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Most people who struggle with assertiveness have the same misunderstanding: they think being assertive means becoming a selfish prick who dominates people, hurts feelings, and starts fights. That misunderstanding is exactly what keeps them passive, resentful, and powerless, because if the only two options seem to be aggression or submission, most decent people will choose submission and call it kindness.

But assertiveness is neither aggression nor passivity. It is the ability to stand up for yourself without trying to control anyone else, and without allowing anyone else to control you. It is how self-respect becomes visible in real life.

The misunderstanding that ruins people

A lot of people hear the word assertive and picture someone loud, intimidating, selfish, or impossible to deal with. They think assertiveness means winning arguments, getting your way, shutting other people down, or forcing your preferences onto the room. So when they try to be a “good person,” they reject assertiveness altogether and become accommodating, overly agreeable, conflict-avoidant, and weirdly proud of how much shit they can take.

That’s the trap. If you think assertiveness is aggression, then every time life asks you to stand up for yourself, you feel like your only options are to become a bully or become a doormat. Most nice guys, people pleasers, and conflict avoiders will choose the doormat option every time, then tell themselves they’re being mature, patient, spiritual, easygoing, or “picking their battles.” Usually they’re just scared.

The result is predictable. You swallow your opinions, go along with things you don’t want, laugh when you’re uncomfortable, stay silent when someone crosses a line, and then wonder why nobody respects you and why you secretly feel like shit. It’s because every small act of self-betrayal teaches your nervous system that peace matters more than integrity.

Assertive, aggressive, and submissive

The cleanest way to understand assertiveness is to compare it with the two things it gets confused with all the time: aggression and submission. Aggression is when you try to control, dominate, punish, or change another person. Submission is when you let them do that to you.

Assertiveness is the third option. You do not go onto their territory and try to run their life, and you do not open your gates and let them trample over yours. You simply hold the line.

The fortress analogy is useful here. Aggression is firing arrows out from your fortress at other people and trying to take over their land. Submission is opening the gate and letting them come in, smash up your place, and rearrange everything. Assertiveness is locking the gate, manning the wall, and refusing entry.

That is why assertiveness is not about “getting your way.” Getting your way at all costs is aggression. Assertiveness is more like refusing to sell out your values for approval, comfort, harmony, or fear. You may not get the outcome you want, but you refuse to abandon yourself in order to chase it.

The electric fence idea

One of the best ways to explain assertiveness is as an electric fence. An electric fence does not chase people, argue with them, or punish them for fun. It just sits there, and if someone tries to cross where they’re not welcome, they get a shock.

That matters because one of the biggest objections people have to assertiveness is, “But what if it hurts someone?” The answer is that assertiveness may upset people, but it does not harm them in the way aggression does. If someone gets an unpleasant response from your boundary, it is because they tried to cross a line you had every right to set.

The fence doesn’t zap them after they step back. It doesn’t go hunting them down in the next town. It doesn’t try to ruin their life for what they did. The moment they stop crossing the line, the problem is over.

That’s why assertiveness is not vengeance, not revenge, and not “an eye for an eye.” If someone behaves badly and you become equally bad in return, they have already changed you. You might feel triumphant for a second, but really you lost yourself.

Why so many people are afraid of it

Most people do not struggle with assertiveness because they’re weak in some abstract sense. They struggle because they were trained to be afraid of emotional discomfort, trained to confuse anger with danger, and trained to believe that a good person keeps everybody comfortable.

For some people that conditioning happened in a very volatile home. Conflict meant screaming, humiliation, violence, chaos, and punishment, so standing up for yourself felt like pressing a button that triggered World War Three. If that was your environment, of course your body learned to freeze, submit, placate, or explode.

For others, the environment was too gentle. There was so little visible conflict that any strong disagreement felt catastrophic. If nobody ever modeled healthy confrontation for you, then the first time you run into friction in the real world, your nervous system treats it like a threat to survival.

Then there’s the moral layer. A lot of people are scared of being “the asshole.” They saw adults who were domineering, selfish, loud, or cruel and assumed that was assertiveness. So now, when they feel the urge to say no, disagree, or call something out, they clamp down on themselves because they think decency requires silence.

