Season 3 – Episode 21: With Dawn Wray
Fitting in at work isn’t just about wearing the right shirt or laughing at the boss’s jokes—it’s about survival. Or at least, that’s how it feels. This week on A Job Done Well, James and Jimmy are joined by Gestalt psychotherapist Dawn Wray to dissect the dark art of “fitting in” and why it’s more psychologically taxing than a Monday morning spreadsheet. It’s not about your social skills. It’s about the ancient, visceral patterns of belonging—or not—that shape how you show up at work, how you hide, and how you might just lose yourself in the process.
Dawn pulls no punches: fitting in isn’t just uncomfortable, it’s exhausting. It’s the constant, unconscious negotiation between who you are and who you think you need to be to avoid rejection. It’s the shirt you tuck in, the opinions you swallow, and the banter you force yourself to laugh at—all while your brain screams, “This isn’t me.” And when the gap between your authentic self and your “work self” yawns too wide? Welcome to burnout, anxiety, and the slow erosion of confidence.
But here’s the kicker: not fitting in isn’t always a bad thing. Sometimes, it’s growth. Sometimes, it’s the friction that forces change. The trick? Knowing the difference between the discomfort of stretching and the soul-crushing drain of pretending. Dawn’s advice? Slow down. Pay attention. Notice when you’re holding your breath in meetings or rehearsing your personality before walking into the boardroom. And ask yourself: Are you adapting, or are you disappearing?
James and Jimmy riff on the absurdity of corporate “professionalism” (read: conformity), the myth of the “perfect fit,” and why the most dangerous employees might just be the ones who never complain. Because if everyone’s nodding along, someone’s lying—and it might be you.
Five Key Points:
- Fitting in isn’t about skills—it’s about survival. Your brain treats workplace rejection like a threat to your safety, thanks to patterns wired in since childhood.
- The cost of conformity: Swallowing your opinions or faking enthusiasm doesn’t just feel bad—it drains energy, fuels anxiety, and can tank your performance.
- Not all discomfort is equal. Growth feels energising; self-betrayal feels like dread. Learn to tell the difference.
- The “professionalism” con. What’s often sold as “professional” is just socially sanctioned masking—tuck in your shirt, shut up, and smile.
- The ultimate question: Are you adapting to thrive, or editing yourself to survive? And if it’s the latter, how long can you keep it up?
Dawn is a Gestalt therapist and co-founder of The Listening Collective. Before becoming a therapist, she worked as an operations director in financial services.
These things are not as disparate as they might seem.
She believes organisations work best when the people, and the teams they are part of, work well. It isn’t enough to focus on ‘individual development’, we also need to pay attention to what goes on between us, and the environments we create. This means embracing complexity and acknowledging that sometimes the thing we want may not be measurable in numbers.
The Listening Collective is all about helping people thrive at work, whether individually or in groups. Dawn is passionate about the idea that work is just a part of life. When people have a safe, confidential space to talk through what’s going on, they can show up more authentically and perform better.
In addition to her work at The Listening Collective, Dawn runs a private therapy practice and is also a student counsellor at Nottingham Trent University. She’s a Fellow of Whole Intelligence and values above all else, honest conversation and finding practical ways to help people sparkle. She talks candidly about how her therapeutic work is vital to getting beneath the things that are driving our organisations. After all, organisations are staffed by people.
The Listening Collective: www.thelisteningcollective.org
Therapy: www.dawnwraytherapy.com
Whole Intelligence: www.wholeintelligence.org
[00:00:00] Jimmy: Hello, I’m Jimmy. James: And I’m James. Welcome to A Job Done Well, the podcast that helps you improve your performance and enjoyment at work.
[00:00:15] James: Good morning. Today, we’re talking about fitting in—something I’ve often felt uncomfortable with. And we’ve got an expert to help us unpack it, because let’s be honest, we don’t always know what we’re talking about.
[00:01:10] Dawn: Hi, I’m Dawn. I’m a Gestalt psychotherapist, supervisor, and teacher. I used to work with James and Jimmy, but now I help people navigate the psychological minefield of fitting in—at work and beyond.
[00:01:43] James: Good to have you back.
[00:02:05] Dawn: Fitting in is hard, and not for the reasons you might think. It’s not just about social skills or whether you “click” with your colleagues. It’s about ancient patterns—how you learned to belong in your family, your upbringing. It triggers something visceral. If I don’t fit in here, will I be rejected? Excluded? That fear goes deep.
[00:03:43] James: It can be that simple, can’t it? Just wearing the same clothes as everyone else. Dawn: Exactly. Because fitting in is part of your identity. Work is a huge part of who you are. So when you’re figuring out how to fit in at work, you’re negotiating how you meet the world—and how the world meets you.
[00:04:20] Dawn: To fit in, people might agree with everything, even if they don’t. They might swallow their real opinions, avoid conflict, or mimic others—just to avoid rejection. But that comes at a cost. If I never say what I really think, I’m keeping everything bottled up. And that affects how I feel at work.
[00:05:20] James: So we do it because it’s safer. Dawn: Yes. Or we stay quiet when we should speak up. Because if I tell you I disagree, I risk not fitting in. And that risk feels huge.
[00:05:42] James: We talk a lot about “professionalism,” but isn’t it just socially sanctioned masking? It’s not about being good at your job—it’s about being the same as everyone else.
[00:06:06] Dawn: Exactly.
[00:06:11] James: Before we dive deeper—is fitting in really a problem? Dawn: It becomes a problem when you’re overriding yourself. When you’re constantly compromising who you are to fit into the organization, it can have serious psychological—and even physical—impacts. It’s one thing to tuck in your shirt because you choose to. It’s another to feel like you have to, every single day, just to survive.
