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organizing a file drawer

I have a two-drawer lateral file cabinet in my office near my desk that I am thinking of organizing soon. I like to plan time in either December or January to make new files for the coming year. The ones I tackle first are the ones I like to label with the current year. For me, they are files for your bank statements, investment statements, and anything tax related.  Typically I never get around to it in December. January comes along and the file drawer calls me. Do you have a sense of urgency about this, too or do you pay closer attention to your files in March during tax preparation season?

Jonda Beattie wrote a great post recently about how to organize your files for our company: Release Repurpose Reorganize. Jonda is primarily a paper person. I have a mix of paper and digital files. This, at the beginning of the New Year, is when I look at both types of files and organize them.

Paper Files First

I tackle my paper files first. As I am thinking about organizing my files I look to see if there is anything I can switch over from keeping in paper form to digital form.

The supplies I have on hand are: my labeler, colored interior files, my shred box, and my paper recycling box. I color code my interior files just because it’s fun to do so and the colors resonate with me.  For me, the red folder is anything tax related, green (think money) is financials, and blue is for DNQ Solutions. If color doesn’t matter to you then use plain manila folders. I have a HUGE shred bin in my garage because I remove any papers that need to be shredded from my clients’ home. This is a service I offer to all my clients.

What can you save digitally?

I don’t know about you but my insurance folders are huge. There is the annual update, plus the original insurance binder, and the receipts. This is something I am going to switch over to being a digital folder. Are you wondering how I am going to do that?

I will call my insurance agent and ask her to send me the binder as a pdf. That’s my first step. Then I will create a file in my documents for Insurance. Inside that folder, I will create a 2022 file for that year’s updates. Just like a paper filing system, you can create a hierarchy of files and have folders nested inside the main category. Under Insurance, you can have Life, Disability, Car, Home Owners, Health, Pet and any other type of insurance. Look at all the space (and paper) you can save when you receive your documents this way.

I know that some people like to have a printed copy of certain things. My suggestion is rather than having the whole document in print form. Scan the document or have it sent to you as a pdf. Find the bits that you want to read more closely, and print those sections.


I love to weed in the garden or in planted pots. When you weed you give the plants you want to flourish space. Weeds clog the space and remove nutrients from the soil that you want the plants to have.

Similarly, there are often papers in files (and digital documents saved) that clog the folders. When I look through the folders I weed out anything that I know I don’t need to keep anymore. There may be an obsolete receipt in a file or an out of date document. Just remove them. Chances are the time has passed to claim a refund if something breaks.

Trouble deciding

Often when we are thinking about organizing we run into a roadblock. We are stopped dead in our tracks by indecision. We can’t decide if we should recycle or shred, keep as a paper document or scan and save digitally. When this happens I recommend a pending file or box if there are many papers requiring a decision. Most often it is not necessary to make an immediate decision.

If you can, go ahead and make a decision. If you can’t, keep the forward momentum going by moving on to the next file to go through. Weed the next file and decide what to do with the contents.

When you let your trouble deciding get in the way you may start overthinking the issue. Just move on. Acknowledge the roadblock. You can always come back to those files or papers another day.

Here’s the thing, though. Be sure to schedule time in your calendar to return to the papers which were creating a roadblock.

Have confidence

You gain a marvelous sense of accomplishment when your files are organized. Whether you opt for mostly paper files or are like me and have mix of paper and digital files you can have confidence that you know where to look for specific documents.

As you are thinking about organizing the file drawer remember you have options. You do not have to keep everything. Besides, if you do keep everything you will run out of room. Ask yourself: what can you remove confidently? What is your comfort level with digital files and folders? If you decide you want guidance Jonda Beattie and I run a clutter support group. We will happily provide you with support, guidance, and accountability.

This post was originally published in 2010. Updated January 17, 2022.

Diane N. Quintana is a Certified Professional Organizer® ,a Certified Professional Organizer in Chronic Disorganization®, Master Trainer and owner of DNQ Solutions, LLC and co-owner of Release●Repurpose●Reorganize, LLC based in Atlanta, Georgia


  • Revisiting paper files is super important! Color doesn’t really matter to me, however, I like to review and update the information and papers, in December. Transfer the tax business and personal files to the accordion folders (one for personal and one for business) and a clear bin that holds the accordion folder and extra personal files not for taxes. This way, as the year comes to a close, everything is ready for tax paperwork that comes in January. Thanks for the tips!

