Enjoy the audio preview version of this article—perfect for listening on the go.
Have you ever felt like the “rules” of therapy you learned in graduate school didn’t quite fit the moment in front of you? That bending them made the work feel deeper—or even more alive? Sometimes, even small departures from the script can lead to clinical breakthroughs. Sure, rules provide structure and guidance, we also know that many times, when we trust our instincts instead of sticking rigidly to the manual, profound moments of honesty, connection, and healing follow.
With this in mind, we reached out to five fearless therapists to hear their stories of therapeutic rebellion—and how, sometimes, bending the rules can make all the difference.
Leaning into My Mistakes
By Ben Yalom
I often admit my mistakes in therapy—which is really to say that I often make mistakes in therapy, and then draw attention to them.
The first part of this is common: we therapists are constantly choosing what parts of our clients’ stories to explore and what questions to ask. And often, we make a bad choice and follow a fruitless path or—even worse—reveal an unkind thought or judgment. These things happen all the time.
But why draw attention to these missteps? After all, people come to see therapists when they’re feeling unsettled and looking for guidance, stability, and expertise. Doesn’t telling them we’ve messed up undermine that expertise? Wouldn’t it be better to sweep it under the rug, maintain our façade of unflappable competence, and move on?
My experience is that expertise isn’t the most crucial aspect of the therapy encounter. The loss of whatever stature or confidence the client previously assigned to me is more than made up for by the closeness that develops from freely admitting my fallibility. Suddenly, I become a fellow human to my client, someone who also screws up sometimes, which normalizes their shortcomings. I’m also willing to share my own, which models vulnerability and opening up.
This reminds me of an early session I had with one client, Patrick, a successful 39-year-old attorney who’d been suffering bouts of anxiety. He wasn’t sure therapy could help, but had come in at his wife’s suggestion. Over the last couple weeks, we’d been engaged in a battle of wits over the cause of his anxiety, which I’d suspected was related to his recent promotion to junior partner at his firm, something he’d long desired.
“This is good news,” he argued. “Why the heck would it make me anxious?” I couldn’t help but see a connection, but Patrick was having none of my interpretation. Something in his demeanor had triggered an unwelcome, competitive impulse inside me, and I’d continued to fall into the trap of trying to convince him to have an insight. Finally, I realized that I wasn’t being therapeutically helpful.
A few weeks later, Patrick came in for our session and sat down on the couch with a defiant smirk that seemed to say, “Well?” He looked ready to pounce.
“Patrick,” I began, “I’m a little nervous to bring this up, but I think over the last couple of weeks I’ve taken us in the wrong direction. I want to apologize for that.”
He chuckled, clearly a bit taken aback.
“I was ready to tell you we weren’t getting anywhere,” he replied, “that this felt like a waste of time. But I guess you knew that!”
“Maybe,” I agreed. “Would you be willing to give me another chance, and we can explore a different path?”
Patrick looked genuinely surprised, then nodded, challenging me to do better.
Did this interaction change everything in our relationship, or open the floodgates of closeness, or cause Patrick to have a sudden epiphany? No, it did not. But between us, something softened. Perhaps it was because he knew that if I could give in like this, he no longer felt like therapy was some sort of competition. But I believe that something else had happened: Patrick developed a small sliver of respect for me, and realized that I cared enough about him and our relationship to admit fault. This allowed us to head in a new, better direction, with less posturing on both of our parts, and more sharing. It led to work that, eventually, Patrick found quite helpful.
Realizing I’ve made a poor choice—as I did with Patrick—or missed an opportunity to pursue a particular direction in therapy is always a little distressing. But by being transparent about this, I can often turn these missteps into useful moments, showing that mistakes are normal and my primary concern will always be my clients and our relationships.
Accepting Imperfection
By Oona Metz
When I graduated with my MSW in 1993, I believed therapy could cure everything and everyone. Supervisors and mentors assured me that with the right mix of warmth, exploration and insight, all of my clients would get better. Those who didn’t were simply resistant, and it was up to me to break through that resistance. When I became certified in group therapy, my mentor told me that everyone on my caseload should also be in a group. Therapy was meant to heal everyone, no matter the circumstance.
Over the last 30 years, I’ve unlearned that lesson many times. The first time was the hardest. In my early days as a therapist, my 28-year-old cousin died by suicide. He’d been diagnosed with bipolar disorder and struggled with addiction—both risk factors for suicide. But he also had a loving family, a therapist, and a psychiatrist. He had an entire therapeutic team. I didn’t understand how he’d slipped through the cracks.
His death devastated me, and his loss challenged my entire professional belief system—just as I was getting started. If my cousin, with a team of professionals helping him, could die, what was the use? Who was I to think I could help someone who was suffering? What if one of my clients died, too? I thought about changing careers. Maybe it wasn’t too late to become a midwife.
