The shrill beep of my alarm pierced the silence at 3 AM, jolting me awake. As I sprung out of bed, squinting at the glowing numbers on my phone, I couldn’t help but wonder, “Why on earth did I agree to this early flight?”
But then I remembered: Derek Sivers.
For the last three days, I’ve been able to sit down and chat with Derek about everything we’re interested in, and that is worth every bleary-eyed moment.
A few hours later, I found myself settling into my business class seat and writing this to you. Now, don’t get me wrong—I’m beyond grateful for where I am today. Building successful coaching businesses has its perks; yes, extra legroom is one of them.
But as I sat there, watching Wellington shrink beneath me as we took off, I couldn’t shake this nagging feeling that something was… off.
You see, I’ve been lucky enough to work with some incredible clients and build businesses I’m proud of. But success? It’s a funny thing.
Success is like a mirage in the desert – the more desperately you chase it, the further it seems to recede.
After selling my last company, I thought I had it all figured out. I spent a year in the trenches with six, seven, and eight-figure entrepreneurs, racking up over 220 hours on Zoom calls. I was the guy with the answers, the problem-solver extraordinaire.
The truth: most of their business problems were just personal problems in a fancy suit and tie.
There I was, dispensing wisdom like a vending machine when it hit me…
What if I’d been chasing the wrong rabbit all along? What if all this ‘success’ was just a distraction from something deeper?
So, as I found myself sitting down with Derek we dove headfirst into the murky waters of life, success, and that sneaky little devil called desire.
“Why do you want to grow your business?” he asked me. Five seconds of silence felt like an eternity as my brain short-circuited. It’s such a simple question, right?
The kind every entrepreneur should have a ready answer for. But in that moment, I felt like a kid caught with his hand in the cookie jar, unsure why he was even there.
That’s the thing about Derek – he doesn’t just make you think outside the box. He makes you question why there’s a box in the first place. And as I sat there, mouth agape, trying to formulate an answer, I realized I was on the brink of something big. Something that could change not just my business but my entire approach to life.
As the plane cut through the clouds, my mind drifted back to our discussions sitting in a museam cafe. The kind where the coffee’s gone cold but the ideas are just heating up. It was during one of these tea-fueled sessions that Derek and I stumbled upon an idea that would change everything for me:
Happiness = Haves / Wants.
Sounds simple, right? Almost too simple.
But don’t be fooled. The true power of this equation lies in its denominator.
Most people focus on increasing their ‘Haves’. But the ‘Wants’ at the bottom of the fraction pack more punch than a double espresso on an empty stomach.
Why? Because while increasing ‘Haves’ often requires time, effort, and luck, decreasing ‘Wants’ is entirely within your control.
Think about it. Double your ‘Haves’, you double your happiness. But halve your ‘Wants’, and you achieve the same result. And you can do that right now, just by deciding to.
It’s like finding a volume control for contentment. Turn down the ‘Wants’, and suddenly, everything you have gets amplified. That old car becomes a chariot of freedom. That small apartment? A cozy sanctuary.
The less you want, the more powerful you become. When you’re content with what you have, you can walk away from bad deals. You become unshakeable.
I’m not saying eliminate all desires. But by consciously managing our ‘Wants’, we gain incredible control over our happiness.
Because sometimes, the key to having it all is realizing you already do.
Easier said than do, I’ll admit, becuase as I sat there, trying to make sense of it all, I couldn’t help but reflect on my own journey. All the goals I’d chased, the milestones I’d hit, the things I’d acquired along the way.
And I had to ask myself: had any of it really brought me lasting happiness?
The answer wasn’t quite what I expected. And it set me on a path of questioning everything I thought I knew about success, happiness, and what it means to live a good life.
The answer hit me harder than my daughter’s soccer ball to the face last weekend.
Don’t get me wrong, I’m not saying success sucks.
As someone who’s built and scaled numerous businesses, I know the thrill of achievement. But chasing it?
That’s a different story. It’s like being on a treadmill that keeps speeding up. You’re running faster and faster, but you’re not actually going anywhere.
The Moments That Matter
So as I sat here, high in the sky, I started reflecting on when I was truly happy.
And you know what?
