Issue #145 The Greatest Lie About The Journey

Over the past two weeks I have found myself returning again and again to the wisdom found in Homer’s The Odyssey. What began as a reflection on Calypso’s island and the dangers of comfort gradually evolved into an exploration of life’s inevitable shipwrecks and the realization that the strengths that carry us through one season are not always the ones that will carry us through the next.

If you missed either of those essays, you can catch up HERE and HERE.

As I continued reflecting on the story and the lessons it seemed to be revealing, I realized something had been quietly bothering me.

I had spent a great deal of time thinking about why Odysseus left Calypso’s island. I had thought about why Homer had chosen to give him a raft instead of another mighty warship. But I hadn’t stopped to ask what may be the most important question of all.

What made the journey worth taking?

After all, why would anyone endure ten years of war, survive a shipwreck, walk away from comfort and continue embracing uncertainty if there wasn’t something on the other side that made every hardship worthwhile?

As it happened, those reflections coincided with something much closer to home.

Last week, Kelly and I celebrated our wedding anniversary.

For several weeks beforehand I had been planning the evening. Truthfully, creating meaningful experiences is one of my favorite things to do. I enjoy thinking through the details, weaving in elements of surprise and delight, and finding small ways to celebrate.

The day ended with dinner at one of our favorite wineries near our home, where the photo above was taken. 

As I reflected on our evening together, I couldn’t help but think about the journey that had brought us there. Looking back over thirty-two years of marriage, the different seasons we had lived through and the countless ordinary moments that had quietly become the story of our life together, I found myself sitting in a quiet sense of awe. 

And that is when I realized that somewhere along the way my definition of accomplishment had quietly changed. 

For much of my life, I measured accomplishment by the businesses I built, the problems I solved and the goals I achieved. Those things mattered deeply to me, and they still do. Entrepreneurship stretched me, challenged me and provided opportunities I could never have imagined.

Yet today, if someone were to ask me what I consider my greatest accomplishment, my answer would no longer begin with business.

It would begin with Kelly.

Building a marriage has become the most meaningful work of my life. Not because our marriage has been perfect. Quite the opposite. Like every meaningful relationship, it has been shaped through seasons of joy and disappointment, celebration and grief, certainty and uncertainty. We have celebrated victories together, endured losses together and weathered more than one shipwreck.

Looking back now, I realize that while I spent decades building companies, the deeper work was quietly taking place somewhere else entirely. It was taking place within our marriage.

The Reason He Went Home

One of the oldest questions we wrestle with is whether the journey or the destination matters more.  The famous poem Ithaka by C.P. Cavafy celebrates this idea, and there is certainly wisdom in it.  The journey changes us. It stretches us beyond our comfort, exposes our weaknesses and teaches us lessons we could never have learned by standing still.

Yet I no longer believe the journey has meaning by itself.

Its meaning is found in the people we share it with and the people waiting for us when we return home. It was that realization that brought me back once again to The Odyssey.

When we think about Homer’s story, we often remember the Cyclops, the Sirens, Scylla and Charybdis or the wooden horse at Troy. Yet the more I have reflected on it, the more convinced I have become that perhaps the most important character in the story is the one who says the least.

Penelope.

Everything Odysseus endured suddenly makes sense when we remember there was someone worth returning home to.

The journey wasn’t simply about surviving; it was about coming home.

The older I get, the more I wonder if we have misunderstood the purpose of our own journeys. Perhaps the journey was never the destination. Perhaps it was always preparing us to come home differently than the person who first left.

The Quiet Longing Beneath Our Ambition

I have had the privilege of meeting entrepreneurs who have built remarkable companies. I have also spent time with individuals who have accumulated extraordinary wealth, influence and recognition. While every story has been different, I have noticed something that has quietly repeated itself.

Very few people, when reflecting on the second half of life, begin by talking about the businesses they built or the accomplishments they achieved. Instead, the conversation almost always turns toward the people who mattered most. They speak about their spouses, their children, lifelong friendships and the relationships that shaped them along the way.

The more I have listened to those conversations, the more I have come to believe that they are pointing toward something much deeper.

Interestingly, science has arrived at much the same conclusion. The Harvard Study of Adult Development, one of the longest longitudinal studies ever conducted on human flourishing, found that more than wealth, career success, status, diet or even exercise, the single greatest predictor of a long, healthy and meaningful life is the quality of our relationships.

The older I get, the less surprising that finding becomes. Beneath every ambition lies a deeper longing that we rarely acknowledge. 

We pursue careers, build businesses, chase significance and strive to accomplish meaningful things, believing that each achievement will somehow satisfy us. Yet once we reach those milestones, we often discover that the satisfaction we believe we will feel when we get there is temporary.

The human soul isn’t ultimately searching for achievement; it is searching for connection.

Not simply to be admired.

Not simply to be successful.

But to be deeply known…and deeply loved.

A Better Scoreboard

What I find most interesting is that this insight isn’t simply supported by decades of scientific research. It is echoed time and again by people who have lived long enough to reflect on what truly matters.

One of those voices is Warren Buffett.

Here is a man who has climbed almost every mountain our culture celebrates. Wealth, influence, recognition and professional accomplishment have all been part of his journey. Yet when asked how he measures the success of his life, his answer had nothing to do with Berkshire Hathaway, investment returns or the billions of dollars he accumulated.

Instead, he said:

“When you get to be my age, you’ll really measure your success in life by how many of the people you want to have love you actually do love you… The only way to get love is to be lovable.”

He went on to explain that money can buy recognition, admiration and almost anything else we might desire, but it can never purchase genuine love.

Coming from almost anyone else, those words might sound cliché or even sentimental. Coming from Warren Buffett, they sound more like the reflections of a man who has already climbed the mountain over a long and full life and from that perspective he is willing to tell the rest of us what he found there.

The older I get, the more this simple but profound truth has revealed itself to me.

In fact, the more I reflect on my recent anniversary celebration with Kelly, and on Odysseus finally returning home to Penelope, the more I believe Buffett was simply describing, in modern language, the very same truth Homer had been pointing toward nearly three thousand years ago.

Odysseus wasn’t risking everything simply to return to a kingdom.

He was returning home to someone he loved.

Reflect and Align

Looking back over these past three newsletters, I have come to believe that Homer was never simply writing about war, monsters or impossible voyages.

I believe he was writing about what it means to become fully human.

Comfort has a way of making us forget who we are meant to become. Shipwrecks have a way of stripping away identities that can no longer carry us forward. Yet it is love that ultimately reminds us why the journey was worth taking in the first place.

My own life has convinced me that each season quietly prepared me for the next. Building businesses taught me confidence. Shipwrecks taught me trust. Yet neither proved to be the destination. Rather, both became part of the journey that was preparing me for something much deeper.

To become someone capable of loving well…

And of belonging.

One of my favourite observations comes from T. S. Eliot, who wrote:

“We shall not cease from exploration, and the end of all our exploring will be to arrive where we started and know the place for the first time.”

The longer I live, the more convinced I become that he was right.

The greatest purpose of every journey is not simply to arrive somewhere new.

It is to return home as someone new.

Someone more capable of loving than the person who first left.

With that in mind, here are three questions worth reflecting on:

• Who are the people that make my journey worth taking?
• Am I investing as intentionally in my relationships as I have in my accomplishments?
• When the work of my life is finished, what do I hope the people I love will remember most about the person I became?

In the end, the measure of a life is not found in the places we traveled, the businesses we built or the goals we accomplished.

It is found in the people who made the journey worth taking.

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