Issue #144 Are the Strengths That Once Made You Successful Now Holding You Back?

Last week’s newsletter generated more responses than I expected. 

Many of you reached out to share your own version of Calypso’s island. Some wrote about businesses that had quietly become comfortable and dulled their sense of purpose. Others shared stories about retirement, relationships, health challenges or seasons where life had gradually drifted into predictability, leaving them with the sense that something important was missing.

If you missed last week’s newsletter, you can catch up HERE.

As I read through your comments, I found myself returning once again to The Odyssey. 

Last week I wrote about how comfort quietly reshapes our lives, causing us to lose sight of both who we are and who we are meant to become. Odysseus’ experience illustrates this perfectly. After enduring the Trojan War and years of hardship on his voyage home, he washes ashore on Calypso’s island. Surrounded by beauty and comfort, he gradually forgets why he ever wanted to leave.

Yet after seven years something awakens within him. The comforts that once soothed him no longer satisfy him because the call to return home has become greater than his desire to remain where life feels easy and safe.

As I sat with that scene, I couldn’t shake the feeling that  many of us eventually arrive at the same place. We work hard to build a life of comfort, only to discover that the life we created can no longer carry us into the person we are meant to become.

And it is here that Homer quietly offers us another piece of wisdom.

The Ship I Thought Could Never Sink

When Odysseus decides it is finally time to leave, he walks to the shoreline expecting to continue his journey home.

There isn’t another mighty warship waiting for him.

The vessel that had once carried him into battle, survived impossible storms and transported him through years of adversity is gone. Everything that had once represented strength, certainty and control has been reduced to scattered fragments along the beach. 

So he begins gathering the broken pieces, not to build another warship.

But a raft.

The more I have considered that image, the more significant it has become for me. 

Surely Homer could have chosen a different ending. A king returning home after twenty years of hardship seems deserving of a magnificent ship complete with sails, a seasoned crew and everything required to complete the journey in confidence.

Instead, Homer gives him little more than a handful of broken timbers lashed together into something that appears painfully inadequate for the voyage ahead.

I don’t believe that detail is accidental. I believe Homer is revealing something profound about every meaningful transition in life: our next chapter cannot be navigated by drawing strength from the identity that carried us through the last one.

That is a lesson I have learned firsthand through my own journey in business.

By 2005, our company was riding high. We had become the largest toy distributor of our kind in Canada. We were launching our own products, expanding aggressively into the United States and experiencing the kind of growth that many entrepreneurs spend an entire lifetime hoping for. 

Over the previous decade we had grown rapidly, received industry recognition and won awards. 

I loved building businesses. I loved solving difficult problems. I loved proving that we could compete with companies much larger than ourselves. Entrepreneurship had become much more than a profession. Somewhere along the way it had become the place where I worked to prove myself.

Without fully realizing it, my identity and my sense of self-worth had become increasingly intertwined with the success of the business. What began as healthy pride in our work slowly became the foundation upon which I measured my own value.

Then, in 2006, we ran into financial difficulties. What initially appeared to be a temporary setback became a two-year struggle to save the company. We fought hard because we genuinely believed we could turn it around. We restructured, negotiated and searched for every possible path forward.

Despite our best efforts, the company entered bankruptcy in 2008.

Looking back now, I realize I didn’t simply lose my business.

I had lost my warship.

The confidence and certainty I had quietly drawn from the enterprise disappeared almost overnight. What remained were the fragments of something I had once believed was mighty and impenetrable. 

My business had become a shipwreck. Only then did I begin wrestling with questions that had very little to do with business and everything to do with my own identity.

Who was I without the company?

What remained when the thing that had defined me was no longer there?

I have since come to believe that this is what every shipwreck in life eventually does. It strips away the identities we have carefully constructed, forcing us to consider who we are yet to become.

The Pieces That Remained

A year after our company’s demise, I found myself in much the same position as Odysseus.

Motivated partly by hope but mostly by fear, guilt and desperation, I set out to build again. The problem was that all that remained were the broken pieces.

The capital was gone, much of the team had scattered and our market clout had disappeared. More difficult still was the realization that my reputation had been deeply tarnished. In many circles I had become a cautionary tale, with the prevailing narrative being that I had been careless and reckless.

Walking into meetings with customers and vendors felt completely different than it once had. Not long before, I had entered those same rooms as the captain of a prominent enterprise. Now I found myself sitting across the table representing a tiny start-up, a handful of loyal people and very little evidence that any of it would work.

At the time, I believed my challenge was rebuilding the business. Looking back now, I can see that life was asking something much deeper of me. It wasn’t asking me to rebuild the enterprise I had lost; it was asking me to let go of the identity I had formed while building it.

