Issue #155 What If Everything You’ve Been Told About Success Is Wrong?

Recently, I was walking home from the mountain near where I live when something stopped me in my tracks.

Standing on a ridge was an enormous buck, his impressive antlers silhouetted against the sky. For a few moments, I simply stood there, taking it in. It was one of those unexpected encounters with nature that leaves you breathless. I hadn’t gone looking for it. I was simply fortunate enough to be there at exactly the right moment.

I spend time on that mountain almost every week. It’s one of my favourite places to disconnect from everyday demands, enjoy the solitude and find perspective.

I also have another reason for being there. I’m a director of our local mountain biking club, where we volunteer to maintain and steward the region’s trail network. Sometimes that means clearing fallen trees and repairing trails. Other times, we’re designing new ones, using the landscape as our canvas.

Nobody pays me for this work. There’s no financial return, and after a day on the trails, I’m usually physically exhausted.

Yet I always come home feeling incredibly enriched.

I’ve been reflecting on why that is, particularly after last week’s newsletter about the difference between having wealth and feeling wealthy. I think it has everything to do with the scoreboards we use, often unintentionally, to measure our progress in life.

The Scoreboard We’ve Been Given

Most of us grow up with a conventional understanding of what it means to be “successful.” It’s actually a word I’ve come to loathe because it’s so ambiguous. We use it constantly without considering what it really means or who gets to define it.

For our purposes, let’s define success as making progress toward meaningful goals.

We work hard, develop skills, build careers or businesses and accumulate financial resources, often imagining the day we’ll finally have the freedom to enjoy the rewards.

Along the way, we look for evidence of progress, and the easiest things to measure tend to be the zeros and ones in our bank accounts (or the accolades, awards and recognition we receive from other “successful” people).

How much do we earn? What do we own? How much influence do we have? How are we perceived by others?

For entrepreneurs, this thinking becomes particularly ingrained. We’re constantly measuring revenue, profitability, growth and financial returns. And for obvious reasons, those metrics are important, but somewhere along the way, it’s easy to allow the scoreboard we use to measure our businesses to become the one we use to measure the quality of our lives.

Nearly 750 years ago, Thomas Aquinas explored the things human beings pursue in their search for happiness, including wealth, honour, power and pleasure. He argued that while these pursuits can provide temporary satisfaction, none can deliver lasting fulfillment when treated as an ultimate goal.

I’ve come to think of these pursuits through a framework I call the 4 P’s: Power, Prestige, Possessions and Pleasure.

There’s nothing inherently wrong with them. Power exercised with humility can create positive change. Prestige earned through meaningful accomplishments can reflect excellence. Possessions enjoyed with temperance provide comfort and security. And pleasure, particularly when shared with people we love, enriches our lives.

The trouble begins when the things meant to enrich our lives begin to define them. In their pursuit, we convince ourselves that the next milestone will finally deliver happiness, only to discover that the satisfaction is fleeting. Psychologists call this the arrival fallacy. Before long, we’re back on the hedonic treadmill, pursuing more.

The insatiable nature of human desire, explored by the philosopher Arthur Schopenhauer, is sometimes compared to drinking saltwater. The more we drink to quench our thirst, the thirstier we become.

But before going further, I’d like you to try something.

What Do Your Favourite Memories Reveal?

Think about three of your favourite memories.

Not necessarily your most impressive accomplishments, but experiences that still bring a smile to your face. Moments you’d happily relive and might hope someone recalls, when giving your eulogy.

When I ask people this question, their answers tend to follow a few common themes.

For some, it’s the people they love: getting married, the birth of a child or an unforgettable adventure with family or friends. For others, it’s overcoming a meaningful challenge, like co-founding a business, running a marathon or accomplishing something they once thought impossible.

Sometimes it’s creating something: writing a book, painting a picture or building something valuable. And sometimes it’s contributing to another person’s life, whether through volunteering, offering support or making a meaningful difference.

Consider your own three memories. What made them special? Who was there? What has stayed with you?

Now here’s what I find interesting.

We spend an enormous amount of time pursuing the 4 P’s, believing that accumulating more, achieving recognition or increasing our influence will make us happy.

Yet I suspect your favourite memories have relatively little to do with how much money you had, what you owned or how important others considered you.

And that reveals an interesting paradox.

We spend the majority of our waking hours chasing the things we believe will make us happy, while giving whatever time and attention we have left to the experiences that actually do.

And with that, we have been sold a misleading definition of success.

The Other Four

When I reflect on the memories that have brought me the greatest meaning and fulfilment, I’ve noticed four recurring elements. I’ve come to think of these as the 4 C’s: Challenges, Connections, Creativity and Charity.