You know, it’s funny how life works. After all these years of chasing success, closing multi-million dollar deals, and launching companies, I finally realized where true happiness lies. And it wasn’t in a boardroom or on a stage receiving accolades. It was right there in my living room on a Tuesday night.
Four little heads finally asleep on their pillows after the usual bedtime circus. My wife Lauren and I, exhausted but grinning, collapsed onto the couch. I had my trusty tub of ice cream (don’t worry, I made it myself), while Lauren was battling with what was supposed to be our dinner but was quickly becoming a charred offering to the kitchen gods.
Just moments earlier, our living room had been a whirlwind of chaos. Our eldest was premiering her latest “interpretive dance” – a performance that seemed to involve a lot of arm-flailing and sound effects. Not to be outdone, our other three daughters decided it was the perfect time to join the dancing, which made our dog run laps around the kitchen. And somehow, in the midst of all this, a rogue splatter of tomato sauce had found its way onto the ceiling. Don’t ask me how. I’ve learned not to question these things.
As I sat there, spoon halfway to my mouth, watching Lauren laugh at the absurdity of it all, I felt it. This overwhelming sense of… contentment. Pure, unadulterated happiness. No desires, no wants, just… bliss.
In that moment, with the house finally quiet save for the scraping of Lauren’s valiant attempts to salvage dinner, I realized we’d stumbled upon the secret.
This – this beautiful mess of a life we’d created together – this is what makes us happy. Not the deals, not the companies, not the accolades. Just us, our four daughters, and the simple joy of being together.
As I pulled Lauren close, both of us still chuckling at the events of the evening, I couldn’t help but think:
“This is it. This is what it’s all about.” All those late nights, all those stressful meetings, all those goals I’d been chasing – they paled in comparison to this simple moment of family bliss.
Don’t get me wrong, I’m proud of what I’ve achieved in business.
But if you asked me to choose between another successful launch and another evening like this?
Well, pass me the ice cream and cue the interpretive dance. I know where my heart truly lies.
The Questions We Need to Ask
Now, don’t get me wrong. I’m not about to sell all my businesses and become a monk.
But this experience with Derek has shaken me to my core…
When I was a Personal Trainer, I’d tell my clients that “one of the best fat loss exercises is running from your problems.” This usually got a chuckle, maybe an eye-roll, from the more serious gym-goers.
After years of sprinting away from my issues, I’ve got to say – my emotional cardio is off the charts.
Olympic-level stuff. I could outrun Usain Bolt if you put my deepest fears behind me. But here’s the thing about constantly running – it’s exhausting. And I’m not just talking about the physical toll.
This kind of bone-deep, soul-crushing exhaustion makes you want to collapse on the spot and question every life decision you’ve ever made.
And trust me, as a guy who once thought the solution to all life’s problems was “earn more,” it’s taken more “healers” than you can poke a stick at, a wide variety of psychedelics, and hours of therapy for me to dig deep to hear the answers that are truest to myself.
Here I am, trying to piece together the ultimate life puzzle. I’m trying to put together something practical and useful that lets me chase my goals and dreams but keeps me in check. I want to make sure that every target I set, every achievement I chase, everything I desire—it’s all in integrity with who I really am, not just who I think I should be.
So here on the plane are the questions I’ve been journaling on…
- Why do I want this? Understanding the “why” ensures that our desires stem from a place of authenticity rather than external pressure.
- Who do I have to become to achieve this? Every pursuit requires growth. This question ensures that your goals are about evolving into someone better, not just acquiring something.
- What am I willing to sacrifice? Desires come with a cost. This helps you weigh the true worth of your pursuit.
- How will this contribute to my overall happiness and fulfillment? It forces you to consider the long-term impact on your well-being.
- What if I fail? Failure is part of any journey. This prepares you for setbacks and builds resilience.
- Who am I doing this for? Clarifying this helps avoid living someone else’s version of success.
- What would my life look like if I didn’t pursue this? Assess the potential regret of inaction.
- How does this align with my values? Ensures that your goals are in harmony with your principles.
- What will this teach me? Beyond tangible results, every pursuit offers lessons. This question keeps you focused on the journey, not just the outcome.
- Is this part of a bigger picture? Helps you stay focused on what truly matters in your life vision.
The Bullshit We Tell Ourselves
Now, here’s where it gets tricky…
It’s one thing to ask ourselves hard questions about what we want in life, it’s another thing entirely to answer them honestly. And let me tell you, I’ve come to realize I’m a master bullshitter – not to others, but to myself.
