Raw Truth: My Top Lesson From A Bittersweet Decade in Thought Leadership
Personal Note: Today's musings are a departure from my usual style. I've always been drawn to the rigor of research, the solidity of facts. But this time, I'm peeling back the layers of my own journey, sharing a slice of my soul with you. I'm venturing into a territory that's both scary and exhilarating – the realm of personal storytelling in the voice of my deeper, more soulful, poetic nature. It's not just about ideas; it's about baring my heart, hoping you'll meet me there. I hope you enjoy…
Extra Bonus For Paid Subscribers: In addition to the full article, paid subscribers get the four ChatGPT prompts that helped me write this article and explore a new way of expressing myself. These prompts can help you take rough ideas about your life experiences and crystallize them into an expressive personal narrative that feels even more authentic.
When I think about the last time we moved homes, it strikes me how life is like a series of homes we live in.
Each one holds our stories, our dreams, our tears.
And then, one day, it's time to leave.
The boxes are packed. The walls are painted. The floors are cleaned. And the only thing left to do is to close the door.
But I have a secret.
Before I close the door, I have a silly little ritual. I like to say goodbye.
I like to revisit each room one final time. Look at the empty walls that used to cradle our family photos. Walk on the bare floors that used to be a stage for our lives.
But the moment is always bittersweet.
For the thing I want to say goodbye to is no longer there. Now, our home is a building— an empty shell.
Then, I remember that I’m not saying goodbye to a house. Rather, I’m memorializing a time in my family’s life that I get to carry with me as a memory.
My last move was in February of last year…
It felt like a mirror to the time my wife and I closed a chapter of our lives back in 2014 when we wrapped up the business we had built together.
Back then, I couldn't see it - how that collapse of my business dream was actually a birthing. A painful, messy, beautiful rebirth. It's odd, isn't it? How life's toughest blows crack us wide open, pouring out a truth so pure, so startling, it reshapes our entire being. This wasn't just a failure; it was an awakening. A heart-wrenching lesson that rewrote the script of how I live and how I work. It was my phoenix moment.
The Exact Moment In 2014 I Knew The Business Was Dead And It Was Time To Move Out
Over 11 years, we had nurtured a business from a seed to a mighty tree, with branches that reached over a million dollars in annual revenue, touching the lives of tens of thousands of students each year with our live events. It was a journey where I found lifelong friendships, where I learned the raw truths of building a business, and where I earned my stripes as an entrepreneur.
But, on the other side of the coin, was a different story.
The walls of the business, once reverberating with ambitious plans, now echoed with a deafening silence. My heart ached not just for the loss of a dream but for the personal sacrifices that came into sharp focus. The times I had pushed myself to grow the business rather than to grow myself. The times I forced myself through discipline rather than unleashing my own curiosity. The times I wasn’t present enough with the kids to witness a first. Or to deeply understand a nuance of their inner world.
I remember looking into my wife’s eyes, once brimming with shared dreams, now reflecting a well of fears about our future. We left the business carrying a heavy burden of personal debt, with no savings as a safety net. The relationships I thought were as strong as oak withered away without the common cause of the business to keep us together. Overall, I was engulfed in a sense of emptiness, a profound sense of loss, and a piercing feeling of failure.
It is said that even the best-fed babies die without loving arms to hold them. The same is true for businesses. I'd lost that heartbeat for our business long before it crumbled. Fear kept me blind to what my soul already knew.
Then came the moment.
It was November 2014, at the United Nations, and we were facilitating a conference for 100 of the country’s top entrepreneurs under 35. In the midst of all that buzz, I found myself walking the corridors, lost in the chaos of organizing the event when I almost ran into my wife and business partner. There was this look in her eyes – like windows clouded over with the storm of unsaid things. Tears brimming, threatening to spill over.
We'd been battling with the United Nations catering service. For weeks, they'd been this impenetrable and unresponsive wall, giving us no hint of what their services might actually cost. Then, right there in the middle of it all, the blow landed – a quote so high it knocked the wind right out of us. Suddenly, our showcase, which we had invested so much time into was drowning in red ink. We would’ve been better off financially if we hadn’t even organized the event.
