Learning how to be assertive won’t happen overnight. You’re going to push up against a lot of psychological resistance you’ve accumulated throughout the years. But, I promise you the following steps will help you stand up for yourself.

Here is a step-by-step guide on how to be assertive:

  1. Set your values & boundaries
  2. Deal with the fear that hijacks you from being assertive
  3. Practice how to be assertive

How to be assertive step 1: Set your values and boundaries

Your boundaries & values are the measuring stick used to assess if someone has crossed the line.

Here are some values and boundaries I’ve come up with:

  • I am honest.
  • I respect others (if deserved) and expect the same.
  • I treat other people well, but don’t tolerate or enable bad behavior.
  • I take care of myself.
  • I am empathetic, but don’t try to caretake other people’s emotions.
  • I go after what I want.
  • I act in spite of fear.

I initially struggled with sticking to my values & boundaries because I couldn’t tell if I was being too sensitive or still being a doormat when I felt disrespected. I found it difficult because I was so used to thinking about what other people thought instead of listening to myself. I was still trying to caretake other people’s emotion even though it wasn’t my responsibility. This happened because I was scared of loss and had poor self-esteem. Ultimately, I felt like I didn’t have the right to set a boundary.

Sound familiar?

As you work on your self-esteem, you naturally will become more attuned to your personal values and boundaries. With that being said, here is a framework you can use to assess if someone if stepping over your boundaries:

  1. List out the events / situations that made you feel bad.
  2. List out the reasons why it made you feel bad.
  3. Ask yourself if the reasons you feel bad are true. Did the other really try to make you feel bad, or is it just your interpretation of what happened?
  4. Drop the issues where you realize you interpreted things incorrectly. All other issues are areas you can practicing asserting yourself.

There will be times it is difficult to pinpoint if someone is just joking around or actually being hurtful. When in doubt, give it some time. If it continues to bother you, chances are you’re running up against something that crossed your boundaries. If something continues to bother you, practice setting the boundary. It is better to ask for forgiveness than to ask for permission. Practicing how to be assertive isn’t about setting the right boundaries right away. It’s about being willing to assert yourself and learn from any mistakes you may make.

You have a right to feel the way you do. No one has a right to dictate how you feel because they’re not you.

How to be assertive step 2: Deal with the fear that hijacks you from being assertive

Advice on how to be assertive often tells you what behavior you should emulate in order to become assertiveness. That is helpful to a certain degree, but the core issue that stops you from actually being assertive is fear. It is fear that makes you freeze up and unable to respond when someone says something offensive to you.

Fear manifests in the mind and body. Here’s how to target each part:


As mentioned in my article on why it’s so hard to be assertive, low self-esteem makes it difficult to stand up for yourself. It perpetuates fear because you feel like you’re not worthy enough to stand up for yourself. You ruminate incessantly over situations where you were stepped on and fear future situations. These thoughts fuel the anxiety you have towards other people.

Behavior flows from mindset (i.e. self-esteem). Fix the mindset, and the behavior will naturally follow.

Mindsets to implement

The following mindsets solidify your sense of self and enable you to be assertive:

Mindset 1 on how to be assertive: Be okay with loss

Why are you scared of losing someone or something? What feelings will losing them / it give you?

I found I was scared of loss because I thought it meant I wasn’t good enough, couldn’t handle the loss, and would never be able to pick myself back up.

Here’s what it took to not let the fear of loss control me:

  • I was in so much pain staying where I was. The pain of my present situation hurt infinitely more than being assertive and potentially losing it all.
  • I realized I had no control to how life would pan out. Before, I had placed my confidence in having nice things instead of my ability to pick myself back up.
  • I accepted shit would happen in life and I didn’t need to worry about things out of my control.
  • I cultivated a sense of faith & destiny: I started to believe I would be able to pick myself back up no matter what happened in life.
  • I started to value myself. Taking care of myself and living according to my values mattered way more than trying to get things to be my way (which was usually out of my control anyways).

When my self-esteem raised, I became okay with losing people that wouldn’t want a relationship with me because of my boundaries. We can’t control others, but we can live authentically by keeping our boundaries intact. The people that respect those boundaries and stay are the ones that are worth it.

Mindset 2 on how to be assertive: Treat everyone as your friend 

Fear is embedded in the worldview of people that struggle with assertiveness. If you act like everyone’s out to get you, then they will be out to get you. If you are focused on your thoughts of being walked on, it will reflect in your body language and you will live life in a reactive state. Unfortunately, people that step on others notice this behavior right away. The vicious cycle continues.

