Want to Become a Winner at Life? Start With This Step

Your Defining Moment?


No matter how useful or useless the rest of this post ends up being to you, your presence means you’ve successfully accomplished the first step to become a winner at life:

You called a time-out.

Most people don’t. They play the game of life like I did for my first 27 years. They sweat and pant through it and shoot in haphazard directions without taking a break to regroup and re-strategize.

But, you did. Whether you did so by accident or not, good move.

What’s the next step?

Figure it out for yourself by defining what “winning at life” means to you.

The following seven questions can help. As you’ll see, I’ve used them to come up with my own definition of winning at life and plan my next move. Use this time-out to do the same for yourself.

Me celebrating winning a game and thinking I'll be happy forever because of it.
Spoiler: I was not happy forevermore.

Is it even possible to win at life?

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

What kind of game is life if you can’t win?

Games you play but can’t win remind me of an old babysitter named Annie. She was a hippy my parents hired to look after my siblings and I who forced us 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:

Chris pointing in the direction he wants to go to win at life.
What’s your 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 defining that mission with 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.)

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, I could still set a mission and perform to the best of my ability at fulfilling it. Life may be less comfortable, but that wouldn’t doom me to be a loser.

Older snobby lady playing DJ and wondering what balance will help her become a winner at life.
Her strategy will almost certainly not work for you.

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

To answer this, I first tried to think of other people who are winning at life.

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

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.

Shouldn’t you just enjoy the moment?

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

Because I have no doubt that my future self will be pissed off at me if I relax too much.

So it’s a balance. As a DJ of my life, 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.

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

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

I don’t think it’s entirely selfless. My mission—and everyone else’s—doesn’t need 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 effort 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.

Putting it all together

My Definition of Winning at Life

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.

Kim lazily skimming through this post on her phone not showing much motivation to try to start winning at life.
Skimming isn’t winning.

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 probably came up with a different definition from mine on what it means to win at life.


Just as we can all have our own life missions, we can all have our own ways of defining if we’re accomplishing them or not.

But I hope you agree with me 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 do anything. To become a winner at life you’ve got to perform.

So on that note, your time-out’s over. Get out there and put on a show.

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Chris and Kim

Kim and Chris started The Unconventional Route in 2018 to share their adventures fighting complacency to win at life. Today, over 150,000 people a month visit the site and thousands more explore a dose of uncomplacent ideas with them every 10 days in their free newsletter, Consider This.

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