It's called "Two blind men crossing a log bridge," and is supposed to reflect to perilous journey to enlightenment over the ever present abyss or uncertainties of life.
Maybe it metophorically means, being "blind" and looking for enlightenment; which their is no obtainment, path, bridge, or guideline. The blind men cannot see the abyss; so in reality it only exists in those that bring it to awareness.
In the case of the professional handicapper, it could mean many things: perhaps the difficulties of trying to uncover profitable angles to help others, but in any event the goal is to reach the other side albeit one step at a time.
We are all apprentices in a craft which has no masters. The fallacy of superiority has been well documented.
Humility is often one of the best indicators of where some one is in relationship to their approach on life regardless of age. We must possess the ability to laugh at ourselves and surroundings; and learn from our mistakes by being a better person that continually grows.
A mind numbing still forest pond examination absent of preconcieved notions to erase all that is known to see things more clearly.
Most times it has little to do with being right or wrong; but how one responds, or does not respond. Marriage can be a good testament.