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

Take a time-out to answer these seven questions that help you define what it means to become a winner at life. Then get after it.


What’s the meaning of winning at life?

What kind of game is life anyway? And 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 can “play the game” of life.

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. Maybe they’ll help you, too.

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

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?

I’m thinking maybe it would be if I cured cancer, stopped climate change, and convinced the entire human race to stop fighting in a single swoop.

But then what? Would I burst into a cloud of fulfillment?

No. After a glorious victory lap, I’d have to find a new game and keep playing.

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.

But if you can’t win at life, what kind of game is it?

Games you play but can’t win remind me of an old babysitter named 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.

Then why should I try to keep on winning? What kind of game is this?

Is God a greater version of Annie? (Shudder.)

I 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.)

What’s the objective?

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

You mean the meaning of life?

Jeez. 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

How I interpret this is that the meaning of life is having a meaning. A purpose. A mission. And, as Frankl recommends, I have to detect that mission rather than invent it.

Another wise guy, Steven Covey, suggests setting a personal mission statement. I like this concept a lot, so that’s what I’ve done.

(Here’s more on how and why I created my personal mission statement.)

My best guess: To become a winner at life, my objective is to fulfill my personal mission statement.

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

How much comes down to luck?

Luck certainly has a huge role in how my life’s performance has gone 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.

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 doesn’t mean I’m destined to lose at life. I could still set a mission 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.

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?

My first instinct, as much as I know it’s not true, 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.” They’re likely closer to winning.

Then I asked myself, do I aspire to one day have their same life?

Not exactly. Because they have different missions. 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 balance that resonates best for us so we perform to the best of our ability.

My best guess: I can’t copy anyone else’s strategy to become a winner at life. I have to find my own harmony.

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.

Shouldn’t you just enjoy the moment?

Focusing on winning at life all the time seems stressful. So why can’t I just relax, be grateful for what I have, and enjoy the moment?

Because my future self will be pissed off at me if I relax too much.

So it’s a balance. As the DJ of my life’s performance, I set a mix, vibe to it for a while, go back to the mixing board to fine-tune, then vibe some more. And I’ll keep going, trying to put on the best show possible and enjoying it to the max.

My future self will decide whether I did a good job or not.

My best guess: I need to find a balance between enjoying life and tweaking with it to make it increasingly enjoyable.

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 collecting welfare checks from other people’s efforts certainly isn’t winning.

I think what’s most important is to perform the best I can at whatever my definition of winning at life is. That way, I’ll inspire others to do the same, 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

If you actually put some thought into the questions above rather than lazily skim through them in search of magical quick-fix answers, you will have come with a different definition from mine on what it means to win at life.


But I hope we agree on two things:

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

So on that note, I’m off to try to put on a great show. Hope to see you out there doing the same, however it is you decide to do so.

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About the author

I'm Chris. Canadian, husband, dad, writer, investor, athlete, and obsessed explorer of the secrets to living a never-boring, always improving, unfollowable life story.

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