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I go about automation in even less efficient way.

I spend many months doing repetitive tasks. And than I realize I should automate them, and proceed to spend hours coming up with scripts/tools to automate them.

Happens way too often...

There are some really clever people here, but as a general rule, you can't truly automate something until you can do it manually to the point where you're fully aware of all the snags and exceptions that may occur.

Once you reach that point, it then becomes a matter of trading-off how much time/money/effort it will take to automate the task against what benefit you get in return.

Agreed, but it's important to include one criterion in the trade-off calculation: I'd much rather be writing automation code than doing most automateable tasks (i.e. repetitive, simple decision tree). Even if I don't save any time, or even if it actually costs me a little time, I count it as a win. Especially since I often discover useful tools and techniques (holy smokes! Someone already wrote a parser for this weird thing I'm playing with!) that end up being valuable later in a completely unrelated project. True story: some colleagues wanted to integrate a departmental Moodle server with some bespoke scheduling software we were running. Turned I already had most of what we needed, because a year earlier I'd gotten irritated at hand-loading class lists into Moodle and hacked together a bunch of code to directly translate entities from one database to the other. I'd even generalized it into a bunch of types and tables that I didn't really need because OCD. All that 'hobby' code ended up being really valuable later.

I believe there is also merit in spending a lot of time repeatedly doing something, before proceeding to automate that workflow. Because only through that, you gain a deep understanding of 'edge/exception' cases which you can directly code into your script later on to manage.

Check out the ski rental problem, it will explain how much manual work to do before automation is right.

I tried googling for this and didn't find anything - do you have a link?

Sure thing.


[...] The ski rental problem is the name given to a class of problems in which there is a choice between continuing to pay a repeating cost or paying a one-time cost which eliminates or reduces the repeating cost. [...]

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