Chubby Rules for 2020

Though he was skinny like me, my dad’s nickname was Chubby. He was plump as a kid (like me), and the “Chubby” nickname stuck for the rest of his life. 

Chubby grew up with no money, no connections, and a basic high school education. He didn’t have a father-mentor (as he was to me) because his dad died when he was young. He started life without the advantages he gave me, but still built a successful, multi-office real estate firm in Cincinnati. 

Unfortunately, many fall short of their childhood dreams, but I’ll bet Chubby achieved more than he ever thought he could. Growing up I observed that a key to his success was structuring his life around a set of simple, yet powerful rules.  

I call them “Chubby Rules,” and thought it would be fun to start the New Year by sharing three of the most impactful to me:

5 Reach-Outs A Day 

Chubby tried to call or write five people a day, five days a week. He might congratulate them on doing something well. He might show appreciation for something they’d done for him. Or he might simply point out how much he enjoyed having them in his life. 

If he fell short of five reach-outs one day, he’d make it up the next. Chubby’s reach-outs were genuine (I heard him make hundreds of calls, and saw many of his notes). He didn’t praise or show appreciation he didn’t mean. 

Chubby was smart, realizing that these five reach-outs each day would likely come back to benefit him. He believed that making someone feel good (genuinely), and benefiting from it, was a win-win for both. 

Chubby’s five reach-outs a day were not a substitute for him doing and saying nice things with no motive in mind. Instead, they were a complement to what we all hopefully do naturally as good hearted, caring people. 

Over the years I witnessed the outpouring of goodwill and reciprocity emanating from Chubby’s five reach-outs a day. It was the best ROI of anything I’ve ever seen anyone do… and it made people feel good too.  


In high school I desperately wanted to be a starter (and star) on the basketball team. The “Big O” (Oscar Robertson) was my hero. So I went out for the team, barely made it, and then rode the bench all season.

I practiced harder and longer than any player on the team. No kidding. But I didn’t have big hands, so I couldn’t dribble, shoot, or pass as well as the kids who could palm the ball. That was one of the most frustrating years of my life. I had a dream, worked like a demon to achieve it, but lacked the God given attributes to realize it.

When I expressed my frustration to Dad, he shared a valuable perspective you don’t often hear. He told me it’s not smart to pursue certain dreams (contrary to many parents’ advice). We should assess our innate capabilities and odds of success first, before going after a dream. Chasing a dream that you have little chance to realize can be a nightmare, like my basketball season sitting on the bench. 

It’s also important to fast forward your mind and be sure you’ll be happy if you achieve your dream. For example, if you aspire to be a high school teacher, will you be okay living modestly? If you aspire to be a performer, will you be okay traveling and living in motels? Chubby’s advice was to assess my probability of success, and then make sure fulfilling my dream would truly be right for me.  

The Definition of  HAPPINESS

When I started in the real estate business, my dream was to accumulate $1,000,000 in the bank, own a luxurious home, and drive a Porsche. I figured that would make me happy. Silly me. 

After achieving those goals, I felt like I needed more… stuff that is. So I started buying a lot of things. After a while, I was spending money foolishly, trying to find happiness in materiality. 

Then one day, having coffee with a friend,  I mentioned that while I wasn’t unhappy, I didn’t feel as invigorated as when I was “going for it.” The advice he then shared has been foundational to my happiness ever since. It became one of my top Chubby Rules even though it wasn’t from Chubby. 

The Definition of Happiness – Happiness is the deep sense of satisfaction that comes from the enthusiastic pursuit of a worthwhile goal of your own choosing. 

The point is that happiness is not about pleasure, it’s about purpose. Purpose is the cake. Pleasure is the icing. 

So with your happiness in mind, I wish you a purpose-filled New Year brimming with intelligently chosen, worthwhile goals, with good fortune and savvy to make them come true.

“It’s really dumb to think you’re smart.”
-Greg Hague
(What I learned after graduating from law school,
thinking I was invincible.)