Question Every Should, Would, and Could

How to tell the difference between what you want and what you think you’re supposed to want

Code V of The Twelve Codes  •  Quietly Disruptive®



I should be on Instagram. I should have a course by now. I should be grateful for these clients. I should be further along. I should work harder. I should want to scale.

Count the shoulds in your average week and you’ll find dozens. Lodged in your decisions like shrapnel, so embedded you can’t even feel them anymore. Each one someone else’s expectation wearing a disguise. Each one quietly directing you away from what you actually want and toward what you think you’re supposed to want.

This code asks you to stop and interrogate every single one.

Where the shoulds come from

Shoulds don’t arrive with a label. No one says ‘here is someone else’s expectation, please internalise it.’ They come disguised as common sense, industry wisdom, friendly advice, or the most insidious source of all: your own voice, repeating something you absorbed so long ago you think it’s yours.

You should be posting three times a week. Says who? The algorithm? The marketing guru who sells courses on social media strategy? Is there evidence that your specific audience, for your specific offer, requires that frequency? Or is it just something you absorbed and never questioned?

You should be scaling. Says who? The business coach who measures success exclusively by revenue? Do you want a team? Do you want the management overhead? Or do you want a lean, precise, boundaried business that serves you and your clients without consuming everything else?

Each should dissolves under scrutiny. Not all of them, some shoulds are valid, and that’s fine. The point isn’t to reject all external input. It’s to know which external input you’ve chosen and which you’ve simply absorbed.

The should I held longest

For years, I held a should that nearly broke me: I should be available whenever clients need me.

This seemed reasonable. Professional, even. The client is paying, so the client’s needs come first. And for a long time, that meant working evenings when they could ‘only’ meet at 7pm. Answering messages on weekends because it showed dedication. Hiding the fact that I had a daughter to collect at 5pm because I thought it made me look less serious.

The day I questioned that should, the day I stopped and asked, who said availability equals professionalism?, was the day my business started to change. Not because I set a boundary (though I did). Because I finally understood that the boundary was mine to set. That no external authority had the right to define what my working hours looked like. That ‘I work 10am to 4pm’ wasn’t an apology. It was a statement of fact.

That single should, questioned and discarded, changed the architecture of my entire business.

The difference between curiosity and rebellion

Questioning your shoulds isn’t rebellion. Rebellion is just reacting, doing the opposite of what you’re told because you’re told to do it. That’s still letting other people’s expectations drive your decisions, just in the other direction.

Curiosity is different. Curiosity asks: why am I doing this? Is this serving me? What would happen if I stopped? And then it listens for the honest answer, which might be: actually, this one is worth keeping. Not all shoulds are worth discarding. Some are genuine wisdom that happens to have arrived from outside.

The skill is in telling the difference. And the only way to tell the difference is to question everything and see what survives.

When you strip away the shoulds, what’s left is usually the thing you actually want to build.

A practical exercise

Write down everything you’re currently doing in your business. Every platform you’re on. Every type of client you serve. Every commitment you maintain. Then next to each one, write down why.

If the honest answer is ‘because I chose this and it serves me,’ keep it. If the honest answer is ‘because I think I should,’ question it. Hard. Ask who said you should. Ask what happens if you don’t. Ask whether the should is protecting you or constraining you in ways that no longer serve.

You might be surprised by how much of your business is built on inherited expectations rather than deliberate choices. And that awareness alone, just seeing it clearly, is where the real change begins.

This is Code V of The Twelve Codes: 12 Principles for Building Your Corner of the World. Read the full Twelve Codes or explore What is Quietly Disruptive®? for the definitive guide to this philosophy.

Onwards and Upwards,

Becky :-)


About the Author: Becky Benfield Humberstone partners with Quietly Disruptive founders to build businesses that change their corner of the world, on their terms. If you started your business because you believed things could be done differently, and you're ready to make that vision real, she gets it. Based in the UK and working globally via Zoom and in-person, she's done this work herself, more than once.

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