How do you know when to stop tweaking questions as a beginner?

Part of me wanted the fancy version with all the tools. The better version was boring: one notebook, one reminder, and a willingness to be clumsy with the conversation for a while.

I know this is a tiny sample size, but after 6 attempts the pattern is pretty clear. When I keep the setup simple, I actually follow through.

Would love to hear how other people handle this. I am especially curious about the version that works on a tired weekday, not just on an ideal Sunday