I Hope I Will Have the Courage and the Capacity

to Tolerate Breaking Her Heart...

by Martha Stark, MD / Faculty, Harvard Medical School


I have just started working, one-on-one, with a highly accomplished, psychologically sophisticated, extraordinarily smart, and rivetingly articulate 65-year-old lawyer – whom I will call June.

Please know that, to protect patient confidentiality, I have modified all identifying data (including her name).

I offered June an initial, complimentary, 45-minute consultation session, which I generally do in order to give both the patient and me an opportunity to experience the “mutuality of fit.”

June used the session well. In fairly short order, I learned from her that, over the course of the previous decades, she had been in multiple, frustratingly disappointing “failed” therapies but that she was now feeling so anxious, restless, dissatisfied, stressed out, and, at the age of 65, such an acute sense of urgency because of “so little time left” that, in desperation, she had decided to try therapy once again.

June informed me that five years earlier, having grown weary of being an underappreciated – albeit very successful – lawyer, she had decided to cut back on her practice of law in order to pursue her dream of becoming an author (of books promoting healthy lifestyle choices and physical / mental well-being) and, hopefully, as an offshoot of success in that venue, a motivational speaker.

Indeed, she had already written three books (well-received by the critics but, from her point of view, not widely enough read) and, over the course of the next five years, had invested over $250,000 in what she now considered to be a misguided and naïve attempt to get her “brand” out there.

June reported that actually, over the course of her life, she had made numbers of “bad and irreversible” decisions – failures that still haunted her and from which she was still suffering.

As an example, she cited the fact that 40+ years earlier she had chosen the wrong law school (more affordable than Harvard or Yale but, regrettably, so much less prestigious).

As another example, 20+ years earlier, hoping to make a killing in the real estate market, she had invested a substantial sum in various commercial properties that were now bleeding her dry financially.

And, as yet another example, three years earlier, she had found herself drawn to Wayne, a handsome, charming, and easygoing man who was in the process both of getting an acrimonious divorce and of losing his home to foreclosure. She had therefore invited him to come live with her and her disabled (adult) son – only then to find out that his consulting firm (marginally successful at best) was going under because of the pandemic and that he was therefore filing for bankruptcy.


June no longer wanted Wayne in her life, but her son had become very attached to, and dependent upon, him – and, June noted, Wayne did help out a lot around the house (which made her life a bit easier).

As a final example (and almost as an afterthought), June noted that she had had a longstanding conflictual relationship with her demanding father (who wanted for her the success that he himself had never been able to achieve in his own life) – and that she could not forgive herself for having had a huge fight with him just prior to his accidental death 35 years earlier (when he was, himself, 66).

June said several times that she was eager to get started in treatment and wanted very much to work with me because she felt I “got” her and would be able to “help” her.

At my end, I was riveted and pained by her compelling story of so many courageous undertakings – only then to be followed by so many perceived failures and so much deep regret and self-recrimination.

My heart could not help but ache for this tormented soul who had spent a lifetime struggling so mightily to get her life right, to gain her father’s admiration and respect, and to do herself (and him) proud – only then to find herself saddled with ever more debt, disappointment, heartbreak, and shattered dreams.


So I did indeed want very much to be able to help her.

But, somewhat uncharacteristically, I also found myself hesitating to make a commitment to take her on as a long-term patient – because I was wondering how I would ever be able to be of use to her.

So I suggested that before we committed to ongoing work (only to find that this too might be a mistake for her and yet another expensive “failure”), we should schedule a series of weekly sessions over the course of the next six weeks, that during this time we should do the best that we could to see how the treatment might be helpful for her, and that at the end of the six sessions we could then revisit the idea of long-term work.


June said she was comfortable with that plan.


Over the course of our first three sessions, June fleshed out one sobering story after the next about both past and present situations in which, despite her best efforts to get it right, she would nonetheless find herself feeling disappointed (in both herself and others) and ever more convinced that neither she nor others would ever be “good enough.”

Although June was remaining steadfastly optimistic that I would be able to help her, at my end – and perhaps not surprisingly – I was finding myself working incredibly hard during our sessions but feeling that I was simply not doing enough and never quite getting it right…

June hadn’t – yet! – told me that she was disappointed in me, but I absolutely “knew” that it would simply be a question of time.

