The ink wasn’t even dry on the deal to exit my company when the question started coming from all angles. We still had a six-month mountain of due diligence before we would ever see a dime. But that didn’t stop everyone – friends, investors, family, everyone – from saying the same thing:
“Congrats! I can’t wait to see what you do next.”
I would nod and accept the congratulations with a wry smile. The kind that says, “Yep. I’ve got it all figured out.” But I most certainly did not have it all figured out. Internally, my stomach would turn and I would have a mini-panic attack every time someone said it. Next?! This was really hard. Now I had to create something bigger and better?
And then, after the panic, the icy hand of fear would grip my heart. What if this is the biggest thing I ever do? What if I got lucky? What if I’m a one-trick pony and people find out that this was all sleight of hand and that I really didn’t deserve this?
The fear would give way to dread. What if I don’t have another good idea? What if it doesn’t work? Then, the death blow: what if I’m not as smart as I think I am?
The problem, of course, isn’t that the question of “what next” was a new one that I had never considered before. That wasn’t what was causing the panic. It’s that they were naming the question I’d already been agonizing over for months, long before we ever started courting buyers. It’s the insidious, unavoidable follow-up question that sneaks in behind the first one: I wonder if I should I sell my company? Then, boom, the dagger: what would I do with myself?
It was precisely this question that had been keeping me up late at night, staring at the ceiling. The truth is, I knew it was time to sell. The market had shifted. More capital had started flowing into the space, and with it, competition had increased exponentially. Our position as an aggregator was under existential threat as the once-inefficient market began to mature. That part was easy to see.
But I had a business partner and employees who were depending on me. Not just any employees, but my two younger brothers, whom I had hired during the gold rush era. We were selling at the peak, sure, but business had been slowing over the last eighteen months, and they were feeling it. I was the idea guy. I had to keep the band together. I hadn’t asked any of them about this; it just felt obvious. I had to figure out what we were all going to do.
Then there was the money part. Thirteen million dollars was a decent start, but long ago I had determined that I needed a hundred million dollars to be rich.
That first real windfall had come from going all in and betting on ourselves. We took big swings, and somehow they kept paying off. I knew that if I was going to turn thirteen into a hundred, I’d have to bet bigger and win bigger. But I wasn’t worried because this wasn’t a fake-it-until-you-make-it situation. I had evidence on my side. Every big bet I’d ever made had paid off.
So when a commercial property came across my desk in downtown Golden, Colorado, I didn’t spend much time asking whether I knew anything about commercial real estate. I knew deals. And this had all the right ingredients to be a great one.
It was in a prime location, and we had plans to modernize the building, add usable square footage in the basement, and increase the rent. We used a 1031 exchange to defer taxes and financed half of the $2.7 million purchase price with an additional $700k construction loan, making my personal cash investment roughly $550,000.
Three years later, we sold the building for $5.56 million. My portion of the proceeds came to $987,000, an eighty percent total cash-on-cash return and a 21.7 percent annualized return.
Now, at this point, you might be thinking that this was a homerun and that I am a legendary real estate investor. And you would be right—on paper. But let’s examine the hidden costs.
After taxes, my net gain was around $758,000. Had I skipped the 1031 I would have had around $450,000 of investable capital. Had I simply invested the same capital in the S&P 500 when we bought the property, I would have ended up with about $594,000 on the day I sold the building. The difference was $163,000.
For that extra money, I spent three years of my life managing this investment. Between sourcing the property, securing financing, planning, permitting, design, due diligence, managing construction and securing new tenants, I spent hundreds of hours. Worse, I got into a disagreement with my partners, and the building became a massive source of stress. I ended up not speaking to my best friend for nearly a year as a result. Not to mention the fact that my capital was locked up in a project in which I did not own the controlling stake, so I had no control over the timeline in which we sold.
As a reward for all of the hard work and stress, I earned an annual “salary” of $54,333. I could have invested in the S&P 500 and spent that time riding mountain bikes with my son or drinking coffee with my wife. At one point, less than two years after my life-changing exit, I found myself unclogging a toilet in a tenant suite, wondering how the hell I had gotten here.
So now to the obvious question: was it worth it? Not in a million years. I traded my freedom of time for what equated to a full-time job that didn’t even get close to paying the bills. The opportunity cost of this decision was staggering.
Perhaps I should’ve learned the lesson with the building. But I’ve always loved learning the hard way. The building was only the beginning. I was on a mission, a rocket ship ride to get to a hundred million by any means necessary, and instead of a warning sign, I took the building as confirmation that I was on the right track. I just needed to go bigger.
