Issue #143 What if the Comfortable Life We Long For is Our Greatest Obstacle?

A few years ago, after exiting the toy business, I found myself living a version of freedom that I had spent nearly three decades trying to create. My calendar had opened up. The relentless cadence of product launches, board meetings, payroll and international travel had finally slowed. For the first time in a very long time, nobody was asking anything of me.

At first, it felt exactly as I imagined it would.

After years of carrying responsibility, I welcomed the slower pace. I slept a little longer. I spent more time outdoors, Kelly and I travelled, and I rediscovered the simple pleasure of having an afternoon with nowhere particular to be. It felt less like retirement and more like finally exhaling after holding my breath for a long time.

But after a season, the novelty began to wear off and something unexpected happened.

A quiet restlessness settled in that I couldn’t quite explain.

Nothing was wrong. In fact, by almost every outward measure, life was very good. Yet underneath all that freedom, I sensed something beginning to drift. I wasn’t unhappy, nor was I eager to jump back into operating another company simply for the sake of staying busy. It was subtler than that. I found myself wondering whether I had confused peace with comfort, and whether those two things were actually very different.

A few mornings ago, during my usual time of reading and reflection, I came across a quote from the philosopher William James that stopped me cold:

“Compared with what we ought to be, we are only half awake. Our fires are damped, our drafts are checked.”

I read the quote once. Then I underlined it. Over the following days I found myself returning to it again and again. I couldn’t shake the feeling that James had managed to describe something I had experienced without ever having the language for it.

The longer I sat with James’s words, the more I realized he wasn’t describing a crisis. He wasn’t writing about failure or tragedy. He was describing something far more subtle; something that often disguises itself as success. Somehow he had given language to a feeling I had carried for years but had never fully understood.

And in my contemplation I began to wonder if perhaps our greatest obstacle isn’t hardship; perhaps it’s comfort.

The Island of Comfort

Based on a friend’s recommendation, Kelly and I recently went to watch The Odyssey. Like most people, I knew the broad outline of Homer’s story. The Trojan Horse, the Cyclops, the Sirens and the long journey home. 

I was looking forward to seeing how one of history’s greatest stories would be interpreted on the big screen. What I did not expect is what ultimately caught my attention. 

It wasn’t one of the battles nor an encounter with a mythological beast, but another particular part of the story that stayed with me.

It was an island.

After years of war and years of surviving storms that would have broken most men, Odysseus washes ashore on the island of Calypso. She offers him everything a weary traveller could want: safety, beauty, rest and the promise that his struggles are finally over. 

No more conflict. No more impossible decisions. No more uncertainty about tomorrow. She offers him a life where the storms simply disappear.  And for seven years, he stays.

What struck me is that Calypso never really imprisoned him. Odysseus had escaped far greater dangers than a beautiful woman and a beautiful island. A locked gate would never have held the man who was capable of surviving everything he already had experienced.  The real danger was far more subtle than that.

She didn’t need to chain him.

She only needed to slowly remove his desire to leave.

I’ve thought about that scene often over the past few days because I wonder if that is precisely how comfort works in our own lives. Rarely does it arrive looking dangerous. Sometimes it comes in the form of something we really need (at least for a time). 

More often it comes disguised as something we’ve earned. It quietly whispers that we’ve worked hard enough, sacrificed enough and climbed enough mountains. It invites us to settle, not because we’ve reached our destination, but because we’ve forgotten why we began the journey in the first place.

What the Lotus Really Represents

Earlier in The Odyssey, Homer tells another fascinating story. Odysseus and his crew arrive on the island of the Lotus-Eaters. The men eat the flower and almost immediately lose all desire to continue the voyage home. They don’t become prisoners; they simply forget.

Home no longer feels important because the comfort of the present moment has replaced the calling that once compelled them forward.

I’ve often wondered whether the lotus was ever really about a plant. Perhaps it is a metaphor for the countless things that quietly numb our desire to keep growing.

