Why Healthy Boundaries Feel Uncomfortable When We First Apply Them

Why The Good-Hearted Find It Difficult to Apply Boundaries

Healthy boundaries are one of those concepts everyone agrees are important, yet few people feel naturally confident practicing, especially good-hearted people who might have learned earlier in life that they are supposed to consider the desires of others and sometimes even defer to them.

The idea of boundaries sounds simple: know your limits, communicate them clearly, and protect your emotional well-being. The idea not only sounds simple but really sounds natural, normal, and almost needless; after all, who wouldn’t set boundaries and who wouldn’t expect that everyone would? I mean, after all, we experienced them our entire childhood, right? Our caretakers set boundaries for us to follow, our schools did as well, and for many of us, so did our churches.

So how can it possibly be new to us?

That’s because boundaries are not new to us; we are very familiar with them; we are familiar and well-versed in adhering to the boundaries of others.

Do you have that friend with whom you know you can only go so far in a subject? Maybe you know that they are very sensitive about their weight, their hairline or style, or maybe their acne? Whatever the topic is, you know how to steer a conversation away or around a topic that you feel is leading in the wrong direction that might approach those sensitive areas, right? I would guarantee every single good-hearted person reading this article has known or has someone in their life right now who fits into this category.

So here’s the thing – we are very familiar with boundaries. In fact, based on the example I just gave, we are even pretty good at understanding the boundaries of others, even if they don’t know it for themselves. Why is this? Furthermore, if we can do it for others without their asking, and we are used to all of the boundaries we had in childhood, exactly why can’t we set them for ourselves?

We might not like the answer, but the reality is that we don’t set the boundaries for ourselves and in our lives because we don’t feel we deserve to have them – yet.

In my experience, the vast majority of good-hearted people fall into this category or did at one time in their life until they discovered the power and the authority to do so. In my coaching, I alert my good-hearted clients to this tragic realization. As a person who grew up feeling responsible for the emotional well-being of others in the household (or at least expected to not cause difficulty), you either became or remained the good-hearted person you were born to be by following these emotionally charged rules, where you first considered your impact on others before you considered your own needs or emotions. How many of you just resonated with that statement? Quite a few I know.

Before I continue, I want to make something very clear; for the sake of this article, I may discuss “setting” boundaries, this is to include the act of applying boundaries and applying the resultant consequences upon those who do not respect the boundaries we set, ok? Setting boundaries is not enough on its own – we must hold others to those boundaries we set. I specify the distinction because I have had clients who have come back after performing their assignment of setting boundaries and keeping note of how the practice worked, and they tell me, “Dave, I told my husband my boundary, but he didn’t follow it.”

We cannot expect people to follow the boundaries we set merely by sharing the boundaries with them; we must apply both the boundary and the consequence (whatever that may be) for not honoring the boundary we provided them.

But when it comes time to actually set a boundary—saying no to a friend, asking for space from a spouse, declining a request, or expressing a need—many people feel a surprising wave of discomfort. When a boundary is first enforced, we can really feel proud of ourselves and very empowered, but until we practice and get used to feeling deserving of having the boundary, guilt, anxiety, self-doubt, and even a sense of disloyalty to earlier learned behavior can rise to the surface immediately following applying it.

This discomfort isn’t a sign that the boundary is wrong; in fact, it’s often evidence that the boundary is healthy and long overdue. Understanding why boundaries feel so awkward when first applied can help us stay committed to them long enough for the discomfort to fade and the benefits to take root.

I like to have my clients think of boundaries like starting a new exercise regimen. The soreness we feel the next day doesn’t mean you’re doing it wrong — it means we’re using muscles we haven’t used before. And we have to remind ourselves of those exercises we did the day before, and then we can almost enjoy that muscle soreness because we’ve begun to work at being physically fit. Working on our boundaries is the exact same situation, working our emotional muscles that we’ve not used before will create that soreness or emotional discomfort, and that discomfort is there to remind us that we are using the emotional muscles we have always had but are now using, and the more frequently we use them, the more comfortable we become.


