Why "Later" Never Comes: Breaking Business Procrastination Chains
Oct 15, 2025I'm The Real Jason Duncan, back with another edition of Beyond the Grind – showing entrepreneurs how to stop being slaves to their own businesses and start building assets that run without them. 🚀
Have you ever noticed how the most dangerous chains are the ones we forge for ourselves?
Not the heavy iron shackles of external force, but the delicate threads we spin with a single word: "later."
"I'll start delegating next quarter."
"I'll hire that operator once this project wraps."
"I'll document our systems when things calm down."
Each "later" feels harmless – reasonable, even.
After all, the business is moving, clients are paying, deals are closing. What's the rush?
But Étienne de La Boétie (aka "E.B."), the French philosopher I've written about previously, understood something most entrepreneurs miss: voluntary servitude doesn't just happen through comfort and perks.
It happens through postponement.
The tyrant's most powerful weapon isn't the whip – it's convincing you that freedom can wait.
The Debt of Delay
Here's what E.B. understood that most entrepreneurs miss: every "later" is a form of borrowed time that compounds with interest.
When you say "I'll delegate next quarter," you're not just postponing a task – you're borrowing energy you don't have.
You're borrowing margin your family deserves.
You're borrowing valuation your future requires.
And like any debt, postponement doesn't stay static. It grows.
The client who "only trusts you" becomes more dependent on your personal involvement.
The decision that "only you can make" trains your team to stop thinking critically.
The system that exists "only in your head" becomes more complex and harder to extract with each passing month.
What feels like maintaining control is actually surrendering it – to the tyranny of urgent over important, to the illusion that tomorrow will somehow be less busy than today.
E.B. saw this pattern centuries ago: people don't just choose servitude through comfort – they choose it through delay.
The chains feel lighter when you convince yourself you'll remove them later.
But "later" operates under different rules than "now."
Later assumes you'll have more time, more energy, more clarity.
Later assumes the problems will be simpler and the solutions more obvious.
Later never comes because later doesn't exist.
The Power Drain of Indecision
Here's what's really messed up about putting things off: it's not just that you don't take action.
It's that your brain keeps chewing on the same decision over and over again.
I learned this the hard way. There's actual research on this – they call it "cognitive load."
This is when every unmade decision is like having an app running in the background of your phone, draining the battery even when you're not using it.
Think about it.
How many times have you had the same internal conversation: "Should I hire that operations manager or keep doing it myself?"
You probably had that exact debate dozens of times before you either hired someone or gave up on the idea.
That's not just procrastination.
That's torture.
Every unresolved decision becomes this little tyrant in your head, demanding attention but never giving you anything useful back.
You're not just avoiding action – you're volunteering to carry around the weight of unmade choices everywhere you go.
Here's what I've noticed about entrepreneurs who actually break free: they get comfortable making decent decisions quickly instead of perfect decisions eventually.
Napoleon Hill studied this pattern decades ago and found that successful people make decisions quickly and rarely change their minds, while unsuccessful people make decisions slowly and change their minds often.
He wasn't talking about being impulsive – he was talking about the ability to gather enough information to move forward without needing perfect certainty.
Not because they're reckless, but because they figured out that the mental cost of going in circles is almost always worse than the risk of being wrong.
When you finally just choose – really choose – something shifts.
All that mental energy that was stuck in the loop suddenly becomes available for actually doing stuff.
And here's the kicker: this is exactly how "voluntary servitude" stays so strong.
It's not just that the chains feel comfortable. It's that deciding to break them takes mental energy you've already burned up debating whether you should break them.
Breaking My Own Chains
I had to learn this lesson the expensive way.
Back in 2018, my business hit $1 million in EBITDA. I thought I was crushing it.
Then I decided to explore selling, and my business coach looked at everything I'd built and said, "Jason, your business is unsellable. It's too dependent on you."
That hurt. Bad.
But here's the thing – I'd been having the internal debate about making myself less essential for months. Maybe even years.
"I should probably start delegating more. I need to document our processes. I really should hire someone to handle operations."
Round and round, burning mental energy on the same conversations with myself.
My coach didn't give me new information. He just forced me to stop debating and start deciding.
That one decision – to actually take the feedback seriously instead of just thinking about it – changed everything.
It led me to develop what became the #ExitWithoutExiting method. It led to writing a best-selling book by that name, launching a podcast, coaching entrepreneurs all over the country, and eventually founding The Exiter Club.
But here's the irony: I'm in the coaching business – the very type of business most people assume can never be independent from the founder. I took that as a challenge.
Today, I only do one-sixth of the coaching inside my mastermind.
I can disappear for 30 days and the business keeps running because I've built a team of five other coaches, strong staff, an incredible assistant, a dedicated VA team, and my former apprentice who now handles all my emails and website backend.
Recently, my wife celebrated a birthday.
Because of the systems we've built, I was able to take the entire day off – no emails, no calls, no "quick check-ins" – and spend it completely focused on her.
Years ago, that would have been impossible.
