There is a steep hill by my house. Steep enough that cars can easily accelerate beyond 40 mph without pressing the gas peddle, causing homeowners to post signs along the road to slow down. Apparently the attraction of the hill was too great for a teenage boy to resist. He went flying down the hill, with cars behind him, without a helmet. Hitting a twig or rock, which are common along the road, could have resulted in serious injury or worse. But he was lucky and ended his ride safely.
Sometimes reckless risks payoff. But the payoff is a function of luck, not skill. Taking calculated risks, understanding what could go wrong and having a plan to address them, makes a lot of sense. But in taking the risk, you should be willing to lose whatever is being placed on the line if going big. What risks are you willing to take?