Why is it So Hard to Be Assertive? 5 Skills You Can Learn

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Why is it so hard to be assertive? There are some very good reasons why it’s such a struggle for so many.

The first reason is that lots of people think they know exactly what assertiveness is, but they actually only know half of the definition.

That missing half makes a huge difference.

Pause for a moment here and think about what “assertive” means to you. Come up with your own definition.

Did your definition describe standing up for yourself? Speaking your mind? Telling people how you feel or what you think? If so, you got it mostly right. This is the aspect of assertiveness which most people are familiar with.

Now let’s talk about the other half. In some ways, it’s the most important half. So, enough build-up. Here’s the true, full definition.

Assertiveness: Speaking up for yourself  — in a way that the other person can hear.

These two aspects of assertiveness, and how they work together, are what make assertiveness a skill which must be learned, rather than a natural ability. Most people have a hard time with the first half or with the second half, and many folks struggle with both. Also, our ability to be assertive varies with the situation, the people involved, and the amount of emotion that we are feeling at the time.

Most people err in one of two primary ways when they try to be assertive: they come across too weakly, making it too easy for the other party to discount their message; or they come across too strongly so that the other party becomes too hurt or too defensive to listen. Once the recipient’s defenses rise, your message will be lost.

No one struggles more with assertiveness than those who grew up in households where emotions were ignored (Childhood Emotional Neglect, or CEN). These emotionally neglectful families do not have the vital skills required for assertiveness because they do not understand emotions, or how they work. They do not know the Five Skills of Assertiveness, so they are not able to teach them to their children.

If you grew up in an emotionally neglectful family, it’s important to acknowledge that you struggle with these skills for a reason. And it is not your fault.

In a minute we will talk about how you can learn the skills, but first let’s consider the skills themselves.

The 5 Skills of Assertiveness

  1. Being aware of what you are feeling in the middle of a difficult, possibly intense situation
  2. Trusting that your feelings and ideas are valid and worthy of expression
  3. Managing your feelings, possibly hurt or anger combined with an endless possible number of other feelings, and putting them into words
  4. Understanding the other person or people involved, imagining what they are likely feeling
  5. Taking into account the situation and setting

When you put these five skills together, you are able to say what you need to say in a way that is appropriate to the setting, situation, and people involved (not too strongly or weakly), so that the recipients can process your message without their defenses being ignited. Keep in mind that talking to a defensive person is like talking to an inanimate object. Your message will not get through.

You can see from these steps why assertiveness requires not just skill, but a constellation of skills. This is why if it’s hard for you, you are not alone.

The good news is that it is entirely possible to build your assertiveness skills. If you keep all five skills in mind, you can work on building them. Follow these special suggestions to learn these vital skills.

4 Ways to Build Your Assertiveness Skills

  • Pay more attention to your feelings all the time.
  • Make friends with your emotions. When you value your feelings, they will become your most valuable life tool. They will tell you when you need to speak up or take a stand. They will motivate and energize you when you need it the most.
  • Begin to build your emotion management skills. For example, increase your emotion vocabulary, and try to use those words more often in your daily life.
  • Take every opportunity to stand up for yourself, as best you can. If you miss a chance or do it wrong, it’s OK! Just review the situation afterward to determine what you wish you had done. The more often you do this, the more you will learn, and the easier assertiveness will become for you.

There is so much more to learn about Childhood Emotional Neglect. Sign up for my Free CEN Breakthrough Video Series!

Growing up in an emotionally neglectful family leaves you struggling with many emotion skills that other people take for granted. To find out if you grew up with Childhood Emotional Neglect (CEN), Take The Emotional Neglect Questionnaire. It’s free.

To learn more about Childhood Emotional Neglect, see my first book Running on Empty. 


Click Here to Leave a Comment Below
Jacqie - March 27, 2024 Reply

Thank you Jonice
I found your book last year and it has become my best friend. I am learning so much about the effects of CEN and the impact it has had on my adult life. It’s an ongoing learning journey and very tough at times. I do live with a lot of guilt, shame and unworthiness. Do you have any advice on how to deal with CEN in the work place? This is an area that I am struggling with at the moment. Not being able to speak up and the lack of confidence I have around people in a higher position. When I do find my voice I will go into a negative spiral and punish myself for rocking the boat. This is where I fawn so much. I’m exhausted with my over thinking, over working and my hyper vigilance. Once again thank you for all the help and support your book has highlighted and started to help me live a happier and healthier lifestyle.
Many thanks

    Jonice - March 27, 2024 Reply

    Dear Jacqie, I suggest you think of this as a life problem, not just a work problem. As you work on finding and expressing your voice in general in your life, you also improve on it at work. If you can start valuing your emotions more, that is a great beginning.

