1/ Sometimes it is useful to sincerely ask why? And sometimes it is useful to sincerely ask why not? The same holds for where, what, when who and how.
2/ These basic questions of life, the 5W+H questions, are how we evaluate every option for action, trivial or profound, in every situation.
3/ Under conditions of low uncertainty, the positive forms of the 5W+H questions are usually more useful. There are default easy answers and few alternatives. You just have to learn to like them.
4/ Under conditions of high uncertainty, the negative forms of the 5W+H questions are often more useful. They help you eliminate premature bad answers and break out of lazy defaults.
5/ It is the transitional zone that is hard to navigate: when there are seductive and easy default answers that are not obviously wrong, and dubious-seeming ones that are nevertheless hard to eliminate.
6/ This is the zone of anomie. A zone where you can thrash between the positive and negative forms of the basic questions about any option, and get nowhere.
7/ Should you go to college? Why? Why not? In 1992, when I was applying to college, the answer was Duh! Today, it's not so easy. It depends on which college.
8/ Drill a little deeper. The thing about high uncertainty is that there are more specific options in the environment that you must interrogate, and higher risk latent in default options.
9/ Under low uncertainty, you have to find a way to like one of the few default options available. Under high uncertainty, you have to eliminate options and avoid premature commitment.
10/ Under low uncertainty, the positive questions capture knowledge, the negative ones tend to be excuses to avoid action.
11/ Under high uncertainty though, the positive questions tend to point to false certainties, the negative ones force you to think and learn.
12/ These questions are subtle though. Why can get you to no, and why not can get you to yes.
13/ What customer need does this satisfy? is often a way to shoot down a great idea. Why not? Is often a precursor to let's just try it. These questions are open-ended thinking prompts, not triggers for knee-jerk yeses and noes.
14/ As another example. Startup investing is mostly a game of saying "No!" a lot. Eliminating options and patiently waiting for the big ones. But saying no to the one Big One can destroy a firm.
15/ What not to do is a way to learn from others' failures and increase your odds where what to do might tempt you buying into snake-oil formulas.
16/ Be careful though: both the positive and negative forms of the questions are most powerful when used on a concrete option, not on entire abstract classes
17/ Why/Why not Harvard? Why/Why not Cook County Community College? Why/Why not Coursera? are all much better questions than Why College?
18/ Whom to trust/not trust are better questions asked one individual at a time rather than one class at a time.
19/ This weakness of abstract classes is a feature of anomie. Norms tend to be be based on abstractions, like college is good, and easily computed rankings based on a notion of good.
20/ Under normless conditions, you have to get specific. Is a Harvard MBA worth it? What about a no-name state college MBA? Are the rankings meaningful? In which parts of the list?
21/ The heuristic of specificity is a good guide to whether the positive or negative form of a question is more useful under anomie. Just ask: which version makes you work harder and learn more to get to the answer?
22/ Under low uncertainty conditions, eliminating options is easy: There aren't many. But finding a way to accept and like the default can be very hard and teach you a lot.
23/ Under high uncertainty: specifically eliminating any given option may be easy. But you have to do a LOT of eliminations. Kiss a lot of frogs.
24/ Under low uncertainty, eliminating a lot of options is the same as deciding to do nothing. But under high uncertainty, it is hard work, trial and error, and learning.
25/ If there's only one startup investment to evaluate in a year, anybody can be a VC. If you have to specifically evaluate 200 and say no to 199, but make sure you don't screw up the 1/200 deal, that's work.
26/ In summary, to navigate anomie, make options as concrete as possible, ask both positive and negative forms of the 5W+H questions, and drill down into the versions that take more hard work to answer.
27/ But since we live in anomic times, that summary easy answer may be the wrong one for you in any particular case.