Boundaries Challenge Old Conditioning

Most of us learn early in life how to stay safe, accepted, and connected. These lessons can be spoken or unspoken because we often learn from the unspoken lessons much more quickly than the spoken ones (the reason why is fascinating but for a different article). But those lessons we’ve learned shape our beliefs about what we’re “allowed” to need or express.

• If we grew up in a family in which saying “no” was punished or ignored, boundaries may feel like rebellion.
• If we learned that our worth came from being helpful, agreeable or low maintenance, boundaries may feel selfish.
• If we were taught to anticipate others’ needs before our own, boundaries may feel like abandonment.

These patterns become automatic. So, when we begin setting boundaries as an adult, we’re not just changing a behavior—we’re actually disrupting a lifelong survival strategy, that which we came to know as normal. And normal to our emotional mind, becomes the new standard. So when we alter that pattern or habit, our emotional system and specifically our unconscious emotional mind interprets this as risk, even when our conscious emotional mind knows it’s healthy.

The discomfort is not a sign of failure. It’s a sign that we’re rewriting old rules; I call these our POOL rules. In my coaching, POOL is an acronym I created for the Primary Occurrence Of Learning – all those rules we learned early on must now be evaluated in our adult life. As a good-hearted person we now have the ability and the need to determine which of those rules align with our unique, individual and authentic belief systems and these new rules are ours and ours alone. Much like the placard of rules on the outside of a community pool, our new POOL rules let everyone approaching our life of the expectations if they intend to enter our new POOL – and know that consequences will be applied should those rules not be followed.
Boundaries Can Trigger Fear of Conflict or Rejection

Many people avoid boundaries because they fear how others will react. Even a simple “I can’t make it tonight” can stir up worries like:

• “They’ll be mad at me.”
• “They’ll think I don’t care.”
• “They’ll leave.”
• “I’ll ruin the relationship.”

These fears are powerful because humans are wired for connection. Historically, being excluded from the group was dangerous. Today, the stakes are emotional rather than physical, but the our emotional mind still reacts as if rejection is a threat to our emotional existence.

When you set a boundary, we do take a risk: we show others our needs and we hope the relationship can withstand them. That vulnerability can feel deeply uncomfortable, especially if we’ve experienced unpredictable or volatile reactions in the past.

But here’s the truth: healthy relationships can tolerate boundaries. Unhealthy ones depend on you not having any. Boundaries don’t harm relationships – they reveal them!


Boundaries Disrupt Familiar Roles

Every relationship - romantic, familial, professional, or social - develops a rhythm or a pattern. People fall into roles, we all do – or we adopt them when caretakers indicate their expectations for us. Maybe we became the fixer, the peacekeeper, the listener, the dependable one, the flexible one or the one who always says yes.
When we start setting boundaries, we change the rhythm or pattern. We step out of our assigned role. And even if the role was draining or unfair, it was familiar or normal and therefore considered by our unconscious emotional mind as safe.

Familiarity feels safe. Change feels risky.

Others may resist the shift, not because the boundary is wrong, but because it forces them to adjust. They may need time to recalibrate. Some may push back. Some may test the boundary. And when you do this for yourself, some may even accuse you of changing.

You are changing. That’s the point. But you’re changing through growth.

Because of this change that people will see, I encourage every single one of my clients to let the people important to them know that they are embarking upon the path of self-discovery with me as their coach and that they will see differences in their behaviors or emotions. If we don’t notify our people of the developing growth, then it’s like we are playing a board game with them all of our lives, and suddenly now are changing the rules – without telling them what the new rules are!

After all, we’ve trained them to know what to expect from us for all of our lives up until this point, haven’t we?
It’s kind of additionally fascinating that when you begin to become very good at setting the boundaries, the people who really never healthily contributed to our lives begin to fade away; it’s kind of like the icing on the cake of having that extra benefit without having to do anything.

