Seinfeld says: "Go for the coolest job"

I'm on board, and so is Gary

“The less secure and confident you feel in the direction, the more surprises and excitement you will have in store. That’s good. So the better the job you’ve done in finding a path for yourself, the more boring and predictable your life is going to be.”

This nugget of career advice comes from Jerry Seinfeld’s 2024 commencement address at Duke University. It’s just one gem I pulled out for those bent on living meaningfully, and willing to risk for it.

Dunno about you, but ‘boring’ and ‘predictable’ aren’t the words I want to describe my existence as a whole. Parts, sure. I am a big believer in roots and foundations, and we can all agree that there will be unglamorous parts to any life and endeavor.

But settling for a life that can, on the whole, be described in such lackluster terms? No thanks. As much as I liked that bit of advice from Jerry, though, my favorite bit of advice was this:

The other thing I see going on that throws a lot of people off these days is thinking, I’ve got to make as much money as I can. I personally believe the real game is I want to have the coolest job. When I started out as a comedian, I did not think I was funny. I thought, I’m a little funny. Maybe I wouldn’t have to be that funny. I just have to be funny enough to feed one person. And I could do that with a loaf of wonder bread and a jar of peanut butter… I just wanted to have this super cool job. And cool is a word not easily defined. It’s really just whatever you think is cool. So just go for what you think is the coolest.

I believe Jerry and my friend Gary would really get along. Gary is an octogenarian beloved youth Sunday School teacher of mine, the one who brought Klondike bars to us undeserving kids and who has the gift of liking people. He is also a retired “river philosopher” (Montana fly fishing guide) and is living proof that a) it really matters what you choose to do for work and b) you can actually provide financially doing work you like.

Speaking of fly fishing and Montana, I still remember the day my siblings and I wandered our way over from Dad’s seat cover shop to the old train depot in Bozeman. They were filming a movie (A River Runs Through It) with some actor named Brad Pitt and we wanted to see what we could see. Everyone’s got a claim to fame, and this is mine.

Anyway, on a recent visit, Gary and I talked about how he never made a lot of money in his work, but that he sure enjoyed it. In his words: “I decided a long time ago that I wanted to do something fun.” It’s enough to almost make a person wonder how much of his persistent sparkle for life came from choosing work that suited his soul¹ and knowing what really matters in life and eternity—and it ain’t money.

If I’ve said it once, I’ve said it twice: “The lucky ones are the ones who find or create something they don’t want to retire from.”² Swap in “interesting” or “worthwhile” or “cool” and we’ve got a consensus between Jerry, Gary, and me, and that feels cool.

Isn’t life rich, and aren’t people interesting? See you in the next one…

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More to Your Life is a reader-supported column about what makes life cool and people interesting. Your hearts (♡) and comments are always appreciated. To receive new posts and support my writing habit, please become a free or paid subscriber.

1. https://www.moretoyour.life/p/be-your-own-person

2. https://www.moretoyour.life/p/lessons-from-the-happys