Are you taking big enough risks?
Mark Twain famously said; “I am an old man and known a great many troubles, but most of them never happened.” What Twain is saying here is that most of the risks we perceive are unlikely to happen. Think of the many things you might want to do but are afraid of trying – ask for a raise, go sky diving, talk to that pretty stranger at the end of the bar – all with high perceived risk, but from a probabilistic perspective those risks are highly unlikely. Evaluating options in terms of the worst possible outcome will result in a state of ultraconservatism that will guarantee mediocre results at best.
Instead, evaluate options in terms of all possible outcomes and the likelihood of each. Asking for a raise might result in a swift and vicious reprisal from your boss, but that is highly unlikely, especially in today’s hyper sensitive HR environment. What is more likely is a career conversation which may result in a promotion, expanded responsibility, or in a realistic worst case scenario – nothing at all. However, not taking action, not asking for a raise, not discussing career ambitions with your management will certainly keep you stuck in the status quo.