My psychologist once called it the “tyranny of should.” I like to call it “shoulding all over yourself”. Either way, the problem with should in business is that every time you tell yourself you should … (insert thing here), you’re piling on invisible rules, obligations, or requirements that no one actually asked of you.
And my question is always: Who says? Whose rules are these? Who really benefits, and at what cost?
Here’s the thing: should is an expectation. Expectations are rarely written in stone, often borrowed from family, peers, or industries that love to measure worth in endless hustle. When you live by “should,” you’re living someone else’s version of business, not yours.
The Psychology of Should in Business
Let’s make this simple. “Should” in business, like life, is the brain’s way of keeping you in line with what it thinks will earn approval, belonging, or safety. Most of us learn it early on from parents, family members, or school. Imagine the stories you might have heard about being “a good girl”, “seen and not heard”, or expectations based on how you looked or your natural abilities. It feels like law, but really, it’s a habit.
Move into the workplace or run your own business, and then every “should” whispers: You’re not enough unless…
- You should have more clients.
- You should be charging more.
- You should be better at marketing.
- You should be more confident.
Sound familiar?
For many of us, especially the high-achieving founder or professional, every “should” fuels the story that they’re failing, or about to be found out. But the truth? Should is not fact. It’s a borrowed belief.
What Should Costs Your Business
There is a mental load that should in business carries. (As if most of us don’t have enough tabs open) It quietly wears us down. How do I know? I’ve tried to shoulder the burden. I’ve watched clients as the tears rolled down their faces as they realised that the weight of being a business owner mostly came from:
- Time wasted overdelivering or procrastinating.
- Energy drained by people-pleasing.
- Money lost through unpaid invoices or underpricing.
- Confidence eroded by constant self-comparison.
- Direction blurred by chasing everyone else’s priorities.
It’s not just annoying or wearing. It’s expensive.
Case Study: From Should to Self-Assurance
One of my clients came to me in tears. Their business was failing under the weight of should in business; every decision was clouded by expectations, and they thought it was all their fault. The shoulds came from:
- competing with siblings growing up,
- people-pleasing to win approval,
- playing the martyr because the struggle felt noble.
It showed up everywhere in their business:
- Clients ignoring invoices and boundaries.
- Staff disregarding instructions.
- And not enough income to pay themselves a living wage.
They were drowning under a set of expectations that started in childhood about accommodating others, that they were only ever expected to make do, and that boundaries were barriers not safety nets. It was a string of should about kindness, worth, sacrifice, staying quiet or keeping the peace, and putting the needs of others above their own.
Here’s what happened when they stopped shoulding and started experimenting with new ways of operating:
- One-third of invoices paid within a month.
- Clearer direction for staff (and respect in return).
- Boundaries set around office hours.
- A communication and marketing strategy.
- More money in their own pocket.
- And most importantly: they felt more confident than they had in decades.
Even a year later, through COVID downturns, they were still holding boundaries, spotting new opportunities, and enjoying their business again. Eventually, they sold it as a going concern and retired on their terms.
That’s the power of breaking free from “should.” Freedom. Happiness. Opportunities.
The Transformation: What’s Possible When You Stop Shoulding
This isn’t just one client’s story. Here’s what’s possible when you replace “should” with can:
- Business seems lighter and less must do and more want to
- Trust is more internal that someone external
- Clarity goes past strategy and on to ability
- Control comes back to you, the owner
- You realise the being you, the owner, is the authenticity people talk about
- Confidence rooted in your own proof, not borrowed rules.
And you don’t need a 12-step plan to get there. Like my client, you start with small, testable shifts — experiments. Say no once without apology. Send one invoice without a discount. Post one piece of content without softening it.
Each time, you gather proof that the world doesn’t end when you stop shoulding in business. In fact, it generally gets better.
Ready to Stop Shoulding All Over Your Business?
If you’re tired of the endless shopping list of shoulds, it’s time for a different approach.
That’s why I created The Confidence Upgrade — a 7-day experience designed to help business owners like you replace “should” with “can.”
Daily prompts. Simple experiments. Tools that help you stop shoulding on your business and start leading it with confidence.
Join The Confidence Upgrade here.Because your business doesn’t need more shoulds. It needs you — confident, self-assured, and ready to run it on your own terms.
