Why You Cannot Say No: The Truth Behind Your Lack of Assertiveness

“If you avoid conflict to keep the peace, you start a war within yourself.” — Cheryl Richardson

Have you ever found yourself agreeing to something you really did not want to do? Staying late at work, taking on an extra project, or attending an event you had no interest in, simply because saying “no” felt too uncomfortable?Maybe you hesitated, worried about disappointing someone, or feared being seen as difficult.

But what if the struggle to be assertive was not really about pleasing others? What if it was actually a sign that you have lost touch with yourself?

Many people mistake a lack of assertiveness for politeness, flexibility, or being easygoing. But at its core, constantly overriding your own needs to accommodate others is not just about avoiding conflict, it is a form of self-abandonment. When you do not clearly know who you are, what you want, or what you stand for, how can you confidently express your boundaries? The result? Silent frustration, burnout, and a growing sense of resentment, toward others and, more painfully, toward yourself.

What I have come to learn over the years, both personally and professionally, is that asserting yourself is not about being rude or difficult, but rather about reclaiming the relationship you have with yourself. Learning to say “no” confidently will actually bring you closer to who you really are, rather than making you feel like you are letting others down.

In this article, I will unpack why assertiveness feels so difficult, the psychological barriers that hold you back from stepping forward, and how reconnecting with yourself (i.e., your values, your needs, and your truth) can help you speak up with clarity, confidence, and self-respect.

Why Is It So Darn Difficult?!

Often, those who struggle to assert themselves are masters of compliance. You have likely been raised in an environment where expressing your needs or opinions was seen as disrespectful, selfish, or outright unacceptable. From a young age, you may have learnt that speaking your truth came with consequences — disapproval, punishment, or even emotional withdrawal from those you loved or depended on most.

For instance, if you grew up with an alcoholic parent, you knew that asserting yourself could end up in extreme conflict. Similarly, if you had a strict, authoritarian parent, challenging their rules was not an option unless you fancied emotional or physical repercussions. Perhaps your parents were emotionally manipulative, meaning they showered you with love and approval when you conformed but would dish out silent treatment or emotional pain when you dared to defy them.

This survival strategy of self-abandonment was essential in childhood. It kept you safe, avoided conflict, and maintained some form of harmony and emotional safety. However, as adults, many of us continue to operate from this outdated mental script, believing that speaking up will lead to rejection, instability, or emotional turmoil.

So, if you have ever wondered why asserting yourself feels so damn hard, consider that your brain has wired it to danger. You are not simply struggling to set boundaries, you are unlearning a deeply ingrained survival response.

But the great news is that you now have a superpower. Yes, you do! Once you learn how to speak up, you have the capacity to be assertive whilst maintaining the empathy and perceptiveness that once made you hyper-attuned to others’ needs. This is a skill that sets great leaders, parents, partners, and friends apart.

Reclaiming Your Voice

Breaking free from fear-based associations with assertiveness begins with 1) reconnecting with your soul-self and 2) reprogramming your response to speaking up. You cannot assert yourself effectively if you do not truly know who you are. The version of you that was pushed aside, the one with opinions, wants, desires, needs, and emotions, needs to be acknowledged and embraced. Two powerful means to achieve this is via psychotherapy and journalling.

So often, people think therapy is a place for the “emotionally broken” or those who need “dealing” with a mental disorder. However, this is hardly ever the case. In fact, none of my patients are “emotionally broken” or only in therapy to work on their diagnoses. I firmly believe that when we are not in alignment with who we are, our psyche will try to tell us by manifesting in symptoms of depression, anxiety, addiction, inattention, obsessive-compulsive behaviours, career dissatisfaction, or relationship difficulties.

In this way, psychotherapy acts as a space where you get to voice what you truly think, feel, and desire without judgment. A well-trained psychologist will be able to guide you towards reconnecting with yourself through intentional questioning and creating a space for emotional reconnection.

Journalling is another powerful tool as it allows you to give language to your inner world. It is a form of self-inquiry that provides clarity on what you truly feel and think. When you document your experiences, you begin to notice patterns — when and why you silence yourself, what situations trigger discomfort, and what narratives are playing in your mind. The act of writing brings self-awareness, which in turn fuels self-trust.

Once you have started reconnecting with your authentic self, you need to begin acting in alignment with it. And that starts with small, everyday decisions. For example, stop outsourcing small decisions. If someone asks what you would like for dinner, state it. It is not about winning the meal war, or being “picky”, but about practising the act of voicing your wants and desires. Similarly, speak up when the risks are low. If you disagree with a minor work suggestion, voice your concerns diplomatically. Small moments of self-assertion prepare you for more significant (i.e., risky) ones.

Expect anxiety and discomfort–initially. The first few times you assert yourself, it will feel like you have just committed social treason. But this discomfort is not a sign of danger, it is a sign of growth in disguise. Your brain needs evidence that asserting yourself will not result in death or a catastrophe. The more you do it, the more evidence accumulates.

These small moments of self-assertion build self-trust. Perhaps you were not able to protect yourself as a child, but you can absolutely stand up for yourself now! You start to get real-life evidence to show that when challenges arise, you are fully capable of handling them.

One of the biggest fears people have about becoming more assertive is that they will come across as aggressive or inconsiderate. This could not be further from the truth. Assertiveness does not mean being a d… doodie-head. It is about expressing your needs in a way that is respectful to both yourself and others. Yes, your early attempts may feel abrupt or even awkward, but this is only because the muscle is not fully trained yet. Over time, you will refine your communication, learning how to balance directness with kindness.

In a Nutshell

Assertiveness is not about learning to say “no” — it is about reclaiming the voice you lost when survival meant silence. Self-abandonment, once a necessary adaptation, is now a self-imposed limitation. The anxiety and discomfort of asserting yourself is not a sign that you are doing something wrong, but rather a sign that you are being brave! You are breaking free from a pattern that no longer serves you.

If you have spent years walking on eggshells, questioning your right to take up space, or shaping yourself to fit the needs of others, let this be the moment that you begin to rewrite that script. The world does not need a more agreeable, accommodating version of you. It needs YOU! Fully seen, fully heard, and unapologetically whole.

I hope this article has provided insight and encouragement. I would love to hear your takeaways from this. Also, any thoughts or suggestions for future topics are welcomed. To make it easy-peasy for you, I have created an Anonymous Feedback Form (click here) where you can share your ideas, experiences, or let me know if this resonated with you.

Now, go forth and reclaim your voice — you have been silent long enough. In fact, why not use this form to start training that muscle?

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