The person who’s willing to go the furthest usually wins. 
Most people are so afraid of losing, though, that they flinch at the first hint of the possibility of losing. 
You back down. You compromise. You hedge your bets. 
You minimize your chances of losing by giving up some of what you would gain in winning. Setting a smaller goal, for example, means a smaller investment and less to lose -- but also a smaller prize if you win. 
The more you try to minimize your risk, the more concessions you have to make in exchange for that safety. 
Repeat this process enough -- lowering your ceiling and raising your floor -- and you're smack in the middle. You can't lose, but there’s nothing to gain, either. 
People are smart. They see that this equation basically means it’s not worth it to start anything. 
So you do nothing. 
This is where most people live the entirety of their lives. 
The alternative is to stare down the possibility of failure. Claim your space and stand your ground, knowing that you might lose. 
But also knowing that the odds are in your favor: Everyone else is just as afraid of losing as you are. They'll probably back down before you do. 
The question is if you have the fortitude to handle that uncertainty. 

Related MasterClasses you should listen to: 
#1109: Deleting Your Anxiety Over The Uncertainties Of Life
#1189: What You Would Accomplish Without Fear In Your Way
#1074: How To Make Moves When Fear is On Your Mind
#332: Eliminating The Fear Of Failure