make mistakes.
... not because you should. just because you will.
No one starts out planning to ruin anything.
We make decisions the way people light cigarettes in bad weather—rushed, hopeful, one hand shielding what the other refuses to let go of. We tell ourselves we’re careful, that we’ve thought this through. That unlike everyone else, we’ll get away with it.
That’s the first mistake.
It’s a sort of arrogance, though you don’t call it that at the time, and it’s not the kind that shouts. It’s quieter, more insidious. The belief that you’re exempt, that you can outthink regret. That with enough overthinking and self-awareness, you can avoid consequence entirely.
You can’t.
….and you won’t.
Mistakes arrive exactly when you’re most sure of yourself. At twenty-two, you move to a city you can’t afford. You mistake debt for identity. You assume being wanted is the same as being loved. You say ‘yes’ too quickly, ‘no’ too late. You think pain is depth. You start calling silence maturity, which, is generous.
These are the early mistakes, the glamorous ones, the ones that ‘build character’. Later, you almost admire them like an old photo where you’re wearing something terrible, but pulling it off anyway.
Mistakes, in the beginning, look like a stranger. Later, you realize they were always just your reflection.
Because you will make mistakes.
This isn’t advice, or encouragement, it’s just a fact.
You’ll call the wrong person. You’ll leave at the wrong time. You’ll stay longer than what’s good for you because somewhere along the way, you started confusing endurance with loyalty. You’ll hurt people. You’ll lie, maybe just once, or maybe in a way that means you’ll never see them again.
You’ll mean well. You’ll mean nothing. You’ll want something so badly you forget how to behave. You’ll even say it out loud.
And then quietly, privately, stupidly… you’ll survive it.
Not all mistakes teach you something.
Some are just… necessary.
We’re taught early that mistakes are avoidable. That if you’re careful, decent, and wear enough sunscreen, you’ll get through life without leaving a stain.
It’s a comforting lie. Color inside the lines, say thank you, don’t interrupt. Learn the rules, preferably before you even know what game you’re playing. It’s in the sticker charts, the report cards, and the way adults flinch when you ask the wrong question.
But at some point, correctness stops being about doing things right and it starts being about pleasing.
You grow up mistaking compliance for character. Thoughtfulness becomes survival and goodness becomes a strategy. You think if you’re careful enough, you’ll dodge regret entirely.
Again, you won’t.
Correctness doesn’t protect you. It just teaches you to apologize for the wrong things and bury the right ones until they rot. And eventually, the muscle memory outlasts the reason for it and you forget who you were trying to please in the first place.
By adulthood, the fear of being wrong feels like instinct. You second-guess a text like it’s a wire transfer. You reread a calendar invite like it’s a legal contract. You reread a three-sentence email fourteen times, not because it’s complicated, but because you’re scared of how it might land.
You learn to disappear in plain sight. Just be good enough, and maybe no one will notice how unsure you are. You tell people what they want to hear and call it kindness. Say less than you mean and call it boundaries. You manage your life thoughtfully and strategically, as if the risk of being misunderstood is too high to bear.
And still, the whole performance is built around one goal: don’t get it wrong.
But of course, you do. Eventually.
We all do.
And when it happens, it’s not the big kind of mistake. It’s ordinary. Forgettable. The kind of slip you only clock if you’ve spent years trying to make sure no one ever had a reason to dislike you, until one day, you realize you kind of dislike yourself.
You follow the rules long enough, and eventually, you lose track of what you actually think. Instinct dulls and you wait for someone else to say it first, so you know it’s safe.
The more you avoid mistakes, the more you become brittle under the weight of endless reasonableness.
And that’s when you start making the mistakes that actually matter.
In our pursuit of never being wrong, we turn ourselves into versions of people no one can dislike, but it comes at a cost.
Perfection wasn’t always about excellence. It was about restraint. Say enough to seem interesting, but never enough to make anyone uncomfortable. Be cool, but not cold. Warm, but not needy. The goal was to be just enough and never too much of anything. To make mistakes, but only the charming kind you can use in a job interview when they ask about adversity and you say, “I’m a perfectionist.”
Yes, that kind.
