To Win at Life, Stop Competing: 8 Can’t-Lose Strategies

This post on how to win at life by not competing is part of Volume 8 of our Unconventional Monthly newsletter on the topic of Super Self-ism.

Life’s Not a Competition (But You Can Still Win)


Here’s the best description I’ve found on what it means to win at life:

“Harnessing all that you are in the service of realizing the best version of yourself so you can help raise the bar for the whole of humanity.”

Scott Barry Kaufman, Transcend: The New Science of Self-Actualization

It’s a bit wordy and highly subjective, but I feel if I come anywhere close to touching this definition, I’ll be giving life all I got and leaving it all out there. When the Grim Reaper eventually takes me out of the game, he’ll be like, “Nice job.”

That’s the idea, at least.

And notice what’s missing from this definition of winning at life: competition. There’s no need to be better than anyone to harness your best self, raise the bar for humanity, and earn a high-five from Death. Life’s not a competition. It’s hard enough to win at life as it is.

Let’s look at some can’t-lose strategies that might increase our chances.

Can't lose when you differentiate so you're the only competition
You can’t lose when you find areas where you’re the only competitor.

1. Play Games You Can’t Lose


The more authentic you are, the less competition you’re going to have.

Naval Ravikant, Naval Podcast

Go where competition is irrelevant because we’re the only ones. This is called The Blue Ocean Strategy in business. And it applies just the same in life.

Our challenge is finding virgin patches of ocean to sail our little self-actualizing boats through. It’s a matter of understanding our unique “jagged profiles” of strengths, weaknesses, interests, and values, then finding somewhere it fits. It’s not easy.

What’s easier is knowing when we’re in the wrong spot. Because we lose. If you lose your job, relationship, or your mind, or you feel lost, you’re in the wrong place playing the wrong game. The right games are those you can’t lose.

Stop and smell the flowers
When you do what you want to do, not what you want the results of, you can stop to smell the flowers along the way.

Score Fewer Goals


“When you sign up to run a marathon, you don’t want a taxi to take you to the finish line.” 

Derek Sivers, Anything You Want: 40 Lessons for a New Kind of Entrepreneur

Goals help us set our direction. That’s good. And scoring goals feels fantastic. Yay.

But then what?

Shoot for another goal? Then shoot for another and another until we fail, give up, or run out of time?

That doesn’t sound like winning at life. As Todd Rose writes in his unconventional-path-finding book, Dark Horse, “If you commit yourself prematurely to a straight path, you may close off numerous winding paths leading to far more satisfying versions of success.”

Here’s an alternative:

  1. Pick a goal. “I want to run a marathon.”
  2. Think of the systems, values, and skills needed to reach it. “I need to join a running group, get a coach to improve my stride, and value my long-term health over short-term rewards.”
  3. Forget the goal and do step two for the fun of it. “I’ve come to love getting outside and going for runs and how my body feels afterward.”

Do what you want to do, not what you want the results of. Odds are you’ll score by accident. “The score takes care of itself.” as legendary NFL coach Bill Walsh said. Either that or, like me, you’ll stumble into playing different games you’d hadn’t considered.

Shoot for What You Can’t Beat People At


Use values instead of goals to determine the actions we take and how we keep score in the game of life.

Avoid competitive values. Shooting for values that are measured relative to others like popularity, image, power, acceptance, and respect is a loser move. Nobody can win forever in those games.

Shoot for values you don’t need to beat anyone to attain. Here are some values recommended by Abraham Maslow, the famed hierarchy of needs creator who dedicated his life to figuring out how to achieve “self-actualization” and “transcendence” (fancy terms for winning at life):

  • Perfection. Struggle to master.
  • Justice. Make it right.
  • Simplicity. Get to the essence of things.
  • Truth. Stay open-minded and curious.
  • Uniqueness. Be your best possible self.
  • Playfulness. You can’t win at life without playing.
When sh*t happens, suck it up and deal with it.
Even when you get in some sh*t and it’s not your fault, it’s your responsibility to deal with it.

Suck It Up and Keep Swinging


The game of life is like playing golf on par a infinity hole. We try to pick the right club from our bag given our circumstances, aim as best we can, and swing.

