We were an hour into lunch when I asked her what it would take for her to leave.
“Damn! You always ask good questions! . . . I don’t know.”
“Yes you do” . . . and I just waited, because silence is the thing that keeps you from avoiding.
She wasn’t trying to dodge me. I know what her dodging looks like. This was a real not knowing.
“I guess I’ve grown complacent. I could do this until I’m done.” She said it like she was reporting the weather. Same voice she’d use to tell me the traffic was bad on the way over.
This is a woman who has run things. Big responsibilities and always knew the answer and as I asked her one question about her own life and she had nothing.
She was complacent. Not burned out because burned out has an exit ramp and everyone understands burned out. Complacent is comfortable, and comfortable is survivable, and survivable is exactly why she’s still there.
Notice where she said it, though.
Not in her office. Not to anyone she works with. She can’t, and she knows she can’t. The second that sentence exists at work it stops being a feeling and becomes a file. She’s checked out. She’s a flight risk. Let’s start planning around her.
So it comes out at lunch with a friend, after the food’s gone. That’s the only room it’s safe in, and she’s been carrying it alone in every other room for years.
She went on to tell me that she probably should have left six years ago. And in those six years something happened that nobody puts in the exit interview.
Her confidence got chipped away. She’s just as great as she’s ever been, but somewhere in there she stopped believing she’d be great at anything else. That’s what staying takes from you. Not your ability. Your nerve.
That’s the compounding nobody warns you about. The longer you stay, the less able you feel to leave and the less able you feel to go, the longer you stay.
Here’s what’s actually happening, and it took me years to see it in myself. I know I stayed longer than I should have. Longer than what was reasonably good for me.
So she’s uncertain because it’s the first time the path is hers to pick. All hers. And she has to bet on herself when they stakes are as high as they’ve ever been.
Just sit with that for a moment . . . .
For thirty years the direction came from somewhere else. Someone else set the strategy. Someone else moved the target. Someone else decided what mattered this quarter. She was brilliant inside it and that’s not a small thing and I’d never call it one. But the certainty was never hers. It came with the job because she became the title. She’s spent three decades being the outcome of other people’s decisions and getting really, really good at executing them.
But what about hers?
When she finally steps back and asks herself what she wants, nothing comes back and she reads it as a malfunction, a failure on her part because how could she not know?
But it isn’t. It’s the first honest answer she’s given in thirty years.
She just doesn’t know.
I know, because I stayed six, maybe even ten years past my own expiry date (as I like to say).
For most of those years I didn’t sit with anything. I was bored and restless, but instead I ignored it all. It was easier to ignore everything. Stuff it under a rug and it’s out of sight. But the pile under the rug got so big that one day I didn’t just trip over it. It was so big that I face planted over it.
That’s what the procrastinating really is. It isn’t deciding later. It’s adding to the pile, while telling anyone who asks that you’re fine and the timing isn’t right and you’ll look at it after the reorg or when the kids are out of college.
I wasn’t waiting for clarity. I was waiting for someone to hand me the answer. Thirty years of being the one who produced the answer for everybody else, and the first time I wanted one for myself, there was nobody to ask. Where was that easy button?
So, if you were the one who didn’t have an answer at lunch last week. If you’ve been reading the not knowing as evidence that you should stay put, that you’re not ready, that you’d better wait until you can see the whole thing before you move.
You’re saying no to your future possibilities right now. Today. You just don’t know what they are, because you’ve never once looked at what’s actually out there. You’ve been so busy being certain inside somebody else’s frame that you have no idea what you’re turning down.
You’re not too old for this. You’re not having a crisis. And you’re not lost. Those are just the easy button excuses, so you don’t have to look.
You’re standing in the first quiet you’ve had in thirty years, and you don’t recognize the sound of it. In fact, that silence makes you very very uncomfortable.
The uncertainty isn’t the thing in your way. It’s the only part of this that nobody else decided for you.
So what’s under your rug?
Clearing it and laying a new one down will feel so much better than that room you redecorated. This is your renovation with an added revelation.
You’ve never made a high-stakes call without counsel. Not once, in thirty-five years. This is the same move, finally pointed at your own life.

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