I don’t know about you, but I’ve always been confused about how sailboats work. I mean, really, how does a sailboat go in one direction when the wind is blowing from the other direction?
Boats with motors and props, I understand. You turn the key, turn the engine on, you steer the prop in the direction you want to go, and it’s easy. I’ve owned a couple of boats in my life, grew up on boats. I understand that. But a sailboat doesn’t make any sense to me. There’s no motor – it’s just a big sheet of cloth and the wind, and somehow the boat is able to go in whatever direction the captain steers it. That has never made any sense to me.
Recently I took the time to look it up. I wanted to figure out how it actually worked. What I found is something that has more to do with freedom than I would have at first thought. As a matter of fact, when I started looking it up, I was just genuinely curious. Now I want to bring it to you here in this article because I think it has a lot to say to us about freedom.
For sailboats, the secret is what’s underwater… something that you don’t see at all. There’s something under that boat called a keel. It’s a long, heavy fin bolted to the bottom of the boat that sometimes can be half as tall as the mast the sail is attached to above the boat. While the boat is sailing, the keel digs into the water and makes sure that the boat isn’t pushed sideways. The sail grabs the wind, and the keel grips the water, and those two fighting each other are the only reason the boat is able to move forward instead of just getting blown wherever the wind goes.
If you remove the keel to “free” the boat from all the drag that the keel might otherwise cause, you don’t get a faster boat – you get a floating object that’s going to only go where the wind blows it. It’ll spin, it’ll go sideways, it’ll slide around, and it never goes where you want it to unless the winds happen to be blowing you in the direction you want to go (which is almost never. Am I right?).
What this tells me is that the part fighting the boat the hardest is the only reason it’s free to go somewhere the wind never wanted to go.
And freedom, if you think about it, works the exact same way. We usually figure the way to get free is to strip things away, take off whatever’s pushing against us. But a lot of the time, that very thing pushing against us is the only reason we can go where we actually want to go.
The Freedom We Celebrate This Week Is the Wrong One
This past weekend, the whole country threw a party for freedom, and honestly, I love it. I love the flags and the cookouts and the fireworks out over the lake. But the version of freedom we’re toasting on the Fourth of July is usually the one that gets us into trouble.
You know the one I mean. The freedom where there are no rules, no limits, and nobody to answer to, where you get to do whatever you want, whenever you want, and not a soul can say a word about it. We treat that like it’s the dream.
That’s a golden cage. The gold is that shiny picture of total freedom, the open road and the empty calendar and nobody in the passenger seat telling you where to go. It looks like the best life a person could ask for.
But look at what that life actually does to somebody. The guy with no limits doesn’t get more done, and he doesn’t get further down the road. He just drifts. He keeps every option open and commits to none of them, and he calls that freedom right up until the day he looks up and realizes he hasn’t actually moved in years.
I Spent Years Sawing at My Own Keel
I can tell you about that guy because for a long time I was that guy.
I’ve started more than a dozen businesses over the years. And for a good stretch there, my whole strategy was to keep my options open. Don’t go all in on one thing. Don’t close any doors. Keep three or four irons in the fire at all times, because if one of them cooled off, well, I had others. No single flop could take me down.
It sounded smart. It felt like freedom. What it actually got me was a life where nothing ever got all of me. A dozen things half running, not one of them really thriving, and me telling everybody, including myself, that I was free as a bird.
I wasn’t free. I was just spread too thin to get pinned down. I’d sawed the keel clean off and called the spinning freedom.
Real Freedom Has a Price, and It’s Your Options
And it isn’t just me. The researchers have been poking at this for years, and what they keep finding is that all those open doors don’t set us free. They freeze us.
There’s a famous study from back in 2000 by two psychologists named Iyengar and Lepper. They set up a little table in an upscale grocery store handing out samples of jam. Some hours they put out 6 jars. Other hours they put out 24. The big spread of 24 pulled in a bigger crowd, no surprise there. But of the people who stopped at that 24-jam table, only about 3 percent actually bought a jar. At the little 6-jam table? Around 30 percent did. Fewer choices, and ten times as many people actually bought something. (The breakdown is here.)
More choices didn’t free those shoppers up. It locked them up. A psychologist named Barry Schwartz wrote a whole book about this and called it the paradox of choice, and the same thing shows up everywhere they look, with chocolate, with retirement plans, even with online dating. Past a certain point, more options quit setting you free and start to freeze you solid.
