I am a Millennial, 26 years old. I also recently took the leap from my 9-5 job to pursue writing and digital marketing consulting full-time. And I'll be the first to admit that the month before I took the leap, I was very hesitant (just like anyone else would be). I had a nice amount of money saved up incase everything went wrong. I had a few projects lined up so my time would be filled immediately. But even still, I found a twisting in my stomach that was difficult to shake.

Taking the leap is scary--until you do it.

Not 24 hours after, and I felt like an entirely different human being. My head was so much clearer, my sights set on exactly what I wanted to work on next. My days were mine to sculpt. Everything I did felt full of purpose because I was choosing to do it for myself. And while there was a realization of responsibility--there would be no paycheck deposited into my account on the 1st and 15th of the month; I had to be the one to put my own food on the table--it felt daunting in all the right ways.

But, I have always been this way. I have always been the one looking to walk my own path. I have always been the loner, the one that didn't quite fit in, the one that struggled to sit in a classroom and follow the rules. So while going through the whole "leap" experience, I really questioned why I felt the way I did.

If someone as predisposed to walking the road less traveled as me still felt uneasy about it, how must other people feel about the decision?

How does someone else my age do the same?

Now that I am on the other side (and truthfully, my leap went absolute best case scenario), I have come to see some of these questions in a very different light. And what I have learned plagues so many of my extremely talented peers from ever taking the leap is this:

They doubt their ability to figure things out as they go along.

You see, with this topic especially, most people stop at the assumption that people don't take the leap because they "fear the unknown." And yes, that's definitely part of it--but it's really just the tip of the iceberg. Unknowns are part of life. Even with a secure office job you still have unknowns. You could be fired tomorrow. Your industry could be disrupted by technology a month from now. The unknowns are still there, they are just much more easily masked.

No, it's not the unknowns themselves that hold people (especially young people) back from ever going all-in on their dreams.

It's their uneasiness as to whether or not they have the confidence, the thick skin, and the patience to be able to sit with those unknowns on their own, for as long as it takes for them to find their own answers.

My theory for why this is the case goes back to our education system. I will never forget a few years ago, having dinner with two of my peers from high school. Both of which were extremely good students, and the girl in particular had always been the President of everything. She had graduated at the top of our class, had gone on to attend a very prestigious university, and had a resumé the length of a football field.

On paper, she was everything we, as students, were ever told to be.

But as we began our dinner, catching up and sharing where we were in our lives a few years out of college, she expressed severe unhappiness. She felt lost and confused in the real world, and at one point actually said, "I feel like I should just go to grad school. I do so much better when someone tells me what to do."

I remember being somewhat shocked by that statement--probably because it was so opposite of my own outlook on life. But something about her saying that stuck with me, and it hasn't been until recently that I feel like I have understood why.

Our education system teaches facts. What it doesn't teach is how to learn. It doesn't teach you how to find your own answers, or how to think in imperfect circumstances. It's learning in a vacuum, and as a result, produces very, very good "followers."

Now, I am not saying everyone needs to be the leader or the entrepreneur. There are plenty of entrepreneurs out there, and extremely successful ones at that, who require someone else to hold the reigns.

What I am saying is that regardless of what you want to do in life--whether it's start your own company, or just take the leap to go work for a different company, or even work for yourself--that decision, in itself, requires you to embrace some sort of unknown. And furthermore, asks that you figure things out as you go along.

And that's something a lot of people struggle with.