What I wish I knew before trying design with a chaotic constraint

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.

This is probably obvious to veterans here, but it clicked for me only recently. housing got easier when I stopped treating every attempt like a final exam.

Context: I am not an expert, just someone trying to make Cities feel less intimidating. I wrote down what worked, what felt awkward, and what I would do differently next time.

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 prototype for a while.