We remember our small victories vividly, and forget the small failures. But when the stakes rise, and more is put on the line, the opposite happens - we remember the large victories fondly, but they don't resonate nearly the same as the great failures do. This is like a built-in mechanism against going for the big prize, and instead to be placated and content with the little victories that occur throughout daily life. A mechanism to not stand out, and to accept the safety of the crowd. However, to turn it around and use either the fear of failure, or previous failure, to push yourself is to truly invest in yourself, and your own success.
If you eliminate the reasons you could use to defend yourself in event of failure, you stand on your own two feet, with either success or failure almost solely dependent on you. I think that is true freedom.