Why I Coach Strivers
Reflections after the first year of building the Strive Better coaching focused on private equity professionals and executives.
When, a little over a year ago, I began introducing my coaching work and describing the system and method I had developed, I often heard a version of the same reaction:
“Oh, so you’re a life coach for executives?”
My answer then was, “Well… yes, and no.”
A year in, I still hear the same reaction. The difference now is that I have enough experience and data points to be more precise about what that “yes, and no” really means.
Much of my work today takes place in and around private equity firms and the companies they back. I work with investors, operating partners, and leaders of private equity-backed companies who are striving to perform at a high level in demanding environments. But the work goes deeper than helping someone achieve the next goal. And it certainly is not about “life design.”
Rather, the work is rooted in a simple belief: human beings possess extraordinary capacities for growth, achievement, and flourishing. Yet many of the most capable people I know, the strivers, struggle to fully cultivate and actualize those capacities.
They are successful, but restless.
Accomplished, but not fully at ease.
The same drive that propels them toward ambitious goals can also pull them away from the conditions that allow them to thrive.
Over time, striving can quietly turn us into something like goal-seeking machines.
Highly productive.
Highly capable.
But increasingly disconnected from the deeper foundations of our humanity.
Magnified by the relentless pressure to achieve the next goal, that disconnection can manifest as burnout, impostor syndrome, and ultimately declining performance.
The work, then, is about developing the human capacities that allow struggle and joy to coexist in every aspect of life. It is not about balance. It is about harmony.
And it is certainly not about eliminating struggle. It is about making meaning of the difficulties we encounter and overcoming them in ways that preserve integrity between our values and our actions.
A year into building this practice, a few patterns have become especially clear.
Insight #1: No One Outgrows the Human Stuff
No matter how much someone has achieved or what title they hold, everyone is still dealing with the same underlying human dynamics.
Fear.
Doubt.
Identity.
The need for control.
The tension between ambition and meaning.
In high-performance environments these forces are amplified. Even among the highest performers, the pressure to perform can make them more pronounced.
Success does not eliminate the human stuff.
Sometimes it magnifies the strain.
Insight #2: Striving Comes with Both Gifts and Costs
The drive to achieve is often one of the most powerful forces in a person’s life. It can produce extraordinary outcomes.
But striving also comes with costs.
Relentless pressure.
Difficulty being present.
A tendency to measure self-worth through achievement.
The leaders who navigate this well are not the ones who eliminate striving. They are the ones who become aware of its costs and make conscious choices about how to navigate them.
Awareness creates the possibility for traditional forms of success, wealth, status, and achievement to exist in harmony with wellbeing.
Insight #3: The Strategies That Create Early Success Eventually Stop Working
When people encounter difficulty or uncertainty, they tend to rely on what worked in the past.
For many high achievers, that means:
Working harder.
Grinding longer.
Applying more effort.
These strategies often work early in a career.
But leadership eventually presents challenges that cannot be solved with effort alone. They require something different:
Self-awareness.
Emotional regulation.
Clarity of judgment.
The ability to step back and see the larger dynamics at play.
These practices place a premium on self-mastery.
After all, how can someone effectively lead an organization if they cannot first lead themselves?
Insight #4: Philosophy and Science Are Converging
For much of modern professional life, conversations about performance have been dominated by tactics, metrics, and optimization.
But something interesting has begun to happen.
Research in psychology, neuroscience, and human performance is increasingly validating ideas that philosophers have explored for centuries.
Concepts like attention, discipline, emotional regulation, meaning, and self-mastery have long appeared in philosophical traditions and are now being examined through the lens of scientific inquiry.
In my coaching work, integrating these two perspectives, philosophy and science, has made the work both more accessible and more durable.
Philosophy provides language for questions of meaning, character, and purpose. Science helps explain the mechanisms through which our thoughts, emotions, and behaviors shape performance.
Together, they make the work more human and less abstract. Less like a laboratory experiment and more like a framework for living and leading well.
And when leaders internalize these ideas in that way, the results tend to stick.
Insight #5: The Most Advanced Performance Environments Are Leading the Way
Some of the most demanding performance environments in the world have already begun applying these principles in practice.
Elite athletics and the military, environments where the margin between success and failure can be extraordinarily thin, have spent decades refining approaches to human performance.
In many of these settings, the philosophy of performance has shifted.
The emphasis is no longer simply:
Train harder.
Push more.
Produce outcomes.
Instead, the focus turns toward something deeper.
Develop the internal capacities required to perform under pressure.
Release attachment to outcomes.
Focus on behaviors that reflect who you want to be and how you want to show up.
You hear this shift most clearly in the words of athletes themselves.
In post-competition interviews, many Olympic champions describe reaching their best performances only after letting go of the obsessive focus on results and reconnecting with the craft itself. They rediscover the joy of the discipline and the freedom to perform.
Ironically, when athletes orient themselves this way, performance often improves.
Not because they are chasing results more aggressively, but because they are fully inhabiting the practices that make excellence possible.
Over time, the insights developed in these environments inevitably migrate elsewhere.
Increasingly, they are beginning to shape how leaders think about performance in private equity firms and the companies they back.
I am excited to play a small part in helping bring the practice of human capacity development into these demanding professional environments.
Because ultimately, that is why I coach. To support ambitious people in thriving while pursuing their goals and, in the process, becoming the very best versions of themselves.