There was one critical trait I always looked for in the analysts and investors I worked with during my Wall Street career: the ability to state a case for buying a stock--and then the ability to immediately state the case against buying that same stock.
The case for any investment is almost always balanced out by an equally powerful contra-case. After all, that's what makes it a market! And, beware: if you find yourself angry with or resistant to the contra-case for an investment you've made, be prepared to get separated from your money. Rudely.
More importantly: if you are using a financial expert and she resists the contra-case for an investment she's selling to you, prepare to really get separated from your money.
As I muddle my way though life, I'm finding this ability to argue the contra-case to be a useful tool far beyond just the world of stock market investing. Seek out this ability whenever you consult an expert in any domain with uncertainty or risk: investing, diet, fitness, healthcare, home ownership, auto repairs, psychology, relationships, careers, and so on.
Look, some things in life are known to the point of obviousness (e.g., you should be nice to your spouse, you should exercise regularly, you should diversify your investments). For things like these, there is no contra-case. However, most things in life are not known (will the stock market go up? Down? Will my investments meet my needs? Is this is bad time/location to buy a house? etc.). For questions like these, it's important to seek out well-argued reasons for both the pro- and contra-case in order to help your decision-making. The experts who provide this--and who won't lull you with decisive, confident-sounding, one-way answers--are the ones to seek out.
Also, keep in mind: sometimes your "expert" may have an agenda. Have you ever had an auto repair person tell you that you didn't need a repair? Have you ever heard a real estate salesperson say you shouldn't own a home? Ask for the contra-case argument and see what reaction you get. If anything, it should give you a window into their soul, and this should help you compensate for their natural bias to sell to you.
So, the next time you consult an expert, ask for her opinion. Then, immediately ask her to argue one or more contra-opinions, and ask her to make those contra-opinions as compelling as the original opinion. It will illustrate the honor, humility and intellectual honesty of your expert. If she can't--or won't--do this, watch out. You've likely got yourself an intellectually arrogant "expert" who's attached to her already-formed opinions more than she's interested in sharing genuine expertise. Run.
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