But are you having fun?
Is success only real if it hurts? How does pride influence us?
The other day, I found myself in a familiar spiral. I was knee-deep in the demands of my Substack, Instagram, TikTok, and everything else I’ve tied my identity to lately. Progress, analytics, engagement—it all looked good, even great. But then someone asked me, “Are you having fun?”
I froze.
I could feel my pride rising to defend itself. Fun? Who cares about fun? Look at how much I’m building. Look at how many kids can’t read. Look at the teachers quitting. But that question lingered, slicing through my defenses. Am I having fun? And why does it feel shameful to admit I am—or worse, that I don’t even know how to anymore?
You act like it's shameful to be having fun.
Gut punch.
Because they’re right. Somewhere along the way, I started to believe that fun was frivolous. I wrapped myself in pride—the kind that tells you progress must be hard-earned, that success is only real if it hurts. Pride became my fortress, but also my prison. It has caught me in cycles I’ve seen before: isolation, fear, overcompensation, and feeling total surrender to forces I can’t control.
You act like it's shameful to be having fun.
Am I ashamed? I might be.
Insisting on joy sounds like rebellion. It sounds loud, messy, audacious. It’s also terrifying, isn’t it? Because if you insist on joy, you must let go of something else—guilt, maybe. Or the illusion of control. Or that voice whispering that suffering is the price you pay to be taken seriously.
For me, shame about having fun didn’t come out of nowhere. It came from growing up in a world where "fun" was either a distraction or a danger. It came from adulthood, where productivity replaced play as the marker of a life well-lived. It came from learning that survival mattered, safety wasn’t guaranteed, and laughter could turn to silence in an instant. Then there’s social media, where fun is curated, staged, and packaged for others’ approval—where it’s easy to lose track of whether you’re actually enjoying yourself or just performing enjoyment for an audience.
I know I’m not alone in this. I’ve spoken to people who feel the same pull: the pride in the grind, the fear of wasting time, the deep and quiet suspicion that joy is a luxury they can’t afford. It’s hard to admit, even to yourself. Fun? It sounds so childish. So unserious. So unimportant.
But then I remember this: We aren’t meant to be a glum lot. If newcomers to a school, program, organization, or system see no joy in our existence, why would they stay? Who would want what we have?
I have to remind myself: life isn’t supposed to be this heavy. My house runs better when it’s in order, when I’m not buried under guilt or remorse. When I stop taking myself so seriously, the weight lifts. And yes, the work matters. It matters to create, to grow, to contribute something real. But so does fun. So does laughing with people who love me. So does watching a ridiculous show or playing a silly game or walking outside and letting the sun warm my face without thinking about how to monetize it.
Am I having fun? Sometimes the answer is hard to face when I ask myself that question. Sometimes, it’s painful because admitting I am not having fun feels like failure. Or, realizing I am having fun feels like a forbidden fruit, something only the privileged educators at the central office get to enjoy.
You act like it's shameful to be having fun.
Pain is a message—it’s a nudge from somewhere deeper, asking me to wake up. To take stock. To re-center.
It’s okay to feel pride in what I’ve built. But it’s not okay to let that pride chain me to the idea that joy is a distraction. Pride doesn’t have to mean isolation. Progress doesn’t have to mean pain.
So I will continue to have fun. Not as an afterthought, not as a guilty indulgence, but as a practice. A priority. A way of reminding myself—and maybe others—that joy is part of the work, too. Perhaps it’s the most important part.
Are you having fun yet?
My action steps:
Stop taking myself so damn seriously and have fun.
Craft.
Create meaning out of what’s in front of you if you feel like it or don’t.
Be responsibly authentic (Thanks, Parisa for this language!).
Great post, I feel that sometimes and I definitely feel like the fun police out there need to read this.
What I mean by that is some people are so wrapped up in their own cause, noble as it is, that they think everyone else should be in their mindset.
”How can you be making a joke or playing a game with your kids when there are children starving all over the world, when there are wars going on?”
Then comes the guilt, because I actually feel deeply, so deeply that I purposely don't watch the news or delve too deeply into those subjects because I know how it affects me and that I took could become that person who can't see the fun in life for the cause.
So I stay in my bubble, where I can breathe, and things don't overtake me. Where I am free to have fun.
Sorry that got long but you're so right we all get so attached to what we're trying to do it blinds us sometimes.