I mistook the planning for progress

I message my friend once a year, on her birthday. Today she told me she'd quit her job.


My friend hides her birthday on Facebook, but I’ve had the date saved in my calendar for years and every year I message her on it. That message is the only conversation we have all year. Today she turned 30.

We did the usual update, work and family, and then she told me she had quit her job because she felt lost. This is someone who was near the top of everything at school and went to good universities, and someone I would bet on before I’d bet on myself. She told me she had started a business, it failed, and now she has another one she wants to start. But she has not started it yet.

I told her it sounded like she already knew exactly what she needed to do, and that something else was standing in the way. She said that was exactly it. It isn’t a shortage of ability. It’s that she overthinks everything.

I told her I do the same thing. I spent my entire 20s planning, and I mistook the planning for progress. All that thinking never made me braver. It made me more lost, the same way she is lost. I ended up with a plan and no confidence to do any of it.

The only thing that has switched the thinking off since I turned 30 is having too much to do. When I’m busy actually doing the work, there’s no gap left for me to talk myself out of anything. I don’t want to turn 40 and find that I spent my 30s the same way I spent my 20s. So that’s the plan now, and it’s the whole plan: enough small steps, close enough together, that there’s no room left in the day to overthink.

I don’t know yet whether the overthinking stops once I start. I know it doesn’t stop while I wait.

This is the first thing I’ve published here, and I’m doing it before I have anything to show for it. She only hears from me once a year, and I wanted this to be it.

She sounded certain when she described her business idea. Not hopeful. Certain. In high school I would have bet on her before I’d bet on myself, and this time I’d bet on both of us.