Meanwhile, our sessions were absolutely grueling for me, labor intensive, exhausting, and stressful. Quite frankly, I was finding myself dreading our sessions and getting very anxious prior to each one.

But last week we had our fourth session – a watershed session that turned out to be incredibly profound for us both.


Just prior to the session, I had found myself thinking about the relational dynamic that might be unfolding between June and me on the stage of the treatment; and I had forced myself to step back from what I now realized might be the part I was already playing in the drama being re-enacted between us.


Indeed, I began to see things a little more clearly and found myself thinking about the significance of the fact that June had been referred to me by a highly respected colleague of mine who had worked with her for about five months but who – fearing she lacked the kind of “life wisdom” and “years of experience” that might be needed to “guide” June at this “important juncture” in her life – had ultimately decided that she was not the appropriate therapist for June. 


Once I began to reflect upon what might be happening in the room between June and me, I came to suspect that, from the very beginning and completely outside our awareness, June and I had been engaged in a mutual enactment in which June, at her end, was unwittingly doing unto me what had been done unto her by her relentlessly demanding and uncompromisingly expectant father and in which I, at my end, had unwittingly taken on the role in which June had found herself in relation to her father and that was now being assigned to me – namely, the role of someone who wanted desperately to provide what was being sought but who was nonetheless fearful that, despite her best efforts and most fervent desire, she might never be “good enough” or able to deliver what was needed.


In essence, June was getting me to experience in relation to her the tormenting pressure that she must always have felt in relation to her father – a dynamic that she had then internalized, such that now she both did unto others what had been done unto her and did unto herself what had been done unto her.


In other words, June was enabling me to experience, firsthand, what it was like to be living inside her tortured soul…  and it felt awful.


I decided to share part of my new-found realization with June.


So with my heart in my throat and surprising even myself with my boldness, I opened our fourth session by telling her about the dilemma with which I was struggling, namely, that, on the one hand, I wanted desperately to be able to help her but that, on the other hand, my fear was that I would ultimately end up failing her miserably (as so many others before me had). I told her I was concerned that her treatment with me would end up being yet another instance of “tremendous effort made” only to discover, at the end of the day, that this too had been a mistake, an absolute “waste” of “time and money” for her, and yet another heartbreaking disappointment that would come to fill her with pain and regret.

As I presented to her both my longing to be able to help and my fear of failing her, June listened very intently, thoughtfully digesting and processing my every word.

And then, after moments of silence, she said the most remarkable thing!


Gently, softly, pleadingly, and oh-so-vulnerably, she said something to the effect that didn’t she get to have this as her issue – a problem to be worked out in her therapy with me – this recurring theme and pattern that she herself was coming to understand as the thing she kept playing out on the stage of her life and was now playing out even in the beginning stages of her treatment with me…

I was absolutely stunned by the tender wisdom in what she (who is not in the mental health field) was saying and found myself responding equally gently and softly with, “Yes, of course, thank you, I guess you’re right – that you would want, need, and should have the opportunity, in your work with me, to recreate that old and oh-so-very-familiar scenario of unrealistic expectations followed by a crushing sense of devastating defeat and deep regret – but that this time you would have the opportunity ultimately to discover the possibility of a different outcome – because were I to be able to handle the pressure of your expectations, were I to be able to survive your inevitable disappointment in me, and were I (in the face of that disappointment, anger, and heartbreak) to be able to stand firm in my good feelings about myself and in my ongoing commitment to you and our relationship, then I would be showing you that there is indeed a different, a better, a more compassionate, and a more viable way to manage expectations.”


I concluded with, “In essence, if you and I can both keep our eye on the prize, if I myself can tolerate breaking your heart, and if you can tolerate having it broken, then we will be demonstrating for us both that it is possible to survive not only being disappointed but also being a disappointment.”

Even I didn’t entirely understand what I had just said, but June appeared to be deeply affected and moved by my answer and, after a few moments of reflective silence, she (clearly choking up a bit) softly murmured, “Exactly…  and thank you…”

It was indeed a very special and precious moment of profound connection between us – deep, mutual understanding, appreciation, and respect.

I find myself choking up a bit as a write this…

I deeply believe that we therapists have as much power to heal our patients as their parents once had power to hurt them.

So I hope and pray that I will have the courage and the capacity to do what needs to be done here…

I would love to hear any and all thoughts that you might have about this case! Your input will be deeply appreciated!   Martha