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Set Boundaries with Parents— But What if I Regret it?

Set boundaries with parents – a phrase that carries immense weight and significance for many of us navigating the complexities of having had unempathetic, narcissistic, or emotionally needy and immature parents.   “What if they die and I regret it?” is a question that involves two societal taboos: the necessity of setting boundaries with parents and grappling with our own mortality. But is there a way to break free from the threat of regret? In this introspective letter, we will dive deep into the transformative power of truly grieving what we never had and how that can free us from the shackles of fear of regrets when we were to set boundaries with parents who are dysfunctional and toxic. 

Despite being hurt repeatedly, many of us are still struggling to set boundaries with our parents, who might be needy, controlling, and emotionally immature, who seems determined to have an enmeshed and dysfunctional relationship with us.

No matter how much reading you do or how many therapy sessions you’ve had, you might still feel rather defenseless in their relentless demand for your attention and validation. They constantly seek reassurance for everything they do, always wanting you to be available, answer their calls, and devote your time and energy to them without considering your needs. And when you try to establish some boundaries, they set up guilt trips, play on your emotions and make you feel responsible for their well-being.


Set boundaries with parents

“I’d assumed that once I’d passed the age of twenty, I’d gained the power to do everything alone. But I’d been wrong about that, and this just brought it home to me, again, that I still had a long way to go.”
― Banana Yoshimoto, Moshi Moshi


The Fear of Regrets – When You Set Boundaries with Parents Who Guilt-Trip

I am sure this is not the first time someone has suggested you to set boundaries with parents who are intruding upon your life.

So, what stops you as you try to set boundaries with parents who are demanding and troubled, even when you recognize that the current dysfunctional pattern is harmful to everyone involved? What specific fears grip you and hold you back from taking that step?

Apart from the typical factors such as your parents’ emotional blackmail, the deeply ingrained sense of responsibility you’ve carried since birth, the fear of societal judgment, and the need to compensate for the actions of your wayward siblings who have seemingly abandoned your parent, there is another significant obstacle that often looms: the fear of regret. 

“What if, when they pass away, I am burdened with regret for not having done more for them?”

“What if I regret causing them emotional pain and feeling like I have abandoned them?”

“What if I will be haunted throughout my life by overwhelming guilt and unending remorse?”

These questions, especially when they are not voiced explicitly, haunt us like a silent ghost at the back of our heads.

The fear of regret can stem from our own imagination, societal expectations, and, unfortunately, at times, explicit threats from them:

“You’ll regret not appreciating everything I’ve sacrificed for you when I’m gone.”

“After all I’ve done for you.”

“Remember, I won’t be around forever. ” 

Despite acknowledging the rational truth that you are not obligated to carry the burden of caring for your parents or rescuing them from their lifelong sorrows, you may find yourself caught in the same dysfunctional pattern of enmeshment and co-dependency.

The deep-rooted sense of duty to care for your parents, whether influenced by societal expectations or shaped by Parentification Trauma, presents significant challenges in asserting your needs and attempting to set boundaries. Thus, the fear of disappointing or causing pain to your parents keeps you trapped in a ceaseless cycle of self-sacrifice and neglect.

Instead of allowing these nameless fears to haunt you, perhaps we should dive a bit deeper. This is when a Socratic method of inquiry could be helpful:

You can ask yourself: What exactly is it that I fear I would regret?

You might hear the Fear of Regret gremlin say, “I fear losing out on the one chance of having a relationship with them.”

But pause for a moment and reflect on what kind of ‘relationship’ that is. Have you ever truly experienced success in establishing a genuine connection with them, or is it all just a fragment of your imagination? A dreamlike illusion? An idealized vision of what a parent-child bond should be?

What is there to lose? As you delve deeper into seeking a concrete answer, you may wake up to the reality that there is no substantial answer beyond an enmeshed, dysfunctional relationship filled with daily grievances for both sides.

Due to their psychological limitations and dysfunction, an authentic and meaningful parent-child bond could never have been. It turns out it has always existed as a mere fantasy created by our inner child who never wants to give up, thus unwilling to let go of the idealized image of having a nurturing parent.

Draw a line with parents

“If the family you chose before your birth no longer supports your path towards fulfilling your true destiny, it is never too late to find a new tribe.” 

― Anthon St. Maarten

Hoped Against Hope

For many, our hearts bear the scars of repeated wounds inflicted by our dysfunctional parents. Until we can put our feet down and set boundaries, we hope against hope, knocking on the same door time and time again, seeking an authentic relationship. But all we receive in return is constant hurt and disappointment.

