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What’s Your Contingency Plan? The Question That Actually Makes Retirement Feel Safe
A couple of weeks ago I wrote an article called “What Would It Take to Make You Feel Secure?” I thought I’d covered it. But I kept having the same conversation at two different parties at The FI Collective here in Longmont, and again at a friend’s birthday dinner, and I realized I’d skipped the…
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You Don’t Have to Sell What You Love. You Just Have to Sell It For a Second.
Every FIRE community has one. (It’s me. Hi. I’m the problem, it’s me.) The person who bought a stock years ago, watched it turn into a meaningful chunk of their net worth, and now refuses to sell a single share because they still believe in the company. Maybe it’s an employer stock they understand inside…
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The 0% Capital Gains Bracket Is a Gift. Are You Using It?
Somewhere out there is a tax bracket that lets you sell your winning stocks, pocket the gains, and hand exactly $0 to the IRS. It’s not a loophole. It’s not sketchy. It’s not something your CPA is going to raise an eyebrow at. It’s just… sitting there. Available. Legal. And almost completely ignored by people…
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Are You Slowly Bleeding Money?
I logged into an old HSA today. Not because I had a sudden urge to relive my benefits enrollment paperwork from a job I haven’t worked in years, but because I was doing a little financial housekeeping, the kind of task that sits on your to do list right next to “clean out the garage”…
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What Would It Take to Make You Feel Secure?
The FI Community has a pretty simple pitch. Save aggressively, invest wisely, hit your number, and then walk away from your traditional W2 job to spend your time however you want, with whomever you want, wherever you want. That’s the whole deal. It sounds simple because, on paper, it is simple. Save 25 times your…
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A Field Guide to In-Person FI Events
You’ve optimized your 401k. You’ve got a spreadsheet that calculates your FI date down to the day, assuming a 7% real return and zero unexpected emergencies, because obviously nothing unexpected ever happens to anyone. You’ve read the blogs, listened to the podcasts (hi), and you can recite the 4% rule like it’s a nursery rhyme.…
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Planning for Healthcare Costs Over a Decades-Long Early Retirement
This is Part 2 of a two part series for early retirees and self-employed households and health insurance. In Part 1 I covered how health insurance works for early retirees and the self-employed in 2026: how to get coverage, why location swings the price so much, how Premium Tax Credits work, and why staying under…
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The Lifestyle Creep You Actually Planned: When Spending More Is the Right Move
Every personal finance article you’ve ever read has warned you about lifestyle creep. You get a raise, you upgrade the car, you start ordering the good guacamole, and suddenly your savings rate has quietly deflated like a balloon three days after a birthday party. The warnings are real and the math is unforgiving. Lifestyle creep…
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Net Investment Income Tax: The 3.8% Surtax Nobody Talks About
You’ve done the hard part. You saved aggressively, invested consistently, built up rental income or a brokerage portfolio worth bragging about, and now you’re watching your passive income roll in like a well-earned wave. Congratulations. The IRS would also like to congratulate you, with a bill. Meet the Net Investment Income Tax, or NIIT. It’s…
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How Health Insurance Works in Early Retirement and Self-Employment (2026)
Healthcare costs in early retirement or self-employment are a high-stakes game. You have to pay attention today, and the wide variability means you also need to plan conservatively over the next few decades. This is part one of a two part mini-series. Here I’ll answer the basic questions about how things work right now, so…
