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Building a Legacy Chapter Two: The Learner

Building a Legacy Chapter Two: The Learner

August 08, 2026

Who Shapes Us? 

If I close my eyes, I can still smell my grandfather's workshop. 

There was always the scent of fresh-cut wood mixed with sawdust, machine oil, and the unmistakable smell of a project in progress. His workbench wasn't neat by most people's standards, but somehow, he knew exactly where everything belonged. There were chisels worn smooth from decades of use, hand planes with polished wooden handles, coffee cans full of screws and nails, and scraps of hardwood that looked worthless to anyone else but somehow always found their way into whatever he was building next. 

As a little boy, I didn't understand craftsmanship. 

I just knew I liked being there. 

I was fascinated by the way something rough and unfinished could slowly become something useful. A pile of lumber became a cabinet. A few pieces of oak became a table. Broken things weren't thrown away; they were repaired. 

Looking back now, I realize my grandfather wasn't just teaching me how to build with wood. 

He was teaching me how to look at the world. 

He believed almost everything had value if you were willing to invest the time to understand it. 

I didn't appreciate that lesson then. 

I do now. 

I was born in Port Chester, New York, but when I was young our family moved to Ridgefield, Connecticut. At the time, it simply felt like where I grew up. Looking back, I recognize how fortunate I was. 

We weren't wealthy. 

We weren't poor. 

We were what I would call comfortably middle class. 

My parents worked incredibly hard. In fact, one of my strongest memories isn't of conversations around the dinner table—it's of how often they were already gone before I woke up and still working when I got home from school. 

As a kid, you don't always understand sacrifice. 

You just assume that's what parents do. 

Only later do you realize how much of their lives they quietly gave away so yours could have more opportunities than theirs ever did. 

My parents weren't chasing luxury. 

They were chasing possibility. 

Only a few generations removed from Ellis Island, they understood something I couldn't possibly appreciate at the time. Every generation has an opportunity—and perhaps an obligation—to leave things a little better than they found them. 

They did exactly that. 

Looking back, I don't remember feeling like we had a lot. 

I remember feeling like we had enough. 

Enough to play sports. 

Enough to take family vacations. 

Enough to attend good schools. 

Enough to explore interests that had nothing to do with survival. 

Enough to simply be a kid. 

Perspective has a funny way of changing our memories. 

As children, we compare ourselves to those who have more. 

As adults, we often realize how incredibly blessed we already were. 

School and I never had the relationship my teachers probably hoped for. 

I enjoyed learning. 

I just wasn't always excited about the classroom. 

I found myself far more interested in people than textbooks, experiences than lectures, and conversations than memorization. 

Looking back, I probably frustrated more than one teacher. 

If I'm honest, I frustrated myself sometimes too. 

I wasn't lazy. 

I just hadn't yet discovered why learning mattered. 

That's an important distinction. 

Curiosity and discipline don't always arrive at the same time. 

Sometimes one has to wait patiently for the other. 

College became one of the first places where I learned that actions have consequences. 

Freedom is an incredible gift. 

It can also be a dangerous one. 

Without the structure of home, I made plenty of decisions that, in hindsight, weren't particularly wise. I wasn't a bad kid, but I certainly wasn't as focused as I should have been. I was enjoying life more than preparing for it. 

At the time, I probably thought I was finding myself. 

In reality, I was mostly learning what didn't work. 

Fortunately, life is often more patient with us than we deserve. 

Somewhere along the way, something began to change. 

I can't point to one dramatic moment. 

There wasn't a lightning bolt. 

No grand revelation. 

Just a gradual realization that the future wasn't going to build itself. 

I began making better decisions. 

Not perfect decisions. 

Better ones. 

I've often told my sons that success rarely comes from making spectacular decisions. 

More often, it comes from making good decisions consistently over a long period of time. 

Looking back, that's exactly what began happening. 

One decision at a time. 

One lesson at a time. 

One mistake at a time. 

The young man who graduated from college wasn't the same young man who arrived there - thankfully. 

As I reflect on those years today, I find myself thinking about the age-old question: are we shaped more by nature or by nurture? 

The older I get, the less interested I am in choosing one side of that debate. 

I think it's both. 

We're born with certain gifts, personalities, and tendencies. 

Then life introduces us to people who either strengthen those gifts or challenge us to overcome our weaknesses. 

Parents. 

Grandparents. 

Teachers. 

Friends. 

Coaches. 

Employers. 

Even the people who disappoint us. 

Every one of them leaves a mark. 

Some become examples we want to follow. 

Others become examples we hope never to repeat. 

Either way, they're teaching us. 

One of the greatest lessons I've learned is that learning isn't confined to childhood. 

It never stops. 

The title of this chapter is "The Learner," but I no longer believe that's simply the first stage of life. 

It's the first stage because that's where we're introduced to learning. 

If we're fortunate, it becomes a lifelong habit. 

Even today, I still find myself learning from clients who have built remarkable businesses, from farmers who understand patience better than most CEOs, from young advisors who see opportunities through fresh eyes, and from my own children, who continue to remind me that every generation asks different questions. 

The learner never really disappears. 

He simply matures. 

Looking back, I also realize something else. 

At the time, I thought I was preparing for school. 

Preparing for college. 

Preparing for a career. 

Preparing for adulthood. 

I wasn't. 

I was preparing to become the man I would eventually need to be. 

The workbench. 

My parents' sacrifices. 

The victories. 

The disappointments. 

The friendships. 

The mistakes. 

Every one of them was adding another piece to the foundation. 

I just couldn't see it yet. 

Foundations are funny that way. 

Nobody admires them while they're being poured. 

They're buried beneath the surface, quietly supporting everything that comes later. 

The same is true of our lives. 

When we're young, we spend a lot of time wondering where we're going. 

Rarely do we stop to appreciate who is helping us become the person who will eventually get there. 

If you're in this season today—whether you're sixteen, twenty-six, or even sixty and starting over—don't rush through it. 

Pay attention. 

Ask questions. 

Listen more than you speak. 

Be willing to make mistakes, and be just as willing to learn from them. 

You may not understand why this season matters. 

You probably won't. 

Very few of us do. 

But someday you'll look back and realize that long before you were building a career, a family, or a legacy... 

Someone was quietly building you. 

Reflection 

Who are the people who helped shape your life before you fully understood what they were giving you? 

Take a moment to thank them—whether in person, in prayer, or simply in your own heart. 

Because none of us arrives where we are alone.