You’re Not Crazy. The System Really Is Screwing You

It’s 11:43 p.m.

You’re lying in bed again, staring at your phone. You’re not scrolling for entertainment. Instead, you’re running numbers in your head.

You checked your bank account an hour ago. Then your credit card balance. Then Zillow, because some small part of you still hopes maybe something’s changed.

It hasn’t.

That house you’ve been watching jumped in price again since last month.

You didn’t move. You didn’t upgrade the houses you’re looking at. You just got priced out.

Your chest tightens when you remember the car insurance auto-draft hits your account tomorrow. Your checking account is just below it.

Maybe the grocery store doesn’t run the charge yet. Maybe your paycheck clears early. Maybe nothing else hits in the next twelve hours.

You’re not broke. But you feel dangerously close. And worse, you feel like this has become normal. You’re not looking for answers anymore. You’re just checking for damage.

You flip over and stare at the ceiling, thinking about the five things you’ve had sitting in your Amazon cart for two weeks. Nothing extravagant, just shoes for your kid, a better backpack, and a winter coat—less than $200 total. But you still haven’t hit checkout.

You tell yourself it’s because you’re being smart. But deep down, you wonder if you’re losing the ability to hope.

You were told that the world worked a certain way. You'd be rewarded if you worked hard, stayed out of trouble, got the degree, and put in the time.

You’d be okay.

But something’s off. And it’s not just a bad month or a bad year. It’s not just inflation. It’s not just your situation. It’s the system itself.

And you’re not alone.

The Contract Changed. Quietly. Without Telling You.

Somewhere between the student loan paperwork, the promotions that came without raises, and the sixth time you moved because the rent jumped again, the staircase you were climbing started moving in reverse.

It used to be simple: Work hard → Make progress → Build something.

Now it’s more like: Work harder → Tread water → Watch it slip away.

They still say the right things. “Put your head down.” “Do the work.” “The economy is strong.” But look around: 73% of workers in America report struggling financially, and more than half believe they’re underpaid for what they do.

You feel it. In your bills. In your anxiety. In the fact that you now double-check your debit card before handing it to the cashier.

Not because you’re irresponsible.

But because you know your margin for error is razor thin.

You’re Playing by the Old Rules in a Game That Quietly Got Rewritten

Since 1978, CEO compensation has risen by over 1,000%. The average worker’s pay? Just 24%. Back then, CEOs made 21 times what the average worker earned. In 2023, it was 290 times.

You’re working longer hours, more connected, more efficient, and more productive than ever. But from 1979 to 2013, middle-wage workers saw just a 6% increase in real hourly wages. It’s unfair and demoralizing.

Even the one escape route people believed in—switching jobs—has dried up.

In 2023, job switchers saw median pay bumps of over 7%. By 2025, that’s dropped to just 4.2%. You’re working just as hard, for less reward, in a world that’s getting more expensive by the day.

The system is indifferent. It’s not rigged in a cartoonish sense—there’s no villain twisting a mustache. But it is stacked. Designed for frictionless wealth at the top and rising pressure at the bottom. It doesn’t hate you. It just doesn’t care if you win.

If you’re a saver like me, you get penalized through inflation. You get punished for loyalty through layoffs. You get priced out of stability while being told you should feel grateful for your job.

And here’s the most maddening part: You’re not asking for luxury. You’re not demanding yachts or private islands.

You’re trying to do everyday things, regular people things, like buying a home or taking a family vacation. Put your kid in karate lessons. You’re trying to live a version of normal that your parents achieved on a single income and with less education and less debt.

That’s not entitlement. That’s erosion.

The problem is that you’re trying to play a game that no longer exists. That’s why it feels like you’re losing even though you’re doing everything right.

You were sold the meritocracy pitch. Work hard, and you’ll be rewarded. Stay patient, and your moment will come. Build a stable life, and eventually, you’ll feel safe.

Instead, you feel exhausted. You feel behind. You feel like every decision is a compromise between “what I need” and “what I can delay just a little longer.”

And the most painful part? You start to internalize it. You wonder if maybe it’s just you. Maybe you’re bad with money. Maybe you’re behind because you made bad choices. Maybe you just need to work a little harder, sleep a little less, hustle a little more.

But deep down, you know that’s not the answer.

You’re Not Crazy. The Math Really Doesn’t Work

The system that told you effort would equal progress is the same system that now charges thousands and thousands for an emergency room visit and $3,200 for a one-bedroom apartment in a mid-tier city.

It’s the same system that requires a master’s degree for entry-level jobs and then pays less than your rent.

It’s the same system that applauds resilience but punishes anyone who needs to stop and catch their breath.

You’re not crazy. You’re not lazy. You’re not broken.

You’re just playing a game where the scoreboard has been quietly disconnected from the field.

And I’m not just saying that as a bystander. I say that as someone who “made it.” I’ve played the game. I’ve beaten the odds. My net worth puts me in the top tier. I’m not struggling anymore.

But I’ve looked at this system from the inside, and I don’t buy the story either.

I know what it’s like to believe in that scoreboard. I once lost everything in the dot-com crash and spent years trying to rebuild my life on systems that couldn’t survive reality. I broke that cycle by rethinking everything I believed about wealth and rebuilding it from the ground up. (I explain how I did that here.)

This isn’t a call to burn everything down, and it’s not a motivational speech about bootstrapping and mindset.

It’s a simple acknowledgment that clarity is the first step to freedom.

You can’t fix a system you’re not allowed to name. You can’t reclaim dignity if you think it’s your fault you lost it. You can’t teach your kids how to thrive if you pretend this is all okay.

Because, frankly, it’s not okay… and I think you agree with me even if, like me, you made it.

You need to stop waiting for permission to think clearly.

In another piece, I wrote about the moment I realized that income wasn’t about effort—it was about proximity to revenue. That single shift changed how I worked, earned, and negotiated. (You can read that here.)

What Happens After the Wake-Up Call?

You rebuild. Not with hustle but with systems.

You create discipline before you have dollars. Structure before status. You start treating the money you have today like it matters.

If you want to know how I started acting like a rich person before I had money—how I built guardrails, systems, and friction to keep me disciplined—I broke down five of the exact (and wacky) moves I made. (That breakdown is here.)

Because you’re not lost. You’re just not where they said you’d be.

But now that you see the truth, you don’t have to stay there.

Double D

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