    • Diane Quintana says:

      I love your system. Sabrina. It’s all about making it easy to dot the i’s and cross the t’s when tax time rolls around.

  • Lucy Kelly says:

    This was such a great way to break down how to “go digital”, Diane. I’ll never do it, LOL, but that’s because I’m ruthless about keeping my files weeded and being sure I’m not filing papers just because I can’t think what to do with them.

    I keep active files right by my desk, where I remember I have them and that things need doing, and then I have a file cabinet (in my laundry room – that’s where it fits best) for paper I hardly ever look at but want to be able to put my hands on immediately when I do.

    I’m also music librarian for the choir I sing with, and those filing cabinets are in my basement. Although some people are choosing to go digital and sing with their music on tablets, most are like me and prefer a “real” paper copy. Organizing those files is a busman’s holiday 🙂

    • Diane Quintana says:

      Digital isn’t for everyone, Lucy. And, I am a fan of mixing paper and digital files. Some things I have only in Digital form and some things I keep only in paper form. It’s all about your comfort level. If I were in your choir I would be reading the music on paper, too!

  • There is something so satisfying about organizing papers and files. And I love that “weeding” out process. Like you, I do it this time of the year too. During the fall, I did a big edit because I was in the “live with less” mode. But when the year ended, I needed to pull out the 2021 financials and get set up for 2022. It felt amazing to reduce the bulk in my file drawer and have more breathing room.

    I often think about how paper and filing cabinets will eventually become obsolete. I still like to keep a combination of paper and digital files. And with projects too, I work in both realms. But our kids are almost completely digitally based. I’m sure that’s true for many people under a certain age. Just recently I was giving a workshop to a group (mixed ages.) Many of the attendees were in their 20’s. When I mentioned something about a filing cabinet, I quickly corrected myself recognizing that most likely it wasn’t an issue they were experiencing. I saw a lot of smiles.

    • Diane Quintana says:

      My children are digital natives, too. I must confess, though, that I have worked on them to have some information in hardcopy form as well as digitally saved.

  • Seana+Turner says:

    Wow, I never thought of asking for the insurance info as a pdf. Those booklets are BIG, taking up a lot of space. I’m happy to report that my husband is working on our files right now. Each year we remove the paper that we don’t need going forward and put it in archived storage, freeing the files up for the new year. My husband is a “keeper,” so we don’t get rid of it all. However, we have a deal for how long we keep most of it. We worked on eliminating a lot of the backlog during the COVID lockdown.

    I would like to move toward more digital files myself, but these things are negotiated. We are getting there!

    • Diane Quintana says:

      Those booklets ARE big! It’s wonderful that you and your husband take on this task together.

  • Julie+Bestry says:

    You are spot-on, Diane1 My favorite client work involves organizing papers. (I am the Paper Doll, after all.) But I’ve been known to dither over whether or not to let something go; when that happens, I make myself consult the document retention schedule instead of letting myself get bogged down. For business and financial papers, I’m more likely to wait until after tax time so that I’m 100% sure I don’t need a document, but these snowy mid-winter days offer the perfect opportunities to go through those personal folders, like recipes, travel articles, reference clippings, and mementos. Nobody feels any FOMO about spending a snowy day with a cup of cocoa, a stack of file folders, and a shred box.

    • Diane Quintana says:

      I can just picture you with your cup of hot cocoa, a stack of file folders, a recycling bin and a shred box! Happy snow day!

  • Your title sparked my interest because I cleaned out my file drawer yesterday!
    I agree that the beginning of a new year is a good time for this project. I keep most documentation digitally and my drawer was organized so it didn’t take long to do the job. I had several phone calls scheduled on the hour yesterday, but none of them took a whole hour, so it worked well to review a few folders between each call to get the job done. I’m left with a small pile of things I want to read before tossing, then the project will be complete.

  • Jill Katz says:

    I love paper organizing and I love this post! Sadly, I forget to review my files annually. This is mostly because I don’t have too many files and they easily fit into my small filing cabinet. I love your tip about creating a maybe pile so you don’t lose momentum and then scheduling time to go back to the pile.