1/Why?
We are vastly more conditioned by society than we realize.
How can we “think outside the box” when there’s a bumper sticker and t-shirt with that emblazoned on it?
The ideas that our culture propagates are difficult to truly examine when

2/when “everyone” accepts them as axiomatically true.
To really understand this, read original books, journals, news articles, and now public, once private, diaries from other eras.
Some ideas and thoughts will ring true, but many will appear laughable to our

3/modern eyes and ears. Focus on the ones that ring true from long ago. They ring true by having withstood the test of time and fashion.
A Zen story about a fish who was a Prince who asked his father to explain water to him.

4/His father, the King, asked him why he wanted to know. The Prince answered he had heard land creatures talking about it and wanted to understand.
His father responded “you were born in the water and you will die in the water.

5/You live in it and it flows through you and around you. It is so much a part of you that you are unaware of it.” That’s why we often feel like a fish out of water when questioning what everyone in society believes. It permeates us so much that we are unaware.

6/We literally don’t know what we don’t know.
How does this affect us? People who don’t ask questions don’t get answers.
NEVER be afraid to ask a question, even if everyone you know thinks the answer is obvious.
We’ll never progress without the simple question, why?

7/It can uncover lots of bad beliefs, if only you keep asking it.
I think many of a society’s cherished beliefs are castles built on sand.
To figure out which ones, ask why. As Keith Richards says: “If you’re going to kick authority in the teeth, you might as well use both feet.”

8/ Addendum: Thinking more about this after reading a couple of books. In "Ego is the Enemy," @RyanHoliday argues that the biggest problems we face aren't caused by external events or people, but rather our own beliefs and attitudes that preclude us from making rational,

9/ objective choices. We abhor chaos and therefore often cling to existing ideas and beliefs like grim death. This is potentially caused by our strong need for an "illusion of control" even where none exists. We impose patterns on randomness and often fool both ourselves

10/ and others, especially if we are persuasive. We are also driven by impulses placed deep in our DNA by evolution. For example, we are wired to pay greater attention to potentially dangerous events than potentially good ones. And our minds many times don't distinguish

11/ between real events and forecasted or projected ones. This is why we normally see the clickbait farms churning out stories and forecasts foretelling impending doom and annihilation. Evolution wants you to click on that link. It's also why the dogmatists of all stripes

12/ tend to truck in disaster and ruin, it simply sells better. Add to this what @Gladwell in his book "Talking with Strangers--What we Should Know about the People we Don't Know" calls the "default to truth" which is another evolutionary bug in our DNA. We tend to believe

13/ and trust people, even those we don't know at all. This leaves us ripe for the pickings by anyone trying to sell us something, be it a market forecast or a worldly philosophy. Gladwell give a myriad of examples of how even the best trained people

14/ (CIA, NSA, police detectives, judges, etc.) are routinely fooled by not only people who are intentionally lying to them but also by innocent people who don't have normal reactions to things. (Gladwell calls this transparency and uses the example of the Amanda Knox

15/ murder trial in Italy) as an almost perfectly formed illustration of how bad things can turn out for you if you give of the wrong "vibe." He catalogs all of the times people are duped because they inherently believe that while others may be bad judges, they are excellent

16/ at getting to the truth. They aren't, but this is another persistent behavioral tic that seems immune to all of the facts and empirical evidence we can throw at it. And when you add this to our default to truth, you have an almost perfect formula for being duped by even

17/ honest-minded projections of impending, apocalyptic doom, be it for the stock market or society in general. The irony is, if we didn't "default to honesty" we'd probably quickly devolve to dystopic hellscape that would make Mad Max look like a walk in the park.

18/ Thus, it pays to keep in mind that there are evolutionary programs running in your mind that you may never have even considered that make you simultaneously easy to fool while filled with certainty that is an almost impossible outcome for you personally, since we also

19/ tend to assign ourselves into the top two deciles for almost any "good" characteristic and the bottom two for any "bad" one. Mother Nature is a wily bitch in many regards, and the only way to overcome it is to constantly and almost obsessively question both our beliefs

20/ and abilities. It's a yeoman's task, and completely unnatural, but if you want to get better calibrated, it's also a required one. @naval said something like "the truth should be predictive" and that might not be a bad place to start. Look at which of your beliefs led to

21/ a correct predicted outcome and which that didn't. If you're honest with yourself (and you most likely aren't, another little present from Mother Nature, but that's for another thread) you'll see that not only are many of your beliefs wrong, some are downright destructive.

22/ I suggest keeping a written journal, because I've noticed how many times my recollection of something I said or believed at a certain time proved to be incorrect and I only realized it after being called a liar in my own handwriting. But however you do it, do it and do it

23/ now. You'll at first be disappointed at how much you get wrong, but if you persist, that will turn to delight as you shed incorrect beliefs in favor of those with an empirically supported win ratio. Remember, they don't teach this stuff in most schools nor are there

24/ many people cataloging how often they've been wrong, but if you can, through persistence and repetition make this a habit, you'll find yourself making much better decisions in both investing and in life, and that, in my opinion, is something that will drastically

25/ improve your outcomes and your life. Finally, remember that even a *slight* improvement in your process often leads to continual improvement in the questions you ask and the answers they receive. Talk about killer positive compounding. As usual, it's up to you. Do it!

26/ Another addendum: As I discuss these ideas with people, I find many people are reluctant to pursue this method seriously because they tend to describe things as they would *like* them to be, rather than as they *really are*. Remember, it's just a map, it's not the territory.