At this point, perhaps I could have stopped and asked myself: where did that number come from? If I had, my first answer might have been, “I don’t know.” It just seemed right. It was a nice round number (that’s how you know there’s no substance behind it) that seemed to be the threshold to private jets, private membership clubs, maybe even private islands. To me, nine figures meant access. It meant arrival. It meant I would finally belong to the room I had spent my whole life outside looking in.
I hadn’t calculated it. It was inherited. Maybe it was in the way I saw the rich oil men nod at the other members who had crossed the threshold, or maybe it was in the way they politely dismissed those who hadn’t. Maybe it was the time my mentor had told me about a guy who did a deal that got him a royalty that paid thirty-thousand dollars a month, who then promptly gave up to go play golf. He was a joke, and everyone knew it, pretending to be rich. The message was clear: don’t be that guy. School was in session, and I was taking furious notes.
When the notification that the wire hit my bank account that night on the Croatian island, had I simply pressed pause long enough, perhaps I would have come up with a better answer to why a hundred million was my number. But I didn’t pause. I couldn’t, not then. Because the pressure was already mounting. I had to build something new, something bigger. I had to deploy the capital I’d just earned into bigger bets. And I had to do all of that because I had accepted and internalized the default that was handed to me: more.
More sits at the center of the entire game. Underneath ambition, achievement, growth, more is the answer to every question we are taught to ask. From birth, our path is supposed to track up and to the right, forever. Think about it. Ever since you were a child, everything you have ever accomplished, earned, or completed, there was a new goal, a new target that appeared immediately after. What’s next isn’t just the question that I was facing after my exit, it’s the question we all face, all day, every day.
When we win a gold medal or a championship, we are immediately expected to start defending the title. A champion doesn’t win once; a champion repeats. When we reach a business milestone, we barely look up before we remember: if you aren’t growing, you’re dying.
The problem with more is that it’s insatiable. It doesn’t allow us to catch our breath because it’s designed that way. We move the goalposts because the system is designed to keep them moving.
This is the dirty secret that everyone knows, but no one says out loud. When you finally climb the mountain of success, achieve the goal, get the dream job, build the company, win the medal, get the money, whatever it is you set out to do, the answer is always the same: you are still the same person you were the day before. It doesn’t feel the way you think it’s going to feel. After the ephemeral high of the celebration fades (and it fades fast), winning didn’t make you whole.
Consider this: you have already reached a goal you said would make you happy. So why didn’t it?
But before you had a goal that failed to deliver, you had a moment that did.
Mine came at sixteen. I was barreling down the road, windows down, wind blowing through my hair. The song on the radio was perfect, and the sun caught the windshield just right. The world was mine.
Now, think back to a time when you were younger, before all the responsibilities, when everything just seemed right somehow. The details matter less than the felt sense of the experience. Close your eyes if you need to, but allow yourself to inhabit the sensation of the memory.
In that moment, you were free.
And, in that moment, do you remember how much money was in your wallet? Do you remember having any money in the bank?
Of course not. Because money isn’t wealth. Wealth is freedom. And freedom is a feeling.
That feeling, the effortless, full-body sense that nothing was missing, didn’t come from achieving something. It came from being completely present in your own life, with nothing deferred and nothing conditional.
So why have you spent every moment since then trying to earn your way back to a feeling that you once had for free?
The answer, for most of us, is that somewhere between that car ride and now, someone handed us a scoreboard. Work hard in school so you can get good grades and get into the right college. Graduate at the top of your class, so you can get the right job afterwards. Start your own company, because you can’t make enough money as an employee. Scale the company, because that’s what companies do. Always growing, always building.
Of course, there is a natural arc to life. But when was the last time you actually stopped and asked: what is all the more for? Whose game am I playing? What does success actually mean – to me?
All of these lead to the biggest question of all: what is wealth?
If you were to strip away all of the cultural norms, programming, standards, and inherited definitions of success, what would you be left with? What is it all for? What are we actually trying to solve?
You already know the answer. You felt it at sixteen, or whenever it came for you. I wasn’t solving for anything that day in the car, and neither were you in your version. You weren’t optimizing, or planning, or managing outcomes. You were just there, in the moment, fully alive, fully present. That is wealth. The feeling itself, the aliveness, the sense that nothing is missing. Wealth, at its essence, is a sense of freedom.
A life of true wealth is multidimensional, meaning that felt sense of freedom is experienced across different domains. One isn’t enough, especially if it comes at the expense of others. This is why optimizing solely for money leaves us empty, and often poor in the areas that matter more.
