Rewrite Your Rules: Drop the Weight of Shoulds

Have you ever laid awake at night, staring at the ceiling, wondering, Did I do enough?

Have you ever closed your laptop at midnight and thought, Was it enough?

Or put the mic down after a speech and asked yourself, Should I have said more?

That relentless pressure, that gnawing feeling that you should have done more, been more, achieved more—it’s exhausting. And yet, we carry it like a badge of honor.

It’s time to put it down.

It’s time to give yourself a permission slip.

Not a metaphorical one—a real one.

A permission slip to:

Drop the expectations that don’t serve you.

Forgive yourself for the ways you think you’ve fallen short.

Replace judgment on what you could have done with compassion for what you were capable of at the time.

Release the shoulds and rewrite the rules.

For years, I let the shoulds deplete my worth. I told myself that if I kept striving, kept achieving, I could outrun the feeling that I wasn’t doing enough.

But no amount of success could silence that voice.

Because the real work wasn’t in doing more—it was in learning to let go.

The Weight You’re Carrying Isn’t Even Yours

How many times have you caught yourself saying:

"I should be further ahead."

"I should have it all figured out by now."

"I should be more productive, more disciplined, more successful… more something."

"I should have said more, I should have done better."

What if I told you that the weight you’re carrying isn’t even yours? That the invisible pressure you feel didn’t start with you—and that you have full permission to set it down, right now.

A client of mine, a powerhouse CEO running a multimillion-dollar business, once told me, “I should really be waking up at 5 a.m. every day.”

“Why?” I asked.

She hesitated. “Because... that’s what successful people do?”

I laughed. “Is your business failing because you wake up at 7?”

She rolled her eyes. “Well… no. We’re doing better than ever.”

“So what do you actually need?”

“More energy. More peace in the morning.”

“So what would actually help with that?”

She exhaled. “Probably… not scrolling my email in bed.”

We laughed together, because this is what we do—we torture ourselves with expectations that don’t even belong to us. We inherit them from books, social media, mentors, culture, and our past. And we don’t even stop to ask: Do I even want this?

So, let’s ask that now.

The Should Audit: Seeing the Pressure You Put on Yourself

At one of my retreats, I asked everyone in the room to write down all the things they believed they should be doing. Within minutes, the lists were filled with things like:

"I should have more money by now."

"I should be a better partner, parent, friend, leader."

"I should never need help."

"I should be further ahead by now."

"I should know the answers."

Then I asked them to reflect: Would I put this weight on someone I love?

The shame cracked open. They would never expect perfection from their best friend, partner, their children, or their mentors.

But they demanded it of themselves.

Now, it’s your turn.

AUDIT YOUR SHOULDS

Step 1: Capture Your Shoulds

Keep a "should log" for 24 hours.

Write down every time you say or think "should."

Step 2: Question Your Shoulds

For each "should," ask:

Whose voice is this really?

What would happen if I didn't?

Is this aligned with my values?

Step 3: Rewrite Your Shoulds

Transform each should into:

A choice ("I choose to..." instead of "I should...")

A want ("I want to..." instead of "I should...")

A release ("I give myself permission to...")

Leading Without the Weight of Should

When you take off the weight of should, you don’t lose your ambition—you gain clarity.

You stop proving and start choosing.

You stop reacting and start leading.

You stop chasing and start embodying.

And that is the real work.

So, what are you giving yourself permission for today?

Language Shifts: From ‘Should’ to ‘Choice’

The words we use shape our reality. Should is a word that subtly (or not so subtly) reinforces shame, obligation, and the feeling that we’re always behind, always not enough.

What if we reframed it?

Instead of:

I should be further ahead.
I am exactly where I need to be, and I choose to trust my timing.

I should work harder.
I am choosing to work in a way that is sustainable and aligned with my energy.

I should have said more.
I am choosing to trust that what I said was enough.

I should be doing more.
Today, that was enough. I choose to celebrate what I did accomplish.

When we shift from should to choice, we take our power back.

Your Should Audit: A Three-Day Challenge

For the next three days, track every time you catch yourself saying should. Keep an inventory—write it down, note how it makes you feel, and then try a reframe.

Notice the weight of those shoulds and how much lighter you feel when you replace them with choice.

Because here’s the truth:

You don’t have to hustle for your worth.

You don’t have to meet impossible expectations.

You don’t have to live by invisible rules you never agreed to.

You get to choose.

And when you start choosing with intention, you stop chasing—and start living.

Write your own Permission Slip.

I give myself permission to ______.

And most importantly—stop shoulding on yourself.


Here’s your daily reminder that you are worthy, capable, and I am rooting for you.

Until next week,

Mandy

P.S. Know someone who needs this reminder? Send it to them and share the love.

P.P.S. New here? Welcome ❤️ Read my favourite post ‘ Stop Chasing Success ‘ HERE

….One more reminder, I always love to hear from you so hit reply if this hit home.