Unsung benefits of a paperless workflow

I implemented a paperless workflow (after reading @macsparky’s Field Guide) primarily to reduce the amount of paper I had to file and keep. Howver, it does have other benefits, as I discovered today.

I was meeting with the guy who manages my workplace’s retirement plans and I learned that I wasn’t able to contribute as much to the plan as he previously thought. So I’ll be getting a check refunding some of last year’s contributions and I have to reduce my contribution for the remainder of this year’s paychecks so I’ll be under the limit this year (and pay a bunch more income tax :angry:).

Because I’m paperless and I have all my old pay stubs in Dropbox I was able to grab my iPad and bring up my total contribution for last year and year-to-date contribution this year right there in the meeting with him. This meant we could get all of this resolved right there in the meeting. If I’d needed to go home and find a physical copy of my pay stub or W2 it would have meant a couple of days and a bunch of emails back and forth. I probably wouldn’t have been able to get the withholding adjusted on my next paycheck.

So, there are other benefits to going paperless beyond just saving space in your file cabinet.


Last year we had a medical emergency, being able to answer every question with just my iPhone in hand accessing it trough Files and 1Password was invaluable.
And at the end of the year we had to evacuate for the Thomasfire. Not having to worry about physical papers other then a small file with deeds and titles was a big relief.


I have been moving towards being paperless for several years. I get unlimited cloud storage through work (which will continue beyond retirement) so began getting rid of the many file drawers full of “stuff.” I could go totally paperless if my wife would stop stashing all her “stuff” in and around her desk. I also find it really handy to be able to call up just about any record from my iOS devices, which has been served me well on many occasions (even when I had to prove my dog had a current rabies vaccination). The other thing that has really helped is that I use logical file names that include the date which makes searching really easy.


Digital is the ONLY WAY to go. I do this method every day and it definitely helps cut down on wasted time chasing paper docs.

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I would love to hear a little more about how you organize all your paperless papers. I had heard Macsparky was going to do an update to his paperless book which was going to be my catalyst for truly getting started.

Almost everything goes in my “Paperless” folder in Dropbox. In it, I’ve got an “Action” folder where every new PDF goes. It has a bunch of Hazel rules watching that rename documents and moves them to the appropriate folder (one for pay stubs, one for car insurance, one for statements from each bank, etc.).

Certain things I don’t want in cloud storage (basically anything with my Social Security Number on it) go in a subfolder in my Documents folder. These get handled manually.

Mine are year (2018). Then in that year I have a folder labeled (example) 2018 XYZ Conpany, and folders for each company that would send me a digital doc that I wound get one from. Another example would be 2018 Verizon. I use Scanner Pro on my IPhone to scan in paper docs.

It’s all very simple and quite easy to do.

Hope this helps!

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I don’t get this. Why would you want a copy of all your old Verizon bills? Aren’t they all downloadable if needed? I used to save stuff like this but then I realized in many years of old phone bills I’d never looked at one again.

Many companies that provide PDF statements will only provide them going back a limited time.


Most of the companies I use that have on-line PDF statements only keep them for 1 or at most 2 years. US Tax law says you could be on the hook for proving expenses for up to 7 years after you file taxes so if you get an extension the time they can audit you also is extended. So I keep those things for at least 8 years. I’m considering standardizing on 10 years as that is easier to remember and easier when doing deletions.


Credit card and Bank statements are often just a year or so. And they will charge if you need to go back in time. Just as easy to download and keep the .pdf.

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I’m new to this. What is Hazel?

Hazel is a Mac app that watches folders that you specify and can move or rename files in those folders based on criteria that you set up.

For instance, I have Hazel set up to watch a folder named “Action” where all of my scanned and downloaded PDFs of bills, statements, and the like get saved. One of the rules I’ve set up looks for PDF files that say “Water Bill” and have my account number in them. It pulls the date of the bill out of the PDF, renames the file “Water YYYY-MM-DD.pdf” and moves it to the “Water Bill” folder.

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That’s really cool. So hazel is kinda like the work flow app ?

Yes and no. I’d say the big difference between them is that Workflow is user initiated; you go to the app or the action extension and choose a workflow, and launch it. In contrast, Hazel lurks quietly in the background and acts when it detects a file that meets the conditions that you’ve set up.

How effective is Hazel at accurately pulling the date off of a statement? Do you have to teach it this so that it is accurate?

I like this. I presume you have a different folder for every company?

Also, what do you do with general receipts for purchases?

Hazel is very accurate, as long as the date was OCRed correctly.

I’ve been finding that different companies format dates differently and getting Hazel tounderstand which of several dates on the statement I want in the file name took a bit of finagling. Once I got the pattern correct it’s worked so far with a test set of 2 months. I expect that if the format of the statement changes it will fail again but that doesn’t happen that often.

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Awesome! Would you be interested in sharing the Hazel rule, or at least a general idea of the algorithm used to make the Hazel rule? Was it necessary to make a different rule for each type of statement - e.g, one rule for ABC credit card statement and another rule for XYZ bank statement, reflecting different placement or formats for the statement dates? Am I correct to I assume that your rule (or rules) would re-format the date into a uniform format such as 2018-10-05, allowing alphanumeric sorting?

My simplistic approach would be to insert today’s date as a text annotation, then use that date to name the file along with some captured text representing the company name or vendor name. If needed, the file’s name could be changed later to reflect the true statement date rather than “today’s” date when the document was received. Not perfect, but simple (like me! :grinning:)