I have two stories to tell you.

Story Number One

I was in a bar in New York City and I was trying to convince a stranger to fly to Buenos Aires. I had never been there, but I knew it was the right place for him.

This man told me that his dream was to run a soccer camp for kids in South America. After tossing out a few possible locations, we both agreed that Buenos Aires would be the perfect place to start.

I asked if he would move there if he had the chance or if there was something keeping him in New York.

“Absolutely, I would move,” he said. “I don’t have family or friends or anything keeping me tied down here.”

We talked about whether he could save up enough money to fly down there. He could, and so I pressed him further.

“Perfect,” I said, “Here’s what I would do, if I were you. Once you have the money saved up, buy a one-way ticket to Buenos Aires. Make sure you have enough to buy a ticket back as well. Get down there and hit the scene hard for as long as you can afford it. If for some reason you can’t make it work by the time your money runs up, then buy your ticket back to NYC and you’re back where you started.”

He smiled, but shook his head and said, “Well, that’s just a dream.”

Story Number Two

I spent a long time preparing to launch my first business. I was drawing sketches of the website on a whiteboard for 4 years before I launched it. Basically, I was in perpetual planning mode.

Eventually, I ran out of excuses, put some money where my mouth was, and launched it. In total, it cost me $1,600 to get a prototype built (I had to pay for some programmers to work on things because I didn't know how to code).

What happened? That business idea made me a grand total of $118.05. For those of you planning to do this at home, this is the opposite of what profitable businesses do. (Thankfully, I figured this out when I quickly moved on to other business ideas.)

What's the point of these two stories?


I get what it's like to feel uncertain and unsure about your abilities. I understand how it feels to finally work up the courage to do that thing you wanted to do … and then fall flat on your face.

Thankfully, I kept pushing, continued to experiment with different business ideas, and I've been a full-time entrepreneur for over 3 years now. Becoming an entrepreneur was one of the best decisions I've ever made. But it wasn't easy in the beginning. There was a lot of self-doubt and fear. And there were plenty of reasons to feel that way.

I've noticed similar feelings in other areas. I wrote for over a year in a private document before I finally worked up the courage to start writing these Monday and Thursday articles. Now look at this place. We have over 47,000 members in our little community.

These fears and uncertainties are everywhere. We feel them with little things like going to the gym. (Will people judge me? What do I look like?) We feel them with big things like moving to a new country. (That's just a dream. I could never drop everything and make it work.)

The Bottom Line

But, and this is the main point of all this, I want you to know that I'm going through it with you. I've said this many times, but I don't have all the answers. I'm just learning along the way like everyone else and sharing what comes up during the journey. But I have no plans of just becoming someone who writes about it and doesn't practice it.

How easy would it be for me to sit here and say, “That guy in the bar was an idiot! He has the money. He has the freedom. He should follow his dreams!”

And I think he should follow them, but have you ever embraced that kind of uncertainty with open arms? Change is hard, but oftentimes the hardest part isn't knowing what steps to take or figuring out what is important to you. The hard part is handling your own psychology, getting over your own fears, and finding the grit to make something happen.

If I could see that stranger again, I’d tell him two things.

First, I’ve been there man. I get it. You’re uncertain and unsure and you doubt that you can make it all work. That’s normal. I felt unsure when I moved to a new country. I felt uncertain when I started my first business. I felt like an amateur when I started writing publicly. It doesn’t make you weak or weird or unqualified. It’s normal.

And second, keep pushing. Don’t chalk things up to “just a dream.” It can be something small like making it to the gym or something big like buying that one-way ticket to Buenos Aires, but if you keep pushing enough, it’s going to be a reality instead of a dream.

If you are lucky enough to find a way of life you love, you have to find the courage to live it.
-John Irving

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