Why being the “cool boss” isn’t the right goal

By Brittany Taylor

Work + Life

How to build your professional reputation

+ become the "cool boss" you admire

by Brittany Taylor

published November 3, 2017

updated June 5, 2018

I haven’t met a person yet who doesn’t crave to be singled out in some way, to be seen as special and valuable and unique. I’m certainly That Person, and I bet you are, too.

There’s something alluring about being cool. It might not be the popularity you want or the crowds or the renown. You might just want to be an introverted hermit who goes out only for margaritas and the occasional Target run, but who people happen to think is exceptionally awesome in some way or other.

(That sounds pretty damn good to me. Your experience might vary.)

Coolness, though, shouldn’t be the goal. Coolness should be the by-product of what you do and who you are and what you mean to other people.

Why “be cool” is a bad goal

The best goals are actionable. There are time limits attached, and there are ways to measure your progress and results. But coolness isn’t quantifiable. It’s not a tangible thing you can hold in your hand or track on a spreadsheet.

Coolness is a concept. And cool people? Well, there are two types of them.

The first kind of cool person is the individual who strives to be cool—and achieves it, somehow. These people are known for being cool…and that’s just about it. Maybe they’re tastemakers, maybe they’re socialites, maybe they’re models. They’re the sort of people you look at and recognize as being unquestionably awesome, and yet awesome is all they are.

The second kind of cool person is the one who does something absolutely kick-ass—and becomes cool thanks to their achievements. They’re geniuses, they’re inventors, their movers and doers and world-changers. They’re the sort of people you look at and admire, not because they’re cool but because they’ve done incredible things.

The first kind of person walks on a popularity tightrope. They’re cool now, but that coolness is flimsy. It could disappear any second, and then they would plunge into obscurity.

The second kind of person stands on much firmer ground. They’ve earned their coolness, and the CV they’ve sweated for won’t vanish when trends change.

You want to be the second kind of person.

Do you want to be cool? Sure. But that’s not all you want—or, it shouldn’t be. Going after coolness for coolness’ sake leaves you vulnerable to a big fall. Your social credit relies entirely on the good favor of the masses, and the masses are a wishy-washy group of people. Their long-term admiration is derived from deeds, not just appearances.


Feeling a little shaky? That's natural when you're a creative person trying to make it. But there are ways to deal and flourish despite your self-doubt.

How to achieve a professional reputation as a "cool boss"

So, how do you do the things that score you long-term, “cool boss” status? The answer is to start small—and to start, period.

Here are a slew of must-dos:
Do things that seem genuinely interesting to you

Following your passions rather than trends will motivate you to continue working when there are few rewards, and to work harder when you’d rather take a break.

Be yourself

Bringing your unique personality to the table lets you stand out in a crowd. It also helps people feel more comfortable talking to you because you come across more genuine.

Build relationships

It’s communities that decide popularity, not random people who never interact with each other. Become a valuable contributor and you’ll see your star rise.

Push yourself to improve

You’ll never get better if you don’t challenge yourself to do things that are beyond your current capabilities. Keep striving for growth. The moment you think you know everything is the moment you’ve become complacent, smug, and uninteresting.

Share your work

If people don’t know what you do, it’ll be impossible to become known for it. Sometimes, sharing your work—particularly your triumphs—can feel like bragging. Shrug off that feeling and do it anyway. We want to see your achievements!

Seek ways to differentiate yourself

Excellence and originality are what will set your work apart. Why do we idolize people like Gloria Steinem, Meryl Streep, and Shonda Rhimes? Because they’re trailblazers at the tops of their respective fields.

Be generous, kind, and ethical

“Niceness” is bland and baseline. Generosity, kindness, and consistent, outspoken ethical behavior endears you to people and makes others want to support you whenever they can.

Stand for something

Have a mission, a tagline, or a movement that you can be associated with. You don’t have to do the same thing for your entire life, but do let your passions carry you along a trajectory.

About me

Brittany Taylor

My name is Brittany, but my friends and clients call me "Britt." Online small business owners hire me to create content strategies and write their blog posts, email newsletters, and social media updates. I work with bosses around the world from the marshes of Charleston, S.C.


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