Perhaps our inner child believes that if we try harder and love them more fiercely, they will finally see us and reciprocate.

Sometimes also, we fail to set boundaries with parents because their empathy is intermittently given; There are moments when they do give us a glimmer of what we crave—a genuine connection, thus making it hard to resist the temptation to keep trying. (For more of this compulsion to repeat our trauma, you may wish to read about ‘Repetition Compulsion’)

But then, like quicksand, this false hope slips into becoming a toxic game; it is an addictive cycle on a slot machine.  

We find ourselves unable to stop trying—to talk to them, to open up and share the intricate details of our lives, and to reveal the person we truly are beyond the puppet- version they groom us to be. Despite our unwavering longing for an authentic connection, we get it never. Their hearts remain guarded; their ears feign attentiveness while we fade into background noise. They impose their own visions upon us, demanding conformity. Their selfish desires take precedence over our own, and they persist in pretending that we are a picture-perfect family.

With each rejection, our hearts break a little more.  The pain and disappointment threaten to consume us, and suffocate us.

Every day becomes a swing between the compulsion to connect and retraumatizing despair.

When we find ourselves trapped in a spiral of trying again and again for something that could not work,  it becomes crucial to heed the timeless wisdom and confront the “one hard thing” we have been evading: grieving what we never had.

hoped against hope 

“Desire is the kind of thing that
eats you
leaves you starving.”
Nayyirah Waheed

Grieving What You Never Had

“What do you mean by grieving what you never had?”  you may ask; “Am I not already sad enough and have been grieving all my life?”

In the realm of psychoanalysis, there is a theory that says depression is a form of denial—the refusal to truly grieve.

Depression becomes a defense mechanism, a self-blinding shield that protects us from the unbearable weight of unmet longings and shattered dreams.

By entering into a state of low-grade depression, you numb your emotions, withdraw from meaningful engagement with the world, and let lingering hopelessness stops you from trying anything that would lead to disappointment— which, of course, includes the endeavor to set boundaries with parents and reclaim your life.

Depression can be seen as a way of preserving a fragile psychological equilibrium, albeit at the cost of joy, authenticity, motivation, spontaneity, and life energy. By refusing to grieve truly, we may ‘win’ a battle, but we lose the war— we are inadvertently prolonging our suffering.

Merely experiencing sadness and responding passively to each disappointment with our parents is not true mourning. By repeatedly allowing ourselves to be triggered by day to day events, day after day, we are actually denying ourselves the potential for transformative healing through conscious grieving. It perpetuates a cycle of longing and disappointment, preventing us from fully confronting the profound pain that resides deep within our being.

In contrast, truly grieving is an act of courageous confrontation—an intentional journey into the depths of our psyche.

This means we, with deep awareness, hold space for ourselves to truly weep, scream, write, draw, punch— whatever it is that we need to do—  to grieve the loss of a cherished fantasy, a profound longing for the archetypal perfect parents that we have yearned for but never truly experienced.

You have this hidden longing and hoped against hope, not because you were foolish or stubborn. It is human nature, and we all do it. The undying longing for the perfect parents is woven and imprinted in our DNA. From fairy tales to ancient folklore, we see this collective yearning for a nurturing presence, unconditional love, and unwavering guidance. From a young age, we catch a glimpse of what could have been. Sadly, when you have dysfunctional, unempathetic parents, your childhood becomes a swinging door between the bitter reality and the sweet fantasy: You see the Fairy Godmother, but all you have is the Wicked Witch. 

Through conscious grieving, we peel back the layers of denial and delve into the rawness of our emotions. We give ourselves permission to feel the depths of the profound loss that we can never get back. It is sad, and it is unfair, and it is what it is.

Finally, we surrender our fantasy of the perfect parents as a distant mirage, and we bravely embrace the imperfect reality as they are.

We free ourselves from the unfulfilled expectations that have held us captive, opening up new possibilities for a different future.

And once you have truly grieved what could never be, a profound realization awaits you: When it comes to setting boundaries with parents, you have exerted your utmost effort, leaving no space for regret.

Given the nature of your parents and the dynamics at play, it is clear that to set boundaries is not just justified but the only viable option. Despite their claims of wanting to be close to you, you have learned from past experiences that anything but to set boundaries is not actually possible. The path to maintaining a healthy connection with them lies in creating the necessary space between— enough for you to breathe. 

When you choose to distance yourself adequately, you prioritize not only your own well-being but also the well-being of your parents. They may grow from this or remain stuck, but that is irrelevant. You recognize that the enmeshed and dysfunctional dynamic does not serve either of you, as it only perpetuates a cycle of pain and discord.

