Issue #142 Why So Many People Reach the End of Life Filled With Regret?

A few days ago, I went to visit someone in the hospital whom I have known my entire life.

We have shared a complicated relationship. We valued different things, saw the world through very different lenses, and over the years I found myself carrying hurt that slowly turned into resentment.

I recently wrote about forgiveness and how it is not the same as reconciliation. Forgiveness doesn't erase the past or excuse what happened. It simply means choosing not to let the past continue to define the present. That choice freed me far more than it freed the other person.

So I went to visit him, and I'm grateful I did.

He seemed genuinely surprised to see me, and by the time I left, I felt a sense of peace and lightness that I hadn't expected. It's remarkable how heavy resentment becomes when we carry it for years, and how much lighter life feels when we finally choose to let it go by choosing forgiveness.

But what stayed with me wasn't just my new found sense of levity nor how much age had changed him.

What has stayed with me were his expressions of regret. 

The Price We Will Eventually Pay

As I sat with what I had heard in that hospital room, I found myself returning to something my father used to say.

He believed that in life we will pay one of two prices: the price of discipline or the price of regret.

Discipline asks something of us in the present. It requires us to make time for what matters before it feels urgent, to care for our health before it begins to fail, to invest in relationships before loneliness exposes what we neglected, and to use our resources generously while we still have the freedom to choose how they are spent.

Regret carries a different cost. It arrives later, when some of those choices are no longer ours to make.

My father would say that discipline weighs ounces, while regret weighs tons. Those words have stayed with me and inform me that nearly every important decision creates two possible futures. One in which we eventually say, “I’m glad I did,” and another in which we are left saying, “I wish I had.”

For years, I understood those words mainly as a call to work hard, get up early, and do difficult things in pursuit of a meaningful goal. But fast forward several years and now sitting in a hospital room with a man that I have long known, the lesson took on a different meaning.

This was no longer about the discipline required to build a business or reach a financial milestone. It was about the discipline required to build a life that would still feel meaningful when external achievements no longer matter.

Walking into that hospital room was like stepping thirty years into my future; a reminder that one day I too will find myself in a vulnerable and compromised state, contemplating the events of my life. 

It forced me to ask the question: What must I pay attention to today so I do not arrive at the end of my life wishing I had invested differently?

He had pursued success through business and career. Financial results were the scorecard by which he measured himself. But now, in a compromised state of health, when he needed help with even the simplest of things, there was this sobering realization that the scorecard he had been keeping no longer mattered.

Instead he disclosed three regrets: 

He wished he had taken better care of his health.

He wished he had loved and cared for his family more deeply.

He wished he had used more of his resources to invest in the relationships that mattered most.

There was nothing about the deals he had made, the stock market picks he was tracking nor the financial ranking relative to his peers. 

To the outside world he was a capable and successful businessman who had spent his life pursuing independence and freedom. Yet in the season when he could no longer be independent, what mattered most was remarkably simple: that people showed up, that people cared, and that someone chose to walk through the door.

I Was Chasing the Same Thing

As I drove home, I was grateful for the opportunity to see him but I was also deeply unsettled as I recognized more of myself in that hospital room than I was comfortable admitting.

For most of my career, I have chased one word: freedom.

Freedom to do what I wanted, when I wanted, the way I wanted, with who I wanted. That definition has been the engine behind almost every life and business decision I made. I set large goals in business and believed that once I hit the milestones that freedom would finally be mine.

While it didn't happen the way I planned, (it  rarely does) I eventually hit the numbers. And in that experience I learned something worth holding onto: never underestimate the power of setting goals and living with intention. As Napoleon Hill famously wrote, "Whatever the mind can conceive and believe, it can achieve." 

I had chased freedom and then one day, I found it.

Life handed me exactly what I had been pursuing for years: space. Room to slow down. Room to breathe. A season to become more intentional with my time.

What I didn't anticipate was that the same season would also become one of profound loss.

Over the span of just a few years, I watched promising business partnerships come to an end and opportunities I had counted on quietly disappear. 

Then came losses that reached far deeper than anything business could touch.

