Years ago, I watched a 60 Minutes interview with Tom Brady that stayed with me. Brady was 27 years old and had already won three Super Bowl rings. He had accomplished what most professional athletes spend their entire careers chasing, yet something about the way he talked about it caught me off guard.
Steve Kroft, the interviewer, was also taken by surprise when Brady said “Why do I have three Super Bowl rings and still think there’s something greater out there for me?” He went on to say, “I’ve done it... And what else is there for me?”
Kroft followed with a simple question: “What’s the answer?”
Brady’s response was even more revealing: “I wish I knew. I wish I knew.”
I wasn’t particularly interested in football when I thought about the exchange later. What stayed with me was the question underneath it. What happens when you finally reach the thing you’ve spent years pursuing and discover that reaching it hasn’t answered the question you thought it would?
I would eventually encounter a version of that question in my own life. Years later, I found myself thinking about it again while sitting on a beach in Thailand.
At the time, I had been working sixty and eighty-hour weeks building my business. I was exhausted enough to know I needed to get away. So I took a vacation to Koh Pha Ngan. Looking back, I sometimes wonder whether I was trying to get away from work or from the version of myself.
Life on the island was simple. There wasn’t much competing for your attention. There was the beach, a restaurant, a bar, your thatched hut, and the people around you. You didn’t need an itinerary to fill every hour.
One afternoon, I started talking with a group of local villagers sitting near the water. They asked what I did for a living, and I proudly told them that I owned my own business. I assured them it’s not easy and I worked very long hours. When one of them asked why I spend so many hours working, I answered without thinking: “So that I can make enough money to afford trips to places like this.”
They looked at one another with puzzled expressions. One of them smiled and said that they didn’t understand why I had to work so many hours just to come to a place like this. From their perspective, they didn’t have to work a certain number of hours before they could enjoy the island. They lived there.
I remember being caught off guard. They weren’t criticizing me, and they weren’t trying to convince me that their way of life was better. They were simply describing their lives. But still, their question exposed an assumption I had never really examined: I had come to believe that the good things in life had to come after the hard things.
Work first. Earn enough. Achieve enough. Then enjoy yourself.
I had never consciously decided that this was how life should work. It was simply how I understood it, and that was what made the conversation so uncomfortable.
Brady’s question and the villagers’ question were completely different. One came from a world-class athlete who had already achieved an extraordinary level of success. The other came from people whose lives looked nothing like mine. Yet both observations made me question something I had taken for granted: the idea that satisfaction was waiting somewhere beyond the next achievement.
The Questions That Follow You Home
There is nothing wrong with ambition, achievement, or wanting to improve yourself. Goals can give your life direction. They can force you to develop abilities you didn’t know you had and push you toward objectives that you thought were beyond your reach.
The question isn’t whether you should pursue goals. The more interesting question for me is why you have the particular goals you have.
From the time you are young, you are taught to push yourself. Work harder. Set goals. Get good grades. Get a good job. Make more money. Move up. And once you reach one goal, set another. I have lost count of how many leaders, entrepreneurs, and successful people I’ve heard give some version of that advice.
What I hear much less often is whether those goals still reflect what we actually want, or whether we are simply following a definition of success we inherited.
For much of my life, I never really asked myself that question. I assumed being driven was a good thing. Each accomplishment felt like confirmation that I was moving in the right direction, and every milestone became the next measure of progress.
If I finished one degree, there was another challenge. If I reached one professional milestone, there was another one to pursue. If I built something successfully, I could build something even bigger.
There was always a reasonable explanation for whatever came next. And that was part of the problem.
Nothing seemed particularly strange about it while I was doing it. Each individual decision made sense. It was only when I looked at the pattern that I began to wonder whether I was actually choosing my direction or simply continuing to move because stopping felt like falling behind.
Blind Spots
Over the years, there have been other moments like the one in Thailand. Sometimes they come from a conversation. Sometimes from something I read or observe. Occasionally, they come from noticing a contradiction in my own thinking that I can no longer explain away.
I’ve become increasingly interested in those moments because they seem to reveal something about how we make sense of our lives. We tend to think we make decisions based on facts, experience, and careful reasoning. Sometimes we do. But underneath all of that are assumptions we may never have examined.
Why does an intelligent person make a decision that seems irrational from the outside but perfectly reasonable to them? Why do we sometimes continue defending an idea after the circumstances that produced it have changed? Why can a question from a stranger stay with us for years while others disappear almost instantly?
And perhaps the question that has stayed with me the longest is this: How many of the beliefs guiding our lives did we actually choose?
The more I think about it, the more I realize something. Many of the things I once considered personal choices weren’t. I had been influenced by ideas I had absorbed long before I was old enough to question them. That doesn’t mean those ideas were wrong. But it does mean I had mistaken familiarity for choice.
Invisible Inheritances
When I think about that episode in Thailand now, I don’t think it was really about work or money. It was about the definition of a good life that I had been carrying around without realizing it.
I had assumed that working harder was inherently better. I had assumed that earning more would eventually give me more freedom. I had assumed that the things I wanted to experience later would somehow be more valuable because I had worked to earn them.
None of those assumptions were completely unreasonable. That’s what made them difficult to see.
An assumption doesn’t have to be absurd to shape your life. Some of the most influential assumptions are the ones that sound perfectly sensible. You don’t stop to question them because everyone around you seems to agree.
Maybe you’ve inherited ideas about what a successful career looks like. Maybe you’ve been taught that a bigger house, a higher salary, a more impressive title, or a certain level of financial security will tell you that you’ve made it. Maybe you’ve accepted the idea that you should keep progressing because the alternative is somehow failure.
There is nothing inherently wrong with any of those things. But are they yours? That’s the question I keep coming back to.
I’m less interested now in deciding whether someone is successful than I am in understanding how they came to define success in the first place. Two people can look at exactly the same life and see completely different things because they are operating from different assumptions about what makes a life worthwhile.
That is what makes blind spots so difficult to recognize. You rarely experience them as blind spots. You experience them as reality.
The conversation I had on that beach didn’t suddenly change my life. I still worked too much. I still chased goals. I still fell back into many of the same habits. What changed was that I had a question I couldn’t completely get rid of.
Every now and then, I still think about Brady asking what else there was for him after accomplishing what he had spent years pursuing. I think about the villagers wondering why I needed to work so hard to enjoy something they enjoyed every day.
Neither experience proves that achievement is meaningless or that ambition is a mistake. They simply make me wonder about the assumptions we attach to both.
How much of what I call ambition is actually mine? How many of the goals I pursue would still matter if nobody else could see them? How much of the life I’m working toward is something I genuinely want, and how much of it is simply a version of success I learned to recognize?
I don’t think the answer is to stop pursuing goals or reject ambition. That would simply replace one script with another.
Maybe the more difficult thing is to examine the script while you’re still following it.
When you look at the life you’re working so hard to build, how much of it did you actually choose?