“Congratulations on graduating, Andrea, now you’re off the payroll,” my dad not-so-jokingly declared on the steps of the Milwaukee convention center outside Marquette University.

I barely had time to take off my cap and gown before they dropped me off in Chicago so I could start my first job at an advertising agency the next week.

My parents generously paid most of my college tuition. At 22, I was grateful to be left with only a modest student loan balance. But I didn’t think he was completely serious. Surely, they’d help me if I ever got into financial trouble.

I was convinced I’d never need it anyway. I was steadfast in my desire to succeed…