It is easy to take risks when there is little a stake. We can remember starting out in our first career move or business venture. The downside of our attempt was really minimal. In most cases we were young and felt we had lots of time should it not work out. We had no kids or marriage to worry about and not a lot of money at risk.
Sometimes we were fortunate and our risks paid off and we embarked on other challenges which were also successful. Others were not successful. In both cases we could end up stopping the taking risks.
The more successful we are the greater our potential loss and so we could end up looking for the sure thing. The more failures we had would result in the same dilemma that is looking for the sure thing.
We need to realize that there is no such thing as risk free. It doesn't exist. We need to know what our risk threshold is and accept that. Not everyone is cut out to take high risk and there is nothing wrong with that.
Knowing our risk threshold allows us to make better goals that we will strive for rather than waiting for the perfect score which will never arrive and would guarantee our having an unhappy life.