For some people the lotus may be endless entertainment or distraction. For others it may be leisure, status or comfort itself. But I suspect for many of the business leaders reading this newsletter it is something much more deceptive, and something I know I have personally succumbed to. We become so accustomed to measuring ourselves by the things we’ve spent decades building that we unconsciously allow those scoreboards to define the whole of our lives.

Revenue, enterprise value, recognition and influence. None of these things are inherently wrong. I’ve spent much of my life pursuing all of them. The danger comes when they slowly become our identity and eventually the only scoreboard we know how to read. In that we keep returning to the places where we are comfortable and already know how to win while other parts of our lives quietly wait for our attention.

I’ve also come to realize that comfort isn’t simply about ease. It can show up in much subtler ways. Comfort is returning to the familiar because it asks less of us. It’s staying with the identity we’ve already built because becoming someone new feels uncertain. Sometimes comfort isn’t the absence of challenge at all; it’s simply the quiet decision to stop growing.

Looking back over my own journey, the seasons that shaped me most were not the comfortable ones. Building businesses stretched me in ways I never anticipated, and in my experience, failing with some of my ventures exposed blind spots I couldn’t have otherwise seen. My relationship with my wife has refined me in ways no boardroom ever could, and raising children has taught me more patience than financial success would ever provide. 

Looking back now, I can honestly say that many of the chapters I would never have chosen are the very ones I now would never want to lose. I’ve come to believe that meaningful struggle has a unique way of revealing our character while expanding our capacity for who we need to become. Comfort, on the other hand, quietly tempts us to remain who we’ve always been.

The purpose of the journey is not merely to arrive somewhere new; it is to become someone new along the way.

Going Home Before Going Forward

While it is important to become aware of the seductive allure of comfort, and how it can impede our growth journey, it is important to point out one additional lesson in Homer’s story.

When Odysseus finally leaves Calypso’s island, he doesn’t immediately go searching for another adventure. He goes home. He restores what has fallen into disorder. He reconnects with the people who matter most and puts his own house in order before looking toward another horizon.

That sequence feels deeply significant to me because, if I’m honest, I have often lived in conflict with this idea.

For much of my life I believed purpose was always waiting on the other side of the next opportunity, the next company or the next challenge. I spent so much time looking toward the horizon, believing that I would find meaning on the other side.  Reflecting on my lived experience, I can see that I have spent much of my life looking toward what’s next while quietly neglecting what we’ve already been given. 

As founders, many of us become so focused on building enterprises that we slowly lose sight of the relationships, rhythms and responsibilities that give those enterprises their meaning in the first place. We assume discovering our purpose will be waiting somewhere over the next hill, when the truth is, it begins much closer to home.

The older I get, the more convinced I become that our businesses are not the destination….they are the training ground.

For years I believed the greatest value of entrepreneurship was what we produced in the marketplace. 

Today I see it differently. 

The deeper work was always producing something in me; character, humility, courage, perspective and, perhaps most importantly, generosity. Long before I could realize it, the enterprise was shaping the entrepreneur.

That may be one of the greatest invitations of leadership. Not simply to build organizations that create value, but to allow the process of building them to transform us into wiser, healthier and more integrated human beings. Achievement in business was never intended to be the finish line; it was simply an invitation to pursue something deeper.

Perhaps William James was right. Perhaps most of us are only half awake; not because life has been too difficult, but because it has become too easy to stop growing.

Comfort isn’t the enemy. There are seasons when rest is exactly what our souls require. My own season after leaving the toy business was a gift, and I wouldn’t trade it. But comfort was never meant to become our permanent address. It is a place to recover, to reflect and to prepare ourselves for whatever meaningful work still lies ahead.

So this week, perhaps these questions are worth sitting with.

Where in my life have I mistaken comfort for peace?

What part of my life has quietly gone unattended while I remained somewhere easier?

What is the quiet invitation I keep sensing that I have been reluctant to follow?

More often than not, the deepest transformations don’t begin when we discover something new. They begin when we remember something we once knew….but like Odysseus, somehow forgot along the way.

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