We soldiered on through that day, playing our parts, ensuring everyone else's experience was top-notch. But inside? Inside, we were crumbling. The catering manager, once a ghost, now hounded us relentlessly. His persistence grew with the passing hours, and by day's end, his ultimatum was clear:
Pay up now, or lose everything (including the event room) tomorrow.
It felt like a trap with no escape. Unfair doesn't even begin to cover it.
In the exhausted aftermath of that conference, we were more than just financially drained and sleep-deprived. Our spirits, our very will to keep fighting, had evaporated. That's how our dream died. They call it burnout.
And standing there at the business’ wake in December of 2014, I couldn't help but wonder…
What did I really have to show for those 11 years? What did I get from all of the sacrifices I made?
It's in these moments of stark emptiness and quiet that we find the space to listen to our own heartbeat, to confront our own truths. And ultimately, to find the courage to step into the next home life offers us.
In the quiet aftermath of those tumultuous emotions of a business dying, I made a sacred vow to myself to do things differently.
It’s now January of 2024, and this article is a reflection on the past 9 years. It shares the #1 lesson I learned and blends life's harsh realities and its mesmerizing beauty.
The Big Lesson: Choose Yourself First
I promised to never again lose myself in the pursuit of a business or a noble cause. I refused to be a martyr, sacrificing my essence on the altar of entrepreneurial success or even global impact.
Instead, I chose to honor myself.
I vowed…
To place myself at the top of my priority list.
To lean into my curiosity rather than stifle it when it seemed off topic.
To create work that I am proud to share with others.
To create time for processing real-time emotional challenges rather than viewing them as distractions from my pre-planned to-do list.
To serve not just with my hands but with my soul.
To commit to a journey of learning, not just for knowledge, but for the evolution of my being.
To engage in activities that make my spirit dance with joy rather than sleep with weariness.
From this place, I decided to craft a path where profit and impact were not goals I was optimizing everything around, but natural extensions of my authentic self. Said differently, rather than creating financial goals and then working back from them, I created the conditions to maximize my own growth, enjoyment, and aliveness and then a designed business model that rewarded this.
For example, my various courses, including the Mental Model Club (co-founded with Eben Pagan), Learning Ritual, and Seminal, were not created based on what had the largest market. They were created from curiosities and passions. Furthermore, rather than optimizing for good enough content, I optimized for high-quality content I would be so proud of that I wanted to share it with everyone I knew.
This shift required a profound unlearning.
At the time, this unlearning felt random and chaotic. But, looking back, it followed sequential stages that others can learn from.
With that said, this is my journey…
My Ninefold Path Through The Labyrinth Of Self
I had to gently unravel the tightly wound teachings of business school, to let go of the manic energy of the Silicon Valley startup culture that I had absorbed without realizing it. It was like learning to breathe again, in a rhythm that was mine alone.
Ancient wisdom says we should change ourselves first before changing the world. The unspoken doctrine of high-achievement culture is the opposite:
Choose business and career first.
Choose the external over the internal.
Choose the glitter of money and prestige that trails behind it, and then, only then, consider everything else.
Do so under the guise of changing the world.
The hypocrisy is subtle and deep.
Yet its unraveling has been the most transformative journey of my life. It's like peeling back the layers of an onion, each one revealing a deeper truth, a more authentic version of myself.
Below are the 9 layers of the onion that I unpeeled (with many more layers surely to come)…
#1. I faced the daunting realization that the traditional markers of success—wealth, accolades, external validation—were like mirages in the desert
In my 20s, I was recognized as an honoree of the BusinessWeek 25 under 25, Inc. 30 under 30, and Ernst & Young Young Entrepreneur Of The Year. Our company held events at the White House, Capitol Building, and United Nations with billionaires, senators, members of Congress, governors, university presidents, and foundation presidents. Our social impact company had a budget of $1M+.
