The Trap Found In The Game That Successful People Play

Written By: Brad Pedersen

A couple of years ago, I was sitting on the beach out front of our place in Florida, with one of my closest friends.

We were having a conversation; the kind that moves between the serious and the absurd, where nothing needs to be performed and nothing needs to be proven.

The night was warm and unhurried, with the sky filled with stars, in a way that makes you feel small. We had good tequila, cigars and music, while the ocean waves rhythmically lapped up against the shore.  

In that moment, I had the quiet realization that I had never felt more alive or more deeply aware of how rich my life truly was. The experience was simply perfect and could not have been made more remarkable. Just two people who knew each other well, being able to talk honestly about the things in life that truly matter.

The memories of that evening have lingered with me and only recently have I started to understand why it felt so different from the many other evenings I have participated in that looked far more impressive on paper.

The Idea I Got Partially Right

For most of my adult life, I’ve believed Jim Rohn’s famous line: you are the average of the five people you spend the most time with. I’ve repeated those words often, with sincere conviction.

But if I’m honest, the way I interpreted the idea was incomplete. I believed it meant that I should aim to surround myself with people who were further ahead. People with bigger companies, larger balance sheets and those whose material results signaled that they had built something significant.

The logic felt clean and aspirational; surround yourself with excellence and excellence will find its way to you. Certainly there is something true in that as I have been genuinely shaped by ambitious, accomplished people who have pushed my thinking and raised my standards in ways I am grateful for. But over time I have come to learn that the more time I spend in rooms where people are subtly trying to impress each other, the less joy I feel being part of them.  

It isn’t because these people aren't quality individuals. Many of them are extraordinary by almost any measure. The issue is the game we unconsciously play. We push each other to grow, however the metrics of that growth are almost entirely external: how much money, power or status can be acquired through the latest growth hack, lifestyle upgrade or profit unlock. And with that, driven by the words “more” and “next,” the frame of reference keeps shifting. What felt like enough last year, no longer feels like enough this year. In this game, satisfaction is never the objective, instead every level offers a new reason to push and run faster.  

It appears to be a very noble game as who would ever fault us for wanting embetterment? It is under this illusion that we play, often without realizing we ever entered the competition. In the process, we outsource our sense of enough to other people, letting their lives set the benchmark for our own.  

Unless you recognize that you’re not just playing the game but being played by it, it will become a deeply seductive trap that will lead to a life of exhaustion and misery.

The Status Game Has No Finish Line

There is a real difference between being inspired by what someone else has built and being envious of it. Inspiration leaves us energized and pointed toward something aspirational; while envy draws us into frustration leaving feelings of emptiness. Inspiration helps us build a life while envy quietly erodes it.

Charlie Munger is credited for saying that it isn’t greed that drives the economy, but envy. The more I’ve reflected on that idea, the more I think he was pointing to a truth that is deeply embedded in human nature.

Over four centuries ago, the French philosopher Montesquieu made a remarkably similar observation. He wrote: “If we only wanted to be happy, it would be easy; but we want to be happier than other people, and that is almost always difficult, since we think them happier than they are.”

In other words, our sense of satisfaction in life was never designed to be objective. As a species, we have made it deeply relative to the people around us. And for most of human history, that comparison pool consisted of your neighbors next door.

Today the definition of “neighbor” has expanded to include almost everyone on earth with a social media profile. Their highlight reels are one scroll away: the vacation, the new house, the milestone post subtly wrapped in a humble brag.  Even when we know better, it is remarkably difficult to watch it all without quietly measuring ourselves against it. None of us are immune.

C.S. Lewis wrote an essay called "The Inner Ring" where he described how human beings are driven to perpetually try to break into the next more exclusive circle. The inner group, the better table, the room where the real conversations are supposedly happening.  He went on to observe that once we're inside that ring, the contentment we imagined we would find there doesn't show up. As a result, our eyes move almost immediately to the next ring, and the whole cycle begins again.

He ended the essay with a line that says it all: "The quest of the inner ring will break your heart unless you break it."

So What Does This Have To Do With Our Network?

Everything, as it turns out.

Who we spend consistent time with shapes more than our habits, mindset and professional trajectory. It shapes our expectations; and as a result our satisfaction and enjoyment in life.

Our life's fulfillment at its most basic level, is largely just the gap between what we expect and what we actually have. When that gap is narrow, life feels full, however when it is wide, life feels like a deficit no matter what you accumulate to try to close it.

When we spend time consistently in rooms where everyone is quietly sizing each other up, where the subtext of every conversation is a comparison, that gap never closes. Because unconsciously the group is subscribing to the comparison game, which is not about how much we have but rather how much we have relative to each other. And in the game no matter how much we add to the pile, no matter how many rings we manage to break into, there will always be another level to aspire towards.

Furthermore, if the main benefit of financial wealth is freedom, envy does the opposite by letting other people’s lifestyles dictate how we feel about our own. The result is a constant sense of scarcity where someone else’s success makes our progress feel inconsequential.

I want to be clear that I am not writing this as someone who is against ambition or financial achievement; I have spent over thirty years scaling companies, and I know what it feels like to want to build something meaningful.

But I’ve come to see a difference between ambition rooted in conviction and ambition rooted in comparison.

Conviction-driven ambition comes from getting clarity about our purpose and with that a genuine desire to create and contribute something; while becoming the best version of ourselves.

Whereas comparison-driven ambition moves us forward for a different reason: the quiet anxiety that comes from pursuing “more” and “next” that is driven by envy.

The Accounting Is More Nuanced Than The Saying Suggests

I do believe that your network will determine your net worth; but the way we typically measure that equation is too narrow. I believe it can mislead a lot of accomplished leaders to chase the wrong metrics.

It is not just about who can open doors for us, or whose trajectory we can learn from. All of that has value; I am not dismissing it. But the deeper question, the one that I think determines more about the actual quality of our life, is this: who recalibrates our sense of enough?

Another way to think about it is asking: Who makes us feel, just by being around them, that the life we already have is worth fully inhabiting?

For me, it means spending more time with friends whose idea of a great evening is simply sitting by the ocean, listening to the rhythm of the waves, and talking slowly about the things in life that actually matter. In those moments, something subtle but powerful happens: my baseline for what a wealthy life looks like, quietly recalibrates.

With the right people around us, gratitude replaces comparison and a deep sense of enough begins to settle in; the ordinary starts to feel extraordinary. Not because we have lowered our ambitions, but because we have stopped measuring our lives against standards that were never truly ours to begin with.

That is why choosing our five should be done carefully. Not just for what they might add to our financial trajectory, but for what they do to our sense of perspective and whether we like the person we become, after we have spent time with them.

So this week, sit with these questions:

• Who in your life quietly recalibrates your expectations in the right direction?
• Are you actually investing enough time with them?
• Where are you still chasing a ring that some part of you already knows won't satisfy you once you're inside it?

If something in here landed for you, send it to someone who needs to read it this week. And if you are not yet part of the Full Spectrum community, this is the kind of conversation we have every single week; accomplished leaders working out together what wealth actually means beyond the balance sheet.

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