And underneath all of that is the simplest problem of all: discomfort. People don’t want the hassle. They don’t want the awkwardness, the tension, the weird look on someone’s face, the racing heart, the shaky voice, the possibility that someone might be annoyed. So they sacrifice truth to avoid a few minutes of discomfort and then spend years paying for that decision.

Anger is not the enemy

One of the more uncomfortable truths about assertiveness is that anger is often part of it. That doesn’t mean rage, abuse, or intimidation; it means anger as energy, signal, and force. Anger is often what helps you finally stop tolerating what fear kept you trapped in.

A lot of people were taught that anger itself is bad. They were punished for showing it, shamed for feeling it, or frightened into suppressing it. Then later in life they wonder why they can’t stand up for themselves. It’s because the very fuel that helps a person push through fear has been labeled forbidden.

Anger does not hurt people by itself. Behavior hurts people. If anger comes out as aggression, that’s destructive. If anger comes out as a calm boundary, an honest no, a refusal to cooperate with disrespect, or a decision to walk away, it becomes healthy.

So the goal is not to become some Zen robot who never feels activated. The goal is to let the activation be there without letting it run the show. You can be assertive while nervous, while shaky, while pissed off, while your heart is pounding. You do not need perfect calm before you earn self-respect.

What assertiveness is really for

The point of assertiveness is not social dominance. It is self-respect. It is the ability to say, “I will not allow myself to be moved off my values just because someone else is uncomfortable, manipulative, intimidating, or disappointed.”

That is why assertiveness and self-worth are so tightly linked. If you repeatedly betray yourself to keep other people happy, you teach yourself that your own needs, feelings, and values are less important than maintaining temporary peace. Over time, that becomes low self-worth.

Self-worth is not just how you feel about yourself in the shower after listening to a podcast. It’s built by how you treat yourself in moments of pressure. Do you back yourself, or do you sell yourself out? Do you speak when it matters, or do you disappear?

And yes, assertiveness also gets you more respect from others, though that should be understood properly. You cannot make people respect you. Some people are too selfish, damaged, manipulative, or immature for that. But when you respect yourself consistently, you get the maximum respect that is available from the people around you.

Why people-pleasing ruins relationships

A lot of people think people-pleasing is loving, cooperative, generous, or good for relationships. Usually it is none of those things. Usually it is fear wearing a polite mask.

If you are never honest about what works for you and what doesn’t, then people can’t really know you. They have to guess how to be in relationship with you. And they will guess wrong, because everybody has different preferences, standards, limits, and sensitivities.

This is why so many “nice” relationships quietly rot. One person keeps making sacrifices to avoid tension, the other keeps walking through the open gate because nobody told them there was a wall there, resentment builds in secret, and then eventually the passive person snaps. From the outside it looks sudden. It almost never is.

Assertiveness gives healthy people the blueprint for how to have a good relationship with you. It also exposes unhealthy people much earlier. If somebody reacts badly every time you say no, every time you disagree, every time you ask for basic respect, then that is useful information. That’s not a failed conversation; that’s a revealed character.

In that sense, boundaries don’t ruin good relationships. They protect them. And they often ruin bad relationships faster, which is also useful.

Stop picking your battles

For conflict-avoidant people, “pick your battles” is often just cowardice dressed up as wisdom. It sounds mature, strategic, and balanced. Most of the time it really means, “I’m too uncomfortable to be honest right now, so I’ll pretend silence is a virtue.”

That doesn’t mean turning every moment into a war. It means refusing to lie through passivity. If someone says something you strongly disagree with, you do not need to launch into a courtroom presentation. But you can say, “I don’t agree,” and let the room be awkward for a minute.

This is where many people get confused. They think if they speak up, they now have to win. They think they must justify, explain, defend, persuade, and out-argue the other person. That whole mindset is already drifting into aggression.

Assertiveness is much simpler. You give voice to your truth. You do not need to dominate the room with it. You do not need to make everyone applaud. You do not need to convert disagreement into agreement before you are allowed to move on.

Headlining: say less, mean more

One of the most practical assertiveness skills is to stop overexplaining. Most people who are anxious about conflict say way too much because they’re trying to soften the blow, pre-answer objections, manage the other person’s emotions, and talk themselves into feeling safe. It usually has the opposite effect.

