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Therapists Open Up About Their Toughest Cases

What therapists learn from the most difficult moments of their careers.

Luke Best, used with permission
Luke Best, used with permission

When Ryan Howes spotted William* on his schedule for the day, he felt a mixture of fear and dread. The California-based therapist knew the session would be intense. William was a blustery, high-powered client who had success in his career but struggled in relationships. He had conflicts with coworkers and, while he wanted to date after his divorce, couldn’t form any meaningful connections.

When William walked into the office, he was angry and skeptical, critiquing every move Howes made. This was early in the therapist’s career, and William would make digs about his experience and intelligence. “This sounds like a real problem. Maybe I should see a real therapist,” he would say. He used condescending nicknames like “Doogie Howser,” referencing the teenage sitcom doctor. William routinely came late to sessions, then plopped himself down in Howes’s chair, putting the therapist on guard. “I was trying to go head-to-head and prove I was good enough and smart enough. It turned into an intellectual pissing match,” Howes recalls.

The power struggle continued for a year as the pair tried to explore William’s emotions. At one point, William left Howes with a letter he had written for his children—but upon learning the following week that Howes had forgotten to read it, William sank into his chair, dejected. Howes probed, and William realized that the oversight reminded him of the hurt he felt after losing his mother at a young age. He inched toward expressing emotion but didn’t believe that Howes could truly understand. Howes decided to put his textbook aside and just empathize. He disclosed that he had also lost his mother as a child, when he was 10, and could feel that loss with William.

That moment changed everything. “I became vulnerable in the session. I showed I could empathize, and that put a crack in his exterior,” Howes says. “We started fresh at that point. Just two people in the room. The real change was not the client—it was me. I was trying to play the role of the therapist and go toe-to-toe with him, but instead I needed to show up and be honest.”

Jovelle Tamayo, used with permission
Katey Nicolai. After painful but necessary choices, restoring trust can be an enormous challenge. When Katey Nicolai had to hospitalize a young woman with an eating disorder, the patient felt betrayed. Talking about it didn’t repair the rift, so Nicolai realized her actions would have to speak louder than her words. “It was one thing to say it, but then I had to prove it—by letting her be mad and then still being available to her.”
Jovelle Tamayo, used with permission

“A Mistake I Will Not Make Again”

The majority of therapy clients are a pleasure to work with. They are engaged in personal growth and development and, to varying degrees, achieve the goals they set at the start of treatment. By virtue of walking through the door, a client signals there is success to be had—if the therapist can protect that instinct and help them find the right path.

But every practitioner also has a handful of difficult cases. Some may be individuals with particular diagnoses, medication issues, or a large and unwieldy care team. It’s not that the client is the problem, but for reasons that can stem from the client, the therapist, or their dynamic, that person is difficult for that therapist.

Many such cases still end in triumph; inevitably, however, a few end in disappointment. Whatever the outcome, the experiences leave their mark. They may test therapists’ boundaries, force them to think in novel ways, or reveal their shortcomings. But what they learn from challenging cases—both the successes and the failures—can prove to be professionally transformative.

In William’s case, Howes’ own self-disclosure—his choice to “be real”—was the answer. As they began working together to tap into William’s emotions, the client learned to express anger constructively, rather than through shows of dominance. He softened in his communication with others. His work relationships began functioning more smoothly, he strengthened his bond with his children, and he found a new romantic partner.

Not all difficult cases work out so well. Early in his career Howes treated another client, named Charlotte. She was older, retired, and widowed. In therapy, she would share what she had done that week—what she had watched on TV or had eaten for dinner. Howes couldn’t find a way to engage her on deeper topics, such as the loss of her husband or the challenges of aging. The sessions felt, candidly, a little boring. Finally Howes told her, “You don’t seem to be feeling much distress right now. Maybe our work here is done.”

Charlotte was stunned. She responded that their session was the most important hour of her week, the only time she really connected with another person. She was deeply hurt by his comment, and the rupture couldn’t be repaired. “I should have asked, ‘How are you feeling about our work together?’” Howes says. “I came in with an assumption that we were spinning our wheels. If I had asked that question, we might have continued to work together. That was a mistake I will not make again.”

“How Come You Didn’t Think to Ask?”

Many therapists’ most challenging cases come early in their careers, when they still have a lot to learn and may seek out more experienced colleagues for guidance. People should talk about hard cases, says Palo Alto–based therapist Marty Klein, “not just to kvetch but to really try to understand what it is they’re having difficulty with.” When a less-experienced colleague asks Klein to consult on a difficult case, he might begin by asking a relevant question about the patient. If the therapist doesn’t know the answer, Klein might say, “I’m wondering how come you didn’t think to ask this question.”

