Point-blank, I recently asked a friend, “What do you do when you don’t like who you’re becoming?”

She replied, “Tell other people about the behavior you’re trying to change. Other people can tell you to stop when you don’t even realize you’re doing it.”

Excellent answer! But there are way too many behaviors I want to change. Which prompts the question, “what exactly don’t I like about myself?”.


My worst self awakens around strangers and acquaintences.

I feel personally responsible for others’ happiness. This is not a good thing. Uncomfortable people make me feel uncomfortable, so I start trying things. Do they need water? Wine? Light conversation? Depth? Chapstick? Do they want to be left alone?

But we can’t read minds. And people don’t tell us what they want. Or even worse, they try to obscure their inner feelings because they’re embarassed or hurt or don’t like us or whatever. And trying to pry that out makes some people feel better and makes other people feel worse.

But then I take it even further. Around some people, my poor mind-reading abilities become thoroughly mixed with a dash of curiosity, two teaspoons of impatience, and four heaping scoops of “needs-validation”.

And so we have the key ingredients to my personal recipe-for-disaster: social discomfort, mind-reading, unbridled curiosity, impatience, and attention-craving. Dowse me in whiskey for extra spice.

This recipe creates a dish with pungent flavors:

I’m not always like this. Around my friends and family, I manifest my values as other mixtures and macro-behaviors. There are a lot of things about those alter-egos I hate. But strangers and acquaintances awaken my alter-ego that I hate the most. And if I don’t change swiftly, I feel like I could become that person forever.

So how do I avoid becoming that recipe-for-disaster?


Invert, always invert: Turn a situation or problem upside down. Look at it backwards. What happens if all our plans go wrong? Where don’t we want to go, and how do you get there? – Charlie Munger

Instead of looking for success, make a list of how to fail instead–through sloth, envy, resentment, self-pity, entitlement, all the mental habits of self-defeat. Avoid these qualities and you will succeed. Tell me where I’m going to die so I don’t go there. – Charlie Munger

It’s easier to not do stuff than to do stuff. For example, it’s generally easier to not run marathons, it’s generally easier to not win hot-dog-eating contents, and it’s generally easier to not speak Italian. So don’t try to become your best self. Simply figure out how not to become your worst self.

This is the core of the inversion principle – some problems are easier to solve with subtraction than addition.

More specifically, pre-mortems are an excellent tool to avoid disasters. Pre-mortems prompt you to imagine all the paths to failure, and then imagine all the paths to get to the failure states.

Pre-mortems are a powerful tool to alleviate optimism biases. You must anticipate average-case scenarios rather than best-case scenarios. If you haven’t been to a gym in months, what makes you think you’ll suddenly have willpower tomorrow? If you’ve been smoking for decades, what will make you quit on New Year’s Day? It’s easy to imagine a rainbow road to success. But if you want to avoid disaster, you have to thoroughly prepare for the common and dangerous routes. And enumerating failure states can be grueling intrapersonal work.

So I’ve already imagined my personal recipe-for-disaster, but what paths will lead me there again and again?

problem behavior possible paths
being too intense for the occasion avoid listening; feel forgettable; dive into dialogue; have topics ready before conversations
craving validation induce imposter-syndrome; imagine yourself as the main character
overpowering others in conversation launch into monologues without giving others a chance to signal disinterest; never ask questions; talk “out loud” instead of thinking quietly
not considering others’ boundaries assume that everybody will “get over it”; assume that everybody enjoys all humor; do things before asking; push every button and see what sticks
flakiness try to find the “best option” instead of trying to be a dependable person; plan everything at the last minute; ignore instructions
not remembering details about people don’t ask questions; think of something clever to say as soon as people start talking; never repeat people’s names; immediately forget birthdays, anniversaries, etc. without written reminders
too much funny all the time cause chaos instead of confronting your own social anxiety; reject all boredom; yearn for acceptance at all costs
almost complete inability to listen fill your mind with internal dialogue instead of actual dialogue; live in the past; live in the future; never echo others’ thoughts; immediately and severely judge people’s opinions; say what I think before I actually understand others; never listen to backstories; think and talk quickly; interrupt people often; consider why people choose what to talk about; repudiate boredom; take advantage of all conversational pauses; immediately engage people with what you want to talk about; kill all silence as soon as it begins
thinking out loud be afraid of forgetting what to say; interrupt others before your thoughts are complete; talk about things before asking if people are interested; never admit ignorance
extreme condescension (which means talking down to people) assume that everybody is stupid; assume that people think you’re interesting; hold a lot of things in your head that nobody gives a h*ck about; state your stance and belittle others’ opinions; assume that people actually want to change your mind
lack of follow-through follow your passions rather than your commitments; never write anything important down; ignore instructions; think of “better” plans and ask people to follow you blindly
making judgements about who I’d find most interesting frequently scan surroundings for things instead of listening to people; favor shallows over depth; disregard whether or not my prescence is wanted
extreme avoidance let fears run free; assume the worst; assume the best
inability to moderate play with fire; try to outrun the hedonic treadmill; plan for the best rather than the worst; fix everything “tomorrow”
treating others as NPCs obsess over your own insignificant details; live in an RPG rather than an MMO
passive-agressiveness feel deeply; embrace cowardice; shun sincerity
severe impatience take personal affront to systemic inefficiency; reject the shortness of life; pretend life can be experienced faster; believe that waiting is something that happens to you; punish others for your boredom; let anxiety abound; expect others to run on your timers
being too honest, too negative, too fast assume that people are eager for criticism; assume that people are eager for your criticism; assume it matters; assume that they haven’t already thought of that; ask pointing questions instead of asking about their inner experience; assume that they want to fix the problem

These insights are full of contradictions. How am I supposed to be more honest and not say what I think? How am I supposed to stop thinking out-loud while quieting my inner-monologue?

Contradictions are okay. Perfection is futile. Everything will be alright.

When we reflect on our worst selves, we cast a dim light on our darkest paths. There are no maps to your “best self”, but this dim light makes the journey less miserable. Avoid the dangerous roads.

Steel your soul, take a good hard look at yourself, and then be gentle.


Your world will whisper who are you becoming. And when you don’t listen, you become the worst version of yourself.