The Millionaire Down the Street Feels Like a Failure Too
I recently sat down with Mike Merkur for a conversation about business, podcasting, and what he’s learning as he gets himself into some pretty fascinating rooms. Mike is relatively new to podcasting, but he’s already finding himself in conversations with millionaires, billionaires, and incredibly successful business owners.
And he told me something that caught my attention. When these people get into a room together and start talking honestly, sometimes it starts sounding a little like group therapy.
One person will admit, “I’m carrying $100,000 in debt right now, and I honestly don’t know what next month is going to look like.”
And someone else will essentially respond, “You’re worried about $100,000? I’m carrying $250,000.”
These are successful people. People with businesses, money, experience, and accomplishments that, from the outside, might look like proof that they’ve figured out some secret formula the rest of us are desperately trying to find.
Yet behind closed doors, they’re saying some version of the same thing so many business owners are saying: "I don’t know what happens next."
As Mike was talking about how much he was learning from being around these people, I told him, “Let me let you in on a little secret. Every single one of them is figuring it out as they go.”
Yes, they may have more money than you. They may have decades of business experience. They may have built and sold companies, spoken on huge stages, created successful podcasts, invested millions of dollars, or accomplished things most of us would consider extraordinary. But there isn’t some magical financial threshold where you suddenly stop being a nervous-system-having human being.
In fact, $500,000 of debt doesn’t necessarily become less terrifying just because you’re a millionaire. It may actually become more terrifying because there’s more weight attached to every decision. There are more employees, more customers, more responsibilities, more moving pieces, and potentially a hell of a lot more money on the line. The numbers get bigger, but your nervous system doesn’t suddenly graduate into some advanced form of humanity where uncertainty no longer scares you.
The Millionaire Doesn't Have It Figured Out Either
I’ve spent about 20 years working as a sex therapist, which has given me access to a version of successful people that most of the world never sees. I’ve had incredibly financially successful people sit in my office completely devastated because they couldn’t figure out their marriage or sex life. They could manage employees, negotiate deals, make extraordinarily complicated business decisions, and earn more money than most people will ever see. Then they’d come home and have absolutely no idea how to talk to the person sleeping next to them.
I’ve had successful men crying in my office asking some version of, "How can I be this successful in business and still not know how to fix my marriage?"
The answer is actually pretty simple: those are two completely different hills. Being brilliant at business doesn’t automatically teach you how to manage conflict. Having money doesn’t teach you how to tolerate rejection. Leading hundreds of employees doesn’t necessarily teach you how to tell your spouse you’re lonely. And being married for 20 years doesn’t guarantee you’ll know what to do when the relationship you’ve built suddenly enters a completely new season.
The millionaire down the street is still figuring shit out too. He just might be figuring out different shit than you are.
I think we forget this because we tend to see other people’s outcomes while living inside our own learning process. We see their revenue, their house, their stage, their podcast, their company, their marriage anniversary, their book, or whatever outward marker tells us, "This person has made it."
What we don’t necessarily see is the Tuesday afternoon when that same person is staring at a bank account, a marriage, an employee problem, or some completely unexpected disaster thinking, "What the fuck am I going to do?"
There Is No Arrival
That’s the problem with the idea that eventually we’re supposed to arrive at some magical level of adulthood where we finally know what we’re doing. There is no arrival. There is just another hill.
Years ago, when I lived in Hawaii, I used to hike near Waimano Pool on Oahu. Part of the hike had earned the lovely nickname Cardiac Hill because climbing it made you feel like your cardiovascular system was filing a formal complaint. But the worst part wasn’t even how steep it was. It was the false endings.
You would climb and climb until you could finally see what looked like the top and think, "Thank God. I made it." Then you’d reach it, look up, and—son of a bitch!—there was another hill. I remember this happening three separate times. Three moments of relief where I thought I’d finally arrived, followed almost immediately by, "Are you fucking kidding me? There’s more?"
Welcome to life.
And business. And marriage. And parenting. And apparently adulthood in general.
You finally figure out marketing, and marketing changes. You finally understand social media, and consumer behavior changes. Get comfortable with your business model, and the economy changes. Learn the technology you’re using, and AI walks into the room and flips over the damn table. Learn how to parent a five-year-old, and suddenly they’re eleven. Figure out one season of your marriage, and your bodies change, careers change, families change, or life throws something at you that neither of you has ever experienced before.
Somehow, though, we interpret the appearance of the next hill as evidence that we failed to climb the last one correctly.
We didn’t.
There’s just another hill.
More Money Doesn't Eliminate the Nervous System
This is the part I think we really need to talk about in business. We often treat financial success as though it should somehow make people emotionally immune to uncertainty.
It doesn’t. A person running a $200,000 company may be terrified about making payroll. A person running a $2 million company may be terrified about making payroll for significantly more people. A person with $20,000 in debt may wake up at 3:00 in the morning thinking about it, while a millionaire carrying hundreds of thousands of dollars in business debt may wake up at 3:00 in the morning doing exactly the same thing.
The numbers change.
But a human nervous system is still a human nervous system.
