Why You Keep Ending Up in Toxic Workplaces
by Tess Brigham, Certified Coach & Licensed Therapist
This article expands on a recent episode of The Gen Mess with Tess, where I explore generational differences, communication, and psychological safety in modern workplaces.
You left the toxic job, took your time reflecting on what went wrong within that workplace, and walked into the next job opportunity with better questions and clearer standards. And yet the new job still feels familiar in a way that makes your stomach drop.
The problem isn't that your checklist missed the mark on what makes an unhealthy work environment. The problem is that your checklist didn’t include enough about you.
What to Review When Leaving a Toxic Job
After a difficult job, most people do a thorough autopsy of the workplace. The bad manager, the dysfunctional office culture, the communication failures. And they build a smarter checklist from the wreckage: red flags to avoid in future workplaces, questions to ask in the interview process, professional standards to hold.
That's useful. It's also incomplete. Because the workplace doesn’t repeat. You repeat.
Not because you're broken or naive. Because until you examine what in you responded to that toxic environment, what you were getting from it even when it hurt, and how you behaved when things got hard, you carry the same blind spots into the next role no matter how good the benefits package looks.
Researcher Amy Edmondson at Harvard Business School has spent decades studying psychological safety, which she defines as the belief that you can speak up, ask questions, and make mistakes without punishment. Her research shows it's the strongest predictor of whether people thrive in a workplace. And yet most organizations don't name it, measure it, or screen for it. So you've never had a framework for evaluating whether an environment is actually safe for you. You've been measuring everything except the thing that matters most.
3 Patterns That Keep You Stuck in Toxic Workplaces
In my work as a therapist and coach, I see the same three patterns underneath the repeat cycle. Most people recognize themselves clearly in one of them.
1. Avoidance.
You learn in a difficult environment that asking questions is dangerous, that your needs are an inconvenience, that going quiet is safer than speaking up. So you go quiet. And then you leave that job and take those beliefs with you. When a new manager sends a short reply to your email, you don't read it as their communication style. You read it as evidence that you did something wrong. And the silence starts again.
Psychologist Steven Hayes, who developed Acceptance and Commitment Therapy, calls this the avoidance trap. Avoidance reduces anxiety in the moment and reinforces the threat over time. Every instance of not speaking up becomes evidence that speaking up was dangerous. The pattern doesn't weaken. It calcifies.
2. Disconnection.
You've spent so long in environments where your feelings weren't welcome that you've stopped checking in with yourself about how you actually feel at work. Not how you're performing. How you feel. Whether you feel safe. Whether you can be honest. So you evaluate opportunities from the outside in: salary, title, reputation, trajectory. And you miss the early signals that something's off until they're too loud to ignore.
Neuroscientist Antonio Damasio's research on interoception shows that physical sensations, the tight chest before a meeting, the dread on Sunday nights, are not background noise. They're your nervous system processing information before your conscious mind catches up. Disconnectors have learned to mute that channel. They mistake the silence for clarity. It isn't.
3. Measuring the Wrong Things.
You know intellectually that how you feel in an environment matters. You just never quite get around to asking. Because the right questions are scarier to answer than the wrong ones. If you ask yourself how you feel in an interview and the answer is unsettled, you might have to turn down an offer that looks great on paper. And that's a harder thing to justify than a salary comparison.
So you focus on what's measurable and unambiguous. And you already know where that leads.
3 Ways To Disrupt the Patterns Keeping You Stuck in The Toxic Workplace Cycle
There's a reason I work as both a therapist and a coach. And it's this: you cannot skip to the action steps. Not because the exercises don't work, but because without understanding which pattern is yours, the exercises don't stick. You do them once and slide back into the same default.
So the first step is honest identification. When you read those three patterns, one of them probably landed differently than the others. A little more specific. A little more uncomfortable. That's the one. That's where your work is.
If you're an avoider
Try graduated exposure, a well-supported clinical approach that involves doing the scary thing in small, survivable doses. Not the difficult conversation you've been putting off for six months. Something smaller. Ask a colleague to clarify something in a meeting. Request feedback on a project. Tell your manager you need five minutes before starting an assignment. Once. Notice what happens. You're not building communication skills. You're building evidence that asking is survivable, that your needs are legitimate, that the world doesn't end when you take up a little space.
If you're a disconnector
Focus on rebuilding a relationship with your own internal experience. Once a day, five minutes, ask yourself these questions:
Where did I feel most like myself today?
And where did I feel like I was disappearing?
Not a dramatic inquiry. Just a habit of noticing. So that when something feels off in a new role, you catch it at week three instead of month six.
If you're measuring the wrong things
Researcher Kristin Neff's work on self-compassion offers a useful frame: we avoid honest self-assessment not because we can't handle the truth, but because we don't yet trust ourselves to act on it.
So the exercise is practicing the questions you've been skirting. Before your next interview, write down the answers to three things:
How do I feel in my body when I'm talking to these people?
What do I actually observe about how they treat each other?
Who am I becoming in this environment? Not what the culture deck says. What you actually notice.
Those answers won't give you a salary to benchmark. They'll give you the information that predicts whether you'll be okay somewhere.
The Map to Psychological Safety at Work
None of what I've described is a character flaw in you. You were handed a map that measures the visible, external, comparable stuff in the workplace, because that's the map everyone gets.
Nobody teaches you to treat your psychological safety experience at work as data. Nobody tells you that how you feel in an environment is the most accurate predictor of whether you'll stay, grow, and actually be okay there.
Gen Z gets a lot of criticism for saying out loud, "This doesn't feel right," or "This is affecting my mental health." What they're actually doing is asking the question every generation should have been asking. Is this worth what it's costing me? Not on paper. In real terms.
You are not behind. You are not broken. You are someone who followed the wrong map faithfully. This is about getting a better one.
The job isn't the problem to solve. You're the territory to understand.
References
Edmondson, A. C. (1999). Psychological safety and learning behavior in work teams. Administrative Science Quarterly, 44(2), 350–383.
Hayes, S. C., Strosahl, K. D., & Wilson, K. G. (1999). Acceptance and Commitment Therapy: An experiential approach to behavior change. Guilford Press.
Damasio, A. (1994). Descartes' Error: Emotion, reason, and the human brain. Putnam.
Craske, M. G., Treanor, M., Conway, C. C., Zbozinek, T., & Vervliet, B. (2014). Maximizing exposure therapy: An inhibitory learning approach. Behaviour Research and Therapy, 58, 10–23.
Neff, K. D. (2011). Self-Compassion: The proven power of being kind to yourself. William Morrow.