[Giveaway] A Detailed Summary of Brooks Duncan’s Paperless Document Organization Guide

Paperless Document Organization Guide

The skinny: a chapter-by-chapter summary on the fantastic resource that is Brooks Duncan’s Paperless Document Organization Guide.

You’ve downloaded my eBook Be The Bos of Paper Clutter. You bought the world’s finest document scanner. You have a host of scanned PDFs sitting on your hard drive and now…what do you do? This guide walks you through how to organize and protect all those digital records in a clear and patient voice.

Note: I’m giving away one Platinum package of this guide. Be sure to check out the end of this post to find out how to enter.

Preface: What’s the deal with this Brooks Duncan?

I link to Brooks on this blog a lot for a multitude of reasons. Here are three:

And now to dive into the guide itself, chapter by chapter to get a basic overview of all this guide has to teach us about digital organization.

The chapters:

What is Paperless Document Organization

The 3 decisions you’ll need to make, the importance of backing up, and what you’ll need to learn in order to organize paper files presented in a sharp rainbow graphic.

Storage Location

Breaks down three of the choices you have for storing your digital documents: local storage, cloud, hybrid (combination of the first 2) and network. Presents advantages and disadvantages for all options.

Folders vs. Software

Poses both sides of a frequent question from many of my own clients: should I use traditional files and folders to organize my digital stuff or a software solution like Evernote?

Naming Convention

“I recommend that whenever possible, you use a consistent naming convention when naming your documents. It is (in my opinion) the biggest thing you can do to be able to find your documents later.” – Brooks Duncan

I advocate this as well, put the date first and your files will fall in line like the world’s most agile and delightful calendar.

This section covers quite a bit of ground: shows you a number of choices of naming conventions, the importance of considering “the future you”, what to do with shared files, project codes, and how to update old files to the new naming convention without tearing your hair out.


Spoiler: There is no one way to organize folders. This makes sense, the same is true when I work with a client on their physical files.

What can be helpful is seeing examples of how other folks do it in different contexts and that’s what’s in this chapter: examples of folding structures from category, date based, legal and accounting/bookkeeping perspectives. With handy diagrams for easy visualization!

Searchable Text (OCR)

Great explanation of what Optical Character Recognition (OCR) is so important when you’re searching PDFs (which are more like photos than documents without it) and how to implement it with various software choices.

Helpful to me when resetting up my ScanSnap settings and a cracker-jack explanation of how Evernote handles OCR and its limitations.


This chapter boasts a very detailed and impressive overview of the many computer and cloud based software choices you have for corralling your documents. My choice Evernote is covered here, but also lesser known candidates like Eagle Filer and Devon Think are discussed. There are over 10 apps and services for Mac and Windows alike covered in detail with helpful screenshots to give you an idea of their unique interfaces and benefits.

Plus a reminder that you don’t need software at all if you’re comfortable with folders and files.


Brooks accomplishes a neat trick here: he gives you all the resources to understand why automation tools like TextExpander (one of my favorites) and Hazel will help your paperless workflow and does it in a concise and appealing 6 pages. (Plus links to some videos to see it action.) The power of automation is one of the strongest reasons to go paperless (your Mac can be a great filing assistant) and this will give you all the tools you need to start down that path.


Tagging seemed to become trendy years ago with the dawn of Web 2.0 – where are we now Web 4.0? Anyway, despite its ancient age in internet time, tagging isn’t always that clear of a concept and can be overwhelming and easy to abuse. Here Brooks does a great job of explaining it, setting some suggested rules, and slipping in an Ikea joke.

As a related side note: after you get the basics of tagging down, I’d recommend checking out how Michael Hyatt uses tagging in Evernote. It’s unique and I think an interesting approach.

Special Situations

Here specific workflows are covered: capturing receipts (strangely Brooks leaves out Expensify even though he’s how I originally found out about it), business cards, emails and downloaded PDFs, and the web app FileThis.

Mobile Organization

Covers how to view, file, and work with documents on iOS and Android. Including coverage of my favorite choice: Readdle’s Documents.

Finding Your Documents

Super useful chapter that shows you how to be a power user within Finder to find documents quickly and accurately. Cool stuff like saved searches and smart folders are taught in a clear manner.


Learning