A better approach is what could be called headlining. Instead of giving the whole article, give the headline. “Don’t come into my room.” “Please don’t interrupt me.” “I’m not okay with that.” “No, I won’t be doing that.”

If you have been speaking for longer than about 30 seconds while setting a boundary, there’s a good chance you’ve slipped into explaining, justifying, or negotiating before respect has even been established. The more you explain, the more it sounds like you’re asking for permission. Assertiveness is not asking permission to have standards.

This is especially important if you get emotional in conflict. When you are activated, go slower, say less, use simpler sentences, and leave long pauses. Not because it makes you look powerful, but because it stops you from getting dragged into the kind of back-and-forth that turns honesty into a messy power struggle.

Setting boundaries is verbal, enforcing them is physical

This is probably the biggest practical distinction of the whole topic. Setting a boundary is verbal. Enforcement is behavioral.

A lot of people think assertiveness means repeatedly telling someone what not to do. It doesn’t. You say it once clearly enough for a reasonable adult to understand it. After that, if they keep crossing the line, you stop talking and start changing access, proximity, cooperation, privilege, attention, or logistics.

That’s enforcement. It is not punishment. It is not revenge. It is not an attempt to make them suffer for what they did. It is simply making it harder or impossible for them to continue hurting you.

If a child throws a toy at you after being warned, the toy goes away for a while. If someone keeps interrupting you in a meeting after you ask them not to, you leave the meeting or stop giving them the benefit of your participation. If a person repeatedly violates a stated condition of the relationship, they lose access to the parts of you that were a privilege, not a right.

This is where people who talk a lot about “boundaries” but never enforce them get stuck. They think repetition is strength. Usually repetition without action is just training other people not to take you seriously.

Do not aim to hurt them

The point of enforcement is never to wound the other person. In fact, the cleaner and calmer the enforcement, the more assertive it is. Smashing someone’s TV with a baseball bat because they disrespected you is not assertive; it’s just another tantrum in adult clothing.

Assertiveness removes privileges; aggression adds punishment. Assertiveness changes what you allow access to; aggression tries to make them pay. The difference matters.

You can still care about someone deeply and refuse to cooperate with their bad behavior. You can still love them and say no. You can still support them as a person while cutting off access to something they misuse.

That’s why assertiveness is often more compassionate than indulgence. Indulgence can look nice in the moment, but it often props up the exact patterns that are making everyone miserable. Assertiveness is willing to tolerate short-term upset in service of long-term health.

Make disrespect a hassle

One of the more blunt but useful ways to think about assertiveness is that bad behavior has to become a hassle. Human beings, including manipulative ones, tend to choose the path of least resistance. If disrespecting you is easy and consequence-free, a lot of people will keep doing it.

That does not mean creating drama over everything. It means that every time someone crosses a line, they run into reality. Not your lecture, not your wounded essay, not your emotional collapse, but reality. Access changes, the meeting ends, the conversation stops, the invitation disappears, the privilege goes away, HR gets involved, the date ends, the call gets hung up.

Manipulation often works one inch at a time. The person doesn’t usually begin by trying to take a mile. They test little things, tiny boundary crossings, just enough that you’ll feel petty for reacting. If you keep surrendering those inches because each one seems too small to address, eventually you wake up and realize your whole life is organized around someone else’s disrespect.

Assertive people are harder to manipulate not because they’re tougher in some macho sense, but because they make small violations visible early. They speak up sooner. They act sooner. They do not train others to expect unlimited access.

Reward cooperation too

There’s another side to this that a lot of people miss. It’s not enough just to make disrespect costly; cooperation should also be easier, warmer, and more rewarding.

This is especially important for recovering people pleasers, because they often do the opposite. They bend over backward for difficult people and then dump resentment onto the people who are actually trying. They make kindness feel strangely thankless while making disrespect weirdly sustainable.

A better pattern is simple. If someone respects your boundary, responds well to feedback, makes an effort, or corrects themselves, acknowledge it. It doesn’t need to be a parade. A sincere “thanks, I appreciate that” is enough.

The combination matters: difficult to disrespect, easy to work with. That is a powerful standard. It protects you while also giving decent people a very clear path to being close to you.

