Michelle: We all have that one friend who gives amazing advice, the one who seems to have it all figured out. But what happens when that person’s life completely implodes? What happens when the expert on problems suddenly becomes the biggest problem themselves? Mark: Right, it shatters the illusion. We want our experts to be bulletproof. It’s comforting to think that someone, somewhere, has all the answers and isn't secretly a mess like the rest of us. Michelle: Exactly! And that's the brilliant, and deeply human, premise of the book we're diving into today: Maybe You Should Talk to Someone by Lori Gottlieb. What's fascinating is that Gottlieb herself wasn't always a therapist. She had a whole other life as a TV executive in Hollywood, working on huge shows like ER, before she made this massive career change to find more meaning. Mark: Wow, from writing fictional medical dramas to navigating real-life human drama. That’s quite a jump. Michelle: It is, and that dual perspective is what makes the book so powerful. It became a massive New York Times bestseller and was nominated for several awards, because it pulls back the curtain on therapy in a way that feels revolutionary. It shows us that the person sitting in the therapist's chair is often just as lost as the patient on the couch. Mark: So she's seen life from both sides—the fictional drama and the real thing. That sets up our first big idea perfectly, which is what happens when the therapist becomes the patient.

Michelle: It starts with what she calls the "Boyfriend Incident." Lori, a seasoned therapist, is in a happy, stable relationship. They're planning to move in together, merge their families. It's all set. Then, one night, in bed, her boyfriend casually drops a bomb. Mark: Oh no. I can feel the tension already. What was it? Michelle: He tells her, "I’ve decided that I can’t live with a kid under my roof for the next ten years." Lori has an eight-year-old son. Her boyfriend’s kids are about to go to college, and he’s realized he wants freedom, not another decade of parenting. Mark: That is brutal. It’s a deal-breaker that was apparently hiding in plain sight. And for a therapist, who is trained to see these things, to be blindsided like that… it must have been devastating. Michelle: Completely. She describes it as her world just detonating. And this becomes her "presenting problem"—the crisis that finally pushes her to seek her own therapy. She, the person who helps others navigate their emotional chaos, is suddenly drowning in her own. Mark: This is what makes the book so relatable. She admits to doing all the things she'd probably advise her patients against. I remember reading that she started Google-stalking him, trying to piece together his new life from social media crumbs. Michelle: Yes! She becomes obsessed. She’s creating entire narratives from a single photo, trying to understand how he could move on so quickly. It’s this incredibly raw and honest portrayal of heartbreak. She knows intellectually what’s happening, but emotionally, she’s just as reactive and irrational as anyone else. Mark: And this leads her to find her own therapist, a man she calls Wendell. What's that first encounter like? The expert walking into another expert's office for help. Michelle: It’s so well-described. She’s hyper-aware of everything—the office layout, Wendell’s demeanor, the box of tissues. She’s analyzing the process even as she’s falling apart within it. In her first session, she just unloads the whole story, sobbing, and Wendell mostly just listens. But then he says something that completely reframes her crisis. Mark: What does he say? Michelle: After she tells him the whole story and says she feels like half her life is over, he gently asks, "I wonder if you’re grieving something bigger than the loss of your boyfriend." He suggests the breakup is a trigger for a deeper grief about aging, about the future she had mapped out for herself suddenly vanishing. Mark: Wow. So the presenting problem—the breakup—is just the ticket of admission to the real show. Michelle: Precisely. And this is a core idea in the book. We often come to therapy with a story about what’s wrong, but the real story is usually buried much deeper. For Lori, the breakup wasn't just about losing a partner; it was about losing a future, a narrative she had built for her life. Mark: It’s fascinating because some critics have pointed out that her level of self-disclosure in the book, these "cringe-worthy" moments of her own humanity, can feel like it blurs professional lines. But it seems like that’s the entire point. Michelle: It is. She’s intentionally demystifying the process. By showing her own vulnerabilities, she’s arguing that therapy isn't about a flawless expert fixing a broken patient. It’s about one human being helping another navigate the messy, unpredictable, and often painful experience of being alive.

