The unknown, the wilderness, the dark. 
In our lives we face all different types of wildernesses. And it scares us. We face little wildernesses all the time. There is a lot in our day that is left to the unknown, many things that could potentially happen, yet every day we move forward. But what causes us to dread these unknowns in our life, why do they cause fear?
And why despite the fact that the wilderness maybe by the way to the best experiences do we remain content and satisfied without taking a single step in that direction? And by making the choice to be content are we cheating ourselves ? Have we become comfortably numb?
Are we missing out on the best experiences of our life because we are afraid of failing, afraid of getting hurt, of having a humbling experience, afraid they we may not be the best.
I was reading an article about firsts, and how your first kiss, your first close experience with death, first experience with heartbreak, first experience with success all of these have a profound impact on your memory. To the point where these are some of the points that you will forever remember. Everyone remembers their first kiss, but who remembers their 100th kiss? And maybe there is a connection their between firsts and risks. I'm sure there are plenty of guys and gals who were terrified the first time they kissed someone. And yet, they took that risk and conquered the "kiss" 
One of the experiences that I remember is when I first started at Brigham Young University. I was moving to a city I had never been to before, moving in with people I'd never met to before. It was scary. But, I knew that attending BYU would be worth that risk. The first week was pretty rough. I remember that my class schedule just had acronyms for the names of the buildings, I had no idea where to go. I didn't know how to get around town, I had no idea where the grocery store was, I wasn't a fan of the non-protected green lights. (I liked having a turn arrow and no yielding.) But, I took control. I learned all the buildings names/acronyms, I Google mapped Provo and saw how best to navigate the city, I began to meet new people, develop friendships and the feelings of anxiety dissipated.
I think that sometimes in life, you can never fully prepare. Sometimes you have to just jump and paddle as hard as you can to float. Somethings you just don't know what to expect until you are in the thick of it. The business world, college, marriage, dating, buy a house, raising kids....
Have you ever noticed that if you driving down the road and there is a car on a cross street wanting to cross over and continue in the opposite direction that they will make a more risky move if there is a line of cars behind you verses just you (one car to wait for). Why is it that a car is willing to take a risk such as that, because they don't want to wait for the long line of cars to pass by? So can we make the assumption that people will make a riskier move if they feel their time is running short or their options are dwindling.
Why do we wait til our options are dwindling to take that risk, to make a move? Perhaps by then the best options are gone. I think we forget to look at situations in our lives as if they won't be there forever, because in reality, they probably won't be. Don't wait around. That job offers end, promotions can pass you by, college applications have deadlines, even relationships without the risk of commitment won't last (Beth and Ben from He's Just Not That Into You) people move on if you won't jump on ride with them. The people in life that get what they want, are the ones taking the risks.
I think that taking risks requires courage, faith, a sense of self worth and humility. It takes courage to face the scary wilderness, and faith that things will work out in the end. Self worth in that if things don't work out as hoped, and the word failure comes to mind, you can separate yourself from being a failure and failing at this one situation. And finally humility, being able to laugh at failing, and to remain level if great success becomes an outcome.
Some of the greatest leaders, talented artists and brilliant minds were told they weren't good enough. If they chose to listen, they wouldn't have left their mark in history.
Life = Risk 