There’s a moment—usually late at night—when it hits you.
That feeling like you’re behind.
Like no matter what you do, you’re not measuring up. Like there’s this invisible checklist of everything you’re supposed to be doing, and somehow, you’re always falling short.
It doesn’t even matter whose expectations they are.
Maybe it’s your parents, expecting you to have a stable job, a respectable life.
Maybe it’s society, expecting you to have your life together by now.
Maybe it’s yourself, expecting to be further along, to have figured things out.
No matter where they come from, expectations have weight. And if you’re not careful, they’ll crush you.
Where Do These Expectations Come From?
Expectations are sneaky.
They don’t show up all at once. They creep in—little comments, little comparisons, little ways the world tells you who you should be.
It starts early.
- “You need good grades to get into a good college.”
- “You need a good job to have a good life.”
- “You need a house, a family, a plan.”
And at first, you believe it. Because why wouldn’t you? That’s just how things work, right?
But then, somewhere along the way, you start realizing—this path doesn’t fit everyone.
Maybe you don’t want the same things everyone else does. Maybe you tried to follow the script, and it just didn’t work for you.
Maybe life just didn’t go the way it was supposed to.
And suddenly, you’re stuck between what people expect and what actually feels right.
The Pressure to Be “Something”
If you’re in your 20s, you know the feeling.
You scroll through social media, and everyone seems to be doing something.
- That kid from high school is married with two kids.
- That old friend just bought a house.
- That random person you barely remember is running their own business, traveling the world, “living their best life.”
And you?
You’re just trying to make it through the week without completely losing it.
It’s like the world is telling you: Figure it out. Hurry up. Stop wasting time.
But here’s the thing: Not everyone’s timeline is the same.
Some people peak early. Some people figure it out later. Some people never figure it out—and maybe that’s okay too.
You are not a failure just because your life doesn’t look like someone else’s.
The Expectations We Put on Ourselves
It’s easy to talk about the pressure from other people.
But what about the pressure we put on ourselves?
That’s the real killer.
Because at some point, we stop blaming the world and start blaming ourselves.
- I should be more successful by now.
- I should be more disciplined, more ambitious, more put together.
- I should have done more with my life.
We beat ourselves up over things we think we should have done, paths we think we should have taken.
And all it does? It makes us miserable.
What Happens When You Don’t Meet Expectations?
So what happens when you don’t live up to what people expect?
You disappoint them.
And that sucks. Because no matter how much we pretend we don’t care, we do.
You see the look on your parents’ faces when they talk about their friends’ kids.
You feel the sting when someone says, “So, what are you doing these days?” and you don’t have an impressive answer.
You start to wonder if they were right. If you should have followed the safer path.
And the worst part?
They might never say they’re disappointed. But you feel it. And that feeling sticks.
How Do You Let Go of Expectations?
Alright, so we know expectations are exhausting.
How do you stop letting them control you?
Question Everything
Who says you have to do things a certain way?
- Who says success means a high-paying job?
- Who says you need to settle down by 30?
- Who says you need to be anything other than what actually makes you happy?
So many expectations are just made-up rules. And you don’t have to follow them.
Redefine Success
Most people’s definition of success is external.
- Money.
- Status.
- Recognition.
But what if success wasn’t about that?
What if success was:
- Waking up without dreading the day ahead.
- Doing something you actually enjoy.
- Being proud of the person you are, even if no one else gets it.
Once you define success on your own terms, you stop chasing other people’s approval.
Accept That Some People Won’t Get It
Here’s the hard truth:
Some people will never understand your choices.
They’ll always think you should’ve done things differently. They’ll always compare you to someone else. They’ll always expect more.
And you have to be okay with that.
Because at the end of the day, you’re the one who has to live your life. Not them.
The Expectation I Can’t Shake
I’d love to sit here and say I don’t care what people think.
That I’ve let go of all expectations and I’m just out here living my truth.
But that would be a lie.
I still feel it. The pressure. The comparisons. The quiet voice in the back of my head whispering, You should be further along.
I feel it when I see my dad and know I’ll never be the son he wanted.
I feel it when I look at my bank account and wonder if this whole “figuring it out” thing is just another excuse.
I feel it when I think about how much I want to leave this town but don’t know if I ever will.
Expectations don’t just disappear.
But I’m learning that I don’t have to live my life trying to meet them.
If You Take Nothing Else From This, Remember This—
Your timeline is your own. There is no deadline for figuring things out.
Success isn’t one-size-fits-all. Redefine it in a way that actually makes sense for you.
Not everyone will understand your choices. That’s their problem, not yours.
You are not a failure just because your life doesn’t look like someone else’s.
And maybe—just maybe—the only expectation you should care about is this:
Be someone you can live with.
The rest? Let it go.
—J
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