I recently stumbled upon this fascinating concept from philosopher Harry Frankfurt about the difference between lying and bullshitting. In his essay On Bullshit, Frankfurt argues that while a liar knows the truth and deliberately hides it, a bullshitter is indifferent to the truth, saying whatever suits them at the moment.
And boy, did that hit close to home.
I started to see how I’d been bullshitting myself for years. I’ve been telling myself I want things because they’re expected or admired, not because they align with who I am. Like that time I convinced myself I needed to launch yet another coaching program after selling my last company because “that’s what successful entrepreneurs do.”
It turns out that sometimes less is more, even in business.
In our quest to align our desires with our true selves, there’s a subtle but dangerous trap: self-deception.
When we bullshit ourselves, we blur reality, convincing ourselves that we want things for noble reasons when really, we’re just trying to fit into someone else’s definition of success.
This self-deception is comfortable, like a well-worn pair of shoes. It allows us to avoid the difficult work of deep self-exploration and settle for surface-level answers that fit neatly into social expectations. We can keep running on the hamster wheel of achievement without ever stopping to ask if it’s taking us where we really want to go.
But the cost of this self-deception is high. It’s the price of a life that may look successful on the outside but feels hollow on the inside. It’s waking up one day and realizing you’ve climbed to the top of the ladder, only to find it’s leaning against the wrong wall.
I’ve had to face some hard truths about myself. I’ve had to admit that some of my goals were more about impressing others than fulfilling myself. I’ve had to confront the fact that I sometimes chase success not because it brings me joy, but because it keeps me too busy to deal with deeper issues.
Breaking free from this self-deception isn’t easy. It requires a level of honesty with ourselves that can be uncomfortable, even painful. But it’s necessary if we want to live a life that’s truly authentic, truly ours.
So now, every time I set a goal or chase an achievement, I force myself to pause and ask: Is this really what I want, or am I bullshitting myself again?
It’s not always easy to answer, but it’s always worth asking. Because at the end of the day, the person we most need to be honest with is ourselves.
And I dont say this lightly.
When you say you’re going to workout… and you don’t.
When you say you will do anything… and you don’t.
It’s the reputation you have with yourself that gets tarnished.
When you didn’t do that extra rep int he gym…
When you said “ok, one more” when your friends were having a beer…
When you didn’t say “I love you” when you had the chance…
That’s sloth and torpor masquerading as self-love.
It whispers to you, “you deserve it, it’s ok”.
When in reality…
You don’t deserve it.
Not if you want to achieve the things you’ve not attained yet.
It’s the reputation you have with yourself that matters.
Because if you can’t trust yourself.
Who can you trust?
The Paradox of Growth and Contentment
Don’t get me wrong, I haven’t gone soft. I still believe in pushing boundaries and achieving great things.
But I’m learning that the real art of living – and business – lies in balancing the desire to grow with the ability to be content. And sometimes, the most profound lessons come from the most unexpected places.
I remember this one client vividly.
Let’s call him Mike. Owner of an 8-figure coaching business, the kind of success most entrepreneurs dream of. Our first meeting was on zoom, and his background was a view that screamed ‘I’ve made it.’ Mike sat upright, impeccably dressed, but with dark circles under his eyes that no designer suit could hide.
We dove into the numbers, and on paper, everything looked great. Revenue was up, client retention was solid, the team was growing. But as we went through KPI after KPI, I could feel the tension radiating off Mike.
His responses became clipped, frustration evident in every word.
“Look,” he finally snapped, pushing away from the table, “the numbers are fine. But it’s not enough. Do you know what James is doing?” He mentioned another coach in the industry. “His business grew 40% last quarter. We’re barely hitting 15%. We’re falling behind.”
I let the silence hang for a moment, watching Mike stare out the window at the city below. In that moment, I saw beyond the successful entrepreneur to the man beneath – tired, stressed, and somehow lost despite all his achievements.
“Mike,” I said gently, “can I ask you something? Why did you start this business in the first place?”
He looked at me, confused. “What does that have to do with anything?”
“Humor me,” I replied.
What followed was a conversation that stretched far beyond the Google Calendar invite suggested. We abandoned the spreadsheets and KPIs and just talked.
