CEO Insider

How Being a Dad Makes Me a Better CEO

Lee Goldstein, CEO, DiMassimo Goldstein (DiGo)

With Father’s Day on the horizon, I’m feeling incredibly lucky to be the father of two very talented, yet different boys. One has taken to the great game of baseball and the other is a budding artist, yet each is absolutely committed to his passion.

Jordan, 14, takes over 100 swings every day to become a great hitter. He works out at least four times a week. His goal? To play D1 college baseball. His intensity and desire to perform is palpable. But, along with that desire comes the innate pressure he puts on himself.

Blake, 11, draws at least two hours every day. He’s a constant learner, watching every YouTube video imaginable on becoming a better artist. He has written and self-published two comic books and has created a dozen commissioned pieces. I’ve worked with Blake to create a system for creating art for many different clients – all framed, packaged, and shipped. I’ve helped teach him the value of his time and unique talents.

Although I’m supposed to be teaching them, I often find them teaching me. Here are five ways that being a father has made me a better leader:

Lean Into Your Strengths

Early on, I tried to get my artistic son into baseball and my baseball-only son to try anything else, if even just another sport. Sure, they humored me, but after a while, it just made more sense to lean into their passions. Same applies in business: putting the right talent in the right seat versus force-fitting is the best recipe for success.

Practice Makes Perfect

My kids are starting to see the payoffs of practicing: muscle memory, whether it’s wing, repeat, or to draw, repeat. Malcolm Gladwell’s 10,000-Hour Rule applies to everything in life. The more you do it, the better you get.

Challenge Yourself With Greatness

Both boys have heroes. My 11 year-old would religiously watch videos of The New York Times bestselling comic-book artist David Finch every week. For his birthday, I asked Mr. Finch if he’d be willing to provide a paid private Zoom lesson after sending him Blake’s work. He responded saying, “There’s no way he’s 11…his work is amazing and I’ll do a lesson for free!” Now we send him updates and he’s become a mentor to Blake. When you practice and work while comparing what you do to the output of your heroes, it can be frustrating and even discouraging. But the more you study that gap, the better you get at closing it. The more you practice with the intention of greatness — comparing your performance to your ideal performance — the better you become.

Work Hard When No One’s Watching

When you’re playing in a game, everyone’s watching. But do you use this same intensity when no one is watching? If you do, you’re more likely to get the results you want. And, of course, the same in real life. Being ready for a big presentation is as much about preparation as it is about being “great in the room.”

Be a Team Player

Caring more about the team than yourself is hard, but if you can learn how to be “other-ish” — as Wharton professor Adam Grant recommends his book Give and Take: Why Helping Others Drives Our Success — you can thrive anywhere. A selfish player, if not corrected, may be an unemployable adult later in life. Always include the client on your team. This builds trust, and trust is everything.

Despite my two-decade career in the “real world,” raising these two boys continues to make me a better CEO. I appreciate both the achiever and the creative mind, two critically important facets of being outstanding in the advertising industry. Little did I suspect that they’d be helping me learn almost as much as I am teaching them, and I wouldn’t want it any other way.


Written by Lee Goldstein.

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Lee Goldstein
Lee Goldstein is the CEO of DiMassimo Goldstein, an NYC-based behavior-change marketing, branding, and design agency working with change agents such as WW, SodaStream, Samsung, and Echelon.


Lee Goldstein is an opinion columnist for the CEOWORLD magazine. You can follow him on LinkedIn.