I’ve been “paperless” for many years now. It can be very daunting to get started. Paper comes at us from all directions. Also, until you’ve lived the paperless life, you don’t really know what will work for you and what won’t.
Therefore, I think the best way to get started is to begin with one type of incoming paper. Either the one that’s the most annoying to you (receipts?), or maybe the one that you’re the most excited about (recipes?).
Receipts are a good category to see the complexity. Let’s start with the deceptively easy one — an online purchase. OK, you’ve completed the purchase — now instead of printing the confirmation, you print to PDF as a web receipt. Great! An hour later, you check your email and you see an email confirmation and now you have a choice: do you print that to PDF as well? Does it go to the Web Receipts folder? The box arrives and contains a shipping invoice: do you scan that? If you make a purchase on your phone, do you go through the annoying steps of trying to get the web page to print to PDF and then save it in iCloud? What if you have multiple computers — do you want to have a one place all receipts end up?
Now after a few months, you’ve got a bulging Web Receipts folder with a lot of unidentifiably-named PDFs. Do you organize them at all? Do you remove the “thank you for your purchase” and “your order” text that many of them begin with, so they alphabetize approximately correctly? Do do add dates to the filenames of multiple purchases from the same vendor instead of macOS’s default habit of adding numbers? Or do you just move them together into a folder by month? by year? and hope that searching will lead you to the right info if you need it?
There are no right answers here.You might have a good guess about what will work for you, but until you run the experiment, you won’t see the flaws in your choices which allow you to refine it. (And yes, sometimes the flaws are that something is “too organized” — meaning it takes too long to get to the perfectly organized system, or that the automated system is brittle and breaks too often, etc.)
I want to get off on the right foot using the simplest process possible.
Let me suggest that is incorrect, as the simplest possible process is to just scan everything (in full color, double-sided, with OCR), throw it all into a folder, and use search to find what you need. (Even simpler: put everything to be scanned into a box (or boxes) and ship them off to be scanned!) This assumes that you’ve got the disk space to hold the results (and to back it up) and an excellent ability to search quickly.
However, what I suspect you really meant was you want to organize the results of going paperless in a fashion that is usable to you. There’s no quick-start guide for this because everyone’s use case is different.
So pick a category, start scanning and organizing. When you find that something is taking too long, or it’s too annoying, or you find mistakes, or you suspect that there is an easier way, then turn to your books for solutions. Or this forum.
If you don’t know what’s annoying or interesting in your build-up of paper, then I suggest receipts. If that seems too complicated (I think it’s the worst), then maybe start with utility bills. They’re regular, there aren’t too many of them, and if you want to set up automation (naming, filing), then they are a good place to begin.
I, myself am back to setting aside 15 minutes each day to process my almost-overflowing paper inbox. I got sick last fall and stopped my weekly handling of paper.