Why It’s So Hard to Say "No": Understanding the Challenges and How to Overcome Them
- Stella Ong
- Apr 26
- 5 min read
Updated: 24 hours ago

Have you ever found yourself agreeing to something you didn't want to do, only to regret it later? You are not alone. Many of us struggle with saying "no", even when it means sacrificing our own needs or well-being. But why is it so difficult to set boundaries, and how can we become more comfortable with it?
The Psychological Roots of Saying Yes
1. Fear of Disappointment or Conflict
One of the primary reasons people find it hard to say "no" is the fear of disappointing others. We often worry that saying "no" will make people think we’re selfish, uncaring, or uncooperative. For some, this fear is linked to avoiding conflict or confrontation. When we agree to something we don’t want, we are often trying to not "rock the boat" and the goal is to preserve harmony or avoid conflict.
This fear can be especially pronounced in relationships where we feel vulnerable or dependent. For example, a client in a marriage might worry that turning down their partner’s request will lead to arguments or tension, undermining the relationship’s stability.
2. People-Pleasing Tendencies
Many individuals struggle with people-pleasing behavior. This need to be liked or to receive validation from others can make saying "no" feel risky. For some, their sense of self-worth is tied to making others happy, even at the expense of their own needs. A people-pleaser may prioritize others’ expectations, often disregarding their own boundaries.
This is a common issue in therapy, as clients often explore the roots of people-pleasing, understanding that it’s driven by a desire for acceptance or love. In many cases, these tendencies can be traced back to childhood experiences where affection was conditional.
3. Cultural or Familial Conditioning
In some cultures or families, saying "no" is discouraged, especially for women or younger individuals. Cultural expectations to be compliant, agreeable, and supportive can make setting boundaries feel unnatural or even rebellious. For example, someone raised in a traditional family where respect for elders is paramount may struggle to say "no" to a demanding parent, even as an adult.
For one of my clients, who is navigating challenges with her mother-in-law, the difficulty in saying "no" stemmed from deeply ingrained cultural expectations about family roles, gender roles and obligations. These cultural norms often complicate boundary-setting, as the fear of guilt or dishonor can be overwhelming.
4. Fear of Missing Out (FOMO)
Fear of missing out is another reason people struggle to say "no". Turning down opportunities - whether social, professional, or personal, can create anxiety about missing experiences or losing connections. FOMO can lead to over committing and exhaustion as individuals say "yes" to everything in hopes of not missing anything important.
This is especially true for those working in high-pressure environments, like my clients in the financial and tech sectors. They often say "yes" to more tasks than they can manage, fearing that refusal might limit their career growth or relationships at work.
The Costs of Not Saying "No"
1. Emotional Burnout
When we say "yes" too often, we risk emotional and physical burnout. Over committing leads to stress, anxiety, and exhaustion, making it difficult to maintain healthy relationships and self-care routines. Constantly putting others' needs first leaves little time to recharge or focus on our own well-being.
In therapy, many of my clients experience this type of burnout. For example, a client working in the financial sector who says "yes" to long hours and extra projects finds himself on the brink of burnout. Learning to say "no" becomes an essential part of maintaining balance in determining how much can we push away before it starts affecting our work performance review.
2. Resentment
Agreeing to things you don’t want to do can lead to feelings of resentment, both toward yourself and others. Over time, this resentment can strain relationships and create a sense of being taken advantage of. When we suppress our true desires and boundaries, it can damage trust and authenticity in our relationships.
For example, a newlywed client struggling with her in-laws felt growing resentment from not setting clear boundaries, which affected her sense of independence and personal identity. This resentment also bleeds into other relationships such as one with her husband.
How to Get Comfortable Saying No
1. Recognize Your Priorities
Before you can say "no", it’s important to know what you’re saying "yes" to. Understanding your values and priorities will help you make decisions that align with your well-being. This is particularly useful for clients who are learning to set boundaries, as it requires an internal shift toward prioritizing self-care.
In sessions, we explore these values to help clients define what’s truly important to them. For example, a client who wants to focus on self-care might need to say "no" to excessive work demands to preserve their mental health.
2. Practice Assertiveness
Saying "no" doesn’t have to be confrontational. Learning assertive communication skills can help you say "no" with confidence and respect. Assertiveness is about standing up for your needs while maintaining empathy and respect for others.
I often encourage clients to rehearse how they will say "no" in different situations, using “I” statements to express their needs clearly and respectfully. For instance, “I won’t be able to take on this project right now because I need to focus on other priorities” is a way to assert a boundary without being defensive or apologetic.
3. Start Small
If saying "no" feels daunting, start small. Practice setting boundaries in low-stakes situations, such as declining a social invitation or postponing a favour for a colleague. As you gain confidence, saying "no" in more challenging circumstances will become easier.
4. Let Go of Guilt
Learning to say "no" often involves letting go of the guilt that comes with setting boundaries. Remind yourself that saying "no" is a healthy part of self-care and personal growth. It’s not selfish, rather, it’s necessary to maintain balance in your life and relationships.
Conclusion
Saying "no" is hard, but it is an essential skill for maintaining your emotional well-being and nurturing healthy relationships. By recognizing the psychological roots of why it is difficult, understanding the costs of not setting boundaries, and practicing assertive communication, you can reclaim your power to say no—without guilt.
Please don't suffer in silence, everyone deserves to lead a happy, healthy and functioning life.
We would love to help, do reach out to us for low self-esteem therapy in Singapore and begin your journey of healing.
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