November 6th, 2025
My dad, nicknamed Chubby, grew up poor. His father died when he was just a boy, leaving his mother to work two jobs to keep food on the table. He had only a high school education and used to joke that he graduated from “the School of Real Life with a minor in Tough Breaks.”
When World War II came, he became a fighter-pilot instructor, the man who taught others to fly fast and stay alive. After the war, he married my mom, hung up his uniform, and took a straight-commission real estate job. No salary. No safety net. Just grit.
He worked brutal hours, sometimes through the night, napping on a green leather couch in his office. He wanted a better life for Mom, my sister, and me. And he made it happen. The man with no college degree built one of Cincinnati’s largest real estate firms, more than 400 agents strong.
Chubby wasn’t highly educated, but he was wise. He taught me that there’s a difference between being educated and being smart. That means living guided by thinking guides, decision-making rules that help us make better choices.
The following are a few of those rules I learned from my dad and other smart people I’ve met along the way.
Know the Life That Makes You Happiest
Dad’s first rule was simple but profound: Understand what makes you happy and what you want from life.
He told me happiness is the gap between expectation and reality. When reality meets your expectations, you feel peace. When it doesn’t, you feel restless. So, define your expectations clearly, not what others want for you, but what you want for yourself. Because if you don’t know what you want, life will hand you what’s left.
Change Your “Happiest Life” Perspective—but Not Too Often
Chubby believed in flexibility but warned against chasing every new thing. “If you keep changing roads, you’ll never reach any destination,” he’d say.
It’s fine to evolve, but constant redirection keeps you chasing mirages. Choose a vision, commit long enough to see it bloom, and only adjust when your growth outgrows the plan.
Identify the People Worth Compromise
Chubby believed that time was the ultimate currency. “Some folks deserve your sacrifice,” he said, “and some only deserve your wave as you walk away.”
Know who builds you and who drains you. Give generously to those who matter; family, true friends, people who lift your spirit and guard your energy from those who only take.
Purpose Is the Cake, Pleasure the Icing
Pleasure, Dad said, is nice but fleeting. “Build the cake before you buy the frosting.”
He was driven by purpose; to give our family security, an enjoyable lifestyle, and my sister and me the advantage of the college education he did not have. Dad was willing to sacrifice short term pleasure to achieve long term prosperity, freedom, and happiness. Daily pleasures alone, like lunch, dissolve quickly when they are not simply an enjoyable interlude from a purpose that excites and drives you.
When You Look Forward to Lunch, You Need a New Job
Chubby once told me, “If the best part of your workday is a break from it, you should explore a new direction.”
He didn’t mean everyone should quit their job immediately. He simply meant that lunch, that break in the middle of the day, is symbolic of anything that's merely a pause from purpose.
If you wake up each morning counting the hours until you can escape what you’re doing, you don’t just need a new job... you need a new direction, a new reason to get up, a new sense of purpose that excites you and stretches you beyond simple pleasures. Life’s richest joy comes not from avoiding the hard parts, but from caring deeply about something worth the effort.
Because the goal isn’t just to make a living.
It’s to make a life that makes you love being awake.
