Rule #17: Learn to Live Cheap
As your father, I think one of the greatest disservices I’ve done for your futures is not teaching you how to live cheap.
When I think of “cheap,” I think first of my parents, who understood the concept well.
Both grew up poor. My dad was raised by an aunt and uncle while your great-grandmother spent seven years recovering from tuberculosis. My mom was also raised by relatives after losing her mother and being abandoned by her father as an infant. They grew up in a world where luxuries were few and far between.
Your grandfather put himself through Drexel on $90 a month from the GI Bill, working nights as a bail bondsman. He lived in old storefronts, tiny rooms, and boarding houses—graduating with no scholarships, no grants, and no debt. He did “cheap” on a whole new level.
He later worked as an engineer and still lives in the same 1,100-square-foot house he bought in 1960 for $10,000. And yet throughout my childhood, I never wanted for anything. I had a good education, clothes, food, and a sense of stability. By the standards of my youth, I felt wealthy and lucky.
But the rules were clear. My allowance of $1 a week ended when I turned 16 and could work. Walking through Sears in 1968, I would never have dreamed of asking for a toy or a shirt. There was an unspoken acceptance of limits, and a deep satisfaction with what we already had.
When I graduated college in 1981, the economy was bleak. With my dad’s help, I landed an underwriting job at $13,500 a year and thought I’d struck gold. It wasn’t much, but I worked nights stocking shelves at the newly opened Toys “R” Us and as a desk clerk at Frog Hollow Tennis Club to save enough to live on my own and eventually get married.
I remember grocery shopping at Montgomeryville Mart—a low-end farmers market attached to a strip club (aptly named Mickey’s Mouse)—because that’s where you could buy off-brand, nearly expired food cheap. Stretching money to last the month was an art form.
And I remember the thrill of qualifying for my first Sears card with a $300 limit. That little piece of plastic bought me my first Christmas tree, stand, and gifts. At the time, owning an American Express seemed impossible. In simple terms, I learned to live cheap.
Fortunately, I found a career I excelled in. Promotions and raises came, and by the time you were born we were moderately affluent. You always had what you needed, and most of what you wanted. But in the process, I failed to give you the pride, confidence, and resilience that comes from living cheaply.
Don’t get me wrong—I never believed in handing you a new car at 16. But you did end up with cars, thanks to help from me, your mom, your grandfather, and your aunt. You’ve all had far more than my father could have imagined for his grandchildren.
The problem is not that you’re spoiled—I don’t believe you are. The problem is preparation. Affluence has dulled an essential survival skill: the ability to live cheap.
There’s a certain cocky confidence that comes from knowing you can start with almost nothing and rebuild. That confidence stays with you through divorce, illness, stock market crashes, or business failures. You know you can survive, and that makes you strong.
Personally, I’ve made millions and lost millions. I’ve had enough to last a lifetime, and then barely enough to last a month. Through those cycles, I had my parents’ example to guide me. Life’s successes are never guaranteed. Rebuilding is part of the game.
Many of my peers crumble under setbacks. Many in the generation after mine look for guarantees—lawsuits, government bailouts, parental rescues. I think it stems from two things parents did wrong: teaching kids to expect life to always be fair, and failing to teach them how to survive on less.
The Greatest Generation—those who endured the Depression and fought World War II—had nothing material but knew how to hold onto freedom and opportunity. My generation, the Baby Boomers, challenged tradition and chased affluence. We raised children with self-esteem, but without survival skills. We told everyone they were winners, but didn’t prepare anyone to come back from a loss.
The truth is, you will face financial ruin two or three times in your life, maybe more. Each time you stare into that cliff of bankruptcy, you’ll need to march back with confidence. You’ll face job losses, economic upheavals, and personal crises. Failure is not an exception—it’s part of life. It shouldn’t be feared, just endured.
So learn to live cheap. Save money. Delay gratification. Distinguish what you want from what you need.
Used furniture, macaroni and cheese, and basic cable are God’s gifts to remind you that you’re in control. There is pride in knowing you can be stripped down to nothing and still survive.
The smirk of confidence you need in life comes not from winning, but from knowing you can rebuild.
Takeaway: Learning to live cheap is not about living without—it’s about gaining the freedom and resilience to rebuild no matter what life takes away.
Love, Dad