“When therapists are having difficulty, frequently it’s not a matter of technique. It’s the therapist coming up against their own personal limitations,” Klein says. Are they uncomfortable exploring a particular topic? Are they overreacting to a patient’s comments or tendencies? Are they unsure how to discuss a specific identity, religion, or experience? Klein, for example, specializes in topics around sexuality, but many other therapists aren’t completely comfortable talking about those subjects, he says, and may not realize how their hesitancy prevents them from fully exploring a patient’s concerns.

Uncovering these limitations can help therapists begin to address them. One way to do that is to see a therapist themselves. “I plan to be in therapy for as long as I’m a therapist,” Howes says, “to continually have a place to explore myself and identify my blind spots.”

With experience, therapists should become better able to recognize the point at which things just aren’t working. “Even the best therapists have clients who drive them crazy because they’re not making progress,” says Clifton Mitchell, a therapist in Johnson City, Tennessee, who writes and consults on resistance in therapy. After exploring different avenues and consulting with colleagues, they may simply need to lower expectations for improvement, Mitchell says. The final step may be letting the patient go. But before that point, there are many promising options to pursue.

“What Are You Not Telling Me?”

Greg and Mary came to see Gina Simmons Schneider early in the San Diego therapist’s career. Greg ran a woodworking business, and Mary did the books. They told Schneider that they couldn’t get along, fought all the time, and struggled to communicate. Mary said Greg made fun of her. Greg said Mary complained about his working late and never wanted to have sex.

The couple’s temperament presented an immediate challenge. “They were brutally cruel to each other and incredibly hostile,” Schneider says. Their meanness came to a head during one session when Greg bolted up and started throwing books off of Schneider’s shelves, then picked up a stone sculpture, poised to throw it at his wife. “I stood up—and this is not a therapeutic intervention I was taught—but I stood up and yelled at him. I used a mad teacher voice and said, ‘You sit down right now and shut up!’” Still standing, Schneider proceeded to scold them both and tell them point-blank why their relationship was deteriorating. Then she told them to get out of her office.

Schneider never expected to see them again after the outburst, but Greg called her the next morning and said it had been the best session they’d had and asked when they could schedule another appointment. “That taught me something,” Schneider says. “Sometimes people, especially people who lack self-control, need someone who is strong and forceful.”

But that was only the first hurdle. Schneider began to suspect that they weren’t telling her something. Although they could be cruel to one another, they also shared knowing glances that almost seemed loving. Greg also had frequent injuries, which he attributed to accidents from woodworking. Eventually, the truth came out: Greg was arrested, and Schneider discovered that almost everything the couple had told her was a lie. Their source of income was not woodworking; they were drug dealers, and Greg’s injuries were due to drug use. Further, they were both having affairs that they hid from each other and from Schneider.

While many spouses “tattle” on their partner in therapy, this couple fostered each other’s lies, making their deception difficult for Schneider to detect. “The lessons I learned there helped me cultivate a flexible curiosity. I don’t immediately assume what a couple reveals is true. I look for evidence supporting and denying what they’re telling me,” she says. “Now sometimes I’ll just say, ‘What are you not telling me?’ Then they’ll look at each other and say, ‘OK, here’s what happened...’”

Christina Gandolfo, used with permission
Christina Gandolfo, used with permission

“I Had to Take That Chance”

A young woman, Lily, proved to be one of Daniel Lobel’s most memorable cases. Lily lived with her parents, with whom she perpetually clashed, lashing out in anger, recalls the Katonah, New York–based therapist. She couldn’t handle criticism or frustration, refused to adhere to her parents’ rules—like not smoking marijuana in the house—and generally had behavior indicative of borderline personality disorder. Lily was enrolled in college, but never went to class. She’d pretend to drive to school but instead go to the home of her boyfriend, a drug dealer. She ended up in an intensive outpatient program, where, in Lobel’s opinion, her therapist had taken an overly sympathetic approach, and she’d made no progress. When she and her boyfriend were eventually arrested for selling narcotics, her parents turned to Lobel.

Sessions with Lily were unpredictable. Sometimes she would be receptive and take some responsibility for her actions. At other times, when she walked in, Lobel knew instantly that something was wrong: She would appear disheveled, perhaps wearing dirty clothes or sporting a new tattoo, and comported herself differently. In these instances Lily lashed out about being in therapy, calling her parents or Lobel “horrible.”

Lobel has expertise in working with BPD patients, so he knew how to handle the anger. He refused to argue, validated her concerns, and posed new ways of thinking. Yet those sessions were still difficult. “It made me feel very sad. I knew that something bad had happened, whether it was a bad experience with substances, a bad sexual encounter, or something I wasn’t even aware of. But I knew this poor person had been through something again.”

