Real Freedom Was Never About Doing Whatever You Want
About this Episode
In Episode 374 of The Real Jason Duncan Podcast, the freest people Jason has ever met, no rules, no limits, nobody to answer to, were some of the most stuck people he’s ever met. This past week, just about everybody was celebrating exactly that kind of freedom. And it’s a lie.
Real freedom was never about doing whatever you want.
In this solo Wednesday episode drawn from his What’s Real newsletter, Jason unpacks one of the most seductive golden cages in the entrepreneurial world, the open road, the empty calendar, the no-limits lifestyle that looks like the best life going. And then watches what it actually does to a person.
He traces it through a sailboat keel, a grocery store jam study, a computer game with three shrinking doors, and an elementary school playground with no fence. And what he finds in all four places is the same truth. The thing fighting you hardest is often the only reason you can go anywhere at all.
In this episode, Jason covers:
The sailboat keel , why the part you can’t see is the only reason the boat goes where you want
Why cutting away every limit doesn’t free you , it turns you into a cork
The jam study from 2000 , why 24 choices produced a tenth of the action that 6 choices did
The shrinking doors experiment , why people burned money keeping options open they were never going to use
The fenceless playground , why kids bunched up near the building until the fence went up
Why keeping every door open and every iron in the fire is exhausting and not freedom
What Jason did when he quit sawing at his own keel , and what that looks like from an RV park in Eureka Springs, Arkansas
What Proverb 25:28 says about walls, cities, and self-control , and why the walls were never the prison
The right limits are what actually set you free. This episode will show you which fences to stop tearing down.
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👤 Who Is Jason Duncan? Jason Duncan is a serial entrepreneur, speaker, and coach who built and exited multiple businesses before dedicating his life to helping other entrepreneurs escape the golden cages they’ve unknowingly built for themselves. Known for his no-nonsense approach to business freedom, Jason hosts The Real Jason Duncan Podcast, where every Monday he interviews guests who believed a dangerous lie about business, money, or success and discovered the hard truth. Every Wednesday, he releases a solo audio edition of his What’s Real newsletter, exposing the lies most entrepreneurs are still living inside. Jason speaks on stages nationally, leads the XOS Coaches Summit, and runs The Exiter Club™, a community for entrepreneurs doing the hard work of building their way out of the business.
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The freest people I've ever met, no rules, no limits, nobody to answer to, were some of the most stuck people I've ever met.
This week, just about everybody's celebrating that exact kind of freedom.
Welcome to The Real Jason Duncan Podcast.
Today's episode is a Wednesday Special Edition. Every week I write a newsletter called What's Real? where I expose the lies most people believe and reveal the truths they were never taught. And every Wednesday, I bring that week's edition to you in audio, right here.
Because the most dangerous lies don't look like lies. They look like golden cages. They look like success. The most successful people are the most deceived, because the lies that trap them look like achievements. That's what this whole show is about.
On Mondays I sit down with somebody who believed one of those lies and discovered the truth the hard way. Wednesdays, like today, I bring you the Wednesday Special Edition. Either way, the mission is the same.
Go to therealjasonduncan.com/articles and subscribe for free to get the What's Real? newsletter delivered to your inbox every Wednesday morning before this episode drops. That's therealjasonduncan.com/articles - link is in the show notes.
This week's post is called "Real Freedom Was Never About Doing Whatever You Want."
I don't know about you, but I have never really understood how a sailboat works. I grew up around boats. A boat with a motor I get, you turn the key, you point the prop where you want to go, and off you go. But a sailboat? No motor, just a big sheet of cloth and the wind, and somehow the thing sails in almost any direction the captain wants, even straight into the wind. For most of my life that made no sense to me at all.
So a while back I finally looked it up, and what I found has stuck with me, because it turns out to be one of the truest things I know about freedom.
The secret to a sailboat is a part you can't even see, because it's underwater. It's called the keel. A long, heavy fin bolted to the bottom of the boat, sometimes nearly as tall as the mast is high. While the boat sails, the sail grabs the wind up top, the keel grips the water down below, and those two things fighting each other are the only reason the boat goes forward instead of just getting shoved sideways wherever the wind feels like pushing it.
Take the keel off to free the boat from all that drag, and you don't get a faster boat. You get a cork. It spins, it slides, it goes wherever the wind blows and nowhere you actually want to go. The part fighting the boat the hardest is the one thing letting it go somewhere the wind never intended.
And freedom works the exact same way. We figure the way to get free is to cut stuff away, strip off whatever's pushing against us. But a lot of the time, the thing pushing against you is the only reason you can steer at all.
