EP330: High Income Earners CANNOT Afford to Make This Mistake

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There has never—in the history of mankind—been a time where it’s easier to create wealth than right now.

But because it doesn’t feel easy, most people assume it must be hard.

But the truth is—it’s not that it’s hard…

It’s just hard for you.

And today, we’re going to show you why it feels so hard—even if you’re earning hundreds of thousands of dollars.
Yes, even high-income earners struggle.

We’re going to walk you through the four biggest roadblocks that keep most people from stepping into real wealth. And when we say wealth—we’re not talking about just getting by.

👉 We’re talking about millions.
👉 We’re talking about overflow.
👉 We’re talking about more than enough, so you can bless others without checking your bank balance first.

A few short years ago, we discovered a truth that catapulted us into owning and managing over $400 million in multifamily assets.

Not because we worked harder—But because we finally understood how money works.

Robert Kiyosaki said, “Wealth is your ability to live forward without working.”

So ask yourself:  If you stopped working today, how many days, weeks, or months could you maintain your current lifestyle?

That’s your real wealth.

➡️ Wealth is the ability to build a legacy that outlives you.
➡️ Wealth is the ability to give without limits.
➡️ Wealth is the ability to live in perpetuity, without punching a clock.

We’ve worked with thousands of investors—doctors, lawyers, tech execs—people making $200K, $300K, $500K, even over $1 million a year.  And yet, time and time again, we hear the same thing: “I still feel broke.”

You’re not imagining it.  You’re not alone.  And no—it’s not just lifestyle creep or bad budgeting.

It’s something far deeper—A set of invisible forces and traps designed to keep even high earners poor.

Today—we’re exposing those forces.  The real reasons the wealthy elite stay rich…

And why so many high earners still feel like they’re running on fumes.

But more importantly—We’ll give you the exact framework to break free and finally build the kind of wealth you can feel.

Here’s a shorter, more approachable rewrite of your content in Jenna Kutcher’s blog style—story-driven, warm, and real-talk honest:

The HENRY Trap: When Earning More Still Feels Like Not Enough

Ever hit a big goal—like a six-figure salary or a shiny new job title—and thought, “Why doesn’t this feel like I thought it would?”

Yeah. That’s the HENRY trap.

High Earner, Not Rich Yet.

It’s like you’re running full speed on a gold-plated treadmill. From the outside, it looks like you’ve made it. But inside? You’re exhausted, anxious, and wondering why it still feels like you’re barely keeping up.

And it’s not just you.

Even folks making $100K+ often say they’d need twice that just to feel comfortable. Because as your income grows… so does your lifestyle, your responsibilities, your taxes, and yes—your stress.

Let’s break it down:

You earn $100K a year.  Before you even see your paycheck, taxes take $27K.

▶️ Housing? Around $30K.
▶️ Car, gas, insurance? About $10K.
▶️ Groceries and eating out? $12K.
▶️ Healthcare, childcare, and the little things that aren’t so little? They all add up—fast.

In the end, your “high income” barely stretches to cover your life.  And that feeling of overflow?

Nowhere to be found.

So if you’ve been wondering why “more” still doesn’t feel like enough… You’re not crazy.

You’re just stuck in a system that was never designed to help you feel truly wealthy.

But the good news?  Once you see it, you can change it.  And that’s where the magic begins. 💫

The Asset Awakening 

Because this is what no one tells you: Wealth is a result. And results follow rules. Daniel Priestley said it best: “Income follows assets.” Read that again. Tattoo it on your mind: Income. Follows. Assets. So if you don’t like your income… Stop asking, “How do I make more money?” Start asking, “What asset do I have that income is following?” Because for most people? You are the only asset. Which means your income is tied to your hours, your energy, your calendar.

Own. The. Asset.

It’s like the difference between working at a gas station and owning the oil wells. The gas station worker trades time for money. The oil well owner makes money while they sleep, while they travel, while they’re doing anything else.

In this example owning an asset is like owning the oil wells.

Unfortunately, we learned this lesson the hard way… We used to run a successful fashion business. On paper? We were winning. Sales. Revenue. A growing team. But what happens when that business disappears?

What happens when the income stops… but the bills don’t?

That’s exactly where we found ourselves. Overnight, it all evaporated. We were worried about everything — the mortgage, our family, the future.

We remember lying in bed, staring at the ceiling, thinking: “Did we build a life that only works if we hustle forever?”

Because to us, money was just what showed up when we put in hours. Clock in. Earn. Pay bills. Reinvest. Repeat. That’s what we thought wealth was. Can you relate to that? 

But now? Wealth feels different. Not because life magically got easier… But because we learned how to build it.

And once we did, we couldn’t help but wonder — “Why did we ever think this had to be so hard?”

