How to Find the Meaning of Winning at Life in 7 Questions

The better (or less badly!) you define your own meaning of winning at life, the better you'll be able to play the game.


What is the meaning of winning at life?

What kind of game is life, anyway? How do you play it? Is it even possible to win?

Your guess is as good as mine—or as bad. If there happens to be one true meaning of winning at life, I wouldn’t be smart enough to comprehend it anyway.

But that doesn’t mean it’s not worth trying to figure out. Because I think the better—or less bad—your definition of winning at life, the better you’ll perform.

Maybe trying to find the meaning of winning at life is the game in itself?

Now I’m confused.

Anyway, here are the seven questions I used to come up with my own rough but helpful definition of winning at life.

Cartoon of person racing to win at life
There is no trophy for winning the game of life.

1. Is it even possible to win at life?

To answer questions like this, I like to think of extremes. For example:

What would be the greatest victory at life imaginable?

Maybe it would be if I cured cancer, stopped climate change, and convinced the entire human race to stop fighting in a single swoop, all the while raising happy kids capable of accomplishing even more than me.

But what would happen after I succeeded at all this? Would I burst into a cloud of fulfillment?

No. After a glorious victory lap, I’d have to find new accomplishments to shoot for.

My Best Guess: It’s impossible to win at life. I can only try to keep on winning.

People dancing and dreaming of winning at life together.
Life is more of a performance than a competition.

2. If you can’t win at life, what kind of game is it?

Unwinnable games remind me of my childhood babysitter, Annie. She was a hippy who forced my siblings, me, and any unfortunate friend who happened to be at our house to play “cooperative games.” As a hyper-competitive 8-year-old, I thought her games were ridiculous and boring.

Still do.

But while competition makes small games in life interesting, I’ve come to realize that life itself is not a competition.

Does that imply life is a giant version of Annie’s boring cooperative game? (Shudder.)

I’ve spent a long time trying to unravel this riddle. And I think I cracked it:

My Best Guess: Life’s not a game. It’s a performance.

Without an objective, how do you know where to go with life? (Consider a personal mission statement.)

3. What’s the objective?

What’s the objective of the game (or performance) of life?

You mean the meaning of life?

Yikes. I’ll defer to Viktor Frankl on this one:

What matters… is not the meaning of life in general but rather the specific meaning of a person’s life at a given moment.

Man’s Search for Meaning

Frankl says we detect these meanings rather than invent them. To me, that’s a matter of keeping on the lookout for problems I want to help with and not shying away from taking action.

Frankl and I both love Nietzsche’s quote, “He who has a why to live for can bear almost any how.”

My Best Guess: To become a winner at life, my objective is to have a “why” behind my every action.

Cartoon of baby getting lucky.
Some are born luckier, but everyone can win at life.

4. How much comes down to luck?

Luck certainly has a huge role my life’s performance so far.

I was lucky to be born in Canada to parents who, aside from hiring Annie, gave me the opportunity to go after anything I wanted. I don’t seem to have much brain damage, I am unusually healthy, and I’ve had lots more luck along the way.

But if tomorrow I got Trading Places-ed into the life of some unlucky buck, that wouldn’t mean I’m doomed to lose at life. I could still find meaning and work toward it to the best of my ability.

My Best Guess: Whatever my situation, I can be a winner by performing to the best of my ability.

Meter balance for winning at life.
Everyone has their own balance that resonates best for them.

5. Is there a proven strategy to become a winner at life?

To answer this, I first tried asking myself:

Who out there is winning at life?

As much as I know it’s not true, my first instinct is to look at rich and famous people like Elon Musk or Oprah.

But then I thought of my parents and other family members who seem to have mostly “figured it out.” Do I aspire to one day have their same life?

Not exactly.

They found different meanings from me. We all do. But we all have the same instruments to fulfill them:

  • Bodies
  • Minds
  • Spirits
  • Relationships

The challenge is that nobody can be at 100 out of 100 on each. So, kind of like DJs mixing a track, each of us toggles these instruments up and down to find a combined frequency that resonates best for us so we perform to the best of our ability.

My Best Guess: I can’t copy anyone else’s approach to becoming a winner at life. I have to find my own.

Cartoon of person enjoying the moment now but regretting it later.
There’s a balance between enjoying the moment and letting your future self down.

6. Shouldn’t you just enjoy the moment?

Focusing on winning at life all the time seems stressful. Why can’t I just relax, have gratitude, and enjoy the moment?

Because my future selves will be pissed off at my past selves for shafting them with painful regrets and shriveled up comfort zones.

A winning life can’t be easy. It’s filled with desirable difficulties that fill life with anti-regrets. The sum total of my past and future selves’ well-being will determine whether I did a good job or not.

My Best Guess: I need to perform in ways that are both enjoyable and rewarding in all areas of life.

7. Isn’t trying to be a winner at life selfish?

I don’t think my mission—or anyone else’s—necessarily has to be to make the greatest possible contribution to the world.

But trying to be a winner at life can’t be entirely selfish, either. Lazing around cashing in welfare checks from other people’s efforts certainly isn’t winning.

I want to be useful. That comes down to performing the best I can at things that others appreciate. In doing so, I’ll inspire others to be useful in their own unique ways, and they’ll inspire others. When my show’s over, that’s the legacy I’ll leave.

My Best Guess: I don’t need to be entirely selfless to be winning at life, but somehow my performance needs to contribute to the bigger picture.

Putting it all together

What Winning at Life Means to Me

Winning at life is putting on the best performance I can given my situation so that, when my show’s over, I feel like I had a blast, others are grateful for it, and my output continues to echo and inspire.

Get Back Out There

You will probably come up with a different meaning of winning at life from mine if you go through these questions. And you probably have other questions to add, too, to further fine-tune your definition.


But I hope we agree on two things:

  1. It helps to take regular time-outs like this to reconsider what winning at life really means.
  2. Thinking doesn’t get anything done. To become a winner at life, you’ve got to perform.

On that note, I’m off to try to put on a good show. Hope to see you out there doing the same, whatever you decide that means to you.

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👋 I'm Chris. Everything you read on is my fault. This site is like a gym for your comfort zone, full of challenges to make your status quo sexier. Join my 'Consider This' newsletter for a fun new challenge every 10 days. Try it!

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The Zag shares my adventures off of the boring beaten paths of life and ideas for finding your own unfollowable path.