33. Asking Questions 🔗

99% of the questions people ask in their 20s and early 30s are roughly the same seemingly “important” ones everybody has always asked at those ages. And 99% come up with roughly the same answers ranging from pretty dumb to reasonably smart regardless of effort.

The 1% different answers people come up with might make them somewhat more famous/rich, but are rarely different enough to change much beyond their own lives. The age-old questions are age old because the answers are in our collective diminishing marginal returns zone.

They are important, like air or water, but they aren’t wellsprings of meaning. How to make money, how to get laid, how politics works, who is good/bad, how to choose friends. You’ll spend 99% of your time on this stuff getting to useful and necessary but uninteresting places.

But if you trace back the most interesting, meaningful things people have done by 40s, you’ll usually find them asking a new question in 20s/early 30s nobody thought was worth asking. The questions are rarely deep/subtle. Many people consider them, but few do so seriously.

Even the most unimportant question can create a lot of meaning if it’s a new question and you’re one of few asking it at right age. This 1% of questions you ask should occupy 20% of your attention. The other 99% important-and-age-old questions deserve only 80% of attention, why?

It’s because the 99% questions have been so milked to death by people asking them over 6000 years of recorded human history and writing down the answers, you can really triage the hell out of them. Most answers that have survived are “good enough”. Pick a lazy one and move on.

If you were a 34-year-old mediocre-intelligent guy and had to choose between spending 10 hours asking one of these questions in say 2009...

1. Is conservatism better/worse than liberalism?

2. Why is “The Office” so funny

3. How to fix economy?

Which one would you have chosen?

Like everybody else, I was asking 1 and 3, and got nowhere interesting. I didn’t do much worse or better than others on those (important) Qs.

What I did right was get bored enough with 1 and 3 to accept lazy answers and move on. Everything interesting in my life came out of Q2.

I’m sure others in their 40s have similar examples. My point is 25-40 is your most valuable, imaginative, intelligent and bold time of life, where your powers are at their peak, your life constraints are at their weakest, and your energy at its most boundless.

Don’t waste this period asking age-old questions everybody has been spending 99% of their youth asking through all history. Triage them, get to good enough, and find new questions that few people are asking. The more average you are, the more crucial this hack.

Exceptional geniuses might find unexpectedly high chunks of new marginal value in age-old actively-worked questions (age-old but abandoned/rarely asked questions are different, almost as good as new, but rarely as easy). You, statistically likely to be a mediocrity like me, won’t

And never let seeming triviality or unimportance stop you from investing demented amounts of energy into the answers. Even if everybody thinks you’re crazy. Novelty never wears its significance and hidden value on the cover.