About his passion for helping people transform their lives. About the rush he felt when a client had a breakthrough. About the dreams he had when he first started, dreams that had somehow gotten buried under the relentless pursuit of more.
As the call wore on, Mike’s demeanor changed. The tension in his shoulders eased, and for the first time, I saw him smile – really smile. “You know,” he said, “I haven’t thought about this stuff in years. I’ve been so focused on the numbers, on beating the competition, that I forgot why I even started.”
Then, I couldn’t help myself. With a slight smirk, I leaned back in my chair and casually dropped the bomb:
“You know, Mike, Peter Thiel once said, ‘Competition is for losers.'”
The look on Mike’s face was priceless – a cocktail of confusion, offense, and curiosity all rolled into one. His mouth opened, then closed, then opened again, but no words came out.
And that’s when I deployed my secret weapon: silence.
That was the turning point. Over the next few months, we didn’t just work on business strategies. We worked on reconnecting Mike with his purpose, his values, his authentic self. We redefined what success meant for him – not in comparison to others, but in alignment with his own vision.
The real key to success in business and life isn’t about outperforming others or hitting arbitrary benchmarks. It’s about running your own race. It’s about building a life and a business that aligns with your values and fulfills you on a deep level. Because when you’re true to yourself and operate from a place of authenticity rather than comparison, that’s when you win.
Success without fulfillment is just a gilded cage. But you find true success when you align your goals with your values and build a life that resonates with your authentic self. That’s when you win the only race that matters – your own.
The Power of Wanting Less
As the plane descended, I felt a strange sense of peace wash over me. I realized that happiness isn’t about having more or achieving more. It’s about wanting less and appreciating what you already have.
On one side, you’ve got the relentless pull of ambition, that voice in your head saying, “More abs! More zeros in the bank account! More!” It’s like your inner drill sergeant had a baby with a motivational poster.
Conversely, there’s this radical idea of being content with what you have. Of looking at your life and thinking, “You know what? This is pretty damn good.”
The way I see it now…
What if you didn’t have to choose?
What if the real art of living is in holding both these ideas at once? It’s like being able to pat your head and rub your belly at the same time, but for your soul.
It’s the holding of this tension where I feel my best.
We’re told to strive, to push, to want more. It’s the fuel of capitalism, the backbone of self-help books, the siren song of social media. “You can be more! Do more! Have more!” the world screams at us. And part of us… Responds with a resounding “Yes!”
Wanting less isn’t about denying this part of ourselves. It’s not about suppressing our ambitions or pretending we don’t care about status. That’s just another form of self-deception, and trust me, I’ve been down that rabbit hole.
No, wanting less is about something far more profound. It’s about holding the tension between these opposing forces. It’s about acknowledging our desires for growth and recognition while simultaneously embracing a deep, soul-level contentment with what is.
Imagine for a moment that you could want what you have as much as you have what you want. Sit with that for a second. Feel the weight of it.
This is the art of wanting less. It’s not about resignation or settling. It’s about finding that exquisite balance point where gratitude meets ambition, where contentment dances with growth.
It’s like that moment when you’re in the gym, pushing your limits. There’s the burn, the desire to stop, to retreat to comfort. But there’s also the exhilaration of growth, of becoming more. The magic happens when you can hold the pain and the potential in perfect tension.
That’s what we’re aiming for in life. To be able to feel the pull of our ambitions, to acknowledge our desire for status and growth, but to simultaneously be so deeply grateful for our current reality that we wouldn’t trade it for anything.
And what I’ve found most interesting is…
When we master the art of wanting less, something magical happens. We become more powerful, more effective, and more alive than ever before because we’re no longer driven by lack or the gnawing fear that we’re not enough. We’re driven by love, gratitude, and the pure joy of existence.
From this place, growth becomes not a desperate grasping but a natural unfolding.
Status is no longer a craving.
We can pursue our goals with passion and intensity but without the crushing weight of need.
So…
What if we could see that everything – the joy and the pain, the triumphs and the failures – is exactly where it needs to be?
Can we hold the paradox of wanting to grow while knowing we’re already complete?
Grasping at nothing.
Pushing nothing away.
Just realize everything is in its own place.
And everything is all there is, in each moment.
Isn’t everything enough?