Most of the time, we are working hard, head down, using what we know.

We get better and better at it. We make little improvements, and keep working. Our expertise and confidence keeps increasing.

We can’t afford to stop and question everything. We can’t go back to school. We have work to do.

Until we don’t.

Last year I left my company, and decided to start a new one.

I wanted to replace my old thoughts with new ones. I had been working hard, doing one thing in one mindset for ten years, and needed to install a new operating system in my brain.

I read a lot of books on business, social psychology, management, behavioral economics, investing, cognitive biases, crowds, marketing, networking, learning, and communication.

But each book that made me feel smarter (“Aha! I think I understand the world better now!”) also made me feel dumber (“Wow, I’ve been an idiot. It’s surprising I survived at all.”)

For example, when I read “What Got You Here Won’t Get You There”, I realized what a horrible manager I’d been - how I’ve been dealing with people all wrong. It felt like the author had been hiding under my desk for 10 years, making a list of what not to do, and he was right. I’ve got so much to learn to be a good manager.

Business experts like Ram Charan, Clayton Christensen, Adrian Slywotzky and Charlie Munger made me feel like a court jester next to a samurai. I long to have their insight and expertise. I could study hard for 30 years and barely catch up.

Plus an ex-employee I’d fired, and an ex-girlfriend I’d broken up with, made sure I knew what a horrible horrible person I am. Not only am I an idiot, I’m dangerous! Destroying others in my path.

It was all very humbling.

So humbling, that I found it hard to do anything at all.

I had designed and announced my new company. I was psyched for it to exist. But when it came down to doing the necessary work, I hesitated and procrastinated. “Who am I to be starting another company? I’m just going to fuck it up like last time.“

After all I’ve learned, I can’t believe anyone actually thinks they’ll succeed in the complex world of business. Don’t they see all the really smart people who have tried and failed?

I can’t believe how foolish I was to start my first company. Just me in my bedroom with no experience, making a little website, when I was up against giant IPO-funded competitors.

I was an over-confident punk, thinking I had the answer, and everyone else didn’t.

But it worked.

And in fact, isn’t that kind of confidence absolutely required to get anything done?

Isn’t the role of the entrepreneur to be the bold, daring, audacious one? The over-confident reckless one who says, “Screw it. Let’s do it!”?

Yes! Of course! It’s the essential final lesson: that all this learning means nothing until you make something happen.

Whether you think you'll win or not - you need to jump in the game, and say, “Let’s go!”

Whether your confidence is naïve, inspired or crafted - you need its high-horsepower engine to get uphill and go anywhere.

And no matter how humbling the lessons of life are, this final lesson is the most important of all.

And thus, I graduated from my self-created Entrepreneur 102 class.

Time to go make something happen.