Lobel realized that Lily wasn’t going to change on her own. She would have to stop using drugs, deal with trauma from her past, and face the dangerous choices she was making. He needed to enlist her parents: They couldn’t keep supporting her while she was making unhealthy, dangerous choices. But the parents disagreed with each other; one thought Lobel was right, while the other refused to cut Lily off or send her away. After a series of meetings with them, Lobel says, “I felt frustrated, but the only way was to go down this path. The parent part of me wanted to somehow rescue her. The clinician in me knew that she had to rescue herself. I was afraid she was going to die. I was concerned the parents would say, ‘We’re done with you,’ but to be effective, I had to take that chance.”

Lily’s parents didn’t fire Lobel. They agreed to intervene, and Lily went to a treatment facility. She then spent six to eight months in a sober living recovery residential program. She engaged in therapy, returned to live with her family, and then went on to live independently.

“I’ve Learned to Be Creative”

Sometimes therapists have to contend with patients who just don’t want to be there. Maybe they don’t believe therapy works, but a partner, friend, or sibling insisted they seek treatment. In these cases, Klein says, a therapist should avoid trying to convince the patient that therapy will help and instead try to get an answer to the question: What do you want to get from our work together?

When patients are resistant to suggestions, Klein says, a therapist needs to talk to them about it: “You seem skeptical that this idea has value. I’m wondering why.” Or, “I’d like you to notice this is the third idea we’ve talked about to experiment with closeness.” It’s important not to bring a critical tone to these conversations or to imply that something is wrong with the client. “Engage in a spirit of curiosity,” Klein says. “Encourage patients to be curious about their own resistance.”

Candace Baker of Plumerville, Arkansas, has encountered her share of patients who didn’t want anything to do with her. She has treated people in a variety of settings, dating back to when she worked as an alcohol and drug counselor treating incarcerated individuals. She remembers one—a drug dealer—who thought the program was pointless and was irritated that he had to be there; he didn’t believe drug use was part of his crime. “This isn’t for me,” he would say, but, in fact, although the man did not use alcohol or drugs himself, he did sell drugs, and a murder related to his selling had landed him in prison.

Baker eventually found that the key to reducing his resistance was working with him to identify the consequences of his behavior: “His social setup supported criminal behavior,” she says. He realized that even though he wasn’t addicted, his behavior was still linked to the harmful consequences of addiction for others. In time, the man progressed through the program, pursued his own alcohol and drug certification, and went on to mentor other incarcerated individuals.

In some cases, it’s not a client who resists therapy but their family, says Tushonda Boyd, a therapist in Gulfport, Mississippi. “I deal with a lot of children, and that means I deal with a lot of parents. Often my kids aren’t the problem—my parents are the problem,” Boyd reports. Some parents, she knows, will seek to micromanage their child’s life, including their therapy sessions, while others won’t accept that anything could be wrong with their baby. “It’s important to look at the whole family,” Boyd says. “I’ve had cases where it’s been four to six months before I get a complete picture of what’s going on.”

One of Boyd’s memorable cases involved a child who was about to be adopted by her foster parents. She was a good kid, very hyper and energetic. But she also had some behavioral problems, which was why she hadn’t yet been adopted. The foster parents essentially wanted a guarantee that if they moved forward with the adoption, she would generally be healthy and not have severe psychological problems. The child worked hard in therapy and made significant progress. But there were still occasional bad days, which would unleash a new wave of indecision about the adoption.

The turning point involved a distinct lesson for each parent. The father needed to learn consistency, and the mother needed to learn flexibility. Boyd couldn’t give them a “mental health guarantee,” and she couldn’t completely eliminate the bad days. But she felt that consistency would certainly help the child improve—having a safe space where she could be herself. “Just because the kid had a bad day, the parents couldn’t say, ‘Oh I don’t want you today.’ It was important that they were going to be consistent no matter what,” Boyd says. That lesson was primarily for Dad. Mom, on the other hand, struggled when the day didn’t go according to plan, so Boyd helped her develop more flexibility. This parental education helped them move forward with the adoption, and the child is doing well in her new family.

Matt Furman, sed with permission
Gina Simmons Schneider. Couples therapists can suddenly find themselves thrust into the middle of a heated fight, acting as referee and trying to guide partners to a resolution. “I look for places to build a bridge,” says Gina Simmons Schneider. “If I can find that common need, even in the middle of a fight, I can say something that softens the situation.”
Matt Furman, sed with permission

“I’m Going Back in Time with Them”

Katey Nicolai of Seattle often treats people experiencing trauma, personality disorders, self-harm, and suicidality, among other conditions, and she knows that hearing stories that are tragic or heartbreaking can leave a therapist emotionally depleted. This has nothing to do with a client’s personality or intrapsychic processes but rather with circumstances that are painful for therapists to bear and that can leave them vulnerable to burnout, compassion fatigue, or secondary trauma.