[00:07:45] James: Yeah. I’ve always worked in development roles, so I was paid to do things differently. I’d wear jeans with a shirt and tie—not because I wanted to fit in, but because I wanted to stand out. But maybe I only did that because I thought I should.
[00:09:09] Dawn: That’s the disconnect. How much of yourself can you be at work? And how much do you have to compromise? When the gap between those two things is too big, that’s when you lose yourself.
[00:09:43] James: I think that’s the key—are you adapting, or are you editing yourself?
[00:10:12] Dawn: Yes. And if you’re being paid to be different, that’s authentic enough. There’s enough of you in that role for you to make compromises elsewhere.
[00:10:20] James: I get that.
[00:10:28] Dawn: My experience in corporate was that there was never room for discussion. It was always right or wrong, this or that. But sometimes, the answers lie in the gray. I felt like I had to be forthright and opinionated, but inside, I just wanted to say, “Hang on, let’s talk this through.” Instead, I tried to fit in by looking like I had all the answers.
[00:12:36] James: It’s not about the threat of violence, though. Fitting in is multifaceted. You’ve told a story about working in a bookmakers during an armed robbery—far more dangerous than the post office, but you felt like you fit in better there. So it’s not just one thing. It’s a whole host of factors.
[00:13:35] Dawn: Exactly. Fitting in is about the contact boundary—how much of yourself you can show at work. It’s not always conscious, but you’re always managing it. In the post office, you were constantly adjusting to a culture you didn’t like. That’s exhausting. Fitting in isn’t just about blending in—it’s about how much of yourself you’re willing to override to do it.
[00:15:37] Dawn: This constant adjusting can lead to depression, anxiety, burnout—all symptoms of the energy it takes to keep up the act.
[00:16:05] James: And it messes with your confidence. You start to think, “I don’t fit in. Maybe I’m worthless. Maybe I’m unhirable.”
[00:16:18] Dawn: Yes.
[00:16:55] Dawn: Both fitting in and not fitting in can feel uncomfortable. But the quality of that discomfort matters. If you’re energized, excited, and growing, that’s one thing. If you’re drained, grumpy, and dreading tomorrow, that’s another. Pay attention to how the discomfort feels.
[00:17:51] James: I’ve got an example. Early in my career, I’d practice what I was going to say before making phone calls. I was scared, but that was growth. Later, I’d rehearse my personality before meetings. That’s not growth—that’s survival.
[00:18:24] Dawn: Exactly. The texture of the discomfort is different.
[00:18:47] Dawn: If you’re constantly drained, that’s a sign something’s wrong.
[00:18:57] James: I didn’t work there much longer after that.
[00:20:05] Dawn: This comes up a lot in my work. People internalize it—they think, “It’s me. I’m the problem.” But often, it’s the organization. The key is slowing down. Pay attention to how you feel. Are you tense in meetings? Holding your breath? That’s your body telling you something’s off.
[00:21:29] James: Are people good at noticing this in themselves? Dawn: No. They’re not. They blame themselves. “I’m not competent. I’m the problem.” But it’s often the culture.
[00:21:36] Dawn: Start by slowing down. Notice your physical reactions. Where’s your breath? If you’re stressed, you might be holding it. That’s a sign to dig deeper.
[00:24:55] James: So awareness is step one. What else? Dawn: Talk to people you trust. Get another perspective. And ask yourself: Can I be more authentic here? What would that look like? Sometimes, small changes—being a bit more you—can make a big difference.
[00:27:10] James: But what if I’m wrong? What if I don’t fit in, and I’m just kidding myself? Dawn: Then test it. Be yourself a bit more. See what happens. Maybe your perception of not fitting in is wrong. Or maybe it’s not—but you won’t know until you try.
[00:27:42] Dawn: That’s the work we do with managers. Challenge them: What if you just showed up as yourself?
[00:29:19] James: So there are three levels: First, be aware—is this a problem? Second, experiment—is it really a problem, or is it just in my head? And third, decide: Do I lean in, or do I leave?
[00:29:41] Dawn: Yes. But leaving isn’t a panacea. You might end up somewhere just as bad.
[00:30:06] Dawn: Be wary of people who always agree with you or seem to fit in perfectly. Are they just compromising themselves to please you?
[00:30:35] James: That’s structural, isn’t it? Organizations reward people who do what they’re told, smile, and don’t rock the boat.
[00:30:54] Dawn: Or stay very quiet. If people are blaming themselves, they’ll internalize it. They won’t speak up.
[00:31:20] James: They’re scared of the consequences.
[00:31:22] Dawn: Exactly. Have the hard conversations. Use one-to-ones to ask the difficult questions. Create a space where people can be honest, not just play the corporate game.
[00:32:12] James: It takes time, though. Dawn: It does. Like your story about the team that took six months to believe you actually wanted them to challenge you.
[00:32:35] James: Right. You have to keep going back: “I know you’re nodding, but what do you really think?”
[00:34:18] Dawn: The biggest resistance to coaching—or any real change—is conflict. People are afraid of it. But if you show up as yourself, it won’t always be smooth. And that’s okay.
[00:34:52] James: I did some research: Harvard Business Review says people who feel like they belong perform 3.5 times better. Dawn: That makes sense. All the energy you spend faking it—laughing when you’re not amused, worrying about what others think—could be going into your actual work.
[00:35:23] James: But belonging isn’t about everyone getting along. Dawn: No. It’s about being authentically you—without compromising more of yourself than you need to.
[00:36:31] James: Good point. Because fitting in activates deep, visceral patterns. That’s why it’s not simple.
[00:37:00] Dawn: It’s always good fun.
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