How to Avoid Wasting Decades on Fool’s Errands

You see casualties all around you, people stuck in lousy marriages, jobs, and ideologies, people pouring their precious life’s work into something you can tell just won’t work.

Maybe you think it can’t happen to you, but why not? It can happen to anyone. There are things you can do to try to prevent it. Here are a few.

1. Never cling to an insight as if it's your last: Live and learn. No matter how powerful, joyous and overwhelming that first kiss, that job offer, or that first insight, and no matter how tempted you are to declare it the once and final revelation, stay open to more, unless you want to risk turning out just like that person you know who thought they’d found the answer and ended up with their head stuck in a trap forevermore.
2. Beware of nostalgic triumphalism: A sign that your head might be stuck in a trap is reveling in past success. Sure, you triumphed way back then. Congratulations, but that’s in the past. The games continue. Enjoy your day in the sun, but if you stay stuck in it, you may well end up in the dark, like some late-life loser who can’t get over his high school touchdown.
3. Beware the bad seeds of self-certainty: The devil is in the details, but not the fine points. People spend years promoting ideas that turn out completely wrong because they’re based on some hidden or overlooked over-confident assumption. Challenge your most basic assumptions.
4. Be an exception bloodhound: When you think you’ve found a pat formula, don’t just collect evidence to support it. Look for exceptions to it, and when you find those exceptions (you will—all supposedly pat formulas have exceptions), attend to them, because it’s in noticing such contradictions that you’ll gain your next insight.
5. Tip the scales against you: People think that critical thinking is the antidote to rhetoric. Not in most people’s hands, it isn’t. Most people use critical thinking to pick apart their opponents’ beliefs and rhetoric to bolster their own. If you want antidotes to self-deception, flip it. Be able to make a compelling rhetorical case for your opposition’s beliefs and apply critical thinking to your own.
6. Ingest a morsel of feedback, no matter how bitter: Don’t be convinced by your quick dismissal of someone’s critical feedback. That’s just you spitting out the taste of something bitter. Let some of the criticism linger. Sleep on it. Digest it. You may gain some insight from it over the days to come.
7. Always consider next questions: Flag the questions that follow from your answers. You don’t have to answer them right away. Still, you’ll make quicker progress to future insights if you recognize that there’s always a next question.
8. Be an actuary and an epidemiologist: Study and generalize from past mistakes—yours and other people’s. Like an actuary (someone who calculates odds of casualties for insurance companies), study the odds of failure. Generalize carefully about how failure happens and, like an epidemiologist, how failure spreads. Study history, recognizing that you are not exempt from human nature. No one is exempt. In reality, we are all human, and therefore prone to failings.
9. How it’s going doesn’t tell you where it’s going: Some of our most productive days feel unproductive, like the day you realized you needed to rethink something big. Some of our least productive days feel productive, like the day when you were smooth cruising along at high speed in the wrong direction. You can drain your bank account for a beautiful binge of a day. You can feel deprived on days when you’re skimping and saving for a better future.
10. Offset success with self-doubt: The natural response to signs of success is confidence that you’re right. That’s one of the main reasons we seek success—for the confidence it earns us. Still, it’s risky. People who slide into the feeling that they can do no wrong, often do lots of wrong, not noticing for way too long. Success, especially a rise in status and popularity, is best offset with more self-effacing humor and doubt. With a rise in status and popularity, you can afford it. Take the rewards in the form of greater capacity for self-doubt, not less need for it.

Finally, keep this in mind: Despite your best efforts to keep learning and growing, you might end up wrong anyway. Just think of how many proud, important people of yesteryear strutted in their day only to be overturned later. That’s a chance we take being alive. Life is guesswork, even with our best effort to guess right.