I buried my father, who was my hero and the man whose wisdom shaped so much of who I am today. I said goodbye to my mother and my grandmother, the matriarchs of our family. I lost a dear uncle in a tragic mountain biking accident. And we lost our family dog, whose quiet presence had been woven into the rhythm of our lives for so many years.

Each loss was different and each carried its own grief; but together they taught me something I could never have learned any other way:

When life falls apart, what you have accumulated matters surprisingly little. The currency that matters the most isn't measured in dollars; it's measured in love.

In those moments, the freedom I had spent decades building couldn't comfort me. The financial milestones, the optionality, the success I'd worked so hard to create couldn't sit beside me in my grief.

What I wanted wasn't more freedom….what I wanted was love and connection.

I wanted the people who knew me beyond my accomplishments, beyond my title, and beyond my balance sheet to simply show up and sit with me in my grief.

I realized that while money can buy comfort, entertainment, distraction, therapy, or even companionship, there is one thing it can never buy: genuine love.

The freedom I had spent many years building could not give me the one thing I needed most.

The Paradox 

In his book The Second Mountain, David Brooks writes about the people of Liberia, who are considered some of the most joyful people in the world. They achieved this status despite enduring years of civil war and unimaginable hardship. Their lives were marked by suffering far beyond anything most of us would likely ever experience. Yet in the midst of that turmoil, they discovered something remarkable.

They learned how to depend on one another.

They made fierce commitments to each other; they risked their own safety for one another. And it was those commitments, forged in adversity, it gave their lives meaning.

Then Brooks turns the mirror on people like me and refers to it as the paradox of privilege.

When life is comfortable and resources are abundant, we begin pursuing things that feel good in the moment but quietly separate us from one another. We buy the larger home with the larger yard. We build lives of greater independence and greater privacy. We mistake convenience for connection, and in doing so, we slowly drift away from the very relationships that give life its deepest meaning.

Then when hardship arrives:

A health crisis.

The loss of someone we love.

A marriage under strain.

A business that begins to unravel.

It is then that suddenly, the things we spent years accumulating become insignificant compared to the people standing beside us.

I found myself reading these words  multiple times and sitting pondering them. I considered my recent visit to the hospital and I now understood exactly why that moment struck me so deeply: I wasn't reading someone else's story anymore….I was reading my own.

Freedom From, or Freedom For?

As I reflected on the life of the man lying in that hospital bed, I can now see more clearly a similar mistake I have been making in my own life.

I have spent years pursuing freedom but it has been freedom from.

Freedom from financial pressure.

Freedom from obligation.

Freedom from demands on my time.

Freedom from having to answer to anyone.

That version of freedom measures success by how few claims other people have on your life. But now I understand I have been chasing the wrong kind of freedom.

What I really longed for was freedom for.

Freedom for being fully present with the people I love.

Freedom for showing up when someone needs me.

Freedom for investing my time, my attention, and my resources into my most important relationships.

The financial metrics themselves aren't the issue. What needs to change is how I choose to use those resources and where I invest my time, attention, and priorities.

The sick man in this hospital bed had achieved exactly what he had spent decades pursuing. He had built remarkable independence. But independence, by itself, is a poor substitute for intimacy.

Freedom without meaningful commitments doesn't end in significance….it ends in loneliness.

When life strips everything else away (and it will), the question will no longer be how much we have accumulated. The question became much simpler:

Who will walk through the door?

What I Want to Leave You With

The older I get, the more convinced I become that life isn't ultimately about accumulating more. It's about investing more.

Investing our time.

Our attention.

Our love.

Our presence.

Because the relationships that carry us through our hardest seasons are not built during the crisis itself. They are built years earlier, through thousands of ordinary moments when nothing feels urgent at all.

So before you move on, I'd encourage you to sit with a few questions:

• Am I building freedom from people, or freedom for people?
• What "big yard" have I built that might actually be creating distance instead of connection?
• If I were the one lying in that hospital bed next month, who would walk through the door?
• More importantly, whose door should I be walking through this week?

One day, every one of us will find ourselves in a hospital room.

The question isn't whether we'll get there.

The question is: Who will walk through the door?

The beautiful thing is that, if you don't like your answer, there's still time to change it.

Because the people who walk through our door at the end of life are usually the people whose doors we chose to walk through long before we ever needed them.

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