For the "Difficult" Truth-Tellers

I’ve been fired nine times in fifteen years. Not for being bad at my job, but for being good at the wrong things.

I was good at seeing problems other people wanted to ignore. Good at asking questions that made people uncomfortable. Good at holding space for ambiguity when everyone else wanted certainty by Tuesday. Good at treating design like it mattered instead of like decoration you apply after the real decisions get made.

Turns out, those are excellent ways to become what companies call a “bad fit.”

For years, I believed them. I internalized each rejection as evidence that something was wrong with me. Maybe I wasn’t collaborative enough. Maybe I pushed back too hard. Maybe I needed to be more strategic, more diplomatic, more willing to pick my battles. Maybe if I could just figure out how to fit better, I could finally keep a job.

Then something shifted. I noticed a pattern: my first emotion after each layoff was relief.

Not fear. Not anger. Not even surprise. Relief. Like I’d been holding my breath underwater and someone finally pulled me to the surface.

Eventually I realized being a bad fit isn’t a personal failing. It’s what happens when you have integrity in a system designed around its absence.

Think about what “culture fit” actually means in most organizations. It means not noticing when the emperor has no clothes. It means absorbing dysfunction without naming it. It means performing certainty about things that should be questioned and staying silent about things that should be said out loud. It means being the kind of person who makes other people comfortable, even when comfort is the problem.

I was never going to be that person. Not because I’m especially brave or principled, but because I can’t unsee what I see. When you’re trained to identify problems - when that’s literally your job as a UX designer - you spot every crack in the foundation. And in dysfunctional organizations, the foundation is usually the problem.

So they hired me to solve problems, then fired me for identifying them. They wanted innovation without disruption. Change without discomfort. Someone who could make things better without suggesting anything was wrong.

The term “bad fit” is brilliant corporate sleight of hand. It puts the failure on the individual rather than the system. It suggests the person is defective, not the culture. It’s much easier to replace a difficult employee than to examine why your environment keeps rejecting people who tell the truth.

Here’s what I know now: being a bad fit for toxic systems is not a bug. It’s a feature. It means your integrity is intact. It means you haven’t been broken down into someone who can tolerate the intolerable. It means you’re still capable of recognizing dysfunction instead of adapting to it.

Everyone’s talking about new year’s resolutions right now: gym memberships, productivity systems, better habits. But the new year is also as good a time as any to stop resolving to fix yourself and start recognizing what’s actually broken. To stop trying to fit into systems that were never designed for honest people in the first place.

This newsletter is for everyone who’s been told they’re not a team player when they were the only one being honest. For everyone who’s been labeled difficult for having standards. For everyone who’s been fired for caring too much about work that other people treated as performance.

You’re not broken. The systems are broken. And being rejected by something dysfunctional is not a failure. Instead it’s proof you haven’t learned to call poison nutrition.

Being a bad fit is sometimes the most honest work you’ll ever do.​​​​​​​​​​​​​​​​

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