The Cost of Trying to Make Everyone Happy

Issue #133: A simple courage practice that unlocks authenticity, growth, and peace.

Nov 22, 2025

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If there’s one theme that has kept showing up in my life lately—from books, conversations, newsletters, and even random quotes—it’s this:

Courage matters far more than skill.

And more specifically…

The courage to be disliked.

In my previous issue, I wrote about how courage can beat preparation. That taking action—before you feel ready—is often the only real advantage you need. This week, that idea evolved into something deeper and more uncomfortable: being willing to take action even when people might not like it.

And if I’m honest, this one hits home.

Why We Hold Back (Even When We Know What to Do)

Most of the time, we know exactly what we want to do.

Send that email. Share that idea. Set that boundary. Raise that price. Have that uncomfortable conversation.

But something stops us.

Not the lack of talent.

Not the lack of clarity.

It’s the fear of being disliked.

You don’t want clients to think you’re difficult.

You don’t want friends to think you’ve changed.

You don’t want your team to think you’re too demanding.

You don’t want strangers online to judge you.

So you soften your voice.

You avoid the tough conversation.

You dilute your goals.

You play small.

And all of this creates a quiet form of self-betrayal.

Warren Buffett once said:

“It takes 20 years to build a reputation and five minutes to ruin it.”

He’s right — but that quote can also become a cage.

For years, I worried too much about how I appeared to others. I avoided anything that might make me look foolish or imperfect. I wanted everyone to like me, online and offline. One misstep and I thought I’d blow my reputation.

But living like that isn’t wisdom.

It’s fear disguised as strategy.

The Invisible Boxes We Live In

This fear shows up in another way: the boxes people put us in.

Andrew Wilkinson (an entrepreneur I admire) once shared a story about his father — a moment that captures this perfectly.

He asked him, “Dad, you’ve always wanted to build your own buildings. Why not become a real estate developer?”

His father replied:

“Once people put you in a mental box, they punish you for leaving it. In their minds, I’m in the ‘architect’ box. If I suddenly pitch a real estate project, it would hurt me more than starting fresh. Everyone hates it when you change boxes.”

That hit me hard.

We all live inside these invisible boxes — titles, roles, expectations, reputations. And the second you try to evolve, people resist it.

When the world won’t let you change, you end up choosing from three bad options:

Hide. Stay quiet. Don’t rock the boat.
Perform. Become a character instead of a human.
Split. Live two lives — who you are and who you pretend to be.

None of these feels like freedom.

The Only Way Out

The only real way out is the courage to be disliked.

Not by being rude or careless — but by being real.

You cannot make everyone happy.

You shouldn’t try.

Growing will disappoint some people.

Honesty will offend some people.

Authenticity will confuse some people.

And that’s okay.

That’s part of the path.

Your job is not to manage everyone’s reaction — it’s to stay true to your direction.

I’ve been reading “Courage to Be Disliked,” and the timing couldn’t have been better.

The central message is simple but powerful:

Your fear of being disliked is often the biggest barrier to your growth.

I’m working on growing my courage muscle so I can stop playing for applause.

Courage Isn’t Always Loud

Courage doesn’t always roar. It often whispers.

It shows up in tiny acts of honesty with yourself.

Sometimes courage is ordering something different from the menu when everyone expects you to stick to your usual.

If you’ve been “the vegetarian” your whole life but want to try meat or wine, allow yourself that curiosity.

If you’re an extrovert, try spending time alone.

If you’re an introvert, walk up to a stranger at a networking event — I usually start with someone standing by themselves.

If a thought has been sitting heavy in your mind, confide in a friend. Or write it down. I often use ChatGPT to unpack complicated feelings and see my fears more clearly.

Courage begins with these little micro-moments — choosing truth over performance.

A Dare for You

Let someone down today — gently but honestly.

Say the thing you’ve been avoiding.

Launch the weird project.

End the fake-perfect situation.

Admit what’s not working.

Watch what happens:

90% won’t care
8% will respect you
2% will dislike you
And you’ll finally feel free

Because the cage only exists if you believe in the bars.

I’d rather have 2% hate the real me than 100% applaud a performance.

🤩 Inspiration

⁠Here’s another line I wrote to myself:

“No matter what you do, you cannot make everyone happy.”

And the moment you accept that, life becomes lighter.

Your decisions become clearer.

And your progress becomes faster.

Here’s to learning, growing, and yes—risking being disliked.

📚 I’m writing a book

Creating this short video for my upcoming book - Peaceful Growth took just 10 minutes — thanks to AI tools like Sora. A few years ago, this would’ve taken months.

Excited to share the first look at my new book — Peaceful Growth.