At the time, I couldn’t see the difference. I was still searching for the certainty that the warship had once provided.

Instead, life was quietly asking me to trust in the uncertainty of a raft.

Learning to Trust the Raft

The more I reflect on the image of a flimsy raft, the more I believe it is one of the most important details in the entire story.

After twenty years of hardship, it seems only fitting that Homer would send Odysseus home aboard another mighty warship. Instead, Homer places him on something fragile, uncertain and almost painfully inadequate for the voyage ahead.

The contrast could not be more striking. A warship is designed for control. It has structure, weapons, a crew and a captain directing its course. 

A raft offers none of those things. It has no rudder to steer with, no sail to harness the wind and no certainty that it will ever reach its destination. Once it leaves the shore, it is completely exposed to the uncertainty of the wind and the waves, with seemingly nothing below but ocean abyss.

I have come to believe that Homer wasn’t simply describing a different vessel; he was describing a different kind of journey.

There are seasons of life that can be navigated through competence, determination and the sheer force of will. The first half of my own life often felt that way. I learned how to build businesses, solve problems and overcome obstacles. Those experiences taught me resilience, discipline and confidence. They were important lessons that would serve me well.

Yet every shipwreck I have experienced has eventually confronted me with the same realization: The strengths that carried me through one season of life are not necessarily what will carry me through the next.

Bankruptcy was simply one of many shipwrecks in my life. There has been loss in business, loss in health and the loss of people I have deeply loved. None of those experiences looked the same, yet each one quietly dismantled something I had relied upon. 

Each one stripped away a source of certainty and invited me to discover a new and different kind of strength.

As difficult as those seasons were, I no longer believe they were interruptions to the journey.

They were an important part of the journey.

Last year I read Bob Buford’s remarkable book Half Time. One of the insights that has stayed with me is his observation that much of the first half of life is spent learning how to use our talents and strengths to become increasingly independent. We build careers, accumulate achievements, prove ourselves and create value in the world. These are worthy pursuits because they prepare us for what comes next.

Eventually, however, life begins asking us a different set of questions.

The second half is no longer about proving what we are capable of accomplishing. It is about discovering what those accomplishments were quietly preparing us for. The measure gradually shifts from independence toward interdependence, from accomplishment toward contribution and from proving ourselves to investing ourselves into others.

The more I have reflected on Buford’s work, the more I have come to believe that Homer was pointing toward the same truth centuries earlier.

The raft was never intended to teach Odysseus how to survive the sea, it was intended to teach him that the journey home could no longer be completed by relying on the same strengths that he had previously relied on.

For years I believed maturity meant becoming increasingly self-sufficient. I assumed wisdom meant accumulating more knowledge, more experience and greater control over life’s circumstances. Today, I find myself seeing it differently.

The older I get, the more I realize that growth is not always about becoming stronger in the ways I once understood strength. Some of life’s most important lessons can only be learned when certainty gives way to trust.

The opposite of certainty isn’t uncertainty. It’s trust. Certainty waits for proof before taking the next step. Trust moves forward without it.

That shift has required me to become more willing to receive help, more willing to surrender the identities that once served me well and more willing to trust that each new season of life is preparing me for something the previous one never could.

And that is why I believe shipwrecks become such profound turning points. Not because loss is good, but because it gently loosens our grip on identities that have become too small for the people we are still becoming.

Reflect and Align

When I look back over my own journey, I no longer see the bankruptcy, the losses or the disappointments as isolated events. I see them as invitations. Each one quietly asking the same question.

Will you spend your life trying to rebuild the warship?

Or will you trust that the raft, fragile as it seems, is exactly the vessel required for the journey ahead?

None of us escapes the experience of shipwreck. Life has a way of dismantling the structures we once believed would carry us forever. It isn’t really a question of if. Given enough time, it becomes a question of when.

What has changed for me is how I now view those moments.

For years I saw them as interruptions to the life I was trying to build, setbacks that needed to be overcome as quickly as possible so I could get back to where I had been. 

Today, I see them as invitations. Invitations to let go of identities that once served us well, but are no longer capable of carrying us into the next season of life.

I now realize the deeper work was never simply what I was building. It was what the journey was quietly building within me. 

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

• Where in my life am I still searching for certainty that a former season once provided?
• What identity might need to be released before I can fully embrace what comes next?
• Where am I being asked to trust the uncertainty of the raft instead of trying to rebuild the warship?

I believe the greatest invitation hidden within every shipwreck is not to recover what was lost, but to discover who we are becoming because of it.

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