Yeah, I don't think paulsutter's post holds up to much scrutiny, except in the limited case where you have to make a decision immediately, or in the near future before you have time to do any meaningful research or calculation on the problem.

A problem is difficult when its potential consequences are serious and the best option is not obvious. But the best option can be non-obvious for two very different reasons: either it requires a lot of information and thus a lot of work to gather that information (like choosing a medical treatment), or it depends on randomness or other variables outside your control and understanding (like choose your lottery numbers, assuming someone gives you a lottery ticket).

For the latter case, it's pretty clear that you can choose randomly and shouldn't worry about your decision. For the former case, it's reasonable to "worry" in the sense that you should feel an urgency to gather the required information efficiently. Of course, it's not really that simple, because you have to optimize the cost of gathering information against the potential cost or gain from the decision itself. Also, the two reasons from the last paragraph are more like a continuum, because "randomness" is often effective randomness, i.e. you can't feasibly predict the outcomes despite them being deterministic.