Cyndi Bennett, Resilient Career Academy — Photo by Rapha Wilde on Unsplash

You worked harder. You got there earlier. You revised the report again. You reworded the email three times before sending it.

And still. It was never quite right.

If that sentence landed somewhere in your body just now, this post is for you.

I know that feeling from the inside.

Early in my career I took on a high-visibility role, building a Program Management Office from the ground up. How it would operate, how teams would collaborate across workstreams, what the reporting routines would look like. There was real opportunity there. A chance to prove myself to a new manager and move my career forward in a meaningful way.

I came in hopeful. Motivated. Ready to do the work.

What I wasn’t ready for was what happened when I brought my drafts to my manager looking for direction. Was I heading in the right direction? Was I missing something important? That’s what I needed to know.

What I got instead was a critique of those drafts as if they were final deliverables.

Every time. On materials that were never meant to be finished yet.

I couldn’t figure out what I was doing wrong. So I worked harder. Revised more. Tried to anticipate every concern before he could raise it. And still, nothing landed as good enough.

I went home crying. Not once. Every night, for nearly a year.

The frustration wasn’t just about the work. It was the creeping, relentless question underneath it: What is wrong with me?

If you’ve ever found yourself in a dynamic like that one, your nervous system was already trying to tell you something your mind hadn’t caught up to yet. The hypervigilance. The dread on Sunday nights. The way you’d replay conversations for hours looking for what you did wrong.

That’s not weakness. That’s your nervous system doing exactly what it was designed to do in an environment that kept signaling: danger.

So how do you know, looking back, that you were working for someone you could never please? Here are eight signs that deserve your attention.

1. You couldn’t predict what a “good job” looked like.

The goalposts moved. What earned praise last month earned criticism this month. You became a student of their moods rather than a practitioner of your actual work. When you can’t build a reliable internal model of success, your nervous system stays in a chronic state of scanning, always alert, never settled.

2. Praise felt like a trap.

On the rare occasions when you did receive positive feedback, you didn’t feel relieved. You felt suspicious. Waiting for the other shoe. That’s not cynicism. That’s pattern recognition. Your system had learned that calm was temporary, and that letting your guard down came with a cost.

3. You took the work home in your body.

Not just in your head. In your jaw. Your shoulders. The way you couldn’t fully exhale on a workday evening. Chronic workplace stress doesn’t stay at the office. It gets stored somatically, and understanding that connection between your professional environment and your physical experience is one of the most important pieces of this work.

4. You started shrinking your ideas before sharing them.

You’d have a thought in a meeting and then quietly talk yourself out of saying it. Pre-emptive self-editing became your default. This is what happens when the environment consistently signals that your contributions are unwelcome or inadequate. You learn to make yourself smaller to reduce the surface area for criticism.

5. The feedback was personal, not professional.

There’s a difference between “this report needs more data” and feedback that somehow always circles back to your judgment, your attitude, or who you are as a person. When correction consistently targets identity rather than output, the cumulative effect on your sense of professional self-worth is significant and worth examining.

6. You worked harder when things were bad, not differently.

Your primary response to the dynamic was to increase effort. More hours. More polish. More vigilance. If you’d known how to work differently, how to address the relational pattern itself, you might have made a different choice. But more was what felt available. That’s worth understanding, not criticizing in yourself.

7. Other people seemed confused by what you were describing.

When you tried to explain what was happening to friends or colleagues outside the organization, they struggled to see it. “But they seemed so nice in that meeting,” they’d say. Behavior that is unpredictable, inconsistent, and primarily directed at you is hard to name, and that difficulty in naming it is part of what keeps you stuck.

8. Leaving felt like failure, even when staying was unsustainable.

You stayed longer than you should have, in part because leaving felt like proof they were right about you. That’s not irrational. That’s a nervous system that had been conditioned to equate endurance with worthiness. Recognizing what kept you there, the beliefs, the patterns, the professional identity that had become entangled with that role, is some of the most meaningful work you can do.

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If it feels safe to do so, take a moment with this.

None of those signs points to a flaw in you. They point to a system that adapted to an environment that was genuinely difficult to navigate. Adaptation is intelligent. Your responses made sense given the conditions.

I know that now. I also know it because of how my own story ended.

When that project wrapped, my manager told his manager about the struggle we’d had. His manager wanted him to let me go. He didn’t. He believed I might do well in a different environment, and he kept me on.

It took me a long time to sit with that. He wasn’t trying to break me. He was trying, in his own imperfect way, to teach me something about attention to detail. And honestly? I carried that lesson with me for the rest of my career.

But here’s what I also know: the way that lesson was delivered cost me something. A year of going home in tears. A year of believing I wasn’t enough. And no professional lesson, however valuable, is worth what that kind of environment does to your sense of self.

Understanding that both things can be true at the same time, that someone wasn't malicious, and that the impact was still real, is part of the work.

Adaptive responses that were necessary then can become limiting now, in new roles, in new organizations, in your relationship with your own professional confidence. Understanding where those patterns came from, and learning to work with your nervous system rather than against it, is the territory where real change begins.

If this resonated and you’d like to go deeper, I explore these themes regularly over on my Substack. You’re welcome to join us there whenever it feels right.

If you are ready to move from understanding what you are feeling to knowing what to do about it, you are invited to join us inside The Resilient Career Academy. I would love to have you there.

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8 Signs You Were Working for Someone You…