Chris - November 2, 2023 Reply

I think I need to read your book a few more times. my reaction to situations where I need to be assertive is first want to yell like a marine corps drill instructor or to bargain and figure why I may be over reacting. uggh.

    Jonice - November 7, 2023 Reply

    Dear Chris, learning to be assertive is a complex skill that you can learn. Consider taking my online Find Your Voice Program which will teach you the skills in a direct way at your own pace.

Caroline - November 4, 2022 Reply

Dear Dr Jonice this is such a great article. I have claimed to be assertive all my life but in truth I’ve been a bit of a fraud! Till now I didn’t really know what being assertive means. Instead I confront things but usually with with a) the wrong emotional language, b) too much emotional, or c) I leave it till later and then explode. (I learnt that last “trick” from my dear mum!)
So I am a work in progress and since reading your book Running on Empty and embarking on therapy (I’m UK based) at the tender age of 58, I am healing from CEN finally.
Thank you for all you are doing for your patients/clients and everyone who benefits from you amazing work.

    Jonice - November 7, 2022 Reply

    That’s wonderful, Caroline. I’m happy for you and I encourage you to keep on healing and learning!

Sandy - July 15, 2021 Reply

I never know how I am feeling. I don’t know how to get in touch with my feelings. I never had any. I don’t know what they feel like. I know what feelings LOOK like; I just don’t know what they FEEL like. If I see someone cry because they are sad (like in a movie), I will cry too, but I’m only crying because they are. I’m 73 years old & I don’t know how to do this.

Beth - October 14, 2019 Reply

How do you build skills for assertiveness if when you try to speak up for yourself you become paralyzed with anxiety and unable to get any words out? Thanks.

    Dr. Nikki - November 13, 2023 Reply

    Hi, my name is Dr. Nikki LeToya White I am a trauma-informed nutritionist and recovery coach at Spiced Life Conversation, LLC I am also a recovered codependent people-pleaser, and I’m in full remission of a sugar addiction and binge eating disorder with a sobriety date of August 2015 with its roots in adverse childhood experiences of abandonment and childhood emotional neglect trauma. Before I write my initial post I would like to thank Dr. Webb for all her work after reading her books I applied what I learned to my sobriety plan and the tools have helped me cope with my struggle with unworthiness, separation anxiety, and feelings of unwanted and inadequacies that cause me to escape with food and self abandon. Without them, I would not be able to help my clients today. Thank you.

Abby - September 13, 2019 Reply

Dear Jonice,

I have found that it takes a lot of practice (and failing sometimes) to learn how to be assertive and yet not aggressive. It has taken many years for me to just speak up at all. The skills that you teach are very helpful to me.

It’s been so important to me to make friends with my emotions, not to label any of them as “bad”, but to understand that they are a valuable part of me which I can act on or not.

The most helpful thing for me has been having a friend who has been a good example of one who is accepting of others but can also be assertive when it’s needed. Being able to just observe another person who has healthy behaviors has been a great gift in my life. This friend I’m talking about is a fairly recent person in my life, just the last few years. The value of a good friend can’t be overstated.

The comments that are posted after the articles you write are also truly interesting and helpful to me.

Thank you so much for your articles and books about CEN!

    Jonice - September 13, 2019 Reply

    I’m delighted to hear that you are working on assertiveness, Abby! And finding a role model is a great strategy to help yourself learn this complex skill. Thanks for sharing!

