The question of when to use the word ‘should’ comes up often in coaching, personal development, and values-based living. We’re frequently encouraged to stop saying should altogether, because it can reflect external expectations, pressure and self-judgement rather than what we truly want – and I often joke with my clients that the word is not allowed in our sessions… Yet not all shoulds are harmful. Sometimes should speaks to fairness, integrity and the belief that people should be treated with care and respect. Understanding the difference between expectation-driven shoulds and values-based shoulds – and recognising when the should word is spoken – can be a powerful step towards living more authentically.
Why the Word Should Has So Much Power
In the world of coaching, wellbeing, and personal growth, the word should is often viewed as a red flag. It usually signals an internalised rule, a belief inherited from parents, workplaces, school, society, or the standards of people we’ve been trying to please for years. Or it might be that you have judged another person in a way you would not like to be judged yourself. But that’s only part of the story.
There is a second type of should that is grounded in values, fairness, justice, and integrity. Knowing the difference is essential, especially if you’re unlearning old expectations and rediscovering who you are after years of living by other people’s rules.
The Unhelpful Should: When You’re Living by External Expectations
This is the version that keeps popping up in coaching sessions. It’s rooted in comparison, guilt, pressure, fear of disappointing others, or it’s a sign that you’ve been judgmental towards someone else.
Common examples include:
- “I should be more organised.”
- “You should be coping better.”
- “I should know what I’m doing by now.”
- “I should say yes — they expect me to.”
- “You should be able to do as well as the person working next to you.”
These shoulds are not about personal choice or core values. They often appear when someone has:
- internalised other people’s expectations
- absorbed old beliefs that no longer fit,
- been masking or overworking to keep up,
- learned to please others at the cost of themselves,
- spent years performing rather than living, or
- made an assumption about another person.
This kind of should leads to guilt, frustration, feeling behind, constant self-criticism, and shame when unrealistic standards are not met.
In coaching, this is the should we explore, challenge, and carefully deconstruct, because it rarely represents what someone actually wants.
The Helpful Should: When It Reflects Fairness, Justice and Values
Not every should is a problem. Some shoulds are healthy, appropriate, and necessary.
They come from your sense of fairness, justice, safety, integrity, and care, rather than from pressure or comparison.
This type of should might sound like:
- “People should be treated with respect.”
- “Organisations should protect the people they serve.”
- “Leaders should take responsibility, not shift blame.”
- “Nobody should be left without support.”
- “Professionals should act ethically.”
These statements don’t criticise you, or another individual. Instead, they point to a gap in justice or humanity. They show what you stand for. They reflect your values.
This kind of should is not restrictive. It’s directive. It helps you articulate what matters and where something is not okay.
How to Tell the Difference: Is This Should Helpful or Harmful?
Here are four simple ways to distinguish between the two:
1. Is the should pointing inward or outward?
- Inward: I should be better → harmful, expectation-driven.
- Outward: People should be treated fairly → values-based and appropriate.
2. Does it make you (or someone else) feel small, guilty, or not-enough?
If yes, it’s likely due to internalised pressure or you’re making a judgement about another person.
3. Does it highlight injustice or unfairness?
If yes, it’s a sign of your integrity, not inadequacy.
4. Does it come from fear or from principle?
- Fear = unhelpful.
- Principle = meaningful and protective.
Why This Matters in Coaching and Everyday Life
Understanding this difference changes everything.
When you catch the unhelpful shoulds, you begin to:
- reclaim your autonomy
- reduce guilt
- stop comparing yourself
- recognise whose expectations you’ve been carrying
- connect deeply with what you want, not what others think you should want
When you recognise the helpful shoulds, you access:
- your values
- your boundaries
- your sense of justice
- your compassion for others
- the parts of you that know right from wrong
In midlife (and this can be especially true for people navigating late diagnosis, life transitions, ADHD, burnout, or rediscovery), this distinction becomes even more powerful. It allows you to let go of outdated rules while holding onto the principles that define who you truly are.
A Coaching Reflection: What Does Your Should Reveal?
Here are simple questions you can explore on your own or in a coaching session:
- Whose expectation is this should connected to?
- Is this should about guilt, or about fairness?
- What value is being honoured or ignored?
- Where in my life am I living by my own values, and where am I living by someone else’s rules?
- If I remove the word should, what do I actually want?
Final Thought: The Real Question Isn’t “Should I Say Should?”
It’s this:
Does this should shrink me, or does it strengthen me?
If it pushes you to meet unrealistic expectations, criticise yourself or another individual, or live by someone else’s standards, then it’s time to challenge it. If it helps you name injustice, protect your values, or stand for what is right, then it’s not just okay – it’s necessary.
Ready to Untangle Your “Shoulds”?
If this article resonated, you’re not alone. Many people carry a lifetime of shoulds, i.e., expectations absorbed from family, work, culture, or roles they’ve outgrown, and wonder why life feels heavier than it needs to be.
Coaching offers a space to slow down, gently question those expectations, and reconnect with what you actually want and value. Together, we can explore which shoulds belong to fairness and integrity, and which ones you no longer need to carry.
If you’d like to explore this further, you’re welcome to book a free, no-pressure discovery call. It’s a relaxed conversation to see whether values-based coaching feels like the right next step for you.