The pursuit of cultivating multidimensional wealth is the mechanism that actually delivers on the promise society told us the money would fulfill. Being rich across dimensions is the recipe for a life well lived. But it only happens by design, not by default. The reason there are so many unhappy financially rich people is because we’re not taught how to translate success into happiness.
Another reason wealth across multiple dimensions is critical is because it makes us antifragile. If your career is in a tough season but you have your health, relational, and spiritual wealth, it might still be hard, but it won’t be shattering to your self-worth. The longest-running study of human flourishing, Harvard’s eight-decade Study of Adult Development, found that the single biggest predictor of how happy people were at the end of their lives wasn’t financial wealth or career success. It was the quality of their relationships. If you aren’t naming and accounting for the other dimensions, difficulty in a single area becomes existential instead of manageable.
The first step is choosing the dimensions yourself. Otherwise, you’ll just be trading one inherited definition for another. Think of the areas of your life that matter most to you, the pillars upon which you build your version of a rich life. You may find yourself listing many; I like to condense them to between four and six. For example, my chosen dimensions of wealth are health, relationships, time, mind, and soul.
Notice that money is not on my list. That’s intentional, because money itself is merely a store of value. Think of money as a battery, used in service of powering the dimensions of true wealth. Money is a useful tool, but it can’t do the work for us.
We can spend money on gadgets and supplements, but to be healthy, we have to move our body. We can buy experiences with friends, but money can’t create the feeling of being seen for who we truly are. We can buy back time by outsourcing tasks, but it can’t guarantee we spend that time wisely. We can buy peace of mind when it comes to resources, but it can’t set us free from suffering. Only we can do that.
A helpful frame for choosing your dimensions is to ask whether two or more related areas can roll up into a single more comprehensive dimension. Fun and adventure matter to me, but they’re already living inside relationships, time, and soul. Naming them separately would be tracking the same wealth three times.
This isn’t meant to be a one-shot exercise. When you have your initial list, I encourage you to sit with it and continue to revisit until the list feels true. Also, keep in mind that the list might shift over time. Years ago, I initially had four, but as my spiritual path deepened over the last decade, I decided to give it its own dimension. That’s the natural expression of how our life actually unfolds.
Once you have your dimensions, the next step is to define what they mean to you. The inclination might be to create an exhaustive definition, but we’re going to resist that temptation. Instead your definition should act as a litmus test, one that allows you to know immediately if you’re on the right track. You’ll know your definition works when you can answer instantly.
The definition for my health dimension is radically simple: snowboard when I’m eighty. But the simplicity is doing some heavy lifting. To be able to snowboard when I’m eighty, that means I need a body that moves freely, that’s strong enough to perform, and a cardiovascular engine that powers the movement. It also means I must be free of disease and maintain high cognitive function. Having a specific desired outcome enables me to design my health routine with precision. I have to work on mobility, strength, and cardio in equal proportions. I have to eat a diet that will keep me free from lifestyle diseases. The specificity of my definition yields clarity through which I can filter my decisions.
The clear desired outcome also gives me information about what not to do. The modern health landscape is overloaded with latest and greatest protocols. If you tried to follow all of the advice, your morning routine would take all day. But I don’t need to concern myself with endless optimization to snowboard when I’m eighty; I need to get the basics right, be consistent over time, and let the rest go.
Because wealth is a feeling, your dimensions of wealth should focus on how you want to feel. Ask yourself: how will you know you are rich in that dimension? When I imagine snowboarding when I’m eighty, I can imagine what it will feel like to be out on a crisp winter powder day. While I might be moving a little more slowly than I do now, my body knows the sensation I get from the experience. It’s an embodied expression of wealth.
So the real question is: how can I feel more free, more of the time? How do I cultivate this felt sense of freedom across the dimensions that matter?
This is precisely the question I wish I had asked that night in Croatia. It took me many years and a lot of pain to finally start from first principles and build the life of my dreams.
The building disaster was an example of solving for the wrong metric. I was chasing financial returns above all else, and as a result, I sacrificed my time, my peace, and my freedom on the altar of more. From that perspective, the building was a terrible investment.
But let me tell you about the best investment I’ve ever made. For two years, my wife and I poured ourselves into creating our dream home. I spent upwards of 20 hours a week overseeing every detail, essentially making it a part-time job. And it was one of the best experiences of my life. The sense of pride that I feel in knowing the painstaking care that went into every detail is indescribable. Our house is routinely described by friends who come to visit as the “coolest house they’ve ever been in.”
Our home has become so much more than a place to live and work. It’s a gathering place where we host monthly dinners that bring together a variety of founders, musicians, artists and athletes. It’s where entrepreneurs and visionaries from around the world come to connect. It’s where I hold my transformative retreats. The energy of the space itself has become a catalyst for growth, both for us and for everyone who enters.
