Because maybe, just maybe, winning the game means losing your soul.
I was twenty-six when I reached what society dictated as "success." Corner office, six-figure income, business cards that read with a substantial title. I wore the designer attire, the condo downtown, and more than enough disposable income to grab takeout without first peeking at my bank account. According to all of the old measurements, I'd "made it."
And yet.
Something was ringing hollow in the win. The finish line I'd worked toward so many years was nothing more than a chalk line painted on the road—transitory and vulnerable to being erased by the next rain. No confetti fell. No deep well of happiness arose. Only a quiet Monday morning and an inbox full of emails labeled "urgent."
This internal revelation drove me down the rabbit hole of questioning what success is, actually—and whether our collective understanding is perpetuating a lovely lie that's poisoning our souls gradually.
The Success Mythology
"Try not to become a person of success, but rather try to become a person of value." — Albert Einstein
Our culture has spun a nice myth around success. We're taught it is the kind that comes in forms of awards, accomplishments, wealth, prestige—external validation supposed to verify our worth. Suppose all of this were just a convenient myth that we all sort of acquiesced in? A myth that makes us keep working, spending, competing—turning business and social success wheels.
Consider how we've dissected success into a to-do list of things:
- Education at the right schools
- Career advancement at the right pace
- Income that exceeds certain levels
- Commodities that confirm our arrival
- Relationships that validate our status
It's no accident this mythology exists. It's a story imposed on us by advertising, media, school systems, and social comparison. From childhood, we're taught these markers of "making it" without taking the time to think about whether they actually get us what we really need: meaning, connection, peace.
The Hedonic Treadmill: Running in Place
Do you recall the first big promotion you received? The raise that at last let you afford your ideal apartment? The moment your business hit six figures? That first high was real—dopamine racing through your blood with the word: "You've done it! You've made it!"
And then an odd thing happened. The rush wore off. The new money became routine. The grand job title became quotidian.
Psychologists call this the "hedonic treadmill"—our tendency to quickly return to a relatively stable state of satisfaction in the presence of large positive or negative life events. We acclimate to our success with incredible speed, which instantly robs them of their ability to sustain our happiness.
James, a client of mine who built a seven-figure business before he was thirty, put it best: "The day I hit my money goal, I celebrated with an expensive dinner. By dessert, I was already planning the next milestone. The finish line I'd fantasized about for years just became another mile marker."
Success as Social Control
Here's a more subversive idea: What if our definition of success isn't merely misguided but actually serves as a kind of social control?
The threat of failure keeps us in line. It compels us to:
- Work longer hours than are good for our wellbeing
- Give up relationships and personal passions
- Endure systems that perhaps don't align with our values
- Delay happiness today for rewards that might never fulfill tomorrow
"The vast majority of men lead lives of quiet desperation," Thoreau observed over a century ago, and perhaps things haven't changed as much as we think. We've simply wrapped our desperation in productivity apps and LinkedIn profiles.
The Soul's Definition of Success
What if we've been measuring the wrong things entirely?
I had asked a hospice nurse one time what people talk about in their final days. Her reply was astonishing: "Never once have I heard someone say they wish they'd gotten that next promotion or bought a bigger house. They talk about love—given and received. They talk about moments of beauty they saw. They talk about living or just going through the motions."
The soul, as it turns out, is operating from a completely different scorecard:
- Did you love well?
- Were you present on the journey?
- Did you honor your specific gifts?
- Did you have the courage to be yourself?
- Did you give back to something larger than yourself?
Maria, a former banking executive who gave up her high-level career to start a community garden initiative, told me: "I thought success was about reaching higher. Now I realize that it's about digging deeper—into relationships, into purpose, into the present moment. My 'successful' life drained me. My 'meaningful' life nourishes me every day."
The Faustian Bargain
There's a time-worn legend of Faust, who bargains his soul with the devil in return for limitless knowledge and material indulgences. It's a parable that endures—the grand warning about sacrificing what is most valuable for what temporarily glimmers.
