There is simply no general recipe for this. Sometimes I put my little tools and libraries in order and then I'm very productive with them and looking back it seems to have been the key enabler to the actual thing getting done. Other times I go dirty mode and just hardcode constants, copy code files under time pressure and looking back it is clear that getting to the same result with the clean approach would have taken months and the benefit for later tasks would be unclear.

I know some are tired of AI discourse, but I found AI can help to sharpen the tools but at the same time I find that my scope grows such that dealing with the tools takes just as much time but the tools have more features "just in case" and support platforms or use cases that I won't often need, but it feels easy enough to just do, but then as I said it still takes long in total.

It's all mostly an emotional procrastination issue underneath it. Though that can go both ways. Sometimes you procrastinate on thinking about the overall architecture in favor of just making messy edits because thinking about the overall problem is more taxing than just doing a small iteration, sometimes you procrastinate on getting the thing done in favor of working on more tightly scoped neat little tools that are easier to keep in mind than the vague and sprawling overall goals.

I don't like that 'yak shaving' has degenerated into a synonym for boondoggle.

Some explanations of yak shaving split it into a complex form of procrastination and also necessary annoyances - friction - obstacles.

Sharpen your Tools often falls into the latter category, and it's always useful to question whether those 'necessary annoyances' are actually necessary.

It is, like you say, not always necessary to tackle those annoyances right now. But it is a situation where both the Campsite Rule and the Rule of Three have some domain. As a person whose entire job is about writing code to replace tedious and error-prone human tasks, you need to interrogate yourself any time you start thinking, "This is my life now." Because if anyone has the power to say 'no', it's us.

It's always worth spending 12-15 minutes most times you do a task that you have to do over and over again in service of trying to reduce the task from ten minutes to five or to zero. The reward for engaging in the task more fully rather than putting it off until it has to be done is that you're working toward a day when maybe you don't have to do it at all (you've automated it entirely or you've made it straightforward enough to delegate).

Hal's example is so funny because he's using both arms to scoop in everything from Column A and Column B at the same time. Everybody gets a laugh. A couple of those tasks actually had to be done. A couple could have gone on the shopping list.

I knew which vid's it gonna be before even clicking. Still hilarious.

Relevant XKCD: https://xkcd.com/349

This only happens when the tools have become so neglected that every single one is broken. You should still take the time to pay down that debt, and in the process learn the lesson to pay the debt in smaller chunks in the future.

You are going to pay it anyway, its not an "if" its a "when"

Weird. I happen to be watching Malcolm in the Middle and I find a link to Malcolm in the Middle

LOL! Well, somebody's gotta shave it!