Was it the most financially lucrative investment of my career? Not even close. But in terms of return on happiness, nothing else comes close. I wake up every morning in a space that reflects my values, fuels my creativity, and supports my purpose. That feeling is worth more than any amount in my bank account.
What if, instead of optimizing for return on investment, you started to design your life with a new metric: Return on Happiness? What would happen, if you asked of every dollar, every career decision, every single moment: does this get me closer to the life that I want to live?
Instead, we often do the exact opposite. We put off our life in the present to serve some imaginary finish line when we can finally start living our life. The five most dangerous words we tell ourselves are: “I’ll finally be happy when.” We all have a version of this. Maybe it’s a monetary goal – the “number.” Perhaps it’s when you make partner, or when the kids are grown, or when things finally slow down. Or maybe it’s when you finally exit, or retire – maybe then you’ll finally have the time to explore that hobby you’ve been putting off or spend quality time with your partner.
The trap isn’t the desire itself; it’s perfectly human to imagine a future state that is better than the present. There’s nothing wrong with wanting your life to be easier, wanting more abundance or recognition. The trap is making that desire a condition for being alive in your own life right now. It’s outsourcing your permission to live to a future event that hasn’t happened yet.
The problem with conditional happiness is that someday never comes, because when it does, we’ve already proven that we’ll just move the goalpost.
The antidote to putting off your life until someday isn’t giving up on your dreams. I’m not telling you to just be happy with what you have. It’s the exact opposite. It’s giving up on the idea that some external condition, whether it be a goal, achievement, or material possession will be the thing that finally makes you happy.
Being rich now doesn’t require you to love everything about your life as it is. The distinction is in embracing that all we have is the journey; it’s recognizing that the finish line is a fairy tale and that a great life is nothing more than a series of great moments strung together and compounded through time.
A founder in my coaching community walked into this realization without even realizing it. He had been laser focused on financial outcomes for the last thirty years, building a massive real estate private equity fund. When I asked him to write down everywhere he was telling himself “I’ll finally be happy when,” his list was long. He said he could have written for another twenty minutes.
He had a number in his head. A specific net worth that he believed would finally shut off the need. He wouldn’t say it out loud — even he knew it was ridiculous. But it had been running his life for three decades. Every morning for thirty years, he woke up clenched, uniform on, out the door to make money. Nothing would stop him from that goal. Even cancer wouldn’t stop him. When he was diagnosed with pancreatic cancer in 2021, he didn’t even tell anyone at his office. He would receive his chemotherapy on Friday and show up to the office on Monday morning, game face intact, refusing to be slowed on his quest.
When I asked him to go deeper, to get really specific on the feeling that he was imagining that reaching the number would finally provide, he got quiet for a moment. Then he named it: abundance. He’d grown up in scarcity, literally on the wrong side of the tracks, and he was determined to end it, for himself and for his family. He knew logically that the number was absurd, that he had passed “abundance” long ago. His net worth was well into the mid-eight figures. He knew that the abundant feeling could happen far earlier than he’d been telling himself. He knew all of this logically. But still, every morning, he woke up clenched, white-knuckling his way through life.
Then something shifted. He said that while he was writing, a subconscious thought had popped into his head, seemingly out of nowhere.
He was head over heels in love with his thirteen-year-old daughter.
Every single interaction with her was mind-blowing to him. He couldn’t believe he had this person in his life. He’d had seven minutes with her that morning before the call, just seven minutes, and he described it as pure bliss. Even though she was a thirteen year old girl, not an easy time for most parents, every moment he had with her was extraordinary.
And then, he said the thing that broke everything wide open: “I actually need the bandwidth and the lack of pursuit of another dollar in order to experience it.”
That realization is the whole game. He had spent thirty years chasing an abstract feeling that was sitting across from him at the breakfast table. The only thing blocking his access to it was the belief that it was somewhere else. He didn’t need a single dollar more to feel what he’d been working his entire life to feel. He needed to stop long enough to notice it was already there.
What if everything you were chasing were actually right in front of you – like your eyelash, too close to even see, but there all along?
When we start to question the game itself, we start to see through the illusion. Money no longer feels like the ultimate prize or the source of our worth. It becomes what it always was: a tool, a mirror, a current flowing through our lives. The frantic striving, the keeping score, and the endless comparison all begin to dissolve.
And in that dissolution, the deeper truth reveals itself: wealth isn’t something you can “get” by reading a book or hitting a number in your bank account. It’s something you live, moment by moment.