Is “Winning” Something We Should Strive For?

winning goal

For months now, I’ve been mulling over an idea that I can’t quite pin down.

I’ll get a burst of insight, start typing it out in my Notes app, and just as quickly as the idea came, it fades away.

A game of peek-a-boo where the idea pops its head up—shows itself to me—and then pops back down, only to return a few days or weeks later in a slightly different form.

If I was too sensitive of a soul, I might take it personally that the idea doesn’t want to stay with me longer. Doesn’t want me to fully take it in and dissect it like a formaldehyde-soaked frog on a high school lab counter.

With every return, this elusive idea is nudging me towards answering the question: Is “winning” something we should strive for?

It all started with this year’s summer Olympics, which thanks to a no-travel-summer I must have had the free time to sit around and watch. Perhaps it was the full year in lockdowns or the mental health focus with Simone Biles, but I became increasingly fascinated with the concept of winning and the value we put on it as a society. And whether that’s a good or bad thing.

On one hand, I was insanely impressed with the supernatural talents of the athletes and their resilience under pressure.

On the other hand, their narrow experience of life also saddened me. (Coupled with watching the Netflix documentary, Athlete A, which highlighted the sad realities within the USA Gymnastics team. Most notably, how overly submissive an athlete has to be in order to be pushed to win a gold medal.

Powerful on the competition floor. Submissive behind closed doors.

This paradox lingered over my head for weeks. What is winning? Is it worthwhile? Does it ruin you or make you great?

Then came another insight. Or rather, the same idea but in a different form: what is the American dream, really? At its core, it’s the belief that anyone can pursue a life of success and happiness on their own terms. But the modern interpretation of the American dream resembled the winning mentality of the Olympics more than a noble quest for personal greatness.

The Olympics of Suburbia. Where you compete to have the best house, nicest care, and 2.5 kids.

There’s power in pursuing such achievements, but there’s once again a submissive nature in being part of this endless chase.

And the American dream isn’t dead. It has simply evolved into the Online dream. Where, once again, the playing field has been levelled and “regular people” can pursue a lit of success and happiness on their own terms. But I’ve noticed that lately it has—once again—taken on the winning mentality of the Olympics.

The Online Olympics. Where keeping up with the Joneses has been replaced with keeping up with personal development gurus. Where the white-picket-fence-and-2.5-kids has been replaced with the laptop-lifestyle-and-6-figure-online-business. And where we’ve replaced the strict 9 to 5 work hours with the perfect five-step morning routine.

We’ve put lipstick on the American dream and called it the Online dream. But are we just repeating the same patterns? Mimicking the herd, wanting validation, competing for our worth, and following a rule book.

These questions and half-formed thoughts are circling my brain, slowly starting to take shape but I still have no clear “Aha!” for what they want me to uncover.

Then earlier this week, another spark of insight came. This time, in the form of a YouTube interview with Tom Bilyeu and Raoul Pal on crypto currencies and the Bitcoin revolution. About how the downfall of all former currencies has come from the interference from human greed and our desire for leverage. The crux of crypto is that it’s here to save us from ourselves. Try as they might, no government can manipulate Bitcoin like they do Fiat money.

It got me thinking—what else does human nature ruin?

Having built my career in the online marketing and thought leadership space, I can safely say: plenty.

Want a Forbes feature story? Just write a cheque.

Want a large Instagram following? Just buy some bots.

Want a bestselling book? Just hire a marketing company that will push your book to #1 on the NYT Bestsellers list.

In the online world, most approval can be bought, which makes it very arbitrary. And when you have arbitrary metrics? You can’t assess real value.

And yet, these arbitrary metrics have become the success metrics in the online world. People are still flexing for going viral on TikTok when the algorithm was literally made to lure in creators with its almost-guaranteed virality.

Powerful in the TikTok arena. Submissive to the algorithm.

But what does winning have to do with the American dream have to do with Bitcoin have to do with the online world?

I don’t know. But I do know they’re taking me on an adventure to think deeper and deeper about success and winning. And the speed of insights is picking up speed lately, which is why—although I don’t have a perfect answer to share today—I know that gathering these ideas on paper and sharing them with you might keep the momentum going.

As I’ve been wrapping up this newsletter, I happened to see a quote online by James Carse from his book, Finite and Infinite Games:

“A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.”

His book is an exploration of what it means to see life as a series of “finite games” to be won vs. seeing life as a single infinite game to play in.

The finite players are only as good as their last win, which is why they are always looking for the next game to win. (The Olympians winning a gold medal and wanting another. The homeowners moving into their new homes and immediately wanting a new car. The 6 figure entrepreneur who all of a sudden needs to be a multiple 6 figure entrepreneur.)

The endless chase for more.

And then there’s the infinite players who have only one prize they’re after: to keep playing the game for as long as possible. Their gold medal is resilience. A pursuit of greatness without sacrificing themselves for short-term wins or status symbols.

Knowing your choice—finite vs. infinite—is crucial because it guides how you pursue growth, learning, and the success metrics that actually mean something to you.

Do you choose the life of winning?

Or do you choose the life of play?

I’m still somewhere in the middle, holding both competing approaches to life in one hand.

I don’t have a clear cut answer on my original question of whether winning is something we should strive for.

But maybe my non-answer is an answer?

Maybe not having an answer and being able to say “I don’t know” is what keeps me in the game of mulling over this thought? Going deeper and deeper instead of settling for a surface level answer?

After all, I’m not here to give you answers.

I’m here to share unique ideas without regurgitating external voices. I write to show my ideas that they can trust me, that they can land on me and I’ll nurture them into beautifully articulated ideas in the world.

So this newsletter is for you, my dear thoughts. I won’t parade you around to grow my following or pay my way to a gold medal. I will commit to bringing you into the world through my writing as authentically as I can.

For now, I’m choosing the infinite game of play and open mind over a simple answer.

And I’ll keep you posted as my mind continues to expand on this topic. In the meantime, please hit reply with your perspectives. I can feel I’m 90% there with this new idea.

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  1. […] Last week, I asked the question: Is “Winning” Something We Should Strive For? […]

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