This is the week the whole country throws freedom a party, and I love it. The flags, the cookouts, the fireworks. But the version of freedom most of us are toasting on the Fourth is the one that gets us into trouble. The no rules, no limits, nobody to answer to, do whatever you want whenever you want version. We treat that like the dream.
That's a golden cage. The gold is that shiny picture, the open road and the empty calendar and nobody in the passenger seat. It looks like the best life going. But watch what it actually does to a person. The guy with no limits doesn't get more done, and he doesn't get further. He drifts. He keeps every door open, walks through none of them, and calls it freedom right up until the day he looks up and realizes he hasn't moved in years.
I can tell you about that guy because I was that guy. For a long stretch my whole plan was to keep my options open. Don't go all in. Don't close any doors. Keep three or four irons in the fire so no single flop could ever take me down. It sounded smart. It felt like freedom. What it actually got me was a dozen half-running things and not one of them really alive. I'd sawed my own keel clean off and called the spinning freedom.
And it's not just me. The researchers have been poking at this for years. There's a famous study from the year two thousand where they set up a table in a grocery store handing out samples of jam. Some hours they put out six jars. Other hours, twenty-four. The big display pulled a bigger crowd, no surprise. But of the people who stopped at the twenty-four-jam table, only about three percent actually bought a jar. At the little six-jam table, around thirty percent did. Fewer choices, ten times the action. More options didn't free those people up. It froze them solid.
There's another one I can't shake. A researcher named Dan Ariely sat students in front of a computer game that paid real money. Three doors on the screen, and each one paid you when you went inside. But any door you ignored started shrinking, and if you left it alone too long, it disappeared. The smart move was obvious, find the best-paying room and just camp there. Instead, the students panicked. They burned click after click running back and forth keeping all three doors open, bleeding money the whole time, over options they were never going to use. Then the researchers changed the rules and said, any door that closes, we'll reopen it for free. Didn't matter. They still scrambled to keep every door open. It cost them nothing to let one close, and they still couldn't do it.
That's most of us. Running ourselves ragged guarding doors we are never going to walk through, and calling the exhaustion freedom. The gold is the lie.
I think about a schoolyard. Picture an elementary school right next to a busy road, and the playground out back has no fence. Every recess, the teachers see the same strange thing. The kids won't spread out. They bunch up near the building, away from the road, and that whole back stretch sits empty. All that open space, and the kids play small.
So the school puts up a fence. All the way around. And next recess, those same kids go tearing out to the far corners they wouldn't go near the day before, playing right up against the fence by the road, the very spot that used to scare them stiff. Nobody made the playground bigger. Not one inch. The fence didn't shrink their world, it handed them the whole thing. Because a kid who knows exactly where the edge is will run all the way out to it.
That's the keel again, just up on dry land.
So a few years ago I quit sawing at my keel and started building one on purpose. I built my business around my life instead of cramming my life into the scraps the business left over. I put a hard line around my work time and a hard line around my off time, and I guard both like they matter, because they do. Those lines are my keel. They're the reason any of the rest of it actually moves.
It's why, as I'm recording this, I'm parked in Eureka Springs, Arkansas, with my wife Kristie, our puppy Marcus getting into everything he can reach, and one of my motorcycles riding along in the back of the truck. This is not me doing whatever I want whenever I want. It's the opposite. This whole week only exists because the fences exist.
There's an old proverb that lands this whole thing in one line. Proverbs twenty-five, verse twenty-eight. "Like a city whose walls are broken down is a man who lacks self-control." A city with no walls isn't free. It's exposed. Anything that wants in just walks right in and takes what it likes, and the people living there never feel safe enough to build anything worth keeping. The walls were never the prison. They were the only reason the city could grow at all.
Read the full post at therealjasonduncan.com/articles. Link is in the show notes.
This whole thing comes down to one idea: the right limits are what actually set you free. And that's just as true with your money as it is with your calendar. Which brings me to this week's sponsor.
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It doesn't drop when the market drops, and it grows whether you're working or not. And when you need capital for an opportunity, you borrow against your own cash value, on your own terms, and the policy keeps growing as if you never touched it. It's a structure. A keel for your money. And the structure is exactly what gives you the freedom to move.
My financial advisor is Mark Willis at Lake Growth Financial. If you want to find out what this could look like for your situation, you can get a free consultation with Mark by going to therealjasonduncan.com/bankonyourself. That's therealjasonduncan.com/bankonyourself. Link is in the show notes.
Build wealth that serves your life, not the other way around.
That's a wrap on this Wednesday special edition. If today you finally saw that the fence you've been trying to tear down was the only thing letting you go anywhere, send this episode to one person who needs to hear it.
The gold is the lie.
As always, I am your host, The Real Jason Duncan, and Jesus is King.