Every Family Should Have a Winner [I Think It Should Be You]
And I think it should be you.
It's Christmas morning, 1986. I'm a senior in high school.
My dad, mom, me, and my two older sisters are gathered around the tree, opening gifts. It's a modest Christmas—it always was—but we're together.
My dad had been laid off from his mechanic job a few months earlier. He'd found an opportunity at a trading firm, penny stocks mostly. Studied hard. Got his license. He was all in on this new path.
As we finish opening gifts, he looks around the room and says:
"Hey, next year will be our banner Christmas. This stock trading job is it. It's what I've been waiting for. You'll see."
Six months later, he asked if I could help with the mortgage.
I was 18. Working at a steakhouse. I gave him what I had stashed away.
That moment hit different.
I walked into his office—really just a spare bedroom with a desk—and saw the piles. Real estate programs. Business ideas. Notes and plans for things that never happened. A graveyard of good intentions.
My parents could never hold onto anything. Promotions, pay raises, even sizable inheritances—like water, they always found their level. Money came in. Money went out. Nothing ever built.
I stood there and thought: I can't let this happen to me. I won't.
But I had zero leverage. I was 18 with a steakhouse job and a vow that meant nothing without action behind it.
Four years later, my daughter was born.
And everything changed.
She wasn't planned. Her mom and I barely knew each other. I was still making $5 an hour stocking shelves at Price Club. No degree. No direction. No plan.
But the moment she arrived, I had something I didn't have before: a why.
Not a vague "I want more" kind of why. A real one. A face. A future that depended on what I did next.
That's the leverage I was missing at 18. The vow was there, but the fuel wasn't.
My daughter was the fuel.
Within months, I enrolled in school. The same guy who graduated high school with a 1.6 GPA—who hated every minute of the classroom—was now showing up early, doing the work, stacking credits.
Not because I suddenly loved education. Because I refused to let my daughter watch me become my father. Promising "banner years" that never came. Asking her for mortgage money someday.
No chance.
I got my degree. Then my MBA. Then a second master's. Every rung I climbed, I climbed because the why was burned into me.
The first job I landed after graduating more than tripled my income. Not because I was smarter than anyone else. Because I had a reason to figure it out—and I didn't stop until I did.
Here's what I've learned:
Every family has patterns. Some build. Some tread water. Some sink.
If you're reading this, you probably already know which one yours is.
The question is: are you going to repeat it or break it?
Someone in your family has to be the one who figures it out. The one who stops the cycle. The one who builds something instead of just surviving.
Why not you?
You might not have a kid. You might not have a dramatic moment where everything shifts. That's fine.
But you need a why. Something bigger than "I want more money" or "I hate my job." Those aren't strong enough to carry you through the hard parts.
Find the thing that makes the "how" irrelevant. When the why is powerful enough, you'll figure out the how. You'll find the time. You'll do the work.
If the why is powerful, the how is easy.
My dad never got his banner year. He stayed stuck—not because he didn't want more, but because wanting isn't enough.
I made a vow at 18 that I wouldn't repeat his pattern. But vows without leverage are just words.
My daughter gave me the leverage. And I used it.
Now I'm the one who broke the cycle. The one who built something. The one my kids won't have to help with the mortgage.
Every family should have a winner.
If you're reading this, I think it should be you.
— Scot Free