Challenges stretch us and provide growth and accomplishment. Connections are the relationships we build and experiences we share. Creativity allows us to imagine and bring something new into the world. Charity is contributing beyond ourselves through our time, skills, resources or influence.

What’s interesting is how often these elements overlap, which brings me back to the mountain.

Building and maintaining trails presents physical and mental challenges, particularly when navigating the interests of different stakeholders. Working alongside people who share a love of the outdoors creates meaningful connections. Designing trails with jumps, berms and other features, using the landscape as our canvas, provides a creative outlet. And stewarding those trails for the broader community, including generations of people I’ll never meet, brings the fulfilment of contributing to something beyond myself.

One activity brings all four together.

While there’s no financial return, there’s an undeniable return on the time invested. It’s a return on experience, connection and contribution. None will ever appear on a financial statement, yet each represents a deposit into a different kind of wealth account.

Which brings me to something I’ve come to believe.

The most valuable things we acquire during our lifetime aren’t actually things, but the meaningful and magical memories we create, particularly with the people we love.

I suspect that when we reach the end of our lives, these are what we’ll cherish most.

And if that’s true, shouldn’t we reconsider where we’re investing our most precious resources: our time and attention?

Valuing People or Valuing Things?

There’s another danger in making the 4 P’s our primary pursuit. They can feed our pride, which in turn fuels greed, gradually shifting our attention inward.

What can I own? Who can I control? What recognition can I receive? What pleasure can I experience?

Notice how often the focus comes back to me.

When we become consumed with acquiring more for ourselves, we can unintentionally begin treating relationships as transactions, valuing people for what they can do for us rather than appreciating them for who they are.

Which brings me to a distinction I’ve been thinking about.

We can spend our lives valuing things and using people to acquire them. Or we can choose to value people and use the things we’ve accumulated to create deeper relationships, meaningful experiences and memories worth keeping.

Viktor Frankl, the psychiatrist and Holocaust survivor who wrote Man’s Search for Meaning, offered a perspective that I love:

“Don’t aim at success. The more you aim at it and make it a target, the more you are going to miss it.”

Frankl believed that success, much like happiness, cannot be pursued directly. Instead, it emerges as a consequence of dedicating ourselves to something meaningful beyond our own self-interest.

Consider the ambition of owning a beautiful mansion. There’s nothing wrong with that pursuit. But imagine the difference between acquiring it as a symbol of status and creating a home filled with family, friends, laughter and shared experiences.

The house might be identical, but the meaning and fulfilment it brings could be vastly different.

The difference isn’t necessarily what we’ve acquired, but what we choose to do with it and possibly what we sacrificed along the way to acquire it. 

And this applies to more than possessions. Throughout our lives, we accumulate financial resources, leadership abilities, influence, knowledge and expertise. Each has value, but perhaps their greatest potential lies in what they allow us to make possible.

Last week, I shared my buddy Mike’s metaphor of money as a battery. It stores potential, but that potential only becomes useful when we put it to work. I think the same applies to our other resources.

Our leadership can help others grow. Our influence can open doors. Our expertise can solve meaningful problems. And our financial resources can provide freedom, create experiences and bring the people we love closer together.

Which brings me back to my opening question about success.

Success isn’t simply measured by the goals we’ve achieved or the wealth we’ve accumulated, but by how we use those resources to fuel a life rich in relationships, meaningful experiences and lasting memories.

What Does Your Calendar Reveal?

There’s one final part of the exercise I’d encourage you to consider.

Go back to your three favourite memories and think about which of the 4 C’s made them meaningful.

Now look at your calendar from the past month.

How much of your time was intentionally invested in the kinds of experiences that made those memories special? And how much was consumed by obligations, expectations and pursuing the next milestone?

I’m not suggesting we abandon ambition or financial responsibility. Building businesses and creating financial security are worthwhile pursuits. But every investment of time carries an opportunity cost, and unlike money, time is a resource we can never replenish.

That’s why I think it’s worth occasionally asking whether the way we’re spending our days reflects what we claim matters most.

When I think about the mountain, two experiences come to mind. An afternoon working with creative expression and an unexpected encounter with a magnificent buck. Neither added a dollar to my net worth.

But both made me feel incredibly wealthy.

Perhaps we don’t need to abandon the scoreboard we’ve been using. We just need to recognize that it doesn’t measure everything that matters.

One Question

If your three favourite memories reveal what makes your life feel truly rich, does the way you’re investing your time today reflect what you’ve learned?

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