Little Flaws

Not realizing that inarticulate, uneducated, obnoxious, unqualified, and crazy people sometimes have the right answers.

Comparing reality with an idealized alternative.

Overestimating the extent to which your insights are different from your peers.

Assuming other people think about you as much as you do.

Emphasizing technical expertise while discounting softer topics like communication and empathy.

Assuming experience in one era prepares you for the next.

An insatiable appetite for the hand that feeds you, or discounting how much you rely on other people.

Overlooking that some of your opinions would change if your incentives were different.

Being persuaded by the advice of those who need or want something you don’t.

Having a hard time distinguishing between what happened and what you think should have happened.

An illusion that other people’s bad circumstances couldn’t also happen to you.

Not realizing that surly people are probably going through something terrible in their life.

The inability to communicate your ideas because you wrongly assume others have the necessary background to understand what you’re talking about.

Assuming history is a guide to the future, when in reality, “things that have never happened before happen all the time,” as Scott Sagan says.

Conflating “I’m good at this” with “Others are bad at this” in a way that makes you overestimate how valuable your skills are.

Mistaking a temporary trend for a competitive advantage, when serendipity masquerades as skill.

Extreme adherence to a specific worldview in a world that changes all the time.

Underestimating the odds of disaster because it’s comforting to assume things will keep functioning the way they’ve always functioned.

Being so emotionally invested in what you do that you can’t delegate tasks.

Exaggerating the importance and influence of your social group.

Incorrectly assuming the views of one person reflect those of a broader group that person associates with.

No preemptive check on your risk tolerance and ambition, causing you to learn the limits only when you’ve gone too far when it may be too late to recover.

An attraction to odds that may be in your favor but whose downside could cause ruin.

Ignoring the role of luck because it’s too painful to consider, causing an overestimation of how repeatable your skills are.

Remembering happy events more vividly than bad ones in a way that leaves you with an unrealistic view of how good the past used to be.

So obsessed with data that you discount how influential squishy things like narratives and feelings can be.

Assuming competency in one field leads to skill in other fields.

Expectations rise equal or faster than results, leading to constant disappointment no matter how much you’ve accomplished.

Avoiding negative information that might challenge views that you desperately want or need to be right.

Ignoring the power of tail events because you’d be bored if you admitted that 99% of news events won’t matter at all in the long run.

Assuming that what you know and have measured is more important than what you don’t know and haven’t measured.

Exploiting all opportunities to the fullest extent possible with no room for error in a way that leaves you vulnerable during the slightest change in future circumstances.

Excessively rosy views about the decisions you’ve made to maintain self-esteem in a world where everyone makes bad decisions all the time.

Having zero tolerance for hassle, inefficiency, and nonsense in a way that leaves you frustrated and in search of a perfect world that will never exist.

Excessive ego in a world where humility is the impressive trait that catches people’s attention.

Being blind to the stress, struggle, doubt, and failure your role models deal with.

Taking your cues and insights from people playing a different game than you are.

Thinking that saying “I don’t know” when you don’t know is a character flaw.

Assuming statistics alone can persuade other people when what really changes minds are stories.

Ignorance of the fact that different phases of your career require different skill sets.

Success leading to overconfidence and complacency which erodes the traits that originally made you successful.

A failure to identify the true costs of something you’re pursuing, with too much emphasis on financial costs while ignoring the emotional price that must be paid to win a reward.

Underestimating the power of compounding, in both good and bad things, because linear thinking is more intuitive.

An attachment to social proof in a field that requires contrarian thinking to achieve above-average results.

Ignoring the important fundamentals of a topic that happen to be boring or repetitive.