Existential Thought - How Much Is Enough For You?

"The trouble with having enough is that we rarely know when we have reached it."

I could have retired around the time I was 30 years old. Really - I really could have … I wasnt rich rich or wealthy in the conventional sense, but I had enough passive income to live a comfortable life - a decent house, a decent car, 2 - 3 holidays a year by deal hunting and - you know spend my days playing golf and learning new languages - that sort of thing. I really could have - because I was there - I had accumulated enough to do that for the rest of my life.

But I was 30 and I wanted more - so what did I do? I leveraged what I had and sought to build more to gain more to increase what I had - because, well, it just wasnt enough.

Age played a part but I knew I just wanted more.

But how do you know when its enough?

The ultimate joke is that since then and because I chose not stop but to instead roll the dice… I have been on the brink of catastophy and bankruptcy more times than I care to mention.

I could have just stopped and perhaps I should have. I told myself that I would retire at 35 because all I could see was nothing but success for the next 5 years but that is not what actually happened. Because here I am years later, still at it.

I have spent much of my life around ambitious people.

Entrepreneurs.

Investors.

Executives.

Dreamers.

Builders.

People who want more.

More success.

More freedom.

More wealth.

More impact.

More life.

And there is absolutely nothing wrong with that in my book.

Ambition coupled with the quest for survival is one of the great drivers of human progress.

Without it we would still be living in caves, hunting and gathering with spears.

But over the years when I have managed to be still, I have noticed that many of us have become extraordinarily good at defining what we want.

Very few of us have ever stopped to define what enough actually looks like.

And therein lies the problem.

Because if you never define enough, then enough can never arrive.

The Moving Goalposts

When I was younger, I thought enough looked like financial security.

Then it became owning businesses.

Then properties.

Then creating something meaningful.

Then creating something that would outlive me.

Every time I reached a milestone, I celebrated briefly before immediately moving the target.

Clearly, the problem was not that I lacked ambition. Quite the opposite.

The problem was that I had unconsciously convinced myself that satisfaction existed somewhere just beyond the next achievement.

"I'll slow down when..."

"I'll relax when..."

"I'll be happy when..."

"I'll feel secure when..."

But when when eventually arrived, it never really arrived.

Because another mountain I couldn’t see before, now suddenly appeared.

This is the human condition. Always chasing.

The Curse of Comparison

One of the greatest obstacles to enough is comparison.

No matter what we have, somebody always appears to have more.

A bigger business.

A larger home.

A better body.

A younger partner.

A more exotic holiday.

A larger following.

More money.

Comparison is dangerous because it continuously recalibrates our expectations.

Which is hyper-inflated in a world of always on social media where you see only the polar extremes existence. Often significantly and disproportionately weighted to reflect the good times and the best versions of people.

Suddenly what once felt extraordinary begins to feel ordinary.

Gratitude disappears.

Enough moves further away.

And we begin chasing a life that is not even ours as we try to “keep up with the Jones”

Theodore Roosevelt famously said:

"Comparison is the thief of joy."

I believe it is also the thief of enough.

The Hedonic Treadmill

Psychologists call it hedonic adaptation.

Humans adapt remarkably quickly to improved circumstances.

The new car becomes your normal car.

The promotion becomes your normal salary.

The dream home becomes simply home.

The extraordinary slowly becomes expected.

And so we continue to chase.

Consume.

Accumulate.

Upgrade.

Repeat.

The treadmill never stops.

And perhaps that is why some of the wealthiest people in the world still appear unsettled and unappreciative.

There is levels to everything but once you reach a new level that becomes your new normal but there is always another level higher.

And no amount of accumulation can satisfy a mind that has never defined enough.

Enough Is Different For Everyone

This is where things become interesting. This is key.

Because enough is deeply personal.

For one person, enough may be a quiet life by the sea.

For another, it may be building a billion-dollar company.

For one person, enough means having time.

For another, it means having significance. Being famous is an ambition shared by many.

Neither is right.

Neither is wrong.

The issue is not what enough looks like.

The issue is whether you have consciously defined it.

Or whether society has defined it for you.

Because many people are pursuing someone else's version of success.

Someone else's dream.

Someone else's enough.

And a lot of this is unconscious. From the moment we are born, we are conditioned by nurture and nature to make it easier for us to fit into the world we live in and the circumstances we find ourselves in. Your parents want you to be a doctor or a lawyer and they want you to marry well and many of us have followed the paths set out for us instead of charting our own.

Too many of us have never defined who we are, what we want, let alone what enough looks like.

What Are You Really Chasing?

This may be one of the hardest questions we can ask ourselves.

What do you actually want?

More importantly...

Why do you want it?

Money?

Why?

Security?

Recognition?

Freedom?

Love?

Respect?

Status?

Most of the things we pursue are not actually the thing itself.

Money is rarely about money.

It is usually about what we believe money will give us.

Freedom.

Safety.

Options.

Validation.

Perhaps if we become more honest about what we are truly seeking, we may discover there are simpler ways of obtaining it.

The Fear of Enough

There is another inconvenient truth.

Sometimes we avoid defining enough because it would force us to slow down.

And slowing down can be frightening.

Because movement distracts us.

Building distracts us.

Achieving distracts us.

Accumulating distracts us.

If we stop...

we may have to confront ourselves.

Who are we without the next deal?

The next goal?

The next title?

The next project?

Perhaps that is why so many highly successful people struggle with retirement.

For decades, their identity has been built around becoming.

And suddenly there is nowhere left to run.

To emphasise the point - how long into a conversation with someone you have just met, do you ask “…And what do you do,” and their response for the most part will initially determine where you place them in your mind for future interactions?

In the world we live in, because what we do is so intricately tied to who we think we are, it makes stopping or defining enough - harder than it ought to be.

Legacy and Enough

I increasingly wonder whether enough has less to do with accumulation and more to do with contribution.

What if enough is not asking:

"How much can I have?"

But rather:

"How much can I give?"

How many people can I help?

How many opportunities can I create?

How much can I leave behind?

Perhaps that is why parenthood changes people.

Why building communities matters.

Why legacy becomes increasingly important with age.

Because eventually, most of us realise that we cannot take any of this with us.

At some point, enough becomes less about consumption and more about contribution.

A Different Question

Maybe enough is not a number.

Maybe it is a feeling.

Enough money to remove unnecessary stress.

Enough time to enjoy life.

Enough health to experience it.

Enough relationships to feel loved.

Enough purpose to wake up excited.

Enough peace to sleep at night.

Perhaps, simply put - enough is the point at which gratitude becomes greater than desire.

And perhaps that is true abundance. True wealth.

Not having everything.

But appreciating what you already have while continuing to create with intention.

Because eventually, another question emerges:

If enough is different for all of us...

then perhaps the most important question of all is not:

"What do I want from life?"

But rather:

"What is my purpose in it?"