Even though they may refuse to admit it, somewhere deep inside, they are aware of how toxic their compulsive need to encroach on your life is. A part of them probably feels guilty for it. But their psychological immaturity and weakness have trapped them in their self-inflicted predicament. When you summon the strength to set boundaries with your parents, who are emotionally too weak to do so,  you are bravely confronting the difficult reality that both of you are entangled in.  In other words, it is an utterly honorable act.

Parents, Boundaries, Page, Imi Lo

“expect sadness
you expect rain.
cleanse you.”
Nayyirah Waheed


Set Boundaries with Parents— But What if They Die and I Regret it?

The Fear of Regrets gremlin in you might be stubborn, and it asks: “What if they die? How would I face myself?”

Let this be the answer:

“Well, in the moment of their passing, you will be very proud of yourself for all that you have done.  

Despite how little emotional nourishment you received as a child, you consciously loved and honored your parent as flawed human being who did their best. 

In spite of the immense challenges of maintaining a tenuous connection with them, you have invested effort, time, and energy to try.

Setting boundaries with them despite their protests, guilt-trip, and manipulation is the most daunting task, yet you persevered, honoring what is best for both of you. As much as you can, you have gracefully navigated the most turbulent time. 

Looking back, you have been the bravest warrior in the family and deserve the utmost respect for all that. 

You have done your absolute best given what was possible”. 


Reframing What it Means to Set Boundaries with Parents Who Can’t

Ideas such as “set boundaries” can sometimes be rendered clichés, especially since they are so overused in the realms of therapy and self-help.

It is not uncommon for many who have been emotional caretakers all their lives to associate terms like “set boundaries” or “keep distance” with cruelty or guilt, as if you are intentionally pushing your parents away, abandoning them, or betraying them.

To navigate and overcome these mental barriers, it can be beneficial to approach setting boundaries with parents from a perspective that resonates with your values and intentions. Rather than perceiving it as a “taking away” of something, consider reframing it as “adding something”—a deliberate inclusion of what is more wholesome, authentic, and aligned with your principles.

Instead of focusing solely on what you might be relinquishing or “cutting off,” redirect your attention toward the possibilities.

In other words, shift the focus from loss to gain, from constraint to liberation.

To start, reflect upon the values you embody and the principles you hold dear when establishing boundaries with your parents. Instead of dwelling on what you are leaving behind, contemplate what you are inviting into your life.  What values could you be honoring? Here are some suggestions;

1. Growth: Consider what is ultimately most beneficial and transformative for both yourself and your parents as fellow human beings. The path to maturity is one that leads to personal development and a deeper acceptance of reality as it is, and it is relevant no matter how old you are. They ought to learn to realize they cannot have all that they want from you, and vice versa. How can learning to set boundaries with parents who can’t do it foster a growthful experience for all involved?

Contemplate the missed opportunities that may arise from this toxic enmeshment. What if setting boundaries could unlock your true potential and bring value to your career aspirations, success in life and in relationships?

2. Honesty: Is living honestly not important to you?  When you express your needs, you are not being intentionally hurtful; you are doing what you need to do. Reflect on times when you may have been dishonest with yourself for the sake of protecting their feelings. You may wish to reflect on how embracing honesty within yourself can extend to being honest with your parents, relatives, and the world and the impact that could make. This step could actually be the doorway to heap of power and energy you have locked up as an intense and gifted person.

3. Authenticity: Do you want to spend the rest of your life painting the façade of a picture-perfect family? Is it not more meaningful to strive for genuine and authentic interactions that acknowledge the complexities and imperfections of human relationships, even when it is not a movie poster and comes with conflicts and tears? Reflect upon the potential consequences of living without authenticity, as it may eventually lead to an existential crisis—a state you might already be encountering or could face at some point in the future.

Are you a bit of a rebel, or do you stick to conventional wisdom? See if you can question the conventional expectations that society imposes on your relationship with your parents. What if you were to redefine what it means to be a “good child” and prioritize your own well-being?

4. Realism: Evaluate what is truly possible based on your experience and instincts. Embrace the truth of what can realistically be achieved in your relationship with your parents. Sad as it might be, grieve the fact that they may not fulfill the role of emotionally attuned and nurturing parents you yearn for. By accepting this reality, you can set boundaries that align with what is attainable and foster a sense of inner peace.

5. Harmony: Despite your parents’ childish demands, excessive closeness and enmeshment do more harm than good. Instead, there is an ‘optimal distance’, an equilibrium that you can strive for to create a harmonious balance within your family system.  Setting boundaries with clingy and demanding parents is to find that very sweet spot for a more sustainable relationship, and at best, you can take action to move the dynamics to align with your discovery.

