I was at a dinner party last month. A financial advisor—friend of the host—spent the whole evening telling everyone what they should do with their money. Downsize the house. Move somewhere warm. Shift to bonds. Stick to the 4% rule. Never touch principal.
Everybody nodded. I thought about Hank.
Hank retired eleven years ago. He broke every one of those rules. His advisor nearly fired him as a client.
He’s doing better than any of us.
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01. HE DIDN’T DOWNSIZE
Everyone told Hank to sell the house. Four bedrooms, big yard, too much space for two people.
He kept it.
Now his daughter’s family comes for a month every summer. His grandkids have their own rooms. He turned the garage into a woodshop. The guest house brings in a little rent three weekends a month.
The house isn’t a burden. It’s the center of his life.
People assume downsizing saves money. Sometimes it does. But after agent commissions, moving costs, and the price of leaving a place you’ve lived for thirty years, the savings are smaller than you think. And what you lose—space, familiarity, roots—doesn’t show up on a spreadsheet.
02. HE DIDN’T MOVE SOUTH
His buddy moved to Naples. Beautiful weather. Pool. Golf course. And the loneliest year of his life.
He didn’t know his neighbors. Didn’t know the pharmacist. Didn’t have a barber, a mechanic, or a single person who’d call him to help move a couch.
Hank stayed put. Same town. Same church. Same poker game. Same doctor who’s known him twenty years.
Your network is worth more than your weather.
03. HE SPENT MORE, NOT LESS
This is the one that drives financial advisors crazy.
Hank’s first five years of retirement, he spent more than he ever did working. Trips with his wife. A new truck. A kitchen renovation she’d wanted for a decade. Season tickets.
Here’s why it’s not as reckless as it sounds. Research from Morningstar shows that real retirement spending naturally declines over time. Most retirees go through three phases—active years, slower years, and quiet years. Spending drops about 1% to 2% a year in real terms through most of retirement.
The money you don’t spend at 65, you probably won’t spend at 80 either. Your knees won’t let you.
Hank figured that out early. Spend it while you can use it.
04. HE IGNORED THE 4% RULE
The 4% rule says you can safely pull 4% of your savings the first year of retirement, then adjust for inflation every year after. It came from a 1994 study by a financial planner named Bill Bengen. One guy. One spreadsheet. Thirty years ago.
Even Bengen doesn’t believe in 4% anymore. He updated his own research in 2025 and now says 4.7% is the worst-case floor. Under normal conditions, he thinks most retirees can pull closer to 5%.
Hank doesn’t use a fixed percentage at all. Good year in the market? He spends a little more. Bad year? He pulls back. He keeps two years of living expenses in cash so he never has to sell stocks in a downturn.
That flexibility has served him better than any formula.
The money you don’t spend at 65, you probably won’t spend at 80 either. Your knees won’t let you.
05. HE KEPT HIS MONEY IN STOCKS
The standard advice says shift your portfolio to bonds as you get older. Play it safe. Protect what you’ve got.
Hank kept about 70% in equities. His advisor told him it was reckless. But Hank did the math. He was 62 when he retired. If he lives to 90—which men in his family tend to do—that’s a 28-year horizon. Over any 20-year stretch in U.S. market history, stocks have beaten bonds. Every single one.
The catch is you need the stomach for it. And you need cash reserves to ride out the bad years without selling low. Hank has both.
He’s up more in the last decade than most people’s entire bond portfolios earned.
06. WHAT HE ACTUALLY GOT RIGHT
Hank didn’t break the rules to be contrarian. He broke them because the rules weren’t built for his life.
The 4% rule was designed for a worst-case scenario that hasn’t repeated since 1966. The downsizing advice was built for people who can’t afford their mortgage, not people sitting on equity. The Florida move works great for some guys—and destroys others.
The point isn’t that Hank’s way is right for everyone. It’s that the standard playbook is written for a version of retirement that doesn’t exist anymore.
The best retirement plan isn’t the one your advisor printed out. It’s the one that fits the life you actually want to live.
That financial advisor at the dinner party? Nice guy. Good suit. Solid advice for someone who fits the template.
Hank doesn’t fit any template.
Neither do you.
— Walter
P.S. Have you broken a retirement “rule” that everyone told you was a mistake—and it worked out? Hit reply. I want to hear what it was.
