First, understand the domain of the problem so you can identify poential downsides. Is this area Black Swan prone? Does this resemble Newcomb's problem at all? What do (I think) the shape of risk is here?

For most things people need to do in daily life, we might just consider the cost of further optimization against cost of remaining ignorant and being wrong as a result of that ignorance. It can ne good to be aware of the biases that Prospect Theory talks about--am I putting off reasonably winning big because I'm so afraid of losing pennies?