Good Boy Syndrome: Letting Go of Who You're 'Supposed' to Be

A few nights ago at the office, we stayed late and drifted into one of those honest, unplanned conversations about life — relationships, family, and how we see ourselves in all of it. At some point, I asked whether “making your parents happy” is still a realistic goal.

I didn’t ask to challenge the idea — I asked to reflect. I was curious if our different upbringings led to different views. But surprisingly, we all shared a similar feeling. Then Pyter said something that stuck with me:
“Maybe we’re not in a place to make them happy. But at least we’re not making life harder for them.”

I’ve heard versions of that before, but this time it landed differently. Then Chris added something else: that sometimes the people who feel most weighed down by the pressure to make others proud... are the ones not actually taking meaningful steps to do it. There’s a kind of mental spiral that comes from constantly thinking about it — without actually doing much about it.

That hit me.

It reminded me of a time when I felt overwhelmed by this unspoken need to “make others proud.” I tried to present myself like I had things together — like I was on track. But underneath, there wasn’t much action, just a performance. I looked stressed and self-critical, but the energy I spent wasn’t really moving me forward. It was more about the image than the substance.

It’s what I’ve come to think of as Good Boy Syndrome — that inner script some of us grow up with: be responsible, don’t disappoint, always try to impress, even silently. But over time, it can morph into something heavy. You're not chasing growth — you’re chasing approval. You're not acting from purpose — you're reacting to pressure.

The stress and anxiety we feel about “not being there yet” often isn’t just about where we are — it’s about where we think we’re supposed to be. It’s not failure that shakes us the most, but the gap between who we are and the ideal image we’ve constructed of ourselves. We become more obsessed with being seen a certain way than actually being that way.

C.S. Lewis said it well: We often worry more about appearing good than actually doing good. And our sadness about our failures is often mixed with pride — not because we aren’t good enough, but because we don’t look like the person we wish we were.

“Do not waste time bothering whether you ‘love’ your neighbor; act as if you did. As soon as we do this, we find one of the great secrets: when you are behaving as if you loved someone, you will presently come to love him.”

In other words, action shapes the heart. Not the other way around.

When I stopped trying to live up to an imaginary version of myself, and instead just showed up — doing what I could, with what I had, where I was, something shifted. I felt lighter. More present. Less anxious. I could connect with people more genuinely, because I wasn’t trying so hard to look like I cared.

Pride and vanity pull us inward — making us self-conscious, competitive, and restless.
But humility turns us outward. It makes room for grace, presence, and real joy. It reminds us that genuine beauty doesn’t come from presentation — but from quiet, selfless action.

In the end, maybe the goal isn’t to be seen as “a good boy.” Maybe it’s to be so free of self-obsession that we can admire our talents and others’ — without competition or insecurity. To be a great artist or a kind child, and then just forget about it.