Money

How to Steward a Financial Windfall

Why we’re not as happy as think we should be

I count my blessings.

Among them, my grandparents paid for my Princeton degree, my dad having predeceased them when I was 15. They had the means to do so, and thankfully they valued education. And because I graduated in 1983, before college cost more than a small country’s GDP, money was leftover.

But at the age of 25, I treated that windfall like a hot potato.

I wasn’t ungrateful.

I was afraid.

Because as fast as some people in my family made money, others squandered it. I grew up hearing stories about my much-older half-brother buying a fancy sports car, among other dumb purchases. And my father, who was both a visionary and an alcoholic, invested the chunk of change he’d been given into two failed business ventures.

The first money pit was building a hotel on Anguilla, a small island off of Antigua, which proved uneconomic in the early ’60s, but 50 years later became the site of the swanky Jumby Bay resort.

The second was a more logical investment, a car rental franchise in the French Caribbean. His drinking got the better of him, and he landed in jail for either tax evasion, check kiting, or…