[0]: http://www.ted.com/talks/ruth_chang_how_to_make_hard_choices

There are endless ways for a decision to actually be hard. One is where the type of impact between options is different and difficult to compare. The difficulty may arise due to: uncertainty, complexity, lack of knowledge, value judgements, brutal trade-offs etc.

i) "Should I stay to treat to the ebola victim or leave with my family?" is hard because it involves value judgements, predictions, risks. It questions who you are. ii) "Should our startup be tightly integrated with facebook?" is hard because the potential impact is massive and requires substantial investigation to understand.

The very attempt to compare options can involve costs and feedback loops e.g. should I pay for an investigation, should I prototype this, should I wait for more info etc. The actions you take to compare options can change the available options. A single decision becomes a nested web of other decisions.

In the most general sense, making a decision is like devising a strategy. Is creating a good strategy easy or hard?

p.s. I'm working on this problem

Email is in my profile, if you'd rather not share here.

"Clarity" is dependent on what level of information you already have and what analysis you've already done.

In some circumstances, you've already done whatever investigation, research, and thinking can reasonably be done. If the choice is still hard, then the choice is likely to be of similar value either way and you may as well choose arbitrarily.

But in other circumstances, there's still investigation, research, or thinking that can be done (at a level of effort which is reasonable based on the importance of the decision.) In that case, one choice or the other may become clearly better if you are patient and diligent in the decision-making process. So be as patient as the decision warrants.

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.

It doesn't matter if the cereal I bought tastes good or bad, I'll always wonder if the other option would have been better. Until I taste the other cereal, I'm left questioning my decision, and being unhappy.

Being unhappy and unsatisfied is the main reason we have the technology that currently exists. If people were satisfied traveling by horse, the automobile wouldn't exist. If people were satisfied with 480p, the HD television would never have been a worthwhile venture. Being continually unsatisfied is what causes us to strive higher.

I never said any of this technology enhances our level of happiness. I just said as a species, being constantly unhappy could be one of our greatest strengths. Otherwise, we might be sitting in a cave, smiling at each other until an asteroid removed us from existence.

Regular people may have been satisfied, but the military wasn't, who drove almost all of the research into the 80s. The consumer market is just a follow-on to that, where choices were presented to "me" as better.

There is a world of difference between freezing in a cave and developing 1080p/2160p/4320p.

However, to survive as a species in the long term, we need to leave this planet. To do that, we need a number of advancements in technology.

So, if we can agree the survival of the species is in our benefit, then we can agree development is considered a good thing, even if it doesn't equate to an increase in happiness for the individual.

In this case you would probably be able to try the other option at some time in the future, so why would you be unhappy? I'd definitely do that, and probably alternate between the two if they seem equally good.