Existential Thought - What Does It Mean To Win?

"It is possible to commit no mistakes and still lose. That is not a weakness. That is life."
Jean-Luc Picard

I prefer mine:

"There are no winners and no losers. Only life... and death."

Despite this, I like winning.

There. I said it. It feels good.

I like winning at business.

I like winning arguments, although with age I am slowly learning that some arguments are probably better left unwon.

I like my football team winning.

I like winning games.

I like proving people wrong when they tell me something cannot be done.

I like being right, though now I know it is not as important as most of us think.

The more important question, in case you were wondering, is:

Are we still able to move forward productively?

I suspect most of us like winning, even those who claim not to care.

But after spending the last few articles questioning success, freedom, wealth, enough, purpose and validation, I find myself confronting another question.

What exactly does it mean to win?

Because winning requires a scoreboard.

And perhaps one of the biggest mistakes we make in life is allowing somebody else to decide what goes on ours.

Who Is Keeping Score?

From almost the moment we enter the world, somebody starts keeping score.

Grades at school.

Goals on the football pitch.

Universities.

Job titles.

Salary.

Promotions.

Marriage.

Children.

House.

Car.

Followers.

Net worth.

Awards.

By the time we reach adulthood, an invisible scoreboard has already been constructed for us.

And whether we consciously agreed to play or not, most of us start competing.

The strange thing is that we rarely stop to ask:

Who created the game?

And perhaps more importantly:

Do I actually want to win it?

Because there is very little point reaching first place in a competition you never really wanted to enter.

Winning Is Relative

The fascinating thing about winning is that it almost always requires comparison.

You cannot come first unless somebody comes second.

You cannot win the match unless somebody loses it.

You cannot be faster without somebody being slower.

You cannot be the biggest without something else being smaller.

But life isn't always a zero-sum game.

And perhaps that's where our obsession with winning begins to betray us.

In many of life's most important endeavours, your success does not require somebody else's failure.

We can both win.

We can build together.

We can create more value together than either of us could have created alone.

And besides, life isn't a 100-metre race.

We didn't all start from the same line.

We don't have the same genetics.

The same parents.

The same opportunities.

The same education.

The same health.

The same money.

The same trauma.

The same luck.

Some people start life 50 metres ahead.

Others begin 100 metres behind.

Some people have coaches.

Some have spectators cheering them on.

Some have people actively trying to trip them up.

And yet somehow we look at the finishing positions and pretend they tell us the entire story.

Perhaps winning cannot simply be about where you finish.

Perhaps it also has to account for where you started.

Sometimes Winning Looks Like Losing

This is something life has taught me repeatedly.

Sometimes what feels like the greatest loss of your life eventually becomes the reason you win.

Losing the job forces you to start the business.

Losing the relationship forces you to rediscover yourself.

Losing the money teaches you how to build properly.

Losing the opportunity sends you towards another one.

And sometimes you simply lose.

There is no hidden blessing.

No inspirational lesson.

No universe secretly conspiring in your favour.

You did your best.

And you lost.

I think we need to become more comfortable admitting that.

Because one of the most dangerous ideas we have created is that good people who work hard inevitably win.

They don't. Not always.

Sometimes good people lose.

Sometimes bad people win.

Sometimes the most talented person never gets the opportunity.

Sometimes the person who did everything correctly still gets sick.

Sometimes businesses fail despite the founder doing almost everything right.

Sometimes life simply happens.

And perhaps maturity is understanding that losing does not automatically make you a loser.

I remember when I was in law school. We usually sat in groups of 4. My particular group had two girls and two boys. It went as follows: girl one was the smartest not just in our group but in the entire class and year according to exam results. I was second (in the group - not the year). Boy two was third and girl two was someway behind the rest of us that she had to repeat a year.

Fast forward 20 years - girl two is a celebrity lawyer and a partner at a large law firm in the city. She was made partner about 8 years ago. Girl One is a lawyer too but only recently made partner at another large law firm. Boy two - dabbled in law for sometime but now mostly spends his time writing children’s books and looking after the kids. And I, as you should know by now, I quit law after a few months and went on this tortuous entrepreneurial journey instead.

The person, I would have hand on heart said was least likely to succeed did much better and the person I thought was heads and shoulders above everyone else finally got there but it sure was not as easy. So what was the difference?

Ecclesiastes 9:11 -

I again saw under the sun that the race is not to the swift and the battle is not to the strong, and neither is bread to the wise nor riches to those of intelligence and understanding nor favour to men of ability; but time and chance happens to them all.

Winning At What Cost?

What did it cost you to win?

Because victory has a price.

You built the company.

But lost your marriage.

You made the money.

But missed your children's childhood.

You got the promotion.

But destroyed your health.

You became famous.

But lost your privacy.

You proved everyone wrong.

But somewhere along the way became someone you no longer recognise.

Did you win?

I don't know.

And neither does anybody else.

Because only you know what you traded to get there.

Every victory carries an invoice.

The question is whether the thing you won was worth the price you paid.

The Pyrrhic Victory

There is an ancient expression for this.

A Pyrrhic victory.

King Pyrrhus of Epirus defeated the Romans in battle around 279 BC, but his army suffered such devastating losses that he is reported to have observed that another victory like it would completely ruin him.

