Re-Imagine Success
Re-Imagine Success Podcast
The Fool's Game: Pleasing People in the Pursuit of Success
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The Fool's Game: Pleasing People in the Pursuit of Success

Why Chasing Approval Will Leave You Exhausted and Unfulfilled

“He who trims himself to suit everyone will soon whittle himself away.”

— Raymond Hull

There’s an old parable about a man, his son, and their donkey. As they set off on their journey, the father, elderly and wise, allowed his young son to ride the donkey while he walked alongside. As they entered the first town, whispers spread through the streets. The townspeople gossiped, criticizing the boy for his lack of respect.

“How unkind,” they murmured. “What kind of child lets his frail father walk while he enjoys the ride?”

Hearing this, the father and son swapped places before heading to the next town. Upon their arrival, the townspeople again whispered and judged.

“What kind of father is this?” they scoffed. “A parent with no mercy, making his young son travel on foot while he rides comfortably?”

Determined to silence the criticism, the father and son decided neither of them would ride the donkey as they continued on their journey. Yet, in the next town, they were met with even more scorn.

“How foolish they are!” the people chuckled. “Why bring a donkey and not even ride it? What a waste of an animal designed to carry a load.”

And so, the man and his son learned an important truth: no matter what they did, people would always have something to say.

I love this parable because it illustrates a fundamental reality: trying to please everyone is impossible. Yet, so much of our lives, especially our careers and our sense of self-worth, are entangled with the approval of others.

The Weight of Expectations

One of my kids is 18 and has just accepted his spot at university to study civil engineering. But a few years ago, when I first asked him what he wanted to pursue, his answer was different.

“Computer science,” he told me.

“Why?” I asked.

“I don’t know,” he shrugged. “That’s what you do if you’re smart. You go into CompSci.”

(Yes, my son is quite smart.)

When I dug deeper, I realized he didn’t actually like any of the potential jobs that a computer science degree would lead to. After two summers of intentional exploration, deep reflection, and countless conversations, he made an entirely different decision one rooted in what genuinely sparked his interest. Now, when people ask him about his studies, he lights up. He owns his choice. He understands why he’s pursuing civil engineering, and he speaks about it with conviction.

Yet, when I meet other young people, the majority don’t have that same clarity. Many are simply following the expectations laid out for them by parents, society, or outdated notions of success.

Parents, We Are Part of the Problem

Too many parents push their children toward high-status careers in medicine, law, and finance not out of proper understanding but because of ingrained beliefs about prestige and security. We assume success lies in these paths without questioning whether they align with our children’s unique interests and strengths.

We spend more time at work than on any other activity besides sleep. We sacrifice years of our lives in pursuit of careers. Shouldn’t that warrant more careful thought and more intentional decision-making?

Yet far too often, careers are chosen based on external validation rather than internal fulfillment. We chase titles, salaries, and admiration instead of meaning, joy, and purpose. This inevitably leads to discontent, burnout, and a life filled with regret.

The Courage to Choose Your Own Path

The reality is this: if you live your life trying to meet everyone’s expectations, you’ll end up pleasing no one, including yourself. The world will always have an opinion. There will always be whispers of judgment, no matter what you choose.

So, why not choose for yourself?

True success isn’t about meeting external expectations. It’s about living a life that feels aligned, meaningful, and worth the sacrifices it demands. It’s about knowing why you do what you do, owning your choices, and finding fulfillment in them regardless of what the townspeople may say.

As always, take care of yourself and those around you.

In Partnership,

Nabeela


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