The hardest kind of activity to get organized is stuff that is routine, but cannot be automated. This is stuff that has trivial meta-content, but non-trivial work content. Even GTD struggles in this department.
Trivial meta-content means it is not hard to plan or schedule this stuff, or figure out and create the necessary enabling pre-conditions. Non-trivial content means the actual work is hard and cannot be automated.
Blogging is an example for me, so I’ll use that. If I had to put it in my organization system, it would simply be write blog post as a weekly calendar reminder. No biggie. But I cannot put the work itself on autopilot.
Small business book-keeping is another. It seems simple enough to just put your receipts in a shoebox, and update your books based on your invoices, credit card statements, receipts and bank balances every month. All you need is an Internet connection and your shoebox. But the work itself cannot be automated.
Why is this stuff hard to get organized? Is it fundamentally hard? What are the consequences if you don’t keep up?