He won.

And yet he lost.

I think life contains far more Pyrrhic victories than we acknowledge.

The marriage maintained purely for appearances.

The successful company drowning in debt.

The impressive lifestyle that requires constant work simply to sustain it.

The argument you won but the relationship you destroyed.

The status you gained at the expense of your peace.

Technically...

you won.

Congratulations.

But did you?

When The Person Beside You Becomes The Competition

Winning in any sort of functional relationship that was never supposed to be a competition.

A marriage.

A friendship.

A family.

A business partnership.

Many relationships begin with alignment but somehow end in competition.

Why is that?

Ego?

Misalignment?

Greed?

Resentment?

The loss of a shared purpose?

These relationships begin with a common objective. Two people decide, formally or otherwise, that they are better together than apart.

The objective therefore isn't for one person to win.

It is to win together.

The relationship is the objective.

And something strange happens when collaboration becomes competition.

If I have to destroy you to beat you, but in doing so destroy the thing we created together, what exactly have I won?

You can win the argument and lose the relationship.

Win the negotiation and destroy the partnership.

Win the asset and destroy its value.

Win the battle and leave your family carrying the consequences.

There are situations in life where one person may eventually emerge with more money, more control, more possessions or even the legal victory.

The scoreboard will declare a winner.

But everyone lost.

Except perhaps the lawyers!

Because the original purpose was never to defeat each other.

It was to build something together.

Perhaps some of life's greatest losses begin when we forget who is actually on our team, and lose sight of what we were building together and why.

Simple enough in a world not run by Sociopaths and Narcissists …

But what if it is? What then?

Winning Against Yourself

Perhaps we have misunderstood the opponent.

Maybe the person we are actually competing against isn't the person next door.

Or the entrepreneur on Instagram.

Or the school friend who seems to be doing better.

Or the billionaire on the cover of a magazine.

Or the partner lying next to us in bed.

Maybe the only meaningful competition is with ourselves.

Am I wiser than I was five years ago?

Kinder?

Healthier?

More patient?

More courageous?

More useful?

More loving?

More at peace?

Am I becoming a better father?

Friend?

Partner?

Leader?

Human being?

That is a very different scoreboard.

And strangely, nobody else can really see it.

Which perhaps makes it the most honest one of all.

Winning And Time

There is another problem with judging who is winning.

We usually measure too early.

At 25, the person earning the most appears to be winning.

At 35, perhaps it is the person building the biggest company.

At 45, maybe the person with the strongest family.

At 55, perhaps the healthiest.

At 65, the person with freedom.

At 75, the person surrounded by people who genuinely love them.

At 85?

Perhaps simply waking up and having someone you love sitting beside you feels like winning.

The scoreboard changes as life changes.

Which makes judging another person's position particularly foolish.

You may simply be looking at the game at half-time.

There Are Seasons To Winning

I have had seasons when everything seemed to work.

And seasons where seemingly nothing did.

Moments when I felt completely in control.

And others when life reminded me how little control any of us actually possess.

Perhaps winning is not a permanent state.

Perhaps life has seasons.

There are seasons for building.

Seasons for surviving.

Seasons for losing.

Seasons for learning.

Seasons for harvesting.

And seasons for starting again.

The mistake is believing that because you are losing today, you are losing at life.

Sometimes surviving the season is the win.

Getting out of bed is the win.

Keeping the business alive is the win.

Being there for your children is the win.

Starting again is the win.

Not becoming bitter is the win.

Nobody gives trophies for these victories.

Perhaps they should... Perhaps we should…

Perhaps I should.

The Final Scoreboard

Which brings me back to validation.

If nobody applauded...

would it still feel like winning?

If nobody knew how much money you had...

would you still want it?

If nobody could see your house...

would you still buy it?

If there were no photographs from the holiday...

would you still go?

If nobody knew your title...

would the work still matter?

If nobody ever knew what you achieved...

would you still want to achieve it?

But perhaps somewhere inside the answers lies our real definition of winning, alongside the answers to the questions we have already been asking:

What is enough?

What is our purpose?

What does real success look like?

And whose approval actually matters?

A Different Definition

Maybe winning is not defeating somebody else.

Maybe winning is reaching the end of your life having become more fully yourself.

Having loved deeply.

Having created something.

Having contributed.

Having experienced.

Having failed.

Having recovered.

Having helped others.

Having laughed.

Having forgiven.

Having been forgiven.

Having left something behind.

And hopefully having enjoyed some of it along the way.

Perhaps the ultimate victory is being able to look at your life, with all its imperfections, mistakes, successes, failures, scars and stories, and say:

I would choose it again.

Not because everything went right.

But because it was mine.

One of my favourite sayings is:

"To make things happen, you have to make things."

And I did.

I lived it.

I chose.

I made things.

I made mistakes.

I learned.

I became.

And perhaps that is what it really means to win.

But there is something hidden inside that final word.

Became.

Because becoming anything requires something from us.

Time.

Sacrifice.

Failure.

Pain.

Discipline.

Loss.

Change.

Everything we become comes at a cost.

Which raises the next thought:

What is the cost of becoming who you were meant to be?