Ever felt like you’re working hard but not really moving forward? That’s what I call circling—and I did it for six years.
In my last piece, I said I spent nearly six years circling my own what now. Here’s what that looked like.When I first realized my work no longer fit, I didn’t step into the truth. I kept trying to fix it. I tweaked the business model. I rebranded. I chased strategies that sounded smart but felt empty. I convinced myself that if I just worked harder, it would eventually click. It never did.
Instead, I found myself going around the same question again and again. Always moving, but never really moving forward. That’s what circling is: motion without direction.
Maybe you know the feeling. On the outside, it looks fine. You’re busy, you’ve got projects, you’re building things. But deep down, you know you’re walking the same loop.
For me, every lap around the circle looked like a new idea that wasn’t quite right, a client that wasn’t a fit, a strategy that never landed. Each time I told myself, Maybe this is it. Each time it wasn’t.
Maybe you’ve done that too—stayed in a job that drained you, held onto a relationship you knew was over, or talked yourself out of what you already knew because the timing never felt right. That’s circling.
I don’t regret those years. They taught me. Every false start made the truth harder to ignore. Every almost-but-not-quite brought me closer to what I actually wanted. In the end, the circle did its job: it kept pulling me back until I couldn’t pretend anymore.
That’s when the reset began. Not in a dramatic flash, but in the quiet moment I finally admitted: this isn’t working.
If you’ve been circling your own what now, here’s what I can tell you: the moment you stop circling and step in, everything shifts.
A place to start: take a piece of paper and write down one area of your life or work where you keep saying “maybe this is it” but deep down know it’s not. That’s your circle. Naming it is the first step out.
Thanks for reading The Art of What Now. These reflections are about finding the courage to realign when what you’ve built no longer fits. If this resonated, feel free to share it with someone else who might be circling their own what now.