Watching a couple argue over a $12K trip to Italy. "That's too much," he said. They have $3.9M. Their plan shows they'll end with $4.5M at age 95. The math says spend. The spreadsheet says spend. I said spend. But 35 years of "save, don't spend" doesn't shut off overnight. The hardest part of retirement planning isn't the numbers. It's convincing people they've already won.