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Picture this: You’re 37, sitting in your corner office with the city skyline view you once dreamed about, and instead of feeling accomplished, you feel… empty.
The six-figure salary, the impressive LinkedIn profile, and the respect from peers; it’s all there, but something’s off.
That gnawing feeling? It’s the realization that you’ve been climbing someone else’s mountain.
I spent years chasing a version of success that was handed to me like a pre-written script.
Good grades, prestigious degree, corporate ladder, financial milestones? Check, check, and check!
However, somewhere around my mid-thirties, the facade cracked. The achievements felt hollow because they were expectations I’d absorbed from parents, society, and a culture that equates worth with wealth.
The brutal truth nobody tells you when you’re 22 and hungry for success is that the hardest battle is discovering, often too late, that “there” was never your destination to begin with.
The inherited blueprint of success
Most of us inherit our definition of success like we inherit our eye color, unconsciously and without question.
Your parents wanted stability, so they pushed you toward law or medicine; your peers were all gunning for tech startups, so you followed suit.
Moreover, society applauded certain achievements, so you collected them like trophies.
Here’s what happens, though: You wake up one day with everything you thought you wanted, yet you feel like a stranger in your own life.
When I was working that warehouse job in Melbourne, shifting TVs and feeling like my psychology degree meant nothing, I actually felt more authentic than I did years later when I’d “made it” by conventional standards.
At least in that warehouse, I wasn’t pretending. The exhaustion was real, the frustration was mine, and oddly enough, so was the clarity that came from hitting bottom.
Think about it: When was the last time you asked yourself what success actually means to you?
The momentum trap
Once you start down a path, momentum takes over.
You get the internship, which leads to the job, which leads to the promotion, which leads to more responsibilities, which leads to… what exactly?
Before you know it, you’re 10 years into a career you never consciously chose.
You’re good at it, sure, you’re successful by every measurable standard but measurement isn’t meaning.
The insidious part is that each step made sense at the time: Of course you took the higher-paying job, of course you worked those 70-hour weeks, and of course you sacrificed your hobbies, relationships, and health for the next rung on the ladder.
Everyone around you was doing the same thing, validating your choices through their own similar sacrifices, but momentum isn’t intention and movement isn’t progress if you’re heading in the wrong direction.
In my book, Hidden Secrets of Buddhism: How To Live With Maximum Impact and Minimum Ego, I explore how Buddhist philosophy teaches us about the danger of unconscious living: Following patterns without awareness.
This is exactly what happens when we chase inherited versions of success.
The comparison game that nobody wins
Social media turned comparison into a blood sport.
You see your college buddy’s startup exit, your friend’s promotion announcement, another acquaintance’s humble-brag about their investment portfolio.
And what do you do? You double down on your own chase, running faster toward a finish line you never chose.
Here’s the thing about comparison: It assumes everyone’s running the same race, but what if you’re a marathon runner forcing yourself to sprint? What if you’re built for creative depth but you’re competing in the breadth game?
The cruelest part is that, even when you “win” at comparison, you lose.
Winning at someone else’s game means losing at your own.
Rewriting your definition mid-flight
So, what do you do when you’re 30-something and realize you’ve been living someone else’s dream? Do you burn it all down? Quit your job and become a yoga instructor in Bali?
Maybe, but probably not.
The real work is more subtle and more difficult. It’s about slowly, deliberately rewriting your definition of success while still honoring the life you’ve built, and about finding ways to inject authenticity into a structure that might feel foreign.
When I made the decision to leave Australia and move to South East Asia, people thought I was having a crisis.
However, it was about running toward something real. Starting Hack Spirit was about creating a version of achievement that actually meant something to me.
You don’t need to blow up your life to reclaim it, but you do need to start asking different questions.
Instead of “What will impress people?” ask “What energizes me?” and instead of “What pays the most?” ask “What challenges me in ways I actually care about?”
The courage to disappoint
Here’s something they definitely don’t teach in business school: Sometimes, the bravest thing you can do is disappoint people who have the wrong dreams for you.
Your parents might not understand why you’re walking away from partner track, your friends might think you’re crazy for taking a pay cut to do work that matters to you, and your professional network might raise eyebrows when you pivot from what you’re known for to what you’re drawn to.
Let them, because the alternative—living your entire life as a supporting character in someone else’s story—is a far greater tragedy than temporary disappointment.
Building authentic success
Real success is about pursuing achievements that align with your actual values, rather than the values you’ve inherited or absorbed.
Start small: Maybe you can’t quit your corporate job tomorrow but you can start that side project you’ve been thinking about, or maybe you can’t rewrite your entire career but you can start saying no to opportunities that pull you further from yourself.
The path to authentic success is paved with small, deliberate choices that honor who you actually are.
The goal isn’t to have a life that looks good on paper, but a life that feels good to live.
Final words
If you’re reading this in your twenties, consider yourself warned!
That success you’re chasing? Whose is it really? If you’re in your thirties and feeling that uncomfortable recognition, know that it’s not too late to course-correct.
The hardest part of success is having the courage to admit when you’ve been climbing the wrong mountain and the wisdom to find your own path, even if it means starting the climb again.
Your thirties don’t have to be about realizing you’ve lived someone else’s life. They can be about finally starting to live your own.
The success that matters is the one you consciously choose, imperfections and all.
Plus, that choice—that conscious, deliberate, sometimes painful choice to pursue what actually matters to you—is where real success begins.