I was going to add this one to the post yesterday, but couldn't quite get it to fit. So I'll let it stand on its own.
In a recent episode of the Tim Ferriss Show—Neil Gaiman — The Interview I’ve Waited 20 Years To Do (#366) (2019-03-28)—there was a sequence near the end from Neil Gaiman (whose books I've never read yet, but never mind that) that I liked:
[1:32:52] The biggest thing, looking back on it, that I learned from Terry was a willingness to go forward without knowing what happens. You might know what happens next, but you don’t know what happens after that, but it's okay because you're a grownup and you will figure it out. There's lots of metaphors for writing a novel and George R.R. Martin, for example, divides writers into architects and gardeners. I can be an architect if I have to, but I'd rather be a gardener. I would rather plant the seeds, water them, and figure out what I'm growing as they grow and then prune it and trim it and pleach it, whatever I need to do to make something beautiful that appears intentional, but at the end of the day you have to allow for accidents and randomness and just, "What happens when things grow?"
I'm not sure which of those categories I tend to fall into most often. On one hand, I do a lot of planning, trying to sort out details before getting started. But I also sometimes just start in order to see what happens. And other times I do the planning, but throw out the plan when getting started, using the methods practiced while planning more than the specific details that were planned, and then enjoying the interesting accidents that occur.
Sometimes it just depends on the stakes, and who is relying on the outcomes. If it's something important and there's time to plan: plan. If other people are working with me or counting on me to get something done and there's time to plan: plan.
But in the main, I think I tend to get started without knowing all the details and tweaking the trajectory as I go along. I enjoy watching the pieces emerge and fall into place. I feel calmer trying to figure out the action as I go—perhaps because there is no worrying about whether or not things are going to plan, or because it's just more interesting to see what happens.
Reminds me of one more thing—perhaps due to thinking of that last hesitation before leaning into something uncertain:
The pleasure of sport was so often the chance to indulge the cessation of time itself—the pitcher dawdling on the mound, the skier poised at the top of a mountain trail, the basketball player with the rough skin of the ball against his palm preparing for a foul shot, the tennis player at set point over his opponent—all of them savoring a moment before committing themselves to action.
—George Plimpton, Paper Lion (1966)