Here’s the truth: Income follows assets. So ask yourself: What asset do I actually own that income is following? Because the goal isn’t just to make more money. It’s to own enough income-producing assets that your lifestyle, your retirement, your kids’ future — all of it — is covered.

Once we realized that, everything shifted. Our mindset. Our priorities. Our future. We became obsessed with one thing: Assets. Assets. Assets.

But most people don’t talk about that. They talk about saving. Work. Earn. Save. Repeat.

That’s how most of us were taught. “Save it for a rainy day. Save for college. Save for retirement.” But here’s what the wealthy understand: Saving money isn’t a wealth-building strategy. Because inflation is slowly draining the value of every dollar you store. [Visual: Pool of money slowly evaporating in the sun labeled “inflation”]

Most people treat money like this big pool: “Look how full my savings account is!” But what if we stopped admiring the pool… and started asking: Is this water even moving?

That’s the real shift: Cash accumulation vs. cash flow.

And between the two? We’ll choose cash flow every single time. Because you could have a million dollars saved… But if nothing’s flowing in? You’re one business downturn or hospital bill away from disaster.

We’ll never forget the moment this all clicked. In 2017, we visited the Dead Sea in Jordan. It was beautiful — calm, peaceful. But here’s the eerie thing: nothing lives in the Dead Sea. Why? Because it has inlets, but no outlets. Water flows in… but nothing flows out. And that’s why it’s dead.

And it hit us: If your money has inlets but no outlets — if it just sits — it dies.

We’ve met people with 7-figure retirement accounts… Still worried about money. Because there’s no flow.

Cash flow is what brings life to your finances. It’s what gives you freedom now, not just someday.

If you can have both — cash flow and savings? Even better. But for us, the breakthrough came when we stopped hoarding money… And started building systems that kept it flowing long after we’re gone.

That’s the dream: Not just cash accumulation… but cash perpetuation. Generational wealth.

Phantom Wealth

Now let’s talk about something more deceptive than the IRS: Phantom Wealth. That illusion of wealth you see on a screen — stocks, 401k, your home’s “estimated value.” It looks impressive… but it’s not spendable.

We call it phantom wealth because it’s like a ghost — you can see it, but you can’t touch it.

Ask anyone who lived through 2008. Or 2020. Millionaires on paper became broke — overnight. I remember talking to a tech executive in 2022. His portfolio was worth $3.2 million in January. By October? $1.8 million. He didn’t change anything. Didn’t make any bad decisions. The market just… decided his wealth wasn’t real.

And here’s the cruel irony: While his phantom wealth was disappearing, his real expenses stayed exactly the same. The mortgage. The private school tuition. The car payments. All of it still due — in real dollars.

That’s because phantom wealth doesn’t make you free. It doesn’t buy you time. It doesn’t lower your anxiety. Only cash flow does that. Only real assets — like multifamily real estate — that pay you every month, no matter what the S&P does.

Look at this difference. On one side, you’ve got the stock market — up 30%, down 20%, up 15%, down 35%. Your “wealth” is a roller coaster you can’t control. On the other side? Rental income from real assets. Month after month. Year after year. Steady. Predictable. Spendable.

But Wall Street doesn’t want you to know this. Because they make money whether you win or lose. While you’re chasing paper gains, they’re collecting real fees. Management fees. Transaction fees. Advisory fees. They sell you the dream — and then they sell your fees.

Here’s what really gets me: They’ve convinced an entire generation that “investing” means buying pieces of paper. Stocks. Bonds. Mutual funds. But the wealthy? They buy buildings. Land. Businesses. Things that exist in the real world. Things that produce real income.

We learned this lesson when we met our first multimillionaire mentor. He drove a 10-year-old Toyota. Lived in a modest house. But owned 47 rental properties.

We asked him: “Why don’t you live like you’re rich?” His answer changed everything: “I don’t want to look rich. I want to BE rich.” “Rich is when my assets pay for my lifestyle — not my job.”

Want to stop being a product in their system? Then stop feeding the phantom. Start building real wealth.

The Comparison Prison

Let’s raise the stakes. Because this next trap isn’t just financial — it’s emotional. It’s the Comparison Prison. And for HENRYs, it’s brutal.

Picture this: You make $300K… but your coworker just bought a G-Wagon. You took your kids to Disneyland… but your college roommate took theirs to Italy. You live in a nice house… but your neighbor just installed a $50K pool.

The data shows nearly 49% of six-figure earners live paycheck to paycheck. Not because they’re failing. But because they’re trying to keep up. We don’t compare down. We compare sideways. Or worse — up.

And social media makes it worse. Every day, you’re bombarded with highlight reels. The vacation. The car. The watch. The house. But here’s what you don’t see: The credit card debt behind the vacation. The 84-month loan on the car. The second mortgage for the watch. The stress behind the smile.

