canyon, and one simple question: what has brought me the greatest joy? Where Desert FI began.