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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…
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Concentration Risk from Success: What to Do When One Asset Dominates Your Net Worth
There’s a financial problem that nobody warns you about when you’re just getting started, because it only happens to people who are doing really well. It’s the kind of problem that sounds almost ungrateful to complain about. The problem is this: you got good at something, or lucky with something, or both, and now one…
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Stop Optimizing for a Retirement You’re Too Scared to Take
Let’s get one thing out of the way: you are never going to get a guarantee. Not from the 4% Rule. Not from a 3.5% withdrawal rate. Not from working one more year, or two more years, or retiring at 55 instead of 50 because the sequence-of-returns risk felt a little spooky that Tuesday in…
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Are You Over-Contributing to Your 401(k)?
You did everything right. You read the personal finance basics, nodded enthusiastically at the advice to contribute to your retirement accounts, and have been dutifully stuffing the maximum amount you can into your tax-deferred account like a responsible adult. Your coworkers are out here buying boats and you’re building generational wealth. Good for you. Except…
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What Your Parents Got Wrong About Money (And What They Actually Got Right)
Your parents did their best. That’s the disclaimer we’re putting at the top, right here, before anything else, because this article is going to say some things about the financial lessons you grew up with that might be a little uncomfortable, and we want to be clear from the outset that none of it is…
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Want More Raises, Better Opportunities, and Actual Job Security? Do These Things.
Let’s get one thing out of the way immediately: becoming invaluable at work has nothing to do with being the person who eats lunch at their desk, answers emails at 11 PM, or volunteers for every committee that’s ever existed. That’s not invaluable. That’s exhausting, and it will eventually make you the kind of person…
