Navigating Workplace Dissent

I've been fired for speaking up. I've also regretted staying silent. After nine layoffs over the last 15 years and countless toxic work situations, I've learned that the problem isn't whether to dissent, it's how to do it without destroying yourself in the process.

The Pattern You're Probably Seeing

Organizations love to talk about "psychological safety" while punishing anyone who tests it. They hold workshops asking for honest feedback, then spend 50 minutes on icebreakers and claim there's no time left to address your concerns. They exclude you from meetings without explanation. Your valid questions get dismissed as negativity.

Sound familiar? You're not crazy. The system is designed to silence dissent while pretending to welcome it.

What I've Learned (The Hard Way)

Start small, not comprehensive. When I worked at an education startup, I had to tell them their entire app was broken. I worked then with a career coach to help me learn to pause, let people process, and focus on one fixable problem instead of overwhelming them with everything wrong. I still got laid off eventually, but I built trust first. Small interventions have a better chance of landing than brutal honesty bombs.

Let the users do the talking. At one company, I couldn't get anyone to listen to my UX concerns. So I ran quick user tests and created a two-minute highlight reel of frustrated people trying to use their product. One user even cried. That video accomplished what months of my feedback couldn't. External voices carry more weight than internal ones, even when we're saying the same thing.

Document everything when you spot the real red flags. I once worked with a manager so hostile that she wouldn't use our names: she'd just call us by our agency name like she was calling her dog. She'd lash out, apologize via text, then repeat the pattern. I saved every email and screenshot. When she later tried to trash my reputation, my agency had proof of what really happened. Documentation isn't exciting, but it protects you when things go wrong.

Know when you're done. During the pandemic, I was on a team with no leadership, watching our transformation head take realtor calls during meetings while bragging about buying a beach house, right after laying off dozens of people. When I finally asked everyone to "please be present," my hands were shaking. He yelled. I got fired. But I was DONE. Sometimes protecting your mental health means choosing to be right over being employed.

The Uncomfortable Truth

Even when you do everything right, like pause at the right moments, frame concerns carefully, document thoroughly, you might still get fired. I learned that at the education startup. But staying silent isn't really an action plan either, especially if your mission is to change things for the better.

The question isn't whether you should change to fit the organization. It's learning to recognize which organizations are wise enough to value what you offer and which ones will punish you for it. Your inability to conform isn't a personal failing: it's potentially a professional superpower. You just have to learn how to use it without destroying yourself in the process.

After nine layoffs, I'm still learning. But at least when I speak up, I have the satisfaction of knowing I tried.

Want to share your own stories about speaking up (or not speaking up) at work? Hit reply—I read every response.

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