Unlearning the Shoulds: How I’m Rewriting the Rules in Midlife

I used to “should” myself into exhaustion.
I should work harder.
I should be more patient.
I should say yes.
I should be grateful.
I should keep going.

But one day, I stopped and asked: Who said I had to?

Somewhere along the way, I became a woman who lived by rules I didn’t remember agreeing to.

I said yes to things I didn’t want to do because I didn’t want to disappoint anyone.
I showed up smiling when I was drowning inside.
I overextended, over-functioned, and over-apologized until there was nothing left of me except the pressure to keep performing.

I had built a life that looked successful, but it was made almost entirely out of “shoulds.”

Then midlife came barreling in. And with it, the patience for pretending disappeared.

It was like my body said, “Cool story. We’re not doing this anymore.”
Suddenly, the things I used to tolerate made me feel sick. The pressure felt unbearable.
And the phrase I kept hearing in my head was: “This doesn’t work anymore.”

Not just the schedule. Not just the obligations.
The whole damn system.

“Why are you always shoulding on yourself?”

I’ll never forget what a friend once said to me during a particularly vent-heavy coffee date.

She looked at me mid-rant, after I’d said “I should…” for the fifth time in three minutes, and asked,“Why are you always shoulding on yourself?”

It stopped me cold.

Because she was right. I was shoulding all over my schedule, my relationships, my identity.
I was operating like there was a checklist of how to be a ‘good’ woman, mother, wife, entrepreneur and I was failing it daily.

That question cracked something open. I started noticing just how often “should” ran the show.
And how often it left me feeling resentful, burnt out, or completely disconnected from what I actually wanted.

The problem with “should”

“Should” is sneaky. It sounds responsible. Reasonable. Even virtuous.
But it’s often just a fancy word for guilt.

“I should do this” usually means “I don’t want to, but I’m afraid of what will happen if I don’t.”

Here’s what I’ve learned:

• “Should” disconnects us from what we actually want.

• “Should” keeps us stuck in other people’s expectations.

• “Should” is the voice of fear disguised as good manners.

And it’s exhausting.

Midlife is the great unlearning

One of the most powerful gifts of midlife is the clarity to question what we’ve accepted for far too long.

We start asking:

• Who made this rule?

• Does this still work for me?

• What do I want instead?

And once you start asking those questions, you can’t unask them.

Suddenly, “I should go” becomes “I don’t want to go.”
“I should help” becomes “That’s not mine to carry.”
“I should stay” becomes “It’s time to leave.”

How I started saying no to shoulds

Here’s how I started breaking up with the “should”s:

• I checked the source. Was this something I genuinely valued? Or something I inherited from family, culture, or capitalism?
  
  

• I paused before committing. If I felt a full-body “ugh” instead of a “yes,” I gave myself permission to sit with it.
  
  

• I stopped explaining. “No” became a complete sentence. Not “No, but…” or “No, because…” Just “No.”
  
  

• I trusted that ease isn’t laziness. If something felt aligned and unforced, that didn’t mean it was wrong. It meant I was finally in flow.

What happens when you stop should-ing on yourself

You create space for:

• Rest without guilt

• Joy without justification

• Decisions that honor your energy

• A life that feels like yours, not a performance for someone else

And maybe most importantly?
You finally start hearing your own voice again.

That part of you that’s been whispering under all the noise:
You don’t have to earn your worth.
You don’t have to prove anything.
You just get to be.
Right here. Right now.

Real talk to wrap it up

Midlife is the season of returning to yourself.

Not the version you were told to be.
Not the role you played to keep the peace.
But the real you…the one who’s been waiting patiently under all the “shoulds.”

So the next time that voice pops up and says, “You really should…”
Pause.
Ask who said that.
And then ask what you actually want instead.

Because you don’t have to live a life full of obligation and resentment.
You get to choose again. You get to choose you.

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