We got good at it, alarmingly good. Editing ourselves in real-time while withholding the honest version in favor of the version that wouldn’t make anyone uncomfortable. Eventually, you forget what the honest version even was. Because real mistakes don’t fit into that framework, do they? Real mistakes make people cringe, they ruin brunch and they certainly don’t trend well.
The culture says it loves vulnerability, as long as it’s over. We like people who’ve grown, not people who are still in the middle of it. Especially if “it” involves anything unflattering, raw, or morally ambiguous.
So we offer up safe flaws. “I’m bad at texting.” “I forget to drink water.” Like that’s the extent of the damage.
Meanwhile, the actual mistake, the one you don’t know how to talk about yet, lingers. It crouches somewhere beneath the story you tell about it, hums under your conversations and makes eye contact at the wrong moment.
You don’t talk about it because there’s no version where you come off well.
We mistake polish for character and curation for maturity. And we punish people who remind us that it was always a performance.
That none of us are as good as we pretend to be.
And that maybe the only honest thing left to do is admit it.
You follow all the rules and still don’t like where you are.
So you break one.
A small lie. A half-yes. A conversation you skip, not because you’re lost for words, but because they sound worse spoken. But you don’t call it a mistake yet. You call it ‘not now’ or ‘next week” or nothing at all, which in some circles still passes for being polite.
Mistakes rarely happen in bold type. They creep in where honesty should’ve been but wasn’t—because saying it felt, well, rude. You keep the peace. Yours, theirs (hard to tell). You give up a piece of truth and hope no one notices the gap, or at the very least, that they’re too well-mannered to mention it.
Sometimes the mistake is just that: refusing to speak plainly.
Other times, it’s bigger. You betray someone and you know you’re doing it, but do it anyway. And while it’s happening, there’s a strange, awful calm. Like watching yourself ruin something you’ll later insist meant a lot.
You were calm… and that’s the worst part. It wasn’t a mistake you stumbled into, you walked right into it with your eyes open and your mouth shut, thinking that somehow made it better. And that’s what haunts you. Not the chaos… but the fact that you meant it.
You learn very quickly that you can be right and still ruin everything.
You can take your time, think it through and weigh every option like it’s fine china. And still, somehow, you’ll pick the thing that breaks.
Because mistakes aren’t always wild, or impulsive. They’re often precise and considered, calm even. Chosen with full awareness, and a little hope you’ll be the exception.
You know better and then you do it anyway. But knowing better doesn’t make you braver, it just shortens the distance between the choice and the regret.
And sometimes, you don’t even regret it. Sometimes it feels justified. Maybe even earned, or necessary? Something you should’ve done sooner, if you were being honest—which, of course, you weren’t. But still.
You’ll tell yourself it’s not that bad, that people have done worse and you’re still a good person. And maybe all of that’s true.
You’ll say you didn’t mean to hurt anyone, but the truth is you did. Just not the part of them you thought would bruise.
You’ll ghost someone you love because you can’t be the version of you they still believe in.
You’ll avoid an apology because saying sorry means admitting you waited too long. (And you did.)
You’ll say, “I didn’t know what to say,” which, let’s be real, is almost always a lie.
Real mistakes are boring. They happen in the pause, in the text you didn’t send, in the truth you almost told. And by the time you realize it, the version of you that made the mistake is long gone and you’re left holding the consequences.
You meant well. You always do.
But that’s the thing about meaning well. It doesn’t leave a mark.
The impact does.
The damage doesn’t care why. It just sits there, like something you forgot to clean up. And after a while, you stop noticing the smell.
For a long time, I believed if I didn’t cause trouble, I’d earn my way into something that felt like safety. That being easy to be around was the same as being grown.
What actually happened was I got very good at shrinking myself to go unnoticed. I called it loyalty. Other people might’ve called it avoidance, or cowardice, or lying by omission. They’d be right. It just sounds worse coming from someone else.
I’ve stayed too long. I’ve left too soon. I’ve said nothing when I should’ve said something. I’ve said everything when silence would’ve been kinder.
The worst part? I meant well.
But that’s irrelevant.
