My friend called last week to vent about her new boss. She just got promoted, and the man training her is cocky and thin on substance, the kind of confidence that isn’t backed by much. She says she finds herself playing small around him. Nodding when she wants to argue. Staying quiet so she doesn’t rock the boat, because ultimately, she has to work for him.
I told her to push back. Don’t let him talk down to you, I said. Find your voice.
She said it’s not that simple. She has to be careful. And she’s right, it isn’t simple, and I know that better than I let on, because I spent years in rooms exactly like the one she’s in now.
I used to work for a lieutenant who wouldn’t turn his chair around when I spoke to him. I talked to the back of his head more times than I can count. And when he did speak to me, he made me feel so stupid. So I understand the eggshells she’s describing. What I didn’t tell her, in the moment, was the part that actually matters. Finding your voice doesn’t come with a guarantee. Sometimes you use it and you’re immediately right and everyone claps. And sometimes you use it and you have to stand in the wreckage for months, not knowing if you were right at all.
Years later, when I was promoted to lieutenant, I let my officers choose their own assignments instead of assigning them myself. I trusted them to know their own strengths, to want to do good work, to rise to being asked instead of told. They were happy. They performed. For a while, it looked like exactly what I hoped it would be.
Then the union got into it with the mayor over something that had nothing to do with me, and my officers, frustrated and fed up, slowed down. Performance dipped. And a commander, a man who’d made it clear from the start that he thought empowerment was a soft word for losing control, said it to my face in front of other people. How’s that empowerment working out for you?
I wish I could tell you I stood there unbothered. I didn’t. I stood there and felt the floor tilt a little, because the numbers, in that exact moment, agreed with him. My officers weren’t performing. My theory looked expensive and naive, and he got to watch me hold it while it looked that way.
That’s the part I skip when I tell this story at a podium. I make it sound clean. I found my voice, and it roared. Cue the applause. What actually happened is I doubted myself for months. I lay awake, wondering if trusting people was just weakness I had convinced myself was leadership. I wondered if he was right, if giving away power really was as foolish as he’d always said, if I’d confused kindness for strategy and was about to pay for the difference. I did not want him to be right. That didn’t stop me from being afraid he was.
It took months for my officers to come back around, for the numbers to climb, for the thing I believed in to look believable again from the outside. Months of him getting to be the guy who called it, and me getting to be the one who bet wrong, at least until I wasn’t.
Here’s what I actually owed my friend, and didn’t give her on the phone. Not “find your voice.” Everyone says that. It’s true and it’s also incomplete, and incomplete advice is its own kind of unkind. What I should have told her is that pushing back doesn’t resolve quickly, and it doesn’t always resolve in your favor on any timeline you can predict.
Sometimes you say the true thing, the confident thing, the thing you know in your gut is right, and then you have to go stand in the doubt for months while someone who was rooting for your failure gets to watch you doubt it too. Nobody warns you about the middle. They only tell you about the roar and the ending.
I think we do this to everyone we hand advice to, not just her. We give people the summary of our courage and skip the part where we weren’t sure it would work. We say push back like it’s a single decision instead of a long season you have to survive before you find out if you were brave or just wrong.
So here’s the real question, not for her, for you. Where in your life are you currently standing in that gap? Where have you made the harder, more trusting choice, and the early results haven’t proven you right yet, and someone is standing nearby, watching, half hoping they get to say I told you so? Are you still holding your ground, or have you quietly started agreeing with the cynic because his version is easier to live inside while you wait?
You don’t get to skip the waiting. Nobody does. But you can decide, in the middle of it, before you know how it ends, whether you’re going to keep trusting your own judgment or borrow someone else’s certainty just because it’s less lonely.
This is your moment of reckoning. Step into it.
