File 000: The Inquiry
Magnifying glass
The High Achiever Files is an ongoing essay series exploring how conditioning shapes success, leadership, identity, and fulfillment. We've spent years and years learning what it takes to achieve. We don't spend even a fraction of that time asking what hyperfocus on achievement does to us.
Before I made the big move of ditching my corporate career to start something new, I found myself questioning everything.
Why was I unhappy when I had accomplished so much?
Why were the people around me a version of the same?
Why had I normalized feeling off?
Why did I immediately move on from the achievement of a goal to form the next?
Why was the system so broken, and why did we all put up with it?
I ask a lot of questions; it's is in my nature. During my darker times, I would even go so far as to say my default state was skeptical, even cynical. It wasn't until I recognized that I wasn't trapped, that I could make my life feel better, that backed off the tendency to view my circumstances through the lens of defeatism and decided to shift to curiosity instead.
Once I found an inner state of neutrality with which to ask questions, I was able to observe in ways that satisfied the scientist within me. It was like putting life under a microscope to see what I could see while actively suspending judgment about what I observed.
That shift allowed me to see quite a bit, and most of it was unsettling.
Successful people who feel disconnected, stretched thin, burned out.
Professionals at all levels who tie their value to their achievements.
Leaders who accomplish what they set out to do but aren't fulfilled
Organizations caught up in generating profit while propagating problematic work environments
All of this sounds basic and obvious. I get it. We've normalized this shitty reality to the point where we take it as a given that this is they way it is. The game you have to play if you want to win the prizes.
Well. Fuck that.
YOU, as an individual, have the power to decide what you participate in. You, as a leader, get to influence your organization to be and do better. When leaders have the gumption to demand more, organizations can go from profit-obsessed to people-centered, putting humans at the center and allowing profits to flow as a result of the realignment.
So. Now that we've established the reality of our circumstances, how do you move forward from here?
Start by acknowledging that you likely didn't choose your definition of success consciously. You were shaped by your family, culture, industry, workplace, and outside expectations around what it means to be successful.
You've been conditioned.
I want to be clear that I'm not asking you to leave ambition behind. I'm asking you to be conscious about the forces that shaped it. Then, you can keep what works for you, ditch what doesn’t, and redefine what it takes to live a better, more aligned life that comes with the kind of success that fulfills and honors you rather than depleting you.
Topics you can expect to be covered in these files:
Achievement
Conditioning
Identity
Organizational dynamics
Spirituality
Fulfillment
Meaning
Culture
I'm not here to convince you or to prescribe a remedy. My intention is to invite you to ask the same question that I continue to ask myself.
What does it mean to succeed without losing yourself?