Drowning in "Shoulds": How We Keep Ourselves Underwater

This week I wanted to talk about "shoulding"—what it is, why so many of us do it, and how to quiet the voice that insists we're not measuring up.

"Shoulding" comes up a lot in my therapy office. It’s not unusual to hear clients tell me:

“I should be more productive”.

“I should be over it by now”.

“I should be grateful”.

“I should exercise more”.

 “I should have your career figured out”.

“I should be a better parent, partner, friend, daughter, son, human”.

And it's not just clients. I've had plenty of conversations with friends and family who find themselves standing at the edge of an "I should" cliff, looking down into all the ways they believe they're falling short.

The problem is that no matter how much they accomplish, the cliff never seems to end. There is always another expectation waiting on the other side.

Maybe you've found yourself standing there too.

Most of us think these thoughts are helping us improve. More often, they're weighing us down, keeping us focused on who we think we should be instead of who we are and what we actually need.

So let's talk about shoulding—where it comes from, why it's so convincing, and how to stop letting it pull you underwater.

The Problem With "Should"

Most of us treat "should" as if it's helpful. Responsible. Mature.

But "should" often has a hidden message underneath it:

"Who you are right now isn't enough."

Every time we tell ourselves we should be different, we create distance between ourselves and our actual experience.

Instead of noticing that we're tired, we tell ourselves we should have more energy.

Instead of acknowledging that we're hurt, we tell ourselves we should be stronger.

Instead of accepting that we're struggling, we tell ourselves we should have it together.

The result? We end up fighting reality.

And reality always wins.

Why We Hold On to Them

The tricky thing is that most of our "shoulds" started out as attempts to protect us.

Some came from family.

Some came from culture.

Some came from religion.

Some came from social media, where everyone somehow manages to have a successful career, a spotless house, emotional intelligence, a six-pack, a thriving marriage, and homemade sourdough all at the same time.

Many of us learned that being acceptable meant being good. Being good meant meeting expectations. And meeting expectations felt safer than disappointing people.

So we became experts at monitoring ourselves.

We became managers of everyone else's comfort.

We learned to push harder, do more, and ignore what was actually happening inside us.

The problem is that survival strategies don't always make good long-term life strategies.

How "Shoulding" Keeps Us Underwater

Imagine trying to stay afloat while someone continuously hands you bricks.

That's what chronic "shoulding" feels like.

Every expectation adds weight:

• I should be further along.

• I should know what I'm doing.

• I should stop feeling this way.

• I should be able to handle this.

• I should make everyone happy.

Eventually, you're using all your energy just trying not to sink.

You become disconnected from what you actually want because you're too busy responding to what you think you should want.

You stop asking:

"What do I need?"

And start asking:

"What am I supposed to do?"

Those are very different questions.

How to Stop Shoulding Yourself: Tools to Keep Yourself Afloat

The goal isn't to eliminate every "should." Some expectations are reasonable. Some reflect genuine values.

The goal is to notice when "should" has become an anchor.

1. Replace "Should" With "Could"

When you catch yourself saying:

"I should exercise."

Try:

"I could exercise."

Notice what happens.

"Could" creates choice.

"Should" creates pressure.

People tend to move more easily toward things they choose than things they feel forced into.

2. Ask: Who Told Me This?

When a particularly loud "should" shows up, get curious.

Who taught me this?

Where did this rule come from?

Would I say this to someone I love?

You may discover that some of your strongest rules aren't actually yours.

3. Separate Values From Expectations

There's a difference between:

"I value being a caring parent."

And:

"I should never make mistakes as a parent."

One is a value.

The other is perfectionism wearing a fake mustache.

4. Practice Describing Instead of Judging

Instead of:

"I should be handling this better."

Try:

"This is harder than I expected."

Instead of:

"I should be over this."

Try:

"I'm still hurting."

Description keeps us connected to reality.

Judgment pulls us away from it.

5. Ask What You Need Right Now

Not what would make you more impressive.

Not what would make everyone else happy.

Not what would make you look like you have your life together.

What do you actually need right now?

Rest?

Support?

Movement?

A boundary?

A nap and a snack?

Sometimes emotional wisdom is surprisingly unglamorous.

Staying Above Water

The truth is, life already comes with enough challenges.

Most of us don't need more pressure.

We need more honesty.

The next time you notice yourself drowning in "shoulds," pause and ask:

What reality am I arguing with?

Because the moment we stop fighting reality, we free up energy to respond to it.

And that is often the moment we start floating again.

Not because everything got easier.

But because we finally stopped carrying so many bricks.