Nicole - September 4, 2019 Reply

Dr. Jonice:
After being involved in an abusive relationship a little more than two years ago, I have had fears about how to be involved and engaged in a healthy relationship. I grew up in a household of physical and emotional abuse that I thought I was in the process of overcoming at the time. I have been able, thanks to your resources, to self-identify myself with CEN and I have spoken to my therapist about this, and used some of your resources as tools, on several occasions. In previous relationships that have gone wrong, I blamed myself for the anger I expressed and how I handled situations. It’s been only in recent months that I’ve come to realize and understand that I can’t be entirely blamed for these situations and in my reaction, I was actually setting up boundaries or a boundary, which of course, I have struggled with in my life due to CEN. I was getting hurt (repeatedly) and I was trying to protect myself. I’m learning now to have confidence in what I’m feeling and using my feelings as a tool in discovering what I want and need, and to also be able to effectively communicate that. I try to learn something even by observing friends in relationships and how they deal with stress and/or arguments, but there’s still that fear. Where’s that line between sticking up/protecting myself and realizing that the other party is human and capable of mistakes as well, and how do I recognize the difference? At least in my next therapy session, thanks to this article, I can say, “Kristin, I have the desire and need to work on and improve my assertiveness skills.” Thanks for this.

    Jonice - September 4, 2019 Reply

    Dear Nicole, it sounds like you’re doing great work! The way to identify the line is to take chances and allow yourself to make mistakes and learn from them! Keep up the good work.

Andrea - September 3, 2019 Reply

Thank you for this article, and all of your articles. They are really helpful to me. There have so many times in my life that I’ve had trouble both identifying and expressing my feelings. This had been so helpful, and I plan to buy your book!

    Jonice - September 4, 2019 Reply

    You’re welcome Andrea! I hope you enjoy my books.

Gary Latman - September 2, 2019 Reply

Dr. Webb,
Your CEN training demands that I operate at a cognitive level, but I am reactive or suppress my feelings. The level of manageability I want, the balance I need to have, is elusive. I am challenged to freeze my reactivity to practice the IAAA you talk about. My therapist tells me my amygdala puts me into a fight or flight pattern. Any suggestions for internal dialogue to calm and/or manage these two extremes?

    Jonice - September 4, 2019 Reply

    Self-talk is very effective. You can say to yourself the word “calm” over and over. I also recommend you learn meditation as that helps you take control over your brain so that it can work together with your emotions.

Hezza - September 1, 2019 Reply

part of assertiveness is also acting in line with your words. That can include resisting attempts to influence you in other directions

    Jonice - September 4, 2019 Reply

    Very true Hezza!

Debbie Thiede - September 1, 2019 Reply

Hi Jonice, I hope you know how many people you help! I am most grateful to you. Many thanks, Debbie

Estelle Nagel - September 1, 2019 Reply

Dear Dr Jonice, many thanks for all these valuable articles and life skill lessons . I am 65 years old and benefit greatly from your advice. I feel that at least know I have some understanding of so many feelings, frustrations and situations in my life that I could not understand or explain. Be blessed and continue with the valuable support you are rending too so many people like me !

    Jonice - September 1, 2019 Reply

    I’m so glad to hear that! Keep up the good work Estelle.

Sierra - September 1, 2019 Reply

Hi Dr Webb,
Thanks for the relevant article. I have decided that learning assertiveness is my new goal so this was a perfect primer. I want to suggest that the tone of your emails, websites and books are a bit on the blaming side for parents. If they were more neutral then I would feel comfortable sharing them with family and friends but I worry the current tone will not be received well.

    Jonice - September 1, 2019 Reply

    I always say it’s not a matter of blame, but understanding what went wrong. I will surely keep your request in mind in future articles.

Harley - September 1, 2019 Reply

I feel like this article is very flippant regarding assertiveness in people who have troubles with it. Our conditioning is usually such that we have zero notion of how we’re feeling due to numbing ourselves. You’re assuming we already have these all skills in place when we don’t.

    Jonice - September 1, 2019 Reply

    No, I am not assuming that at all Harley. I offer many resources in addition to this article for getting in touch with your feelings and learning the emotion skills.

      Philip - September 1, 2019 Reply

      Dr. Webb,
      I wanted to share with you how your book Running on Empty helped me enormously with assertiveness. I had read books on assertiveness many years ago but didn’t use the information I read about and remained largely passive. It wasn’t until I read your book and had the revelation that I wasn’t a second class citizen and had every right to speak up for myself and set boundaries. I
      then could assert myself appropriately without hesitation. It was like having the shackles of feeling not good enough fall away and I was free to speak up. It was the realization those feelings about myself came from not being emotionally validated that made all the difference. Thank you for your wonderful books and the freedom they have given me.

        Jonice - September 4, 2019 Reply

        Dear Philip, it makes me very happy to read this! I’m glad Running On Empty helped you realize what’s wrong and that it’s not your fault!

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