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The Stoic Truth About ‘More’: Why Winning Never Felt Like Winning

The Stoic Truth About ‘More’: Why Winning Never Felt Like Winning

The moment I got the promotion I spent 3 years chasing, I felt … empty. I wasn’t jealous of others; I was addicted to a future version of myself. Here is how “Destination Addiction” rewires your brain to enjoy the climb but hate the view — and how to fix it.

“Climb mountains not so the world can see you, but so you can see the world.”

I remember the exact moment I got the promotion I had spent three years chasing.

The handshake was firm. The title on the offer letter was bold. The salary bump was significant. My boss smiled and said, “You earned this, Gary.”

I walked back to my desk, accepted the congratulations, and waited for the feeling to hit me. I was waiting for euphoria. I was waiting for the cinematic moment where the music swells, and you finally whisper, “I made it.”

But that moment never came.

I remember sitting in my car in the parking garage that night. The engine was off. I had the new title. I had the raise. But instead of joy, I stared at the concrete wall for 20 minutes, feeling a tightness in my chest. I wasn’t celebrating; I was already calculating the timeline for the next promotion.

I had won the game, but I couldn’t stop running.

For 40 years, I thought this drive was a superpower. My inability to rest on my laurels was what made me successful. I wasn’t envious of my peers; I was too busy competing with my own potential.

But looking back, I realize it wasn’t a superpower. It was a psychological glitch.

I was suffering from Destination Addiction. And if you are a high achiever, you probably are too.

“I wasn’t competing with my colleagues. I was competing with my own potential. And potential is a cruel opponent because it is infinite.”

 

The Science of “More”

We tend to think of ambition as a character trait, but it is essentially a chemical reaction.

For decades, I was running on a fuel called Dopamine. In pop culture, we call dopamine the “pleasure molecule,” but that is a misunderstanding of neuroscience. Dopamine is not the molecule of enjoyment; it is the molecule of craving.

Neuroscience tells us that dopamine is designed to propel you toward a goal. It spikes when you are pursuing the deer, not when you are eating it.

As the graph above illustrates, once you achieve the goal — once the promotion is signed — dopamine crashes below baseline.

This is why the “Post-Achievement Blues” are authentic. I spent my 30s and 40s confusing this chemical crash for a lack of ambition. Every time I reached a summit and didn’t feel happy, I assumed the problem was the mountain.

“This wasn’t the right goal,” I’d tell myself. “The REAL happiness is at the next level. The VP level. The C-Suite level.”

 

The Hedonic Treadmill

Psychologists have a name for this trap: The Hedonic Treadmill.

The theory states that no matter how fast you run or how much you accumulate, your baseline level of happiness eventually resets to its previous level.

I spent 40 years running at full speed to stay in the same emotional place. I was living in what Dan Sullivan calls “The Gap.”

The Gap is when you measure yourself against an Ideal (an unreachable standard).

The Gain is when you measure yourself against your Past (which is real).

When you live in The Gap, you are constantly measuring yourself against a phantom. As soon as you make a million dollars, your “Ideal” shifts to ten million. As soon as you become Director, your “Ideal” shifts to VP.

You are treating happiness like a horizon. No matter how fast you run toward it, it remains the same distance away.

 

The Objection: “But won’t I become lazy?”

Since I started writing about leaving the corporate grind, I’ve had people ask me a terrified question:

“Gary, if I stop chasing the next level, won’t I stagnate? Is this just an excuse to give up?”

This is the fear that kept me trapped. I believed there were only two options: Relentless anxiety or total failure.

But there is a third option. The Stoics (and modern psychologists) teach us that there are two types of drive.

Deficiency Ambition: “I need to achieve X to prove I am enough.” (This burns you out).

Inspiration Ambition: “I want to achieve X because it is good work.” (This sustains you).

Deficiency Ambition bullies you. Inspiration and Ambition fuel you. You can still climb the mountain — you have to stop believing that your self-worth is buried at the summit.

 

The Stoic Solution to “Next Level” Syndrome

Seneca, the great Roman Stoic, warned us about this trap 2,000 years ago.

“It is not the man who has too little, but the man who craves more, that is poor.”

The Stoics didn’t preach laziness. They preached non-attachment. They understood that “Enough” is a decision, not a dollar amount or a job title.

If you cannot find a way to be satisfied right now — in the messy, incomplete, imperfect middle of your career — you will not be satisfied when you get the promotion. You will be a Director with the same anxiety you had as a Manager.

“The next promotion won’t fix you. You have to decide to be ‘enough’ right now, or you never will be.”

 

Breaking the Cycle

I wasted years waiting for my life to “actually start.” I was rehearsing for a play that never opened.

If you are reading this and you feel that familiar itch — the feeling that you need just one more win to relax finally — try this exercise tonight.

The biggest mistake I made over those 40 years wasn’t chasing the wrong job. It was believed that the “enough” I craved was housed inside a title or a salary. I was trying to solve a philosophical problem — *what is a good life? — *with a business solution — what is the next promotion? That equation will never, ever balance.

The true wisdom of the Stoics isn’t about quitting the game; it’s about changing the scoreboard. It’s about recognizing that the “more” you chase is merely a phantom — a distraction from the one thing you can truly possess: peace in the present moment. Once you stop needing external success to validate your soul, the anxiety of “what’s next” finally dissolves.

The ‘Reverse Gap’ Exercise: Before you go to sleep, do not write a To-Do list for tomorrow. Instead, write down three things you did today that the “You” of 10 years ago would have considered a dream.

Force your brain to see the Gain, even if just for 30 seconds.

Don’t let your ambition bully you out of your life. The view from the top is nice, but the hike is all you really have.

 

 

 

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