The backup plan nobody talks about

There is a hidden factor underneath a lot of failed assertiveness: dependence. If part of you believes you cannot survive without this person, this job, this friend group, this relationship, or this approval source, then your brain is going to slam on the brakes every time you try to risk losing it.

That’s why a backup plan matters so much. You do not need to want the relationship to end, but you do need to know how you would survive if it did. If speaking up to your boss gets you fired, what then? If setting a relationship boundary ends the relationship, what then?

The clearer that answer is, the easier it is to act with integrity. Not because you become reckless, but because you stop relating to assertiveness as if it opens a trapdoor into death. It becomes a real risk with a survivable next step.

Codependence and assertiveness do not mix well. The more you believe someone is your oxygen supply, the less willing you will be to confront them honestly. Real strength grows when you know you can collaborate with people, love people, and build with people without making them the sole source of your security.

The real goal: nothing to lose

The long-term destination of assertiveness is not perfection. It’s not becoming some superhuman who never feels fear and always says the perfect line. It is developing what could be called a nothing-to-lose mentality.

That means integrity outranks outcome. Approval, money, comfort, smoothness, popularity, and even certain opportunities all drop below the question: can you respect yourself after this?

Paradoxically, that is often when life starts going better. People can feel when you are no longer trying to cling, appease, or maneuver your way into safety. The manipulative ones tend to move on. The healthy ones tend to trust you more.

It doesn’t happen overnight. For many people it takes practice, coaching, mistakes, and a lot of very uncomfortable repetitions. But every step toward that mindset makes your life cleaner. You stop living as a hostage to reactions.

The moment that makes it worth it

There’s a particular kind of shame that comes from knowing you should have said something and didn’t. Almost everyone who struggles with assertiveness knows that feeling. You go home replaying the moment, rewriting the scene in your head, wishing you had backed yourself when it counted.

The deeper promise of assertiveness is not that every confrontation goes well. It’s that when the real moment comes, the one that actually matters, you have a chance of showing up as the person you want to be.

That might be standing up to a bully in public. It might be finally saying no to a manipulative boss, partner, parent, or friend. It might be calling something out even though your voice shakes and your heart pounds and everyone around you goes silent. The details change, but the principle is the same: you would rather face the consequences of honesty than the self-disgust of cowardice.

That’s really what assertiveness offers. Not dominance. Not invulnerability. Not a life free of discomfort. It offers the chance to stop abandoning yourself. And once you stop doing that, respect has somewhere to live.

A Serious Invitation to Coaching

If this post resonated with you, there’s a reason.

Most men who end up working with me aren’t looking for motivation, hacks, or surface-level confidence. They’re tired of circling the same problems with information overwhelm but not implementing successful changes.

They know what they should do. They’re just not consistently doing it.

Coaching is not for everyone. It’s not therapy, it’s not cheerleading, and it’s not about “fixing” you. 

It’s a structured, honest working relationship focused on behaviour change, taking responsibility for yourself, and improving the way you make decisions—especially the ones you keep avoiding.

This work is for you if:

• You’re functional and capable, but something fundamental still isn’t working.
• You’re done with intellectualizing your patterns and want them to actually change.
• You’re willing to be challenged, not reassured.
• You’re prepared to take responsibility for your choices instead of waiting to feel ready.

I’ve spent years making these mistakes myself and over a decade helping others stop repeating them. The difference coaching makes is not insight—it’s traction.

What working together looks like

• Clear diagnosis of where you’re self-sabotaging (not just why)
• Practical, uncomfortable actions that build real confidence
• Direct feedback when you drift back into old patterns
• A focus on integrity, not image or performance

If we work together, it will be because it makes sense—not because you were persuaded.

A no-pressure first session

I offer a free initial trial coaching session with no obligation to continue.

You can use it to see how I work, ask hard questions, and decide whether this is something you want to commit to.

If it’s not a fit, that’s fine. If it is, we’ll be clear about what comes next.

👉 Apply for an initial coaching session here

I only work with 8 clients at a time, and only with those prepared to take this seriously. I have 5 intro session spaces available each month – you may need to go onto a waitlist.

Dan Munro

If you’re looking for reassurance of your victim-story, this isn’t it. If you’re ready to change how you actually live, let’s stop messing around.