Mark: That idea of shared humanity really comes through with her patients. Especially this one guy, John. He sounds like an absolute nightmare. Michelle: (Laughs) He is, at first. John is a successful Hollywood producer who comes to therapy complaining that he’s "surrounded by idiots." His wife, his coworkers, the dental hygienist—everyone is an idiot. He’s arrogant, dismissive, and constantly on his phone during their sessions. Mark: I think we all know a John. The person who is never, ever the problem. So how does a therapist even begin to work with someone like that? Michelle: Well, initially, Lori is just as annoyed as anyone would be. She finds him insufferable. She has to repeat a mantra to herself: "Have compassion, have compassion." But then she starts to notice something. John's behavior in the therapy room—his way of keeping her at a distance, of deflecting any real emotion with rants and insults—is a microcosm of all his other relationships. Mark: He’s acting out his life story right there in her office. Michelle: Exactly. This is what therapists call working in the "here-and-now." And as Lori is struggling to connect with John, she has a realization. His way of dealing with pain—by blaming everyone else and refusing to be vulnerable—is a more extreme version of what she’s doing with her own breakup. She’s obsessing over her ex-boyfriend to avoid her deeper fears about her future. Mark: Whoa, so he’s a mirror. His dysfunction is reflecting her own, just in a different form. Michelle: It's a perfect example of what she calls the "parallel process." She and John are "mirrors reflecting mirrors reflecting mirrors, showing one another what we can’t yet see." Her frustration with him is actually a clue about her own unprocessed feelings. Mark: That’s a powerful concept. It suggests that the people who irritate us the most are often our greatest teachers, if we’re willing to look. Michelle: And it’s not just about negative feelings. Lori eventually finds a way into John’s world through his dog, Rosie. He talks about this "ugly" dog with such underlying affection, even while denying he loves her. It’s the first crack in his armor, the first glimpse of the vulnerable person hiding behind the "idiot"-hating facade. Mark: It’s a reminder that there’s always something likable in everyone, as one of her supervisors told her. You just have to find the entry point. Michelle: And that entry point often reveals that the anger is just a cover for something else. For John, it’s fear, loneliness, and a deep-seated grief from his childhood that he’s never dealt with. His anger is like a bodyguard protecting a very fragile core. Mark: This also touches on another fascinating part of the book—the limitations of modern therapy. I’m thinking of the chapter "Therapy with a Condom On." Michelle: Yes, her description of doing therapy over Skype. She has a session with John while he’s on a chaotic TV set, and it’s a disaster. The connection is bad, he’s distracted, and she realizes that so much of therapy happens in the shared physical space—the non-verbal cues, the energy in the room. Technology, for all its convenience, creates a barrier. It’s like there's a condom between them, preventing true intimacy and connection. Mark: It’s a great metaphor. You can go through the motions, but you lose the essence of the experience. The real, messy, human connection.

Michelle: And that messy human connection is at the heart of the book's most moving stories, which are about a different kind of grief—not for a person who has died, but for a life that will never be. Mark: You’re talking about the "Welcome to Holland" story. I have to say, that one really stuck with me. Can you lay it out for us? Michelle: Of course. It’s an essay by Emily Perl Kingsley that Lori shares with a patient. The analogy is this: planning to have a child is like planning a fabulous vacation to Italy. You buy the guidebooks, you learn a few phrases in Italian, you're filled with anticipation. But when the plane lands, the flight attendant says, "Welcome to Holland." Mark: And you're completely disoriented. This isn't what you planned for. All your dreams were about Italy—the Colosseum, Michelangelo, the gondolas. Michelle: Exactly. You’re in Holland. It’s a different place. It's slower-paced, less flashy than Italy. But if you spend your life mourning the fact that you didn't get to Italy, you'll never be free to enjoy the very special, the very lovely things about Holland… the windmills, the tulips, the Rembrandts. Mark: That’s such a profound way to frame it. It's not about pretending Holland is Italy. It's about grieving the loss of Italy, and then, and only then, learning to see the beauty where you are. Michelle: And Lori uses this to help her patient, Julie, a young newlywed who is diagnosed with a terminal cancer. Julie’s "Italy" was a long, healthy life with her husband, maybe having kids. Her "Holland" is this new, terrifying reality of illness and a shortened future. Initially, Julie is furious about the analogy. She feels like her Holland is a desolate wasteland. Mark: Which is a completely understandable reaction. It’s not a simple, "look on the bright side" platitude. It acknowledges the pain of the loss. Michelle: It does. And over time, Julie starts to find her own version of Holland. She starts focusing on what she can do, on finding joy in the present. She even starts planning her own funeral, which she rebrands as a "going-away party," complete with a theme and a playlist. She’s finding a way to live with vitality, even in the face of death. Mark: It’s a powerful shift from "why me?" to "what now?". And Lori realizes this applies to her own life, too. Her grief isn't just about "Boyfriend." Michelle: Right. Her "Italy" was the future she had meticulously planned: marriage, a blended family, a life partner. Her "Holland" is being a single mother in her forties, facing an uncertain future. Her therapy with Wendell helps her see that she has to grieve the loss of that imagined life before she can fully embrace the one she actually has. Mark: It’s a universal experience. We all have a "Holland" in our lives. A career that didn't pan out, a relationship that ended, a dream that died. The book gives us a language for that experience.

Mark: So when you put it all together—the therapist needing therapy, the difficult patient as a mirror, and this idea of grieving for the life we planned—what's the one big takeaway from this book? Michelle: I think it's that the healing process isn't about finding easy answers or getting 'fixed.' It's about the courage to be seen in our messiness. Gottlieb shows us that growth happens in relation to others. We are, as she says, 'mirrors reflecting mirrors.' The book’s power isn't in offering solutions, but in showing that the most universal human experience is the struggle itself. Mark: And that our 'idiots,' our 'breakups,' our 'Hollands'—they aren't just problems to be solved. They're invitations to look inside. They’re the start of a conversation, not the end of the story. Michelle: Exactly. It leaves you with a powerful question: What's the 'Holland' in your own life that you've been resisting? And what beauty might you find if you stopped mourning 'Italy'? Mark: That's a great question for all of us to think about. We'd love to hear your thoughts on this. Join the conversation and share your own 'Welcome to Holland' moments with the Aibrary community. Michelle: This is Aibrary, signing off.