We’ll never forget this conversation with a client. He’s a surgeon. Makes $400K a year. Came to us because he felt “broke.” I asked him: “What does your ideal life look like?” He pulls out his phone, shows me an Instagram post. “I want to live like this guy.”

So we did some research on “this guy.” Turns out, he was $2.3 million in debt. Filed for bankruptcy six months later. But the Instagram posts? Still looked amazing.

Here’s the irony: The people you’re comparing yourself to? They’re just broke at a higher level. They’ve got debt, stress, and leased happiness.

Think of it like an iceberg. Above the water? The lifestyle everyone sees. Below the water? The debt, the stress, the sleepless nights. 90% of what’s really happening is invisible.

But here’s what’s really insidious about the comparison trap: It’s not just about wanting more stuff. It’s about redefining what “normal” means.

When we lived in a middle-class neighborhood, a Honda Civic felt normal. When we moved to an affluent area, suddenly a BMW felt normal. Same income. Same family. Same needs. But different “normal.”

And that’s how they get you. Your reference group determines your spending. If your friends lease luxury cars, you feel pressure to lease one too. If your colleagues take European vacations, Disney World feels “cheap.” If your neighbors have designer everything, Target feels “beneath you.”

We call this Reference Group Inflation. And it’s more dangerous than regular inflation. Because regular inflation affects everyone equally. But reference group inflation? It’s personal. It targets your insecurities. Your need to belong. Your fear of being “less than.”

Here’s the brutal truth: Most high earners aren’t trying to get rich. They’re trying to look rich. And there’s a massive difference.

Getting rich means building assets that pay you. Looking rich means buying liabilities that cost you. One builds wealth. The other destroys it.

So ask yourself: Are you building wealth? Or are you building an image? Because you can’t do both.

The Invisible Forces

And now we go even deeper. Because it’s not just your spending or your mindset. There are forces at play you never saw coming. Forces that have fundamentally changed the game.

We call them the Big Three: Housing. Student Loans. Childcare. They’ve exploded in cost while wages stayed flat.

Let’s start with housing. A house that cost $100,000 in 1990? Now $377,000. That’s not inflation. That’s wealth extraction.

But here’s what’s really happening: In 1970, the median home cost 2.2 times the median income. Today? It’s 5.6 times the median income. So even if you’re making good money, housing eats up a massive chunk.

We were talking to a doctor in San Francisco. Makes $350K a year. Sounds rich, right? His mortgage payment? $8,500 a month. That’s $102,000 a year. Just for housing. After taxes, that’s nearly half his take-home pay.

Then there’s student loans. The average graduate now leaves school with $37,000 in debt. But for professional degrees? Law, medicine, MBA? We’re talking $150K to $300K in debt.

We know a lawyer who graduated with $280,000 in student loans. Her monthly payment? $2,800. That’s $33,600 a year. For the next 25 years. She’s paying almost $840,000 total for a degree that cost $280,000.

And here’s something few people realize: Student loan debt can’t be discharged in bankruptcy. It follows you to the grave. Literally. They can garnish your Social Security.

Then there’s childcare. The average cost of daycare in major cities? $30,000 per year. Per child. We have clients spending $60K a year on childcare for two kids. That’s more than many people’s entire salary.

But wait, it gets worse. These aren’t just big expenses. They’re fixed expenses. You can’t negotiate your mortgage down because you had a bad month. You can’t skip your student loan payment because you want to take a vacation. You can’t tell your kids they don’t need daycare this week because you overspent.

For most high earners, 70-80% of their income goes to fixed costs. Housing, loans, childcare, insurance, taxes. What’s left? Maybe 20-30% for everything else. Food, clothing, entertainment, savings, investing.

And let’s talk inflation. If you made $175K in 2021, you need over $200K today just to have the same purchasing power. That’s not progress — that’s survival.

But here’s what’s really insidious: The things that matter most — housing, healthcare, education — are inflating faster than everything else. While your TV gets cheaper, your mortgage gets more expensive. While your phone gets better, your health insurance gets worse.

The economy isn’t just unfair — it’s predatory. And if you’re not owning assets, you’re the asset.

The Inner Game

Even if you’ve beat the numbers game, you haven’t escaped the inner game. Because your brain is wired for hedonic adaptation. You hit a milestone. You feel good… for a second. Then your brain resets the baseline. And the hamster wheel starts again.

We call this the Horizon Effect.

Wealth always feels just one milestone away.

Remember when you thought $50K would solve all your problems? Then $100K became the magic number. Then $200K. Then $500K. Each time you hit the target, the target moved.