My lack of assertiveness was so evident at one point even some of my high school friends start to shit on me. Talk about a low point. Fast forward a few years later: I had started working out, was happy with my career, and had been through some shit. I felt damn good. My friends’ behavior was a lot different when they saw me again. It wasn’t what I had accomplished that made them respect me. It was the fact I respected myself. I viewed them as old friends to catch up with, not people to defend verbal barbs from.

Try to look at things through this lense: “Everyone’s my friend, let me focus on having a good time with them”. This shifts your worldview from fear to someone that is interested in having a good time. Your headspace won’t be in the perceived lack of respect you’re getting, but will be about being present with the people you’re with. Your attention and state will follow where your mind goes.

Wayne Dyer said: “If you change the way you look at things, the things you look at change.”

Mindset 3 on how to be assertive: Don’t expect people to read your mind or try to caretake other people’s emotions 

You are responsible for getting your needs met. Other people can’t read your mind, and it’s your responsibility to voice your concerns and needs. Your locus of control is on you only, not on external things you can’t control.

You are not responsible for how people feel, and don’t need to try to please them. It is their responsibility for making themselves feel good. You’re no longer a “nice guy” that feels like he needs to do things for people to please them because that’s not what you’re only good for. You and your needs matter.

How to implement the mindsets

Raising your self-esteem will naturally integrate the mindsets I listed above.

Here’s a simplistic way to raise your self-esteem: Disconnect from the disempowering points that run through your mind and fuel fear. Right now, you’re in a state of fear, anxiety, worry that makes you freeze up when you are faced with an opportunity to be assertive. Once you shut down the disempowering thoughts that fuel the state of fear, you’ll feel better about yourself and be empowered to act when someone tries to step over your boundaries.

We think we are our thoughts, and we equate them with our identity. This is not true. I think of random things all the time (i.e. fighting ninjas), but I don’t believe I’m someone who fights off ninjas on the regular. It’s a silly example, yet we closely identify with the thoughts that make us feel shitty and fearful.

The key to disconnecting from the disempowering thoughts isn’t to resist them and force yourself to think of something else. Resistance fuels fear. If you want to disconnect from your negative thoughts, become an observer of them. Being an observer takes the wind out of the negative thoughts because you no longer associate them with your identity.

Here are some techniques you can use to disconnect from disempowering thoughts:

  1. Noting: Raise attention to a negative thought that comes in by simply noticing you’re having this thought. For example, if a negative thought comes in, I think: “Interesting, I notice I’m thinking of [insert negative thought].”
  2. Labeling: You can disempower a negative thought by labeling the emotion behind it. For example, if there’s a situation that makes me tense and angry, I notice the thought and label it as “anger”.
  3. Making the thought into a movie and then reducing the size of it: When you start feeling the onset of the negative thoughts and emotions, start to observe your thoughts on a projector screen you’re watching. View the screen in blank and white, and then start to minimize the size of the screen.
  4. Watch yourself as a neutral 3rd party: Observe the thought in your mind as if you were another person observing yourself. Start to zoom out until your observation of yourself is super tiny.

With all of the above techniques, take deep breaths as you practice the technique.


People freeze up when faced with an opportunity to become assertive because fear is embedded in their body and overrides all rational thought. It becomes impossible to just think your way into being assertive. Fear manifests as rigidity and tension in the body, so the key is to take on a practice that will help you ease the tension in your body.

Here are some ways to start relaxing your body:

Deep breathing

I mentioned deep breathing in the section on disconnecting from disempowering thoughts. When you consciously breathe in deeply and exhale slowly, it will relax your body. Breathe in deeply, and exhale slowly. Doing this for a count of 10 (or more), and then see how you feel.


Yoga is another great way to relieve tension in your body1https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3193654/. To keep it short and sweet, yoga relaxes your body and helps you sleep better if you incorporate it as a practice.


As cliche as it is, exercise promotes relaxation and helps relieve anxiety2https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3151311/. It decreases muscle tension, and helps you calm down. Studies have even shown that being on a training program for 10 weeks or longer has been shown to decrease overall anxiety in research participants3https://www.ncbi.nlm.nih.gov/pubmed/1828608. The less anxious you are, the easier it is to stand up for yourself.

How to be assertive step 3: Practice how to be assertive

Keep the following in mind to effectively practice how to be assertive:

  1. Learn what to practice
  2. Set the right success metrics
  3. Start small

Learn what to practice

Assertiveness is learning how to stand up for yourself without being an asshole about it. This section is on the specifics of how to do that.

Speaking assertively primarily comes in three formats:

Format 1: A light, humorous response

This format indicates the other person took things a bit far but uses humor to defuse the tension. Humor is a great way to be assertive without making the other party feel intensely awkward, and is best used when the other party transgresses across a minor boundary. Your response level should match the severity of the boundary crossed.