But I didn’t change careers. Instead, I worked with children in the Boston public schools. Most of the time, therapy worked. I made connections easily, student behavior improved, and teachers were pleased with the outcomes. When I walked into the cafeteria to pick up a student for their appointment, a swarm of kids raised their hands high in the air, pleading, “Pick me, Miss Oona, pick me!” Therapy didn’t work all the time, but for the most part, those kids got better.
After a decade in community mental health, I transitioned to private practice, specializing in treating women navigating divorce. When I first led divorce support groups, I reveled in their success. Women who were sad, angry, and fearful became happier, stronger, and more empowered in just a year or two. Therapy was working! Women who attended the group were practically guaranteed to feel better post-divorce.
In my second year of leading groups, I was surprised when one of the group members didn’t get better. She was sad when she arrived, even sadder throughout her divorce, and eventually left the group feeling just as depressed as when she’d entered. I wondered if she needed a different therapeutic modality, or more time to heal. I finally had to accept that she might not ever feel significantly better. Sometimes therapy can’t compete with a stubborn diagnosis, a traumatic past, or ongoing stressors.
Accepting this truth continues to be humbling. Early in my career, when therapy didn’t help, I felt like I’d failed. With time, I’ve learned that some people need a different kind of therapeutic intervention. Sometimes a new job, a new love, a new medication, or more sunlight is far more therapeutic than a 50-minute hour. Therapy is one path, but it’s not the only path. And for the most part, it works.
Taking the Scenic Route
By Kathryn Hall
In graduate school, I learned that therapy was supposed to be deep, that therapists should probe beyond symptoms. I believe this to be true. I was instructed that therapists shouldn’t spend precious therapy time or energy on superficial topics. Sure, pleasantries were fine, but then get down to business. Start with the symptom and drill down. My problem is that I’m directionally challenged. Drill down? That requires a directional ability I just don’t have. I don’t know north from south or east from west. These challenges followed me into the therapy room. My therapy GPS kept taking me on the scenic route when I was supposed to be exploring the depths of my clients’ psyches. My curiosity about seemingly irrelevant subjects looked directionless, and I was asked by my supervisors whether this was due to my anxiety about the deeper work of therapy. I worried about that for a while.
And yet, despite my best attempts to focus, my curiosity kept getting the best of me. I’d invariably go sideways and ask my patients about superficial subjects: “You spent the night reading because you couldn’t sleep. What was the book? Was it good?” I couldn’t seem to stop myself. This went on for years.
Finally, I embraced my sideways approach to therapy when I started working with Luis. Luis was dejectedly describing his recent “dating fiasco.” He’d planned a romantic evening with his girlfriend, and prepared a lovely dinner. But after dinner, when they were having drinks and kissing, Luis found that he wasn’t getting aroused. Embarrassed, he withdrew, which led to an argument and a breakup. I knew I should focus on Luis’s sadness and embarrassment, but I was curious about what he’d prepared for dinner. The voices of past supervisors screamed in my head: Go deeper, drill down! But I went sideways, and asked about the dinner. Luis went on to describe an elaborate meal—and all was going well, except for the scalloped potatoes that sat uneaten on his girlfriend’s plate. As I commiserated with Luis about how much time they take to prepare, he told me how the uneaten potatoes were occupying his mind as he’d sat kissing his girlfriend. This led to us talking about how he relied on his observation of small details to alert him to trouble ahead. From there, Luis finally disclosed that he’d been abused as a child.
Over the years, I’ve learned to treat my meanderings not as distractions, but as pathways to my clients’ inner worlds. At the very least, my curiosity shows my patients that I’m interested in them. Really interested.
Rethinking “Ethical Therapy”
By Terri Cole
I’ve been a practicing clinician for almost 30 years, during which I’ve watched our field evolve in important ways, and I’ve learned that some of the most meaningful clinical decisions happen in the gray areas that training can’t fully prepare us for.
Early in my career, many of my clients were Broadway performers. I’d worked as a talent agent before becoming a therapist, so I understood the world of theatre, and my clients knew it. These performers often came to therapy carrying a mix of heightened sensitivity, relentless self-scrutiny, and early attachment injuries that had been amplified by the demands of their job.
Occasionally, when it felt clinically appropriate and if I was invited, I’d attend a client’s performance. If a client was an understudy finally taking on the lead in a Broadway show and extended the invitation, I trusted my clinical judgment. I didn’t bring flowers or linger backstage, but I watched, witnessed, and showed up—and the work remained in the therapy room.
One experience that stuck with me involved a 20-something client who was pursuing stand-up comedy. He’d finally landed his first five-minute set at Caroline’s Comedy Club. For most people, five minutes would barely register, but for him, this was everything. His parents had been emotionally neglectful and openly rejected him because he was gay. He’d been sent to boarding school, and when everyone else went home for Christmas, he stayed behind. He wasn’t welcome at home. Nobody had ever shown up for him.
So, on a Wednesday night, from 10:00 to 10:05, I went to Caroline’s. I sat in the dark. I listened and laughed. I clapped. And then I left.
