Dear Ryan,
I’ve been at my firm for 11 years. Built a lot of it. Know where the bodies are buried. And lately I’ve been doing something I’ve never done before – I’m doom-scrolling job boards at night. I haven’t told anyone that until right now.
It’s not one big thing. That’s what makes it hard to trust. The comp is fine. My team is good. The book is healthy. But somewhere in the last 18 months something shifted and I can’t quite name it. The leadership conversations feel hollow. There’s a new voice in the room that gets more airtime than it deserves, and I feel myself getting smaller in response to it. I used to leave difficult meetings feeling energized. Now I leave them feeling tired.
I’m not ready to blow up 11 years over a blip. But I’m also aware that I’ve been telling myself “it’ll get better” for longer than I’d like to admit. So here’s what I actually need to know: How do you tell the difference between a real signal and a hard season?
– Fine on Paper
Dear Fine on Paper,
Eleven years. A healthy business. A good team. And you’re checking job boards at midnight. I want to start there because the fact that everything looks fine on the outside and something still feels broken on the inside isn’t confusion. That’s data. Here’s the diagnostic I’d use:
There’s a difference between being tired of the work and being tired of the place.
Burnout from a hard stretch is real, but it’s usually specific: a difficult client, a season of too much, a team that needed more than you had to give. What you’re describing is different. It’s cumulative. It’s ambient. It showed up in the people closest to you before it showed up in your own words. That’s not a hard stretch talking; it’s something structural.
The “new voice in the room” detail didn’t slip past me either. When someone who built something starts feeling smaller inside the thing they built, that’s rarely about fatigue. That’s about fit. And fit, once broken at the leadership level, almost never quietly repairs itself.
So here’s my honest answer: you’re probably not burned out. You’re probably right.
But before you do anything, get rigorous about one question: Is there a version of this place that you’d want to stay for?
Not the version you’re currently in. A realistic, achievable version. If you can picture it clearly and there’s a credible path to it, have the hard conversation with the people who could make it real. You owe yourself that. You owe clients that. You owe your assistant that.
If you can’t picture it, if the honest answer is that the version you’d want no longer exists, stop calling it a hard stretch.
You already know the difference. You just needed someone to say it was okay to trust yourself.
– Ryan
Ryan George is the Chief Marketing Officer of Docupace.