The business would have demanded my attention, and I would have convinced myself that "just this once" I needed to handle something urgent.
That's the real payoff of breaking free from voluntary servitude: it's not just about business metrics. It's about being present for the moments that actually matter.
The shift didn't happen because I suddenly got smarter.
It happened because I stopped living in the mental loop of "should I or shouldn't I" and started making decisions that moved me toward freedom.
The Pattern Breakers
The entrepreneurs who actually escape this trap all have one thing in common: they stopped trying to figure it out alone.
Take Landon Dirickson, one of the members in my Exiter Club. He told me, "The Exiter Club encouraged me to hire employees and free up my time for higher-value activities."
That sounds simple, but here's what really happened: Landon had been debating whether to hire for months.
He knew he "should" delegate more.
He had the money.
He understood the theory.
But being in a room with other entrepreneurs who expected him to act on what he knew – that's what broke the mental loop.
It wasn't more information he needed.
It was accountability from people who refused to let him keep having the same conversation with himself.
Another member told me, "Just being in the room with people further ahead made me stop making excuses. I could see my own blind spots clearly for the first time."
That's the thing about isolation – it lets you live in your own mental loops indefinitely.
You can debate the same decisions for years because there's nobody there to call you on it.
But when you're surrounded by people who've already made similar decisions, who've already broken similar chains, the mental energy shifts.
Instead of burning brain power on whether you should act, you start focusing on how to act.
And here's what I've noticed: every entrepreneur I've worked with who actually achieved freedom had some version of outside perspective pushing them forward.
Sometimes it was a coach.
Sometimes it was a mastermind.
Sometimes it was just a trusted advisor who wouldn't let them stay comfortable.
The point isn't that you need me specifically.
The point is that "voluntary servitude" thrives in isolation.
When you're alone with your thoughts, "later" always sounds reasonable.
When you're accountable to people further ahead than you, later starts looking like what it really is – another word for never.
Why Taking Action Now Matters
Here's why I'm bringing this up: procrastination doesn't just delay progress – it compounds the problem.
And I've watched this pattern play out repeatedly.
Entrepreneurs spend months telling themselves they'll get serious about freedom "next quarter."
They'll start with fresh energy, clear priorities, all that good stuff.
But here's what actually happens: next quarter comes, and the same mental loops that kept them stuck are still running.
The same unresolved decisions are still draining their cognitive battery.
The same voluntary servitude that felt comfortable before still feels comfortable later.
Nothing magical happens when the calendar flips.
The entrepreneurs who actually change their trajectory make different choices.
Instead of coasting toward the future, they use the present to make the decisions they've been avoiding.
Not because timing is some special factor for transformation – but because they realize that "I'll start fresh later" is just another version of postponement.
And we've already established that later never comes.
If you've been debating whether to get serious help with building a business that doesn't need you every day, that mental debate is costing you energy right now.
Today. This week. Every week you spend revisiting the same decision instead of making it.
The question isn't whether you'll eventually need to break free from being the center of everything.
You will.
The question is whether you'll make that decision while you still have energy to execute it, or whether you'll wait until burnout makes the choice for you.
The cycle doesn't break itself.
The Way Forward
So here's what I'm suggesting: stop trying to muscle your way out of this alone.
Not because you're not smart enough or tough enough, but because isolation is exactly what keeps voluntary servitude alive.
When you're stuck in your own head, debating the same decisions over and over, you need perspective you can't generate by yourself.
Whether that's hiring a business coach, joining a mastermind, or just putting yourself in a room with entrepreneurs who are further ahead than you – the key is breaking the pattern of trying to figure it out solo.
I'm not saying you have to work with me specifically.
But I am saying that every entrepreneur I've seen actually build a business that runs without them had some version of outside accountability pushing them forward.
Because here's the thing about freedom: it's not a solo project.
The chains of voluntary servitude are strongest when you're carrying them alone.
They get lighter when other people can see them clearly and refuse to let you pretend they're not there.
If you've been going in circles on the same decisions about delegation, hiring, systems, or stepping back from daily operations, that mental loop will continue running.
Unless you make a different choice right now.
Don't continue the same patterns you've been running.
Make the decision to get the help you've been debating, and then use the energy you've been burning on indecision to actually build something that doesn't need you every day.
Your freedom is waiting on the other side of a decision you keep not making.
Words of Wisdom
"Plans fail for lack of counsel, but with many advisers they succeed." – Proverbs 15:22
The plans you've been making in your own head – to delegate more, to hire that key person, to finally step back from daily operations – those plans keep failing for a reason.
It's not because you don't know what to do. It's because you're trying to execute them without the counsel that makes success possible.
The entrepreneur who stays trapped in mental loops about the same decisions isn't lacking intelligence.
They're lacking perspective.
They're missing the advisers who can see what they can't see and push them past the comfortable delay of "later."
Wisdom isn't about having all the answers yourself.
It's about surrounding yourself with people who won't let you keep asking the same questions without acting on them.
Until next time...
Go beyond the grind,
The Real Jason Duncan 🚀