This choice was client-centered and therapeutically intentional. I wasn’t trying to become this client’s friend or his parent. I was offering something his nervous system had rarely received: appropriate, attuned witnessing. I never regretted this decision.
What I’ve learned, slowly and through experience, is that ethical therapy isn’t about rigid rules as much as it’s about ongoing discernment. It requires us to keep asking, Who is this for? Does this serve the client’s healing? These questions continue to guide my clinical choices.
This same mindset informs how I think about self-disclosure. Early in my career, an NYU professor said something that stayed with me: disclosure is neither inherently helpful nor harmful; its value depends on timing, intention, and the needs of the client. Over time, I’ve found that carefully considered self-disclosure can sometimes help a client feel less isolated or less defective in their experience. Used thoughtfully, it can support regulation and deepen trust.
Nearly three decades into this work, I don’t assume any single approach is right for every clinician or every client. What I do believe is that psychotherapy is a relational discipline that asks us to hold complexity, tolerate uncertainty, and remain accountable to both ethics and humanity. My training gave me a foundation, but my lived experiences taught me how to practice.
Embracing Laughter
I have a soft voice—and a big laugh. A really big laugh. The kind of laugh that has startled strangers and made baristas turn around. Years ago, I shared an office space with a therapist I admired deeply. She was smart, seasoned, and a friend. Our offices were adjacent, and most mornings we’d sip coffee and ease into the day with gentle conversation.
One afternoon, after a session where my newly widowed client and I had shared a couple of hearty laughs, my colleague stepped into my office. She smiled, but her eyes were serious. “Just so you know,” she said, “we heard you laughing. My clients in despair don’t necessarily want to hear others’ joy.”
I froze. I blinked, I smiled awkwardly, and fumbled through an apology for being too loud. The moment she left, I began searching online for the strongest white-noise machine I could find. But her comment stuck with me. I replayed it in my head for days, wondering if I’d crossed some invisible ethical line. Had I been unprofessional? Unwise? A less-than amazing therapist because I dared to laugh?
This was early in my career, back when I still believed the implicit grad school message: Great therapy is serious. Intellectual. Slightly aloof. Minimal laughter, please.
Eighteen years in, I can confidently say this: I’ve belly-laughed, cried, sighed, and shared countless deeply human moments with my clients. And those moments have been some of the most healing.
Of course, not all laughter in therapy is the good kind. Sometimes it lands, well, sideways. When a client laughs from anxiety, or cracks up while describing something that is objectively not funny—like abuse or profound loss—I gently name the dissonance.
Humor can be a brilliant coping strategy, but it can also be a clever way to keep pain at arm’s length. It works for a while, but therapy invites something more intimate. When a client seems to be masking their pain with humor, I’ll point out how their laughter doesn’t quite match the story they’re telling, and invite them to explore the messier feelings underneath.
Yes, therapy is a container for insight, healing, and growth, but it’s also a place where our clients get to rediscover glimmers of hope. When those glimmers disappear—when joy, levity, or even a single amused exhale becomes rare—it’s a sign that someone’s emotional world is getting heavy.
Laughing in session isn’t a silver lining. It’s not toxic positivity. And it’s not pretending that something sad, hard, or horrible didn’t happen. It’s a breath of fresh air. A moment of shared humanity. It’s a recognition that life is absurd, beautiful, painful, and hilarious—often all at once.
It’s a reminder that despair and joy don’t cancel each other out. They often coexist.
Benjamin Yalom
Benjamin Yalom, PhD, AMFT, is a psychotherapist, theater-maker, and writer. He practices narrative and existential therapy, focusing on aligning one’s values with one’s way of living and unlocking creative approaches to work and life. Prior to his work in marriage and family therapy, he was the visionary force behind foolsFURY, an influential experimental theater group which helped transform San Francisco’s performing arts scene between 1998-2020. More at www.yalomtherapy.com
Oona Metz
Oona Metz, LICSW, CGP, is a psychotherapist and speaker near Boston, Massachusetts. She writes about divorce, group therapy, and parenting. She’s the author of Unhitched: The Essential Divorce Guide for Women. Visit her website at oonametz.com.
Kathryn Hall
Kathryn Hall, PhD, is a licensed psychologist with a private practice specializing in the treatment of sexual and relationship problems. Her book, Reclaiming Your Sexual Self, was honored as the best self-help sexuality book by the Society for Sex Therapy and Research. Contact: drkathrynhall.com
Terri Cole
Terri Cole is a licensed psychotherapist and global relationship and empowerment expert and the author of “Boundary Boss” and “Too Much.” For over two decades, Terri has worked with a diverse group of clients that includes everyone from stay-at-home moms to celebrities and Fortune 500 CEOs. She inspires over a million people weekly through her blog, social media platform, signature courses, and her popular podcast, The Terri Cole Show. For more, see terricole.com.
Chinwé Williams
Chinwé Williams, LPC, is a trauma specialist extensively trained in EMDR. She’s the author of “Seen: Healing Despair and Anxiety in Kids and Teens Through the Power of Connection.”