Rob Perry retired, then bought a Vermont screen-printing shop for $115,000 and named it Shirt Happens — because retirement, apparently, sharpens the pun reflex. He's 68. And here's the part that makes the joke work: he's got $1.5 million saved, $3,600 a month in Social Security, and the shop throws off $50,000 to $60,000 a year. The business isn't the meal. It's gravy on a plate that was already full. That's the whole trick, and the Journal's July 9 profiles keep proving it — incorporations by 55-to-64-year-olds are up 22% in a decade, and the ones who do it right all share one quiet habit.
They size it. Margo Clayson, 68, runs The Mighty Microgreen about 15 hours a week for maybe $800 a month on top of $3,043 in Social Security — nobody's fortune, and that's exactly the point. Roger Smith, 58, put $430,000 into a golf-simulator franchise, which sounds reckless until you see the denominator: under 10% of his $5.5 million net worth, with a sub-3% mortgage he's in no hurry to pay off while T-bills yield more than the loan costs. This is where a CFP earns the fee the Journal can't — Cash-Flow & Special Circumstances, Modules 5 and 9. As general planning principles: cap in advance what fraction of net worth the venture can consume and treat that ceiling as non-negotiable; stress-test the entire retirement plan with the business earning exactly zero; and plan the exit before you enter, because a business that only runs while you run it is a job you bought, not an asset you can sell. The failure mode we see isn't the first check — it's the third and fourth ones written to rescue it.
You don't need to know how year one turns out to know whether the structure holds — and that's the point of looking now rather than later. If you can already see how the encore-business idea sits against your plan, that's the moment to check the roof, not after the weather turns. A review runs about 15 minutes. Bring your statement, and we'll size the thing like a position instead of a lottery ticket with a lease attached.