Sorry, But Not Sorry

Disappointing People (and Why You Should Try It More Often)

There’s a unique form of Western guilt that bubbles up when we consider disappointing someone— particularly someone we love.

Let’s simply just call it people-pleasing. Here’s how the story goes: Between childhood gold stars and corporate team-building seminars, many of us picked up the belief that being a “good person” means never letting anyone down.

I call bullshit—or more appropriately, I call upon Zhuangzi, who reminds us:

“A path is made by walking on it, not by following others.”

When Italy Becomes a Prison

A friend of mine—let’s call her H —called me recently in a moral crisis. She was expressing upset over the phone, not because she didn’t know she needed to end the relationship she had with her life partner, but because she felt awful about it.

Why?

Because her boyfriend had just recently bought them two tickets to Italy.

Now mind you, this wasn’t a spontaneous getaway. This was a calculated romantic bribe disguised as a Tuscan fantasy. She already knew the relationship had expired like an old bottle of limoncello—but canceling meant disrupting his plans, his dreams, his hopes for permanency in the relationship.

“I just don’t want to ruin it for him,” she said, with emotion in her voice.

I paused, then offered this: “But aren’t you ruining it for you by staying?”

Silence. Then a sniffle. Then a damn.

And just like that, her trip became a metaphor for so many of our lives—postponed departures we delay out of politeness, fear, and habit. We would rather betray our inner compass than face someone’s frown, disappointment, or rage full disappointment.

The Audacity of Being True

In Taoism, one of the most subversive acts you can take is to follow your own nature—your ziran (自然)—your spontaneous authenticity. Not your curated persona, not your good intentions, but the current of who you actually are.

But let’s be real: that’s easier in theory than in practice, especially when other people’s feelings are involved. Over the years, I’ve disappointed a few friends, a few partners, and at least one highly ambitious person who wanted me to be a part of his business.

Every time, it felt like emotional treason. But looking back, the moments I chose me—clumsily, awkwardly, with a bit of Taoist shrugging—were the moments that nudged me closer to my real path.

Confucius Had Boundaries, Too

Even Confucius, that champion of duty and harmony, understood that sincerity had to be rooted in self-respect. He once said:

“To see what is right and not do it is want of courage.”

And let’s be clear: disappointing others is not cruelty. It’s not recklessness. It’s not ghosting someone the night before a wedding. It’s just temerity—boldness—to act in alignment with what feels true for you.

Sometimes the right thing feels like the wrong thing because it’s unfamiliar. Because it interrupts someone else’s expectations. But integrity is not the same thing as predictability.

The Freedom to Change Your Mind

We live in a culture that treats changing your mind like a character flaw. But Taoism teaches that life is a constant form of transformation. The water doesn’t apologize for turning into steam. The mountain doesn’t beg the valley for permission to erode.

So why do we? Why do we say yes when we want to say no? Why do we pack for Italy when our soul is already checked out?

There’s an old Zen saying:

“Let go or be dragged.”

Most of us are being dragged—not by tyrants, but by our own fear of being the bad guy. Of being seen as flaky, selfish, ungrateful, or—God forbid—human.

Your Tao Ain’t Theirs

If there’s one truth I’ve learned, it’s this: You can’t follow the Tao and follow everyone else’s expectations at the same time. One of them has to give.

Choose yourself. Tenderly. Truthfully. Even if it means canceling the damn trip to Italy.

Because maybe that trip wasn’t meant to be taken anyway. Maybe the real destination was coming back home—to yourself.

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Diamond Michael Scott — aka The Chocolate Taoist