I tend to err on the side of not gambling. In many respects, I think this can be considered a problem because the less you risk, the less you stand to gain.
Aside from my lack of interest in actual gambling (poker, sports bets, etc etc)...I see a need to take bigger gambles in my life. In the past few months...I have made a few gambles that I am now seeing returns on (or the beginnings of returns). Some of them have turned out to be mind-blowingly great and better than I originally hoped for. Some of them are less than great...but may open opportunities for greatness in the near future.
All things considered, I am glad I took those risks and moved in the direction I did. I may not currently be happy with some of the results...but that is part of the gamble...and I am willing to try something different in a new gamble to make my game the best it can be.