I think this makes a lot of sense if you tilt your head a little and look at "business-ing" as a creative position. What the author describes sounds a lot like

I think this makes a lot of sense if you tilt your head a little and look at "business-ing" as a creative position. What the author describes sounds a lot like an ordinary iterative design process. You have some idea of what you want to do/make, but you aren't completely clear on 100% of the nitty-gritty specifics. You don't necessarily know if every little bit of your plan will work from the get-go, but you'll learn more as you move forwards and ferret out those loose ends. If your original idea does turn out to be untenable, there are likely going to be changes that you can make in order to take things in a new, more plausible direction. The author says that they have trouble thinking like this, but I wouldn't be surprised if they did so naturally with their hobbies; writing, learning to play an instrument, software projects, hardware hacking...you face the same sort of cycle of vague direction, experimentation, validation or failure, and repeat. Ultimately, it comes down to confidence in your ability to be able to find a path forward and keep moving when you do run into issues; I think that just sort of comes naturally when you're doing something for fun. One of my favorite quotes springs to mind, by Bill Gates: "We always overestimate the change that will occur in the next two years and underestimate the change that will occur in the next ten. Don't let yourself be lulled into inaction."