Why Searching for the Best is Actually the Worst

The Genius Who Chose Less

Herbert Simon wore one brand of socks,

ate the same breakfast every morning for decades half

a grapefruit, oatmeal, and black coffee owned exactly

one beret at a time, lived in the same house for 46 years,

and believed a person only needed three sets of clothes:

one on the body, one in the wash, and one in the closet.

Despite these sparse daily routines,

he was one of the most decorated thinkers of the 20th century.

He won the Nobel Prize in Economics,

received the Turing Award in computer science,

helped establish the field of artificial intelligence,

and made breakthrough contributions across six different disciplines.

Yet, his primary focus throughout his career centered on one question:

how do human beings actually make decisions?

The Philosophy of Satisficing

For Simon, the act of making a decision was an explicit cost.

Whether selecting an appliance or choosing a life partner,

searching for the absolute best requires time

and cognitive energy that most people fail to account for.

As a result, Simon argued that the optimal strategy

was not optimizing at all;

it was finding an option that was good enough and stopping.

He termed this approach “satisficing,”

a blend of the words satisfy and suffice.

When faced with a decision, he evaluated a few alternatives,

made a choice, and moved on without agonizing or second-guessing.

For much of the 20th century, mainstream economics

relied on the “rational actor” model,

assuming that individuals evaluate every available option

to select the optimal choice.

Simon countered that true rationality is impossible.

To identify the absolute best choice,

an individual would need complete knowledge of every alternative,

the ability to predict every possible consequence,

and unlimited mental bandwidth to compare them all.

Because humans operate under incomplete information

and bounded mental capacity, the endless search itself

becomes a costly trap that leads to decision paralysis.

Maximizers vs. Satisficers

Decades of research following Simon’s work have confirmed

that chronic maximizing carries high psychological costs.

Studies evaluating individuals on a scale between “maximizers”

and “satisficers” reveal clear behavioral divides:

• Maximizers strive for the absolute best outcome. They are consistently less happy, less satisfied with their choices, more prone to chronic regret, and more likely to engage in endless social comparison. They also tend to favor reversible decisions, which prevents them from fully committing to a path.
• Satisficers focus on finding an option that is good enough for their specific goals. By setting a practical threshold rather than demanding perfection, they remain content with their choices instead of being haunted by unselected alternatives.

Committing to a sufficient choice frees up cognitive resources

for living life,

rather than draining those resources wondering how to live.

Fredkin’s Paradox and The Illusion of Choice

Agonizing over choices often peaks when the stakes

are at their lowest.

This dynamic is illustrated in Robert Frost’s poem,

The Road Not Taken.

While frequently interpreted as an anthem of bold individuality,

the text states that both roads were virtually identical,

equally worn, and covered in untrodden leaves.

Frost wrote the poem to tease a friend who constantly stalled

over which path to take on walks

and inevitably regretted his choice by the end.

This behavior exemplifies Fredkin’s Paradox:

people spend the most time and energy on decisions

where the differences between options matter the least.

When two choices are nearly indistinguishable in quality,

identifying an advantage becomes difficult,

tricking the brain into expending massive effort

on a functionally meaningless distinction.

The Modern Dilemma of Infinite Optimization

Modern society has embraced maximizing across

nearly every domain, giving rise to trends focused

on optimizing everything from career earnings

and physical appearance to sleep and diet.

Today, individuals have access to vastly more options

than pre-industrial ancestors,

while digital platforms function as endless comparison

engines that frame “good enough” as settling.

Newer technologies and artificial intelligence threaten

to expand this menu of choices even further,

increasing the likelihood of comparison-induced paralysis.

The tragedy of this mindset is captured in a story

by Haruki Murakami, where a young man

and woman encounter each other on a street corner

and realize they are a 100% perfect match.

Rather than accepting the connection, they wonder

if finding their ideal partner was too simple.

They decide to separate as a test, believing that if they

are truly meant to be, they will inevitably cross paths again.

They walk in opposite directions, and despite being an ideal match,

they never see each other again.

Striving perpetually for an elusive ideal often destroys

the value of what is already present.