Perhaps, consider also the long-term consequences of harboring bitterness and resentment towards your sibling who might have ‘gotten away’. What if you were to free yourself from the burden of bitterness and jealousy, and focus on your own journey?

6. Respect: As we transition from a child-like state to becoming adults, we must remind ourselves that being respected as a human being is more important than ‘being liked’ or pleasing people. Respect is not just doing what others demand. You can validate their frustrations to respect their right to feel, but that does not mean you need to comply every time.

Please feel free to adapt and personalize these the above value list to suit your unique journey. Explore what resonates within you and aligns with your growth and well-being. It is in your ability to create a connection that honors your needs while allowing your parents to embark on their own journey of growth. Ultimately, you must reclaim a sense of trust for yourself- that you know what you are doing and that it is congruent to your soul.

feeling guilty about setting boundaries with parents

“Each one of us continues to carry the heart of each self we’ve ever been, at every stage along the way, and a chaos of everything good and rotten. And we have to carry this weight all alone, through each day that we live. We try to be as nice as we can to the people we love, but we alone support the weight of ourselves.”
― Banana Yoshimoto, Goodbye Tsugumi

Ask Different Questions

We have discussed some questions your Fear of Regrets gremlin might have asked. But consider how, on the other side of the picture, equally valid are the questions that self-respect would prompt you to ask:

“What if I deeply regret compromising my well-being and sacrificing my happiness just to please my parents?”

“What if I regret letting myself trapped in Transgenerational Trauma and not cutting the chord for myself and my (potential) child?”

“What if it is too late when I finally feel ready to rewrite the story of who I am beyond being a ‘good child’ for them?

“What if by not spending so much time being entangled with their unreasonable demands, I could have gone further in my career, found my soulmate, and enjoyed my freedom?”

“Will I come to regret the compromises I made, realizing the toll it took on my self-worth, identity, and ability to have authentic relationships?

“Do I have to be trapped in lifelong bitterness and resentment towards my sibling who seemed to have gotten away?”

By asking these questions, I hope you can recognize that your intentions to set boundaries with parents who cannot do it is not an act of rebellion or abandonment but a declaration of your self-worth and the pursuit of a life that aligns with your deepest values and aspirations.

Life goes on, Imi Lo

“In three words I can sum up everything I’ve learned about life: it goes on.”
― Robert Frost

Finding You Again

As you embark on the arduous journey of setting boundaries with emotionally immature and demanding parents, you will realize that you did not create their dysfunctional encroachment and should not be a part of it. Their wounds existed before you were born, and you were nothing more than an unwitting victim caught in the crossfire of their brokenness.

You have been trying to let go by going back and forth, up and down, always on the verge of breaking through a toxic cycle.

Finally, you turn back and take a step away from the swinging door, reclaiming your self-worth and coming to terms with the fact that these are the parents you were given and will not change. You also embrace the truth that their inability to love you as you need it does not diminish your value.

As time passes, you realize that the closed door is a testament to your strength rather than a reflection of your failure. You have the courage to face your pain, confront the ghosts of your past, and transcend their hold over you. Your scars become symbols of resilience, demonstrating your ability to overcome adversity.

You might even find others who understand your pain, your stories weaving together like threads in a tapestry of solidarity.

As you reclaim your power and truth, you are gifted with a vast horizon of possibilities.

Your world has now expanded, regardless of your age.

The wounds are still there, but they no longer define you. You have emerged from the shadows of your past as a being of strength, empathy, and compassion. Healthy anger and feelings of hatred and resentment can exist, but you are not trapped in a cycle of striving for unattainable love and experiencing re-traumatization. Nor are you falsifying forgiveness merely to feel empty inside.

Always remember, dear ones and your inner child, that the love you seek resides within you.

Set boundaries with parents

My dear,
In the midst of hate, I found there was, within me, an invincible love.
In the midst of tears, I found there was, within me, an invincible smile.
In the midst of chaos, I found there was, within me, an invincible calm.
I realized, through it all, that…
In the midst of winter, I found there was, within me, an invincible summer.

Albert Camus



Written in solidarity and with love,

Imi Lo.


Imi Lo
Consultant and Author at Eggshell Therapy and Coaching | Website

Imi Lo is a mental health consultant with extensive experience in mental health and psychotherapy across diverse international settings. She specializes in working with highly sensitive, intense and gifted adults. Her books, 'Emotional Sensitivity and Intensity' and 'The Gift of Intensity' are internationally acclaimed and available in multiple languages. She integrates psychological understanding with both Eastern and Western philosophies, such as Buddhism and Stoicism.