If a crocodile emerges from the water hazard and sits on your ball, too bad for you. Suck it up and deal with it. When a sudden gust of wind carries your otherwise perfect shot into a bunker, boohoo. Suck it up and deal with it.

Not everything’s our fault, but everything’s our responsibility. Moaning, “Why did this happen?” doesn’t help. All we can do is suck it up, ask ourselves, “What can I do about it?” and keep swinging.

Beat Competition with Cooperation


Vince Lombardi, another legendary football coach, said, “Winning isn’t everything; it’s the only thing.” So what gives?

He does.

He later clarified he meant “the will to win” or “making an effort.” Neither of those requires making life a competition. Life isn’t a football game and we’re not keeping score, anyway. We can accomplish more by helping each other find and fix our weaknesses and teaming up to take on bigger challenges.

But what about motivation?

Competition motivates for sure. But so can a lion chasing a group of fat kids in the savannah to make them exercise. Both motivate for the wrong reasons. More rewarding (and less deadly) motivation comes from finding a calling that ignites a “rage to master” under our asses. Focus on finding that flame and cooperate rather than compete.

Contagious can't-lose mindset for winning at life
People respect unanxious types who do their own thing.

Attract Respect Rather Than Chase It


“When you are content to be simply yourself and don’t compare or compete, everybody will respect you.”

Lao Tzu

When we live like we can’t lose, it matters less what other people think of us and what they’re up to. Social anxiety fades, freeing up the energy to be more creative, explore further, and take more risks. Mistakes are no longer embarrassing, but useful lessons.

And a funny thing happens when we keep at it. People recognize and respect what we’re doing. What others who view life as a competition so anxiously chase after comes to us naturally.

I’m not saying to stop giving a single baby rabbit’s pellet of a crap what other people think of you. Only psychopaths have zero social anxiety. Just worry a lot less. And focus most of that worry on the one person we tend to give the cold shoulder…

Only Impress One Person


“A healthy feeling of inferiority is not something that comes from comparing oneself to others, but from one’s comparison with one’s self.”

Ichiro Kishimi and Fumitake Koga, The Courage to Be Disliked

We only have to worry about impressing one person to win at life:

Not our present selves. We’re too easy to please with ice cream, video games, or scrolling through Instagram. 

Not our past selves. The problem with the Pinterest wisdom saying, “My only competition is the person I was yesterday,” is that when our win streaks inevitably end, we risk falling down a deep spiral into Loserville.

Our future selves. If our future selves will be proud, we know we’re on the right track. Try this thought exercise:

Imagine you had an Instagram account followed by 1000 future yous from all moments in the future between now and your death. What could you do and then post about to get the most likes?

Nobody impatient ever accomplished anything noteworthy (…but they probably didn’t die of thirst running through the desert either).

Play the Long Game


“The difficult is what takes a little time; the impossible is what takes a little longer.”

Fritjof Nansen

Our most common adversary to winning at life is impatience. It’s so big and boring to combat that we prefer to compete elsewhere and get easy wins. Then we feel we’re too far behind to go after something substantial.

First, stop worrying about where you’re at. As David Epstein writes in his book, Range, “You probably don’t even know where exactly you’re going, so feeling behind doesn’t help.”

Then worry about your legacy. What’s the story your life will tell? Keep in mind that, “A story is a character who wants something and overcomes conflict to get it.” You can edit the story as you go, but you only get one story to tell. Take your time to make it a good one.

The Can’t-Lose Mindset to Win at Life

To recap:

Play your own game and make it something you want to do, not what you want the results of. Life’s not a competition, so cooperate when possible and forget about the spectators. The only person you need to impress is your future self. Play the long game to leave a legacy, aiming for values, and keep swinging regardless of your situation.

Follow these can’t-lose strategies and you’ll have a great chance of “harnessing all that you are in the service of realizing the best version of yourself so you can help raise the bar for the whole of humanity.” And you’ll get a high-five from Death. That’s winning at life.


Thanks to Francisco (stay tuned for his Mediterranean towels), Luis, and Blair for their input!


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Chris and Kim

Kim and Chris are exploring better ways to do... everything. Think, travel, exercise, work, relate, you name it. Every week-ish, we share a new idea in our newsletter, "Consider This."