Some clients “have been through something that you just know in your heart should not be part of human experience,” Nicolai says. During her internship, she worked with a college student who was the victim of years of abuse and incest, someone who’d had to overcome so much before she could even step into the office. For this girl, being in sessions was itself healing, as it can be for other clients. “They’re not alone anymore. Even reliving the experience, I’m going back in time with them,” Nicolai says. “That can be enough to change a person’s life.”

Every therapist has strategies for avoiding burnout; for Nicolai, they’re “coffee, sleep, and love.” She relies on support from her husband and levity from her children, and she plans tiny things to look forward to, such as a tasty lunch or a hot shower. When she knows a session will be particularly heavy, she schedules time for a short walk afterward. Such practices are especially crucial when managing boundaries with challenging clients.

Oscar began working with Nicolai because of conflict in his relationship. He had a significant history of abuse and
neglect by his father and was perpetually angry—at work, with his partner, and in therapy. Nicolai was keenly aware of her potential vulnerability and was never alone with him. “He was a large man, and you could see it written all over his body and his face when he was upset,” she says. “I was intimidated when he was physically angry.”

Oscar also struggled with suicidality, feelings that often emerged after a conflict, and he would text and call Nicolai at all hours, as would his girlfriend. She knew she had to establish clear boundaries and demonstrate consistency, but he repeatedly tested her. “He would call in the middle of the night or send a cryptic text, like that he was in danger, to see if I’d respond, to see what the limit was.” Nicolai sometimes felt caught between wanting to support him and wanting to support herself. “How do I manage the right amount of empathy and boundaries?” Nicolai says. “There was a lot I had to pour into that case.”

Compassion fatigue involves being in an empathetic position for a long period of time and feeling depleted as a result, explains Robin Stern, cofounder and associate director of the Yale Center for Emotional Intelligence. “When stories are intense, horrific, and difficult to listen to, the more emotional energy you’re expending and the greater your risk of compassion fatigue—especially if it’s over and over again,” she says.

While keeping her boundaries firm, Nicolai helped Oscar develop an internal set of resources to cope with his emotions. Instead of bursting into anger and begging for support—by calling his girlfriend or his therapist—he learned how to support himself. This led to fewer conflicts in his relationship and at work; he even joined a recreational sports team and made friends. Finally, he had found a way to function independently. “I’m smiling,” Nicolai says, “because it was a good outcome.”

Edmund Fountain, used with permission
Edmund Fountain, used with permission

“I Didn’t Know Anything”

As the saying goes, “Insanity is doing the same thing over and over and expecting different results.” This encapsulates a central principle of helping difficult clients: changing the approach. “If what you’re doing isn’t working, quit doing it and do something different,” says Mitchell.

It can be challenging to identify why a strategy isn’t working with a client, to find a creative solution and then perhaps another, and to keep at it until arriving at the right approach. It often goes against natural instincts. “When most people hit resistance, they go faster. But you should slow down,” Mitchell says.

Often, the need for a change in approach emerges only after a patient has been in treatment for several weeks, months, or even years. In those cases, a therapist may want to switch gears but not know how. One strategy is to identify metrics of success and track them across time, says Chicago-based therapist Scott Miller, founder of the behavioral health nonprofit, the International Center for Clinical Excellence. Miller works collaboratively with a client to identify and measure metrics of progress from week to week, such as through scales that track outcomes like distress or well-being. The pair may discuss a particular coping strategy in session and then see what happens over the course of the week. Which ideas led to small but noticeable improvements—or to impairments? Monitoring success also provides a framework that both patient and therapist know will be followed. “Therapists need to be measuring their results and asking for feedback,” Miller says.

The best approach is to remain ready to make adjustments. Realistic expectations help. In most cases, therapy or other potential interventions will eventually achieve a client’s goals, but in a small percentage of cases, the therapist and client may need to explore other services or go outside of psychological practice altogether.

Miller was once called in to consult on treating a teenage girl diagnosed with bulimia and depression. She was significantly underweight, had a restricted diet, and had been hospitalized for suicide attempts. She had been in and out of psychiatric facilities and had seen a therapist for a year, but she wasn’t improving. Miller wanted to explore her physical health more fully, so he referred her for a medical examination. That evaluation revealed that she had a rare tumor wrapped around her heart. This was what had led to her symptoms: Eating increased her heart rate, which then led her to vomit. She was immediately sent to the hospital and, after a complicated surgery, began to recover. Today, she’s thriving. When her family asked Miller how he knew just what to do, he told them, “I didn’t know anything. All I knew was that we were continuing to use the same tools over and over again. We needed to look outside our usual way of thinking.”

*Patients’ names and some identifying details have been changed to respect their privacy.


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