Why You Can't Say No: What's Really Underneath People-Pleasing

People-Pleasing and Boundaries: What's Really Underneath

When I think of the word people-pleasing, the first memory that comes to mind is always the same: feeling like I couldn't say no, feeling responsible for how others felt, and sensing that my own feelings didn't really matter.

Even when I wanted to say no, I couldn't. I felt frozen. I didn't know how to put the words together without sounding harsh. As a child, I had only seen conflict, anger or avoidance (brushing things under the carpet) when people disagreed…

Also, it was safer to push down my own emotions.

People-pleasing shows up in many ways — some obvious, some subtle. Sometimes it's saying yes to things we don't really want to do and feeling resentment.

Other times, it's small things: nodding to opinions we don't agree with, listening to someone talk endlessly even when we're not interested. It might even be something as simple as always making coffee for others whilst forgetting to make one for ourselves.

"Why do we do it? Out of fear? Out of habit? Or because we genuinely care?"

None of this is inherently wrong, but it's worth noticing. If it's fear or habit, what would happen if we experimented with saying no, with expressing our needs in situations that aren't too intimidating at first?

The Symptom vs. The Root

When I see someone struggling to set boundaries, it often comes from a deep sense of unworthiness. Maybe as children we weren't taken into consideration, so we learned to stay quiet, to adapt, to keep ourselves small.

People-pleasing is not the real problem — it's the symptom. Like addiction or any other surface behaviour, it signals that something deeper is at play.

If we only address the symptom — learning to say "no" or "yes" in certain situations — we risk repeating the same patterns without awareness. We might even swing to the opposite extreme, becoming harsh or dismissive, thinking that boundaries mean not caring what anyone else thinks. But that's not genuine change either.

True transformation happens when we start exploring what lies underneath. This is where we discover not just what we're doing, but why we're doing it.

Beneath the Smile

Beneath the helpfulness, there is often sorrow, sadness, anger, loneliness, and the sense of "I am not enough."

Some of us are naturally more caring or drawn to connection, which can make people-pleasing feel like part of who we are. Perhaps you've always known you wanted to work with people, to help others feel good, to make sure everyone's included. Wanting to support, help, or nurture others is beautiful — but it becomes important to notice why we do it and to whom we're giving our energy.

There's nothing wrong with putting others first sometimes, but we need to understand whether we're doing it from a place of genuine care or from fear. For example, as a parent, you'll often put your children first — and you can still find ways to look after yourself. Or when your pet gets ill in the middle of the night, you naturally prioritise their needs. This kind of caring comes from love and connection, not from fear of rejection or feelings of unworthiness. Self-awareness can help us continue to care for others without losing ourselves in the process.

The Fears We Carry

What are people really afraid of when they can't say no? (this list isn't exhaustive)

• Rejection

• Abandonment

• Not being loved for who they are

• Judgement

• Fear of not being a good person

• Fear of being judged as selfish

These fears drive the constant need to prove worth, to deliver, to accommodate. Sometimes these patterns are reinforced by family, society, or generational expectations — subtle messages that our needs don't matter, or that prioritising ourselves is selfish.

If someone could gently peek beneath their people-pleasing mask, they might find grief, sadness, anger, loneliness, and a profound sense of unworthiness.

Awareness: The First Step

Awareness is the doorway. Without it, we can't begin to change the patterns that shape our lives. Awareness allows us to pause, to notice our habits, and to reconnect with our own needs, feelings, and boundaries. It creates the space to treat ourselves with the same compassion we often show to others.

An approach that can be useful: Start by listing the behaviours that show up as people-pleasing in your daily life. Ask gently, "What's really underneath this?" Move slowly, with curiosity and kindness, nudging just a little beyond comfort without becoming overwhelmed.

Remember, everyone's journey is different. Some people can move faster, others need to be more careful. What I can promise is that this awareness will change your life — how it unfolds is deeply personal and unpredictable.

The Paradox of Self-Worth

Here's something that might seem contradictory: before we can genuinely connect with others without fear, we often need to build that solid foundation within ourselves first.

When we start validating ourselves, approving of ourselves, and meeting our own needs for attention and care, something shifts. We stop needing others to make us feel safe or worthy. Ironically, once we have this inner solidity, we can let go of the desperate need for approval — and that's when real connection becomes possible.

We can be curious about differences rather than needing everyone to be the same. We can be kind and connected — not out of fear or obligation, but from a place of authenticity.

The Ripple Outwards

When more people start connecting with what lies beneath the surface, it ripples outwards. We begin to understand ourselves, and through that understanding, we can begin to understand others.

We can share our experiences honestly — not as a pity party, but as genuine connection. When someone acts out, we remember our own moments of being less than perfect. We recognise that we've all rolled our eyes, said things we didn't mean, or behaved in ways we're not proud of.

This doesn't mean we accept poor treatment, but we can respond with understanding rather than judgment. It's challenging when someone's being unkind, but we can do this together.

Creating Connection

I'm not trying to fix the world, but I do hope we can create conditions for people to feel free to be themselves. No one needs to pretend they're perfect because perfection doesn't exist anyway.

When we stop disconnecting from ourselves, we can start connecting with others authentically. We can be genuinely curious about how different people experience life, rather than needing everyone to be like us. We don't even see the same colours, so of course our experiences are completely different — and that can be fascinating rather than threatening.

Awareness is the doorway. Through awareness, compassion, and gentle exploration, we can start to live with more freedom, honesty, and connection — with ourselves and with the people around us. People-pleasing and weak boundaries are just the surface. What lies underneath is where transformation begins.

A short, guided visualisation for better boundaries plus a PDF guide.