The Donkey Dilemma:
Why Trying to Please Everyone Will Drown Your Dreams

The Old Man, the Boy, and the Donkey

An old man, a boy, and a donkey were going to town.

At first, the boy rode the donkey while the old man walked. Soon, they passed a group of people who shook their heads disapprovingly. "How shameful," they muttered. "The young boy rides while the old man walks."

Embarrassed, they switched places.

Later, another group scoffed. "Imagine that," they said, "a grown man riding and making a poor child walk."

Frustrated, the old man and the boy decided they’d both walk.

It wasn't long before they encountered more critics: "How foolish. You have a donkey—why aren't you riding it?"

So, together they clambered onto the donkey.

But soon enough, another set of onlookers gasped. "How cruel to overload that poor donkey!"

Feeling trapped, the man and boy tied the donkey's legs to a pole and tried to carry it. Crossing a bridge into town, they lost their grip. The donkey fell into the river and drowned.

The lesson was brutal and clear:

Yet, today, millions live the modern version of this ancient fable.

And most don't even realize they're carrying a donkey.

The Invisible Chains of Approval

The Silent Epidemic: Approval Addiction

While the Aesop's Fable above is over 2500 years old, it is even more relevant today than it ever has been, social media, the internet and media has made everyone worried about everybody's opinions.

A recent poll states that 57% of Gen Z (and 41% of all adults) want to be "influencers."

It starts innocently enough.

As kids, we learn that smiles, praise, and gold stars follow "good" behavior. Approval becomes currency. We become dealers and addicts at the same time, trading tiny pieces of ourselves for nods and likes.

Fast forward to adulthood, and the stakes are much higher.

Instead of stickers and smiles, it's validation on social media. It's job titles. It's approval from peers, parents, partners, and perfect strangers. Many young men spend their lives adjusting their behavior, words, and dreams to fit what "everyone" expects.

But here's the ugly truth:

"Everyone" doesn't exist.

You can't please "everyone" because "everyone" is just a swirling mass of conflicting desires, values, and expectations. Pleasing one group often offends another. Winning applause from one person may earn contempt from another.

The quest to please everyone is chasing a moving, contradictory target that doesn't even have your best interests at heart.

The Real Cost:
Who You Could Have Been

When you try to please everyone:

• You sacrifice authenticity.
• You waste time and energy trying to read minds and predict reactions.
• You dilute your talent, voice, and power until there's nothing left to recognize.

Most tragically, you lose the very thing that makes people worth following: a clear sense of self.

History doesn't remember people who fit in perfectly.

It remembers the ones who stood for something.

Alexander Hamilton. Bruce Lee. Malcolm X. Miyamoto Musashi. Steve Jobs. Kobe Bryant.

Every single one of them angered "everyone" at some point. They weren't trying to piss people off—but they weren't bending over backward to win approval either.

They chose their values. They chose their vision. They lived (and sometimes died) by them.

And that's why they mattered.

You cannot lead—yourself or others—if you're afraid of being disliked.

How to Break Free

1. Choose Your Audience

Not everyone deserves a vote on your life.

Pick the few whose opinions actually matter: mentors, true friends, people whose lives embody the values you aspire to.

Everyone else? Background noise.

2. Decide Your Values

Approval-seekers drift.

Leaders anchor themselves to a set of principles: honor, courage, loyalty, resilience, excellence. Define your code—or the world will impose one on you.

3. Accept the Cost

Freedom isn't free.

Some people will dislike you. Some will mock you. Some will leave.

Good.

4. Build the Muscle of Self-Respect

Every time you stand firm on your principles, even when it's uncomfortable, you grow stronger.

You don't find self-respect.

You earn it—in battle, moment by moment, choice by choice.

5. Remember the Donkey

Whenever you're tempted to twist yourself into knots to please someone, remember the image: an old man and a boy trying to carry a donkey across a bridge, only to lose everything.

You are not here to carry anyone's donkey.

You are here to walk your path with honor.

Putting It On the Mat:
The Real Test of a Warrior

There was a kid I worked with on a jobsite, barely 18, who reminded me of the boy and the donkey.

Let's call him Danny.

Danny was a good kid. Worked hard. Wanted to do well. But he was obsessed with being liked.

If the foreman joked with him, Danny would laugh, even if he didn’t get the joke. If the journeymen teased him, he'd laugh along, even when it was cruel. If someone asked him to do a job two ways at once, he'd nod "yes" to both—then panic when he couldn't deliver.

I watched Danny slowly crumble under the weight of everyone else's expectations.

He wasn't failing because he lacked skill. He was failing because he lacked a spine.

One day, after a brutal 12-hour shift, I pulled him aside.

"You trying to make everyone happy, kid?" I asked.

He nodded sheepishly.

"You won't," I said. "You can't. You don't need to. You just need to be solid. Do your job right. Stand tall. Take pride in your work. Let the chips fall where they fall."

It took time, but Danny changed.

He toughened up.

He started setting boundaries.

He learned when to say "yes," when to say "no," and when to say nothing at all.

Years later I bumped into him, he's running crews twice the size of the one that nearly broke him.

Not because he became better at pleasing people.

But because he stopped carrying donkeys.

Your turn:

If you've been feeling crushed by everyone else's opinions—stop.

Put the damn donkey down.

Pick up your values. Your goals. Your standards.

Decide who you are—and then walk like a man who means it.

Because in the end, it's not about who claps for you.

It's about whether you can look in the mirror and respect the man staring back.

That's the real test.

That's the way of the warrior.

Let's get to work.

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