two tall stacks of paperwork and files

Paperwork Challenge Q & As

Last week’s paperwork challenge gave me the opportunity to hear what troubles you most about paperwork – here are my answers to the top three most popular questions I’ve received.

Shouldn’t I Be Scanning All This Paperwork?

Only if you love tedious tasks with no visible reward. What I’ve found is that even when people scan in important (and not so important) documents, they’re still reluctant to let go of the original paperwork. And so you end up with digital clutter as well as tangible clutter.

Since scanning paperwork is so boring and time-consuming, the project rarely gets finished. I once hired my preteen who was desperate for money to scan some photographs for me, and she quit after half an hour. She wanted the money but not THAT badly. The time will come when you realize how deeply you’re resenting the time and effort scanning takes and you’ll abandon the project. But which papers have been scanned and which haven’t? It gets confusing and you end up keeping it all just in case. My suggestion: skip the scanning.

If you still want to scan, try this reality check: do you keep up with your shredding or is there a big bag or pile waiting for you to get round to it? Both shredding and scanning are tedious, boring tasks you won’t do. No reflection on you, life’s short – sort the paperwork and take the shredding to a professional shredding company and be done with them both.

How Do I Organize Files in My Filing Cabinet?

I got quite a few questions from people asking about the placement of their files in the cabinet. Shouldn’t it be alphabetical? Alphabetical by category and then within the category? To which I say, if that pleases you and your brain works that way, go for it. And if it doesn’t, trying to keep up that system will be work – which means you’ll put off filing in the future. My suggestion is to group your files by categories within your filing cabinet. So if you have a four-drawer cabinet, the top drawer might be for categories you use fairly often. It’s convenient, no bending down, you can just open it and see what you have. So, paid bills, ongoing projects that have been gathered together in a file folder such as Jason – IEP, this year’s tax folder, would all be good candidates for that drawer. Think of it as your active storage.

The second drawer might be for medical files. The third drawer for financial papers you’ve saved, and the bottom drawer would be a good place to store past tax returns. Within each drawer, you can arrange the folders alphabetically if you like but if you don’t, you’ll still be able to find things. You have the category assigned to the drawer and your brain will soon get used to the fact that Baxter is two-thirds of the way back with a right-hand tab in the second drawer.

Same goes for color coding folders and labels – you can do all that if you enjoy it but it’s not necessary for an efficient filing system. The important thing is, once you’ve decided where something goes, stick with it. If you keep rearranging and tweaking your system, your brain will have a hard time keeping up and you’ll stop filing. Let your system be simple enough to maintain and remind you of the value of good enough organizing.

Don’t I Need an Index?

If your categories and file folders are too detailed, yes, that would be useful. And difficult to maintain. Instead, I suggest you consider broadening your categories so you know which general area of your filing cabinet to look in. If you have a separate folder for each different possible house you might want to buy and label it with the street address , but each folder has only the flyer you picked up when you walked by it, you’ll have an easier time of it if you have one folder for all those flyers and call it something like Should I buy this house?

Did I Miss Your Question?

Email me and I’ll include it in a second Q & A post about this paperwork challenge.

P.S. Did you miss a day? Here are all the previous Paperwork Challenge posts:

If you enjoyed this series of paperwork challenges and would like to have a cool pdf overview, send me your email and I’ll give it to you.

If you’ve realized that paperwork is something you’d rather have support with in person, I’m offering a Pandemic Paperwork Special during covid. Let’s take advantage of this time to take care of your paperwork problem.


  1. I’d say we are slowly reducing our paper load. Kind of going the way Linda described. I have concerns about everything being digital – seems like some “secure” site gets hacked every day. That said, it isn’t possible to be all paper anymore, so it has to be done. I’m not much for color-coding. I like it all the same.

  2. What a fabulous wrap-up for your great series, and you KNOW that paper is my absolute favorite thing to organize (and to talk about organizing) so you got my attention right away. My favorite part was the serious reality-check about scanning. So many people who have hardly ever bothered to keep their papers in order think they’ll make time to scan it all, and just…no. Essentials, but not everything. There has to be a system.

    Congrats on creating such a wonderful resource.

    1. Thank you, Julie! I’m all about reality checks – it’s tough to sneak past perfectionism, so I always appreciate a good hearted, “Really? That will happen?” myself to help me wriggle back from the edge.

  3. I really like how you broke this down step-by-step, including what to put in each drawer. It makes so much sense and I know it’s going to be helpful for anyone who needs tips for organizing papers.

  4. This is an AMAZING resource. I struggle with when/what to digitize. You bring up an important point through experience with clients inclined towards keeping too much. Thanks for sharing!

  5. It’s an interesting comparison you make between shredding and scanning. If you have a big pile of shredding, there’s a good possibility that you will handle scanning in the same way. One thought is that to see if “digital” works, you can experiment with having various bills and statements sent by the vendors in digital instead of paper form. If that works, then you can move forward digitally, and work on reducing the older paper. Eventually, you will have less paper coming in, so you’ll only be dealing with the backlog.

  6. Filing paperwork is a never ending question for some. I love the way you answered it. Do what works and forget the rest. It’s so important to stick with what works. Other systems may be prettier or intriguing but they won’t work if your brain doesn’t think that way.

    1. Thanks, Diane – I’ve had some pushback over the years with clients who wanted pretty over functional but they’ve thanked me later for saving them money and giving them a system that finally works for them!


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