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The Problem With Optimizing For Outliers

The road to unhappiness is paved with good intentions.

Go to school, get a job, get married, buy a house, have kids…

This was THE path we were told growing up. It’s become a status symbol to ignore this life path and do things your own way.

Where in our infinite wisdom, as 20 year olds, did we think we knew better than generations of our family and friends around us.

I’ve been thinking about this quote from Konstantin Kisin a lot this week:

"In the modern world, way more people are lost. They don't know what they're supposed to do. In the past we had trajectory to follow. Which hurt some people because it wasn't the trajectory for them. But, when you take away all trajectory, then everybody's lost."

One of the core themes I keep revisiting is that our problems in the western world are a result of overabundance not scarcity. People have to make their lives harder with cold plunges and 75 Hard to remind themselves of how easy we have it.

  • Too much food > obesity

  • Too much social media > depression

  • Too much entertainment > decision paralysis (anxiety)

  • Too many cheap goods > overspending

  • Too many beautiful people on Instagram > body dysmorphia

And the topic of today’s newsletter: Too much freedom > Nihilism.

There is a reason that the most walked paths are often paved. It’s because the people before us had the forethought to ensure that path stayed preserved for a long time.

That doesn’t mean some people shouldn’t walk on the gravel paths, or that mountain bike trails should be avoided. It means that the paved road is the most likely way for people to get from point A to point B.

For the purposes of the metaphor, assume point A is where you are now and point B is the end of a fulfilling life.

By optimizing for freedom of choice we’ve told people that all paths are equal, which simply isn’t true. As I eluded to before it’s become popular for people bushwhacking their way through the forest to tell people they’ve found the best path to a fulfilling life.

Take this woman, who’s hungover and thriving after a Beyonce concert. (810K views)

Making sure everyone knows that it’s important to not have kids at 29 so you can go out and enjoy your single life. A quick reminder that 80% of women that end up childless never intended to be childless.

Or how about the stay at home husband? (25.7M views)

Men are 10% more likely to need ED medication if their wife even slightly outearns them. Being the breadwinner increases stress and insomnia for women. You’re also much more likely to get divorced if you make less than your wife.

Here’s a few more trendy paths whose popularity exceed their traveler’s happiness level:

  • Van life

  • Activism

  • Onlyfans

  • Polyamory

  • Tiny homes

  • Digital nomads

  • Red pill/MGTOW

  • Professional gaming

  • Long term cohabitating

  • Vegan/Keto/Carnivore Diets

  • Androgynous clothing styles

  • Using your kids for online clout

  • NFT Trading (and associated get rich quick ideas)

It’s not surprising to me that more and more people are becoming overwhelmed by their options, choosing something new for the novelty, discovering the path leads them in the wrong direction and then becoming nihilistic by asking “what’s the point if these options all make me unhappy.”

If you’re unhappy, stop trying to be the adult version of an emo kid and go back to basics.

Go to school, get a job, get married, buy a house, have kids…

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