In some cases, success actually creates new forms of stress because there is more to lose. More employees and customers depend on you. More money is moving. More people are watching. More decisions have consequences.
That’s why I don’t think the goal of becoming successful can be, "Eventually I won’t be scared anymore." That’s probably not coming.
A much more useful goal is becoming increasingly capable of learning, deciding, experimenting, recovering, and adapting while uncertainty is still present.
We're All Learning Faster Than Ever
And right now, there is a hell of a lot to learn.
AI is changing how businesses operate.
Technology is evolving constantly.
Social media today barely resembles the social media many of us originally learned to use for business.
Consumer expectations are changing.
Buyer behavior is changing.
Trust is changing.
Meanwhile, we’re trying to adapt to all of it while simultaneously running businesses, paying bills, managing employees, raising children, maintaining relationships, taking care of our bodies, and occasionally remembering that humans apparently require sleep.
Of course you don’t know everything. Nobody does.
The bigger problem begins when you interpret not knowing yet as evidence that you’re failing. That’s when a normal learning curve turns into a shame spiral, and shame makes learning much more expensive.
I understand this particularly well as a therapist, but unfortunately I also understand it because I do it myself. I can shame spiral with the best of them. When that happens, learning takes longer because instead of putting all of my energy toward understanding the problem, part of my brain turns against me: "I should already know this. Why haven’t I figured this out? Everyone else seems to know what they’re doing. Maybe I’m just bad at this."
When I'm in a shame spiral, I’m no longer simply learning something new. I’m trying to learn while simultaneously defending myself from the perceived threat that maybe I’m a failure. That costs time and energy, and when you’re running a business, it can cost actual money. You may hide a problem longer because you’re embarrassed, avoid asking for help because you think you should already know the answer, make a bigger and more expensive decision because you’re desperate to finally “fix” whatever you think is wrong (with you or your business).
Meanwhile, the millionaire you think has everything figured out may be sitting in another room admitting that he’s scared too.
Confidence Comes at the End
One of the strangest expectations we put on ourselves is believing we’re supposed to feel confident when we’re doing something new.
That’s backwards. Confidence usually comes near the end of the learning process, not the beginning. The learning curve looks much more like anxiety → awkwardness → familiarity → competence → confidence.
You don’t get to skip the awkwardness, uncertainty, mistakes, or the occasional experience of looking slightly ridiculous while trying something you’ve never done before. Then, just when you’ve finally become confident, you discover the next hill and get to become a beginner all over again.
That’s not evidence that you’re failing. That’s what growth actually looks like.
Who Are You Learning Around?
Maybe that’s one of the most valuable things Mike is getting from being in these rooms. He’s not simply getting access to wealthy people. He’s getting access to the truth about wealthy people. He’s getting to hear what happens when successful people stop performing success for one another and start admitting what they’re actually trying to figure out.
There’s tremendous value in that because imagine being in an environment where everyone pretends to know exactly what they’re doing. Nobody talks about debt. Nobody admits they’re scared. Nobody says, “I don’t know.” Everyone performs competence because being seen learning feels dangerous.
Now imagine sitting in a room where someone can say, “I’m carrying $100,000 in debt and I’m scared,” and instead of everyone recoiling, somebody across the room essentially says, “Yeah. Me too.”
Maybe their number is $250,000. Maybe their problem is completely different. But suddenly the struggle isn’t evidence that you don’t belong in the room.
The struggle is part of being in the room.
That’s what healthy learning environments can give us. Teams, mentors, colleagues, peer groups, communities, and conversations like the one Mike and I had can remind us that we aren’t uniquely defective because we haven’t figured everything out yet. We’re humans learning alongside other humans, and sometimes simply hearing a successful person say, “I don’t know what the hell I’m doing with this either,” gives everyone else permission to stop pretending.
The Millionaire Down the Street Feels Like a Failure Too
I think that’s what I wish more people understood. The millionaire down the street does not possess the secret adult instruction manual you somehow failed to receive. Neither does the billionaire. They’re learning too. They’re figuring out AI, customers, employees, debt, marriages, kids, their bodies, and themselves. They’re climbing Cardiac Hill just like everybody else.
Maybe they’re standing on a different section of it, or they’ve climbed a few hills you haven’t encountered yet, or they have resources, money, relationships, and experience that make certain parts of the climb significantly easier.
We don’t need to pretend those advantages don’t matter. They absolutely do. But none of those things eliminate uncertainty, vulnerability, fear, or the experience of reaching the top of one hill only to realize you’re a beginner at whatever comes next.
So perhaps the goal isn’t to finally become successful enough that you never feel uncertain again. Maybe the real competitive advantage in business, relationships, and life is becoming exceptionally good at not knowing yet.
Stay curious. Cultivate a beginner’s mind. Surround yourself with people who can tell the truth about what they’re learning. Test things, make mistakes, ask for help, and use your mistakes as information instead of turning them into evidence that you don’t belong here.
And the next time you look at somebody farther up the mountain and think, "God, they must have this figured out," remember that they may be looking at their own next hill thinking, "Are you fucking kidding me? There’s more?"
Yep. There’s more.
We’re all still learning.