While standing on those esteemed stages, accepting accolades, a part of me swelled with pride. These were not just trophies or titles; they were tangible proof of my discipline, my relentless drive, and the audacious goals I once thought impossible. There was a genuine thrill in each achievement, a momentary fulfillment in surpassing boundaries I'd set for myself.
Yet, alongside this pride, a quiet undercurrent of discontent persisted. As I navigated through the elite circles at the White House, United Nations, and the US Chamber of Commerce, I found myself wrestling with a paradox. These achievements, as dazzling as they were, began to feel like mirages in a vast desert. They promised fulfillment but offered only a fleeting satisfaction. It was as if the more I achieved, the more parched my soul became, yearning for a deeper, more sustaining nourishment.
The nights of celebration were overshadowed by a lingering question that followed me into the quiet of the night:
Amidst all these achievements, had I lost sight of what truly mattered?
#2. I realized that I was addicted to shaming myself in order to be more disciplined
At a 2015 entrepreneur mastermind, in a moment that seemed as ordinary as any other, a close friend casually asked me:
Why are you so tough on yourself?
His words landed softly, yet they shattered something within me – a way I had always seen myself. I had never realized it before, but in that instant, I felt the truth of his observation seep into my bones. I was always pushing, driving, demanding more from myself. I had mistaken this for motivation, for the necessary fire to achieve my goals. But here was this simple, profound question, gently tossed into my lap, and it began to quietly unravel years of self-imposed strictures.
In the years that followed, like a seed nurtured by introspection and care, this realization grew. It bloomed into an understanding that shifted the tectonic plates of my psyche. I had always believed that if I wasn’t relentlessly pursuing my goals with everything I had, something was inherently wrong with me, or I would drift toward failure. That shame was my motivator, my relentless taskmaster. I built layers upon layers of accountability, a fortress to keep my perceived inadequacies at bay. Yet, in the quiet corners of my soul, a whisper grew louder – perhaps I wasn’t the problem.
This whisper became a conversation, a dialogue with my inner self that I had long ignored…
What if, instead of overriding this inner voice, I listened?
What if the solution lay in the very part of me I had been trying to silence?
What if I gave that inner self the freedom to fully express itself?
As I explored these questions, I noticed several surprises:
I actually became more motivated. I stopped using many forms of accountability as they were no longer needed.
I compared myself to others less often. Comparing myself to others, once a sharp blade against my pride, began to dull.
The deep-seated fear – that I harbored some irrevocable flaw – started to dissipate.
From the ashes of self-criticism, I rose with a newfound compassion for myself. It was no longer about external validation but about inner fulfillment.
#3. I realized that there were a few critical, universal, foundational ingredients of a solid life
Next, I saw that no achievement could ever replace the value of:
Health (living pain-free, feeling good, and having energy)
Money (making more than you spend)
Relationships (having at least a few close relationships based on unconditional love and trust)
Purpose (doing things that are meaningful to you)
Said differently, no amount of prestige can replace the feeling that comes from a good night’s sleep.
From that revelation, I understood there were mere handfuls of daily rituals, like the keys needed to unlock the human organism that I needed to master—sleep, exercise, posture, stretching, etc, in order to fuel these buckets. I was exhilarated by the fact that each of them could be filled with just some discipline in a short amount of time. In other words, to form these habits, I didn’t need to wait decades or depend on luck. As I journeyed, ticking off the boxes of self-improvement one by one, I felt a surge of progress, a tangible sense of growth.
But then, along came a whispering realization…
#4. Just like each achievement had its horizon, so did each foundational, external success ingredient
Like running on a beautiful trail that suddenly narrows, I saw that more isn't always better. More exercise, more hustle—they promised health but sometimes led to exhaustion, even injury. More sleep could be healthy, but past a certain point, it can make you groggy. It's like holding a bouquet of relationships; a few can be life-giving, their fragrance enriching your soul. But an armful? That can become a weight too heavy to carry. I learned that it's not about accumulating more but about finding the right amounts and then the rhythm that makes your heart sing.
But there was good news…