Most of us are making Faustian mini-bargains on a daily basis:
- Exchanging health for riches
- Selling presence for productivity
- Swapping authenticity for approval
- Sacrificing curiosity for certainty
- Traders in connection for accomplishment
Sarah, who worked 80-hour weeks for years to be brought in as a partner at her company, had this to say: "When I finally got what I wanted, I realized that I'd lost myself along the way. I couldn't remember when I last read a book for pleasure, and not for work, or when I last engaged in a proper conversation instead of one at work. I'd won at the game, but I didn't remember how I wanted to play it for."
The Paradox of Success
This is where things really become interesting. Individuals who appear most satisfied tend to have a paradoxical relationship with traditional success—they are not against achievement, but they do not cling to it. They view it as just one aspect of a rich existence, not the defining characteristic.
Positive psychology studies confirm this result. Research shows that beyond the minimal requirements, there is no significant effect of higher earnings on happiness. What has a strong correlation with wellbeing? Autonomy, mastery, purpose, relationships, and presence—attributes often put aside in pursuit of conventional accomplishment.
This is a profound truth: What we assume will make us happy and what actually makes us happy tend to be opposite of each other. We chase the illusion while overlooking the oasis in front of us.
Redefining Success on Your Terms
"To be yourself in a world that is constantly trying to make you something else is the greatest accomplishment." — Ralph Waldo Emerson
The challenge here isn't to abandon ambition or success. It's to reclaim the definition of success from outside sources and rewrite it on the basis of your most inner values.
Redefining is a highly personal exercise. For others, it could be:
- Success is creating work that showcases your unique gifts
- Success is having time and energy for the ones you love
- Success is being in alignment with your values
- Success is growing and evolving as a person
- Success is contributing back to something bigger than yourself
Thomas, a teacher who had turned down administrative promotion to stay in the classroom, explained: "My colleagues think I am not ambitious because I have rejected the career path. They do not understand my definition of success is influence, not title. My measure of success is the twinkle in my students' eyes when they get something for the first time."
Beyond the Binary
Or perhaps the most liberating awareness is that success is not a dichotomy—you haven't either "made it" or "failed." Success is not a destination but a continuous search for what truly counts.
This frame of mind transforms our relationship to achievement. We can appreciate achievements without identifying ourselves by them. We can strive for excellence without equating our worth with outcomes. We can
honor our ambitions while remaining connected to more basic values.
The Courage to Question the Game
"It is no measure of health to be well adjusted to a profoundly sick society." — Jiddu Krishnamurti
The most radical thing to do might be to inquire whether the game itself is worth playing—least as it currently exists. That requires courage because we've so invested in the prevailing story. It requires facing the chance that we've been on a treadmill rather than journeying towards something of substance.
Elena, who drastically reduced her life after a health crisis, explained it in the following words: "The hardest part wasn't giving up the trappings of success. It was giving up the image I'd cultivated about being a 'successful person.' I was confronted with the terrifying question: Who am I outside of my accomplishments? The answer was both terrifying and liberating."
The Soul's Invitation
Perhaps the hurt we experience—even when we've achieved all on our list—is the beckoning of the soul to a richer dialogue. It's encouraging us to look over the finish line to what's most important.
What if the best successful life is not the most dazzling resume life or the most financially flush bank account life, but the life of greatest presence, purpose, and love?
What if winning the standard game costs us something much more valuable?
What if success, as we have been conditioned to strive for it, is a lovely lie—and the truth is both simpler and deeper than we ever thought?
These are not easy questions to answer. But asking them might be the start of a life that feels successful, not just on paper, but in the depth of your own soul—where it counts.
Because maybe, just maybe, the real finish line isn't measured by external achievements but by being able to look back and say, "I lived well. I loved deeply. I was truly here."
And perhaps that's the only victory that will matter in the end.
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