You think you’ll know the moment you’ve fucked everything up. That there’ll be some noise, some fallout, a clear moral of the story.
But real mistakes are dull. Almost, administrative.
You don’t call it a mistake, you tell yourself it’s not the right time, or hold the truth a little longer, like that makes it easier to carry. Something you tell yourself sounds responsible, even though it never really is. You say “I’m fine” until it stops sounding like a lie, even to you, because you don’t want to be seen as difficult.
You think you’re buying time but what you’re actually doing is spending your life in tiny, polite increments. It’s only later, when the dust doesn’t settle and the silence stretches—that you’ll find a way to frame it that sounds reasonable. Timing, maybe. Bad luck. Literally anything but what it actually was: you.
At some point, you stop asking if you’re doing life “right” and start wondering if you’re doing it at all. Not managing or optimizing it. Just… living. Poorly, occasionally. But honestly.
You realize the goal was never flawlessness. It was just to feel something, contact, friction… anything that reminds you: I’m here. I’m not getting this right, and thank god.
You’ve met the people who get it “right” all the time. They’re exhausting and they’re certainly never the ones you call when your life blows up. They would just say something tasteful, vaguely sympathetic and completely useless.
Give me the people who’ve tanked the relationship, told the lie, lost the job, disappeared for a while. The ones who’ve humiliated themselves and still made it to dinner. They’re the ones who don’t look away when you say the quiet thing out loud—they’ve said worse, and they remember what it cost them… and they’re the safest people in the room.
Mistakes don’t exile you from being human. They’re how you get invited back in.
And that’s the slow, ridiculous art of showing up again.
What I’ve made of my life, if you can call it that, hasn’t been shaped by wise choices. Just mistakes, mostly. A series of course corrections, a mess of aftermaths. It wasn’t the wise choices that left a mark, it was the ones I had to live through, then live with.
There’s freedom in getting it wrong, in saying yes to the thing that scares you. In walking straight into the wrong job, the wrong city, the wrong person.
Mistakes have this annoying habit of revealing you. They rip away the story you’ve been telling and leave you with the actual one. Not always flattering, but always true.
This isn’t an argument for recklessness, it’s an argument for honesty. And honesty is often what gets us into trouble. It’s honest to admit you’re lost. Honest to say “this isn’t working” even when everyone else thinks it is. Honest to ask for more, less, or just something else.
We don’t outgrow mistakes, we just get better at disguising them. They show us our blind spots and where we haven’t been yet.
Look at anyone who’s ever built something real, they didn’t get there by avoiding mistakes. They walked directly into them and they didn’t treat failure as an exception, they treated it like a step along the way.
There’s a difference between being wrong and being bad, we forget that sometimes. Most mistakes aren’t sins, they’re just miscalculations or misunderstandings. Usually, they’re the result of trying too hard, or wanting more than you were supposed to.
Mistakes will keep happening. You’ll let people down. You’ll let yourself down. You’ll say the wrong thing. Try again. Repeatedly. Spectacularly. Sometimes in public. Sometimes alone, in ways only you will notice.
And you’ll keep going anyway.
And there’s a kind of grace in that. Not the grace of perfection, but the grace of persistence. Of showing up, again and again, in spite of everything. Of refusing to be silenced by your own imperfection.
After all, that, more than anything, is what it means to live.
You don’t get clarity, you get aftermath. You get to watch yourself learn the hard way, again, and still try to pass it off as timing, or character development, or something slightly less pathetic than what it actually was. You survive it. Barely. Quietly. Then you do it again.
Which, unfortunately, might be the whole point.
File Under: The Fine Print of Growing Up.
The Ash Files—Where life’s unexpected moments get filed away—sometimes neatly, sometimes under “figure it out later.” From writer/creator ASH, expect weekly musings, honest stories, and a reminder that no one has life entirely figured out [least of all me].✨
You are spot on with all of this, as per usual. The trick I find is not to file it only under "The Fine Print of Growing Up." But, rather to also file it under, "I won't carry the guilt of my mistakes around for the rest of my life." Brilliant writing, and I hope the scars you build only make you both stronger and kinder.
I definitely needed to read this. Thank you.