Then there’s the one I can’t get out of my head. A behavioral economist named Dan Ariely sat a bunch of MIT students down in front of a computer game that paid them real money. Three doors on the screen, and every time you clicked into a room, you earned a little cash. Simple. But there was a catch. Any door you ignored started shrinking, and if you left it alone too long, it disappeared for good.
The smart move was obvious. Find the room that pays the best and just camp there. That’s it. Instead, those students panicked. They burned click after click sprinting back and forth across the screen just to keep the other doors from closing, bleeding money the whole time, over options they were never even going to use. (Ariely wrote about it here.)
Then the researchers changed the rules. Now a door that vanished could be brought right back, free, no penalty at all. Didn’t matter. The students still scrambled like crazy to keep every single door open.
Think about that for a second. It cost them nothing to let a door close, and they still couldn’t make themselves do it. It was never really about keeping the options useful. They just couldn’t stand to watch one shut. And that, right there, is most of us, running ourselves ragged guarding doors we are never going to walk through, calling the exhaustion freedom. The gold is the lie.
Then There’s the Schoolyard
There’s a picture that’s stuck with me for years, and it makes the same point without a single statistic.
Picture an elementary school sitting right next to a busy road. Out back there’s a playground, but there’s no fence around it, nothing standing between the kids and the traffic. And every recess, the teachers notice the same strange thing. The kids won’t spread out. They bunch up tight near the building, in the safe middle of the yard, and they leave that whole back stretch by the road sitting empty. The swings out there go unused. The far corners might as well not exist. All that open space, no fence, and the kids actually play smaller.
So the school puts up a fence. A real one, all the way around the property line.
Next recess, those same kids explode outward. They go tearing to the far corners they wouldn’t go near the day before. They play right up next to that fence by the road, the very spot that used to scare them stiff. The same kids who hugged the wall are now using every square foot of the place.
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. Take the edge away, and he never leaves the wall.
That’s the keel again, just up on dry land.
Real Freedom Lives Below the Waterline
So a few years back, 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 whatever scraps the business left over. I put a hard line around my work time and an equally hard line around my off time, and I guard both of them like they matter, because they do. Those lines are my keel. They’re the whole reason any of the rest of it actually moves.
It’s why I take real trips all year long, not the someday kind. Long, slow weeks in the RV with my wife. Hard, good miles on the motorcycle with my buddies. They go on the calendar months ahead of time, and the business keeps right on humming while I’m gone, because I built the thing to run without me hovering over it.
In fact, as I write this to you, I’m parked in Eureka Springs, Arkansas. Kristie’s here, our puppy Marcus is underfoot chewing everything he can reach, and one of my motorcycles rode out here in the back of the truck. This is not me doing whatever I want whenever I want. It’s the opposite of that. This whole week only exists because the fences exist. The keel is what set me loose. (It’s the flip side of what I wrote last week, when being your own boss turned out not to make anybody free.)
In my book, Exit Without Exiting, I write about a guy named James who figured this out way before I did. He built his company on purpose from the very start, and by year four the thing ran just fine without him in the building. So he spent his afternoons coaching his kid’s lacrosse team and actually made it to every game. It’s the same boat in the same wind, just with a keel. The very thing that looked like it would tie him down turned out to be what set him free.
Words of Wisdom
There’s an old proverb that lands this whole thing in one sentence.
“Like a city whose walls are broken down is a man who lacks self-control.” – Proverb 25:28
A city with no walls isn’t free. It’s exposed. Anything that wants in just strolls right in and takes whatever it likes, and the people living there never feel safe enough to build anything worth keeping. The walls were never the prison. The walls were the only reason the city could grow at all. Tear down every fence in your life in the name of freedom, and you don’t end up free. You end up as a city anybody can walk into and sack.
What To Do Now
So here’s what I’d do this week. Go find the keel you cut off, or the one you never bolted on in the first place.
Maybe it’s your off time, the time you never actually protect, so the work just leaks into every hour of it. Maybe it’s the work itself, with no walls around it, so it sprawls all over the place for years and never really arrives anywhere. Pick one. Build the fence back this week, even a small one.
And if the keel you’re missing is in your business, the one that would finally let the thing run without swallowing your whole life, then start there. I put together a free training that walks through exactly what to fix in your business before you ever try to step back or sell it. Go watch it at whattofixbeforeyouexit.com.
And if you’d rather just talk it through, one on one, you and me, book a call with me over at therealjasonduncan.com/talk. We’ll find the one fence that hands you the most freedom back.
– The Real Jason Duncan
