The 5-Year Mistake That Taught Me Everything
"Preparation" isn't preparation at all. It was procrastination dressed up in productive clothes.
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I spent five years getting ready to start.
Five years reading every book on entrepreneurship. Taking every course on marketing. Planning every detail of my future business. Creating elaborate spreadsheets. Drawing wireframes. Writing business plans.
I researched the perfect microphone for podcasting for six months. I studied content creation frameworks for a year. I planned my “content strategy” down to the smallest detail.
I became an expert on starting a business.
I never started a business.
Meanwhile, my friend Jake—who barely graduated high school—launched a pressure washing company with a $200 Craigslist machine and a beat-up truck.
His first website looked like it was designed by a blind person having a seizure.
His pricing was all wrong.
His customer service was amateur.
His equipment kept breaking.
But he had something I didn’t: customers.
Real money coming in. Real problems to solve. Real feedback to iterate on.
While I was perfecting my theoretical understanding of business, he was building an actual business.
Today, Jake owns three pressure washing crews and just bought his second rental property.
I was still optimizing my business plan.
The Lie We Tell Ourselves
Here’s the uncomfortable truth I had to face:
My “preparation” wasn’t preparation at all.
It was procrastination dressed up in productive clothes.
Every book I read, every course I took, every plan I refined—it all felt like progress. I was learning. I was growing. I was getting ready.
But I was really just avoiding the one thing that would actually move me forward:
Starting.
The ancient Greeks had a word for this: they distinguished between theoria (contemplation) and praxis (action). Aristotle understood that while thinking about virtue is valuable, you only become virtuous by acting virtuously.
You don’t become an entrepreneur by studying entrepreneurship. You become a writer by writing badly, not by perfecting your understanding of prose. You become confident by doing scary things, not by reading about confidence. You become anything by doing it badly first, then getting better.
But our education system taught us the opposite. We learned to study first, then apply. Master the theory, then attempt the practice.
This works in school.
It fails spectacularly in life.
The Seduction of Perpetual Preparation
Preparation is seductive because it feels productive without requiring risk.
When you’re researching and planning and learning, you feel like you’re making progress. You’re busy. You’re improving. You’re being responsible and thorough.
But you’re not risking anything.
You’re not facing the possibility of failure, criticism, or discovering you don’t know what you thought you knew.
You’re staying safe while feeling productive. It’s the perfect drug.
But there’s something deeper happening here. Something more sinister.
Preparation becomes a way of avoiding the fundamental terror of being responsible for your own existence.
When you’re preparing, you’re not yet accountable for results. You’re still in the realm of potential. You haven’t committed to being the kind of person who builds businesses or creates content or takes risks.
You can still be anyone.
The moment you start, you begin the process of becoming someone specific. Someone who succeeds or fails. Someone who creates or doesn’t. Someone who matters or doesn’t.
This specificity—this collapse from infinite potential into concrete reality—is what the existentialists understood as the source of human anxiety.
Kierkegaard called this “infinite reflection”—thinking so much about what to do that you never actually do anything. He understood that at some point, all the analysis in the world becomes a substitute for living.
But infinite reflection isn’t just intellectual paralysis. It’s existential cowardice disguised as prudence.
It’s choosing the safety of eternal potential over the danger of actual becoming.
Why Starting Badly Always Wins
Here’s what I learned watching Jake build his business while I perfected my knowledge:
Starting badly gives you something that no amount of preparation can provide: contact with reality.
Not the sanitized, theoretical reality you encounter in books and courses. The messy, unforgiving, immediate reality that doesn’t care about your plans.
This isn’t just about business efficiency. It’s about the fundamental difference between two kinds of knowledge: the knowledge that comes from thinking about the world, and the knowledge that comes from engaging with the world.
The philosopher Karl Marx understood this distinction: “Philosophers have hitherto only interpreted the world in various ways; the point is to change it.”
When you try to change the world, the world pushes back. It tells you where your theories are wrong. It reveals the gaps between your assumptions and reality. It teaches you things that no amount of contemplation could ever reveal.
Real customers telling you what they actually want (not what you think they want). Real problems that force you to develop real solutions. Real constraints that spark actual creativity. Real feedback that teaches you faster than any book ever could.
When Jake’s first pressure washer broke down mid-job, he didn’t have time to research the optimal replacement. He had to figure it out immediately or lose a customer.
That crisis taught him more about equipment in one afternoon than I learned in six months of reading reviews and specifications.
But more than that, it taught him who he was under pressure. It taught him that he could solve problems he’d never anticipated. It taught him the difference between theoretical knowledge and practical wisdom.
Every challenge he faced was simultaneously teaching him about business and about himself.
I was learning about business in the abstract. He was discovering what kind of person he was in the concrete.
Reality is the harshest teacher, but it’s also the most honest.
Every day you spend preparing is a day you’re not discovering who you actually are when it matters.
The Preparation Trap
The cruel irony of over-preparation is that it actually makes you less prepared for what matters.
You become prepared for the hypothetical world you’ve imagined in your research.
But the real world is nothing like that.
Jake wasn’t prepared for his equipment to break down constantly—but he learned to fix it. He wasn’t prepared for customers to demand services he’d never offered—but he figured it out. He wasn’t prepared for seasonal fluctuations in demand—but he adapted.
I was prepared for none of these things, despite years of study.
Because you can’t prepare for problems you haven’t experienced.
You can only develop the ability to solve problems as they arise.
And that ability only comes from actually facing problems.
The Action Advantage
Starting badly doesn’t mean starting carelessly.
It means starting before you feel ready.
It means prioritizing speed of learning over perfection of planning.
It means choosing feedback from reality over feedback from books.
Here’s what happens when you start badly:
Week 1: Everything breaks. You feel stupid. You want to quit.
Week 2: You fix some things. You realize what you don’t know. You start learning what matters.
Month 1: You’re still terrible, but you’re terrible at the right things instead of being perfect at the wrong things.
Month 3: You’re competent at the basics. You understand your real problems. You know what to learn next.
Month 6: You’re better than most people who are still preparing.
Year 1: You’ve lapped everyone who’s still getting ready.
Meanwhile, the preparers are still preparing.
The Question That Changes Everything
Instead of asking “Am I ready?” ask “What’s the fastest way to get feedback from reality?”
Instead of “What if I fail?” ask “What will teach me the most, fastest?”
Instead of “How do I avoid mistakes?” ask “How do I make mistakes faster so I can learn faster?”
The goal isn’t to avoid failure.
The goal is to fail faster than your competition is learning.
What I’d Do Differently
If I could go back and advise my younger self, I’d say:
Read one book, then start. Take one course, then launch. Make one plan, then begin.
Let reality teach you what you actually need to know.
Let customers tell you what they actually want.
Let problems show you what skills actually matter.
Let the market correct your assumptions before they become elaborate theories.
The person who starts badly today will beat the person who prepares perfectly for years.
Not because preparation is useless, but because the best preparation is practice.
The water doesn’t care if you’ve studied swimming.
It only cares if you can swim.
Start Now
Whatever you’ve been preparing for, you’re ready enough.
Not perfectly ready. Not completely ready. Not as ready as you’d like to be.
But ready enough.
Because ready enough + starting beats perfectly prepared + waiting every single time.
Jake didn’t know this when he bought that broken-down pressure washer.
He just knew he needed money and someone was willing to pay him to clean things.
That was enough.
What’s your pressure washer moment?
Thank you for reading.
– Scott