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The Case Against Cool

Hipness's hefty price, not just in cash but in relationships and career.

Key points

  • Many decisions stem from prioritizing coolness.
  • People may choose romantic partners and careers based on the "cool" factor.
  • Purchasing decisions can also be influenced by what seems cool, including fashion, vacation destinations, and even where to live.
ZeraDodich, Pixabay, Public Domain
Source: ZeraDodich, Pixabay, Public Domain

A client asked me what car he should buy, and I asked what factors were important to him. Near the top of his list: coolness. I swallowed because coolness tends to be inversely correlated with reliability, which, to this uncool coach, should be the dominant factor. A car is basically an appliance. Its job is to start every day and get you from point A to point B without having to worry much about servicing, let alone breaking down.

That made me think more broadly about coolness:

Romantic partner

Many failed relationships stem from prioritizing coolness: S/he swaggers or sashays in, casually removes the sleek sunglasses, and bestows a smile to the “worthy.” S/he craves adventure, physical or in appearance—s/he is fashion-forward even at the risk of appearing fashion-foolish. Of course, all that hoo-hah has little to do with whether a relationship will work. I'd even conjecture that it's inversely correlated.


Many of my clients seek a cool career, for example, in entertainment, nonprofit, or the arts. They do that so often that I wrote a book, Cool Careers for Dummies . Paradoxically, you may be more likely to have a cool life by choosing an uncool career. That’s because the competition for decent-paying, reasonably stable jobs in a cool career is fierce. Unless you’re unusually talented, dogged, and/or lucky, you may well end up in a decidedly uncool job in that cool career, for example, paid little to pitch for donations to a cause that's not distinctly more worthy than myriad other causes the prospect could donate to.


The cool are more likely to buy stuff they see in fashion mags, for example, Vogue or GQ. That may appeal to the cool pool but could make some mainstream people wonder whether a person's focusing on his or her packaging is meant to distract from the less impressive product within.


Cool people pay a hefty price to live, recreate, and vacation in a cool locale. Some would rather live in a modest home in an immodest zip code, pay big to join a golf or tennis club when there’s a perfectly good municipal facility nearby. They’ll vacation in the Hamptons or Newport Beach even if a couple of nights costs as much as the average person pays in rent for a month.

The takeaway

What are you willing to pay or do to be cool? Or do you think that only fools try to be cool?

I read this aloud on YouTube.