To me this quote hits all levels. The emotional quality of this quote is pretty relevant to all ages and all humans. It reminds me of how technology is changing rapidly but people don't change. The system of life has a platform that hasn't changed since day one. It's a kill or be killed world still or playing the game and drinking the kool-aid to be successful. In certain situations you have to swallow your pride and move on.
In the book Santiago has a tough time realizing with every risk there's the possibility of a reward. Once he starts fearing failure that is when he losses and lets that fear make failure come easier. Confidence is key and just keep pushing forward life is full of obstacles and overcoming those obstacles is part of lives stories. Every time Santiago feared something he stop from moving on and improving instead he stood still in a way and got nothing done. No one is going to walk up to you and just hand you a million dollars you need to earn it.
What this quote ideally means to me if you go into something unsure and uncomfortable the outcome isn't going to be as great as you aspire it to be. Why be fearful of the universe that you're apart of. You own and control it and have history to guide and educate you.