For examples, let’s say someone kept poking me and I wanted them to stop. I would say: “A bit touchy today aren’t you? Keep your hands to yourself (with a smile on my face).” In this case, there’s no need to state “You’re making me really uncomfortable when you keep poking me” unless the person continues to ignore my boundary and continue with that behavior.

Some other examples of using a light, humorous response are as follows:

  • “Whoa, easy there”
  • “Damn, someone’s bringing the heat today”
  • “Damn, bringing out the big guns and putting the pressure on me today, huh?”

The whole point of the light, humorous response is to call out the behavior with a smile and give the other person a notice that their behavior is on the edge of crossing your boundary.

Format 2: A question

This format is quite simple: You ask the other person to stop their behavior that’s crossing your boundary. For example, let’s say someone keeps interrupting me when I speak. I would say: “Can you please stop interrupting me when I talk? Thank you.” This format should be used when the boundary the person is crossing is a bit more severe and you need to be upfront their behavior is making you uncomfortable. You can add a “thanks” or “thank you” at the end of your request to soften the blow a bit.

Format 3: A question + statement

This format is the same as format 2 with the addition you add in a statement about how you feel when the person crosses your boundary. For example, let’s say a friend is perpetually late to events and other friends have had to wait on him / her. In this case, I would say: “Can you be more on time when all of us are hanging out? When you’re not on time, we feel like we’re wasting time and also feel like our time isn’t respected.” When you make the statement, don’t blame the other person (i.e. “you always do this”, “you’re so inconsiderate”). Instead, focus on how you felt and mention the behavior that made you feel that way. Focusing on your feeling gives the other person insight into how their behavior is affecting you and also doesn’t put them on the defensive. If you start accusing them of being an asshole / jerk, they’ll shut down.

As you might guess, use format 3 when the boundary the other person is crossing is severe and you need to make a point how their behavior is unacceptable.

You may find it helpful to practice these formats in front of a mirror. It may seem silly, but it definitely does work. I’ve used this trick countless times to practice for interviews and presentations, and it makes me feel more comfortable when I need to be in the spotlight.

Set the right success metrics

The way you measure success will determine if you continue practicing assertiveness or fall off the wagon. I found it difficult to practice assertiveness in the past due to the following reasons:

I put way too much pressure on myself to be assertive right away

I would beat myself up if there was an instance where I should’ve been assertive but wasn’t due to the intense pressure I put on myself to be an assertive man. It was easy to lose sight about how learning assertiveness was a process. Beating myself up only fueled the anger and anxiety I had in me, making it even more difficult to be assertive because it seemed like I had to “perform” every time there was an opportunity to be assertive.

I measured success based on how other people responded to my assertiveness

When I first starting to learn how to be assertive, I still used people’s responses to my assertiveness to validate that I was becoming more assertive, confident, etc. This was a losing battle because my success metric was still based on something out of my control.

Your success metrics for practicing assertiveness should be the following:

  • It is a success if you at least tried to be assertive.
  • It is a success if you opened your mouth and said something, even if what you said just croaked out.
  • It is a success if you reflected on your attempt at assertiveness in order to improve the next time around.

Setting success metrics based on your effort empowers you because it is the sole thing you can control. It is so much easier to remain motivated and feel empowered because everything is within your grasp.

Start small

As mentioned above in setting the right success metrics, putting too much pressure on yourself will make it more likely you won’t continue with your practice. You do not have to be assertive in every situation at once. Build up to the big situations by starting small.

For example, let the waiter know your order was wrong and send it back to get it fixed if your food order was messed up at a restaurant. When you start small, you practice assertiveness and gain confidence that standing up for your values is possible. You also learn that you won’t die from being assertive, and that most of the worst-case scenarios that went through your mind usually don’t happen. You become more comfortable with being assertive, and can use this to springboard onto more difficult situations.

If you are having difficult even starting with the smallest of baby steps, here’s a question you can ask yourself to flip the script:  “Why if I just said something to see what happened?” Asking this question takes the pressure of you to assert yourself and instead makes it an experiment.  When you are interested to see how something will go, it automatically empowers you because you’re doing it out of choice instead of forcing yourself into it.


Learning how to be assertive will dramatically increase the quality of your life. Your relationships will improve, you’ll feel more confident, and you won’t be as stressed.

I hope you found my advice helpful in your journey to become assertive. If you have any questions or comments, please leave them in the comment section below.

Peace and courage,


References   [ + ]

1. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3193654/
2. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3151311/
3. https://www.ncbi.nlm.nih.gov/pubmed/1828608