Is Being Impressive Really Worth All that Effort? (and how the Game of Life is really more like Chutes & Ladders)

Did you ever meet someone who impresses you right away? The way they carry themselves, their presentation, their job. And you think, “Man, I want to be like that when I grow up.”

Then you find out you’re the same age?

That happened to me twice last month. Once, of all people, by the guy who was Best Man at my wedding. And it made me wonder what the hell I’m doing wrong.

So I did what any normal adult does when they have a question. I asked my dad.

And like every great dad, he had the perfect answer.

(Side note—dads are awesome.)


Now, before I unveil his wisdom unto you, let me back up and give you a quick recap of my career. Don’t worry. CliffsNotes version.

I studied sports marketing in college and landed my first big job at a PR agency in New York. Didn’t like it, but it did lead to a game night gig with the Rangers — so I checked that off my bucket list. From there I went to a sports agency, which led to a rather notable run in field marketing. I tried my hand at sales for a while, but I missed marketing. So I doubled down on the content train and have been riding high ever since.

Howzat for concise?  (#humblebrag)

Now, dear reader, I have a question for you. What was your favorite job? Not your most important job, but your favorite job. Go back to the beginning. We’re talking all time.

Me? I worked at a movie theater during high school. Free popcorn for days. Previewed every new release. Snuck my friends through the back door. And had great after-work parties.

Looking back, I didn’t learn anything from that job. But it was my favorite. Now, I love what I do today and I’m super happy doing it. But man, that was fun.

And that brings me back to my very impressive friend and the sage advice from my father.

El Padre pointed out that my buddy never had those fun jobs. He was taking prep classes while I was slinging popcorn. He was on the executive track when I was bucket listing the Rangers. And he was putting in 60+ hours at the office while I was putting in 12 at a luxury suite.

Remember the board game, Life? Well, I think Life should have been more like Chutes & Ladders. Here’s why.

My friend is now a CFO for a Fortune 500 company. He spun nothing but 6’s and climbed straight up that corporate ladder. I hit a few chutes along the way and my ladders weren’t always connected. But I worked my way around the board. And while neither of us has reached that 100th square yet, I’m catching up fast.

He and I are both exactly where we want to be. Successful, happy, fun lovin’ guys with great lives & solid resumes. He may have the better title, but my ladder was more fun to climb.

Writing this reminded me of something my favorite professor told me. “Don’t worry about what you want to do with your life. Just decide what you want to do next.”

That professor now runs a very prominent marketing agency. Prior to teaching, he was a prison guard.

Pretty impressive.




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