Boundaries Require You to Prioritize Yourself—Which May Feel Unnatural

For people who are used to prioritizing others, putting themselves first can feel uncomfortable, even wrong. You may feel:

• Guilty for disappointing someone
• Selfish for choosing your needs
• Uneasy because you’re not used to being cared for
• Exposed because you’re showing vulnerability

But self-prioritization isn’t selfishness. It’s self-respect.

Healthy boundaries are not about controlling others - they’re about managing your own energy, time, and emotional bandwidth. They allow us the ability to show up authentically rather than resentfully or requiring us to be insincere.

The discomfort comes from shifting our internal compass from “What do others need from me?” to “What do I need to stay healthy and whole?” And by the way, being able to stay healthy and whole contributes positively to absolutely every single person within families as well as our sphere of influence, which is a benefit to everyone.


Boundaries Expose the True Health of a Relationship

One of the outcomes of setting boundaries that many consider unsettling at first is that they reveal things we may not want to see.

• People who benefit from your lack of boundaries may react negatively to you now.
• People who respect you will adjust to them, even if it takes a moment.
• People who only value you for what you provide them usually distance themselves because you no longer exist solely as a service to them.
• People who genuinely care about will support and encourage you in your path and often follow your lead and become very interested in doing the same; you become magnetic. I firmly believe the magnetism is because we all inherently seek to expand into independence after childhood. And the safety in the confidence that is exuded from an individual who comes to know who they are, what they will accept and what they expect is very alluring to others.

Boundaries act like a wonderful filter, they really reveal who is capable of mutual respect and who is not.
That clarity can be painful, especially if it challenges hopes or illusions about a relationship.

But that clarity is also freedom.


Boundaries Require Practice, Not Perfection

Most people expect boundaries to feel empowering right away. In reality, they often feel clumsy at first. You may over-explain, apologize excessively, or second-guess yourself. You may set a boundary and then immediately want to take it back.

This is normal.

Boundaries are a skill, not a personality trait. Skills require repetition. The more you practice, the more natural they feel. Over time:

• Guilt fades
• Anxiety decreases
• Confidence grows
• Relationships become more balanced
• Your sense of self strengthens exponentially

Eventually, boundaries stop feeling like confrontation and start feeling like what they truly are - self-care.


Discomfort Is a Sign of Growth, not a Red Flag

Like I mentioned earlier, the early discomfort of boundaries is similar to the soreness that comes from starting a new workout. It’s not a sign that you’re doing something wrong - it’s a sign that you’re using muscles you haven’t used before. Just like that new workout, if we don’t feel uncomfortable at first we probably aren’t doing it right!

Growth rarely feels comfortable in the moment, but it leads to strength, clarity, and emotional freedom. If growth was easy, quick and automatic – everyone would grow, but as we know, a significant percentage of people never do; at least not in a positive way.

Healthy boundaries create:
• More authentic relationships
• Less resentment
• More energy
• Greater self-respect
• A deeper sense of safety
• A clearer identity

The discomfort of setting and applying boundaries is temporary; the benefits are life-changing and ever-lasting.


Conclusion

Healthy boundaries feel uncomfortable at first because they challenge old conditioning, they disrupt familiar roles, and require vulnerability. They ask you to prioritize yourself in ways you may not be used to. They will also reveal the true nature of your relationships; and as a good-hearted person, you deserve to know the true nature of every one of your relationships. But they do push you into emotional territory that will feel unfamiliar – at first.

But remember, the discomfort is not danger. It’s transformation.

With practice, our boundaries become less about fear and more about freedom. I promise you, they become a natural extension of self-respect and empowerment. And they create relationships where you can show up fully—without overextending, over-giving or disappearing in the process.

When you endure and last through the discomfort you will discover the freedom, the power and the magnetism that results from you caring enough about you to stand up for yourself, your beliefs and your requirements.

Your new boundaries will truly help you become the “me” that you were meant to be.

- Dave Jones