This One Question Will Help You Stop Comparing Yourself to Others

Paul Ollinger
5 min readNov 12, 2023

In the old game show, Let’s Make a Deal, host Monty Hall tempted audience members to trade moderate cash winnings for the opportunity to take home a much bigger prize, like a new car, by taking a risk on Doors #1, 2, or 3.

But all decisions were final and those doors were equally likely to reveal worthless booby prizes like a goat, 100 pounds of baking soda, or a stack of old shoes. These ridiculously-outfitted contestants gambled and often lost because they had to take the whole deal or no deal at all.

block wood reading “envy”
“Envy is a mofo.” — Socrates

This is the image I keep in mind when thinking someone else has it better than I do. When I find myself coveting aspects of another person’s life, I ask myself this question: “Would I take the whole package, with no possibility of refunds or exchanges?”

You’ve heard the Teddy Roosevelt saying that “comparison is the thief of joy.” And boy is it ever. It blinds us to the great things in our own lives while irrationally glorifying those of others. But comparison is also one of the most childish instincts we have because it ignores the stark reality that each of us is an indivisible bouillabaisse of strengths and foibles.

We think: “I’ll take their money, but not their marriage,” or “I’ll take his six-pack abs, but not his low I.Q.” Sorry, but it doesn’t work like that. As Bret Michaels taught us, you don’t get the rose without the thorn.

The more time I spend in conversation with very accomplished people, the more I am convinced that extrinsic success is just one factor in a multivariate equation of life. These ballers possess all the outward signs of achievement, but I don’t find them to be much happier overall than the average person.

At the moment, there’s no better example of this than the late Friends actor, Matthew Perry. He starred on one of the most successful TV shows of all time, earned tens of millions of dollars per year in mailbox money, and dated the most glamourous women on the planet, including but not limited to, Natasha Wagner, Yasmine Bleeth, Neve Campbell, and Julia goddamn Roberts.

Last week, he died alone in a hot tub. The cause of death has yet to be determined, but whether it was an overdose or a heart attack is immaterial. This is the most Hollywood cliché ending any writer could contrive and it is not at all surprising. Last year, I read his memoir, Friends, Lovers, and the Big Terrible Thing, which is little more than a litany of his savage addiction, recoveries, relapses, and broken relationships — the likes of which I wish on no one.

Would I love to have Matthew Perry’s money and fame? Oh yeah! Would I trade my imperfect life for his? Not a fucking chance.

Matthew Perry sitting in a hot tub, wearing headphones and looking over the lights of Los Angeles
One of the last photos of Matthew Perry. From the outside, it looked like a great life.

He’s just one of innumerable examples. Do you envy the hundreds of millions of dollars that come with being the co-founder of a children’s toy empire? Well, then you also have to accept the “existential dread” that has followed Melissa Bernstein of Melissa & Doug’s Toys since her earliest moments on this planet.

This condition and her business success are not mutually exclusive. When we spoke on the podcast, she told me she never could have designed the hundreds of toys she created without an intellect that sees the world through a non-typical lens. That same brain has also led her to contemplate suicide on a daily basis since she was a child. I’m guessing that doesn’t sound better than your life.

Consider Andy Dunn, the co-founder of Bonobos. He sold his company to Walmart for $300 million and now sits on several corporate boards. Yet, as he explains in his book Burn Rate, Andy lives with what he calls his “ghost,” a manic-depressive counter-ego that is with him every day, even when he feels “normal.”

Want the comedic success of Stephen Colbert or Molly Shannon? I sure would! But did you know that Stephen’s father and two brothers died in a plane crash when he was ten years old? Or that Molly’s mom and cousin died when her probably-drunk father drove their car into a tree? I can’t imagine carrying around the lifetime of trauma experienced by six-year-old Molly who was also in the car. So, on second thought…

We simply don’t know or — more likely — choose to ignore how rough those around us have had it. We fool ourselves into thinking that some shiny aspect of another’s life makes them more important, better off, or happier than we are.

I can’t think of anyone objectively cooler than Anthony Bourdain and no one had more discerning taste than Kate Spade. Yet both of these beautiful souls chose to hang themselves instead of facing another day with the darkness that is so often the flip side of an intensely creative mind. It’s a package situation and it’s non-negotiable.

a little girl wearing a birthday hat, sulking. A mom and two other girls are sitting on a picnic blanket in the background.
“Why does she always get the big piece of cake?”

Comparison is not only a childish tendency, it’s also completely unfair to you because you’re grading yourself against a fictional scoreboard. If you can take a step back and evaluate your life non-emotionally, you might realize that you’re doing okay. A lot of folks out there, including 18-year-old you, might be pretty impressed with what you’ve managed to pull off.

So ask yourself, “What assumptions am I making about this other person’s life that — on the surface — looks so much better than my own?” You’ll probably find it’s not as peachy as you might think.

And for the parts you still admire, ask “How did that person achieve what she achieved, and what can I learn from it?”

Be kind to yourself. When you think you want what someone else has, remember that it’s an all-or-nothing deal. It might look like a shiny new car but it’s equally likely to be 100 pounds of baking soda.

THE END

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Paul Ollinger

Comedian. Host of the Crazy Money podcast. Proud former Facebook and Yahoo! sales person/leader. http://PaulOllinger.com/podcast