On Leading With Greatness
On Leading With Greatness
Just Do It! … Like a Boss
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Just Do It! … Like a Boss

He who establishes his argument by noise and command shows that his reason is weak.

Michel de Montaigne

Cartoon of man in suit with arms folded and a smug look standing next to a weathervane with a small green bird perched on his head.

You know the phrase “like a boss?” It was the liveliest, hippest phrase in English a few years back. But, alas, it suffered an untimely and completely meaningless death upon the 2020 release of the the megaplex mediocrity Like a Boss. Prior to that, the phrase was inescapable, but what did it really mean?

Let’s look it up! According to the Cambridge Dictionary, like a boss “is used to say that someone does something well.” Wow. If that inane movie had failed to suck all the life out of like a boss, it would be Cambridge Dictionary for the kill! At least the dictionary helpfully uses the phrase in a sentence for us. Let’s check it out! “I'm going to teach you to draw like a boss.”

That’s just sad.

But have no fear! The Urban Dictionary is on the job with its typical flourish of gratuitous offensiveness. According to the TUD, like a boss describes “a man who's confident in his skin. Knows his shit. Gives a shit if others have a problem. The shit. The man.” Well hold onto your second-class citizenry, little ladies, the boss is not only a man but is the man! And clearly a shit. Whadda surprise!

Let’s see if we can do better than the professional lexicographers. Do you remember the term “simile” from eight-grade English? Your teacher probably told you that a simile is a comparison using “like” or “as.” It’s important to note that a simile is not supposed to be literal. If I say, “your friend sings like Pavarotti on Ozempic,” I don’t think your friend is actually a world-class tenor who is taking weight-loss drugs. I just see a similarity between your friend’s voice and what I imagine a shrunken operatic tenor sounds like. Like a boss is also a simile. If you say, “he ties his shoes like a boss,” you probably don’t mean that bosses have a specific way of tying their shoes. No one gets promoted from cashier to night manager and suddenly stops making bunny-ear loops. No, you mean that he does it with skill and confidence, taking command over those shoelaces, knotting them with authority, bunny-ear loops or not.

Then what is a boss?

In the most basic sense, a boss is someone in charge of others, which is why the term gets used interchangeably with leader. Both have people who are functionally subordinate to them, but that’s where the resemblance ends. Here’s a key difference: a boss tells you what to do while a leader inspires and empowers you—in the immortal words of the sneaker slogan—to just do it. Leaders attract and guide others, not push them to comply. It’s true that bosses sometimes lead, but leaders rarely boss even when they are the boss. Therefore, a boss can be like a leader, but a leader will seldom be like a boss. If you are confused, it is because we use these words carelessly without distinction, but they mean radically different things.

So let’s do a thought experiment. Imagine someone telling you, “she walked into the party like a boss!” Whom does your mind cast in the role? Maybe you picture the great Meryl Streep—as accomplished a thespian as this age has produced! But is it the hard-ass Meryl Streep from The Devil Wears Prada or the tragic, doomed figure she embodies in Sophie’s Choice? It’s gotta be the Prada Streep, right? Menacing, mercurial, and commanding respect while underlings cower before her, cow-towing to her every whim. They are overawed by her power even as they are repelled by her behavior. Did I nail her character? Frankly, I don’t actually know because I’ve never seen the movie! All I have to know is that Streep plays a hard-ass boss in Prada, and the rest falls in line. Streep’s character may be a bloated version, but that’s the essence of like a boss!

And let’s face some facts. Bosses look tough, but, as Michel de Montaigne observes, they are generally weak-minded as evidenced by their empty bluster. Here’s a rule of thumb: a boss is like a skittle—hard shell on the outside, mushy goo within, also a source of empty calories and a promoter of tooth decay. Frankly, acting like a boss takes all the self-mastery of a weathervane and nearly as much brainpower too. You just climb to the top, wait for a stiff breeze, and point.

No, for my money, the real challenge is to be like a leader. Walk into the room like a leader and what happens? People will find themselves drawn to you but not driven toward you. Leadership is a firm but gentle tug, not the insistent and sometimes violent shove of bossing. Leaders get more out of a certain charisma, the subtle gesture, the well-timed word, or the meaningful look than bosses do wielding their titles and positions, flaunting their control as they swagger about.

So, the next time you hear someone say, “he ate that hamburger like a boss,” picture your least favorite boss ever eating that hamburger. Pathetic, right? It just doesn’t mean much, does it? The bottom line is that you can act like a boss or you can be a leader—your call. Remember though that one of those choices is just acting, pretending, while the other choice is leading.


When have you heard the phrase like a boss used? What does the phrase mean to you?

Great leaders must control the urge to act like a boss particularly when they are the boss, and I can help.

If you want to learn more about how to become a great leader in this world of bad bosses, visit GuidanceForGreatness.com.

Visit Guidance for Greatness

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On Leading With Greatness
On Leading With Greatness
Each Thursday I share new ideas for leaders and aspiring leaders on mission clarity, self-awareness, and human skills — a slightly irreverent kit of Tools+Paradigms for leaders and aspiring leaders like you. Visit GuidanceForGreatness.com