That’s why so many high earners keep chasing — but never feel wealthy. Because the finish line moves every time you get closer.

Here’s the psychological trap: Your brain adapts to your new normal within 6-12 months. The bigger house stops feeling big. The luxury car becomes just your car. The fancy vacation becomes expected, not exciting.

And suddenly, you need more to feel the same level of satisfaction. It’s like a drug tolerance — you need bigger hits to get the same high.

But here’s what’s really happening: You’re measuring wealth by accumulation instead of freedom. You’re asking “How much do I have?” instead of “How much do I need?”

We remember talking to a client who made $800K a year. He said: “I feel poorer now than when I made $80K.” Why? Because at $80K, he had simple needs and simple pleasures. At $800K, he had complex needs and expensive tastes. His income went up 10x, but his expenses went up 12x.

The wealthy understand something different: True wealth isn’t about earning more money. It’s about owning more assets.

And until you redefine what “earning” means to YOU — you’ll never arrive.

So how do you break free from a system designed to keep you running?

The same way we built $400 million in real assets while others chased phantom wealth. Here’s the exact framework:

1️⃣ Identify Your Freedom Number Forget net worth. That’s phantom wealth we already talked about. What matters is this: Can the assets you own cover all your monthly expenses?

Most people chase a net worth target — $1 million, $5 million, $10 million. But net worth is just a number on a screen. Your Freedom Number is different. It’s the monthly cash flow you need from assets to cover your lifestyle.

Here’s how to calculate it: Add up all your monthly expenses. Everything. Housing, food, insurance, entertainment, travel — everything. Let’s say that’s $15,000 a month. That’s your Freedom Number: $15,000 in monthly cash flow from assets.

Not $15,000 from your job. Not $15,000 from your business. $15,000 from assets that pay you whether you work or not.

Once your assets generate more than your Freedom Number? You’re financially free. You can work because you want to, not because you have to.

This is why net worth is a trap. You could have $2 million in your 401k and still be broke. Because that money doesn’t flow to you monthly. It just sits there, hoping the market doesn’t crash.

But if you own assets generating $15,000 a month? You’re rich at any net worth. Bec

2️⃣ Identify What Type of Assets You Should Own Not all assets are created equal. Some pay you monthly. Some pay you yearly. Some never pay you at all. The key is matching the right asset to your timeline and risk tolerance.

You’ve got stocks — volatile, unpredictable, but liquid. You’ve got bonds — stable, but low returns that barely beat inflation. You’ve got businesses — high potential, but require your time and expertise. You’ve got real estate — our personal favorite.

We pick multifamily real estate because it gets you there the fastest with the best risk-adjusted returns. Here’s why: Monthly cash flow from day one. Appreciation over time as property values rise. Tax benefits that can save you thousands every year. Inflation protection — as costs rise, so do rents. Leverage — you can control $1 million in assets with $200,000 down.

But here’s the real secret: Multifamily real estate is recession-resistant. People always need a place to live. During 2008, while stocks crashed 50%, our rental properties kept paying us every month.

The wealthy don’t just own assets. They own assets that produce predictable, growing income streams. That’s the difference between looking rich and being rich.

Now, to make this easier for you, we’ve created a free Freedom Formula worksheet that walks you through this entire discovery process. It helps you calculate your exact Freedom Number, compare different asset classes, and create your personalized wealth-building strategy. You can download it using the link in the description below — it’ll save you hours of research and guesswork.

3️⃣ Take Action and Deploy Today This is where most people fail. They learn the strategy. They understand the concept. But they never take action.

Analysis paralysis kills more wealth than bad investments ever will. You don’t need to find the perfect deal. You need to find a good deal and get started.

Here’s the truth: The best time to buy real estate was 10 years ago. The second best time is today.

Every month you wait is another month your money sits in a savings account, losing value to inflation. Every month you wait is another month you’re not building cash flow. Every month you wait is another month you stay trapped in the HENRY cycle.

We’ve seen too many high earners spend years “researching” and “learning” and “preparing.” Meanwhile, their less educated, lower-earning friends who took action are now financially free.

Don’t let perfect be the enemy of good. Start building your asset portfolio today. Even if it’s small. Even if it’s not perfect. Because assets compound over time. And time is the one thing you can’t get back.

The goal isn’t to own one perfect asset. The goal is to own enough cash-flowing assets that you never have to worry about money again.

The system wants you compliant. Wants you spending. Wants you just comfortable enough not to question it. But you’re not here to blend in. You’re here to build something different. So the question is: What are you going to do about it?

So if you would just do those four things, wealth doesn’t become a possibility—

It becomes inevitable.

And if you want to know exactly how we would build my real estate business from scratch— If I had to start all over again with nothing but the knowledge I have now—

Then we’ll see you next video.