To become bold, you must make the bold choices…
“When you cannot make up your mind which of two evenly balanced courses of action you should take — choose the bolder.”
W.J. Slim
What is the downside of bolder action? If the choices are genuinely even, then the risk/reward for each should be the same. However, this question’s very nature highlights that a “bolder” decision carries an additional risk or the potential for failure.