The Blog
Real strategies, real numbers, and real opinions on retiring early — without the fluff
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The HSA Receipt Reimbursement Strategy That Pays You Years Later
By Antonio Hill Pay your medical bills out of pocket, keep the receipts, and you can reimburse yourself tax free at 45 for a dental bill you paid at 33. The money sits in your HSA compounding the entire time. No waiting period. No age gate. No paperwork beyond your own folders. Oh yeah, did…
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How Big Should a Taxable Brokerage Bridge Account Be In Early Retirement?
By Antonio Hill There isn’t one number. For the same couple, retiring at the same age, spending the same money, I can defend a taxable brokerage bridge of $920,000 or $1.54 million. Both are correct. They’re just answers to different questions. So what actually decides it? Not your age. Not the five year conversion ladder…
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Which Accounts to Withdraw From First in Early Retirement
By Antonio Hill Every retirement article hands you the same withdrawal order. Spend your taxable brokerage first, then your traditional 401(k) and IRA. Save your Roth for last. It isn’t wrong, exactly. It’s just built for a 65 year old with Social Security coming in and a 30 year retirement to fund. You’re 40. You’ve…
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Roth Conversion Ladder vs 72(t). At 40, It Is Not Close.
By Antonio Hill You better have a good plan. That is the first thing I think when somebody tells me they are looking at a 72(t). Not “great idea.” Not “here is how.” Just, I hope you have thought this all the way through, because you are about to make a promise to the IRS…
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The Guardrails Withdrawal Strategy Explained Simply, And Why It Retires You Years Sooner.
By Antonio Hill Same portfolio. Same risk. Three fewer years sitting at a desk you’re already tired of. That’s the actual pitch for the guardrails withdrawal strategy in my opinion, but almost no one frames it that way. Here it is simply. You pick a starting withdrawal rate. You draw one line 20% above it…
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Roth Conversion Ladder Example With Real Numbers, and the 2026 Trap A Lot of People Miss
By Antonio Hill Here’s the ladder example with real numbers. A married couple retires at 40 spending $120,000 a year. They want to move traditional 401(k) money into a Roth so they can spend it decades before 59½. How much can they actually convert this year and keep their health insurance subsidy? Thirty thousand dollars.…
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A Retired Couple Can Pull Six Figures a Year and Pay $0 Federal Tax. On Purpose.
By Antonio Hill The first time I ran this math, I assumed I’d typed something wrong. A married couple with no paychecks can realize $131,100 of income in 2026 and owe the IRS nothing. Nothing. It isn’t a loophole. It’s two numbers printed right in the tax code, waiting for anyone willing to be intentional…
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The $84,600 Cliff. How Early Retirees Keep Five-Figure Health Subsidies in 2026
One dollar over the line costs a family of three $8,872 a year. Here’s the one number early retirees manage to keep five figure health subsidies in 2026.
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The Money’s Locked Until 59½. Here’s How Early Retirees Get To It Anyway
By Antonio Hill A guy at work found out I plan to retire at 40 and hit me with the “Must be nice. Most of my money’s locked up until 59½.” No it isn’t. A portion of his money sits in one account with one rule on it. And he let that one rule decide…
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Sequence of Returns Risk: The Thing That Actually Wrecks Early Retirements
By Antonio Hill Your FI number can be perfect. You can run the math ten different ways, hit the target to the dollar, and hand in your notice right on schedule. If the market drops 30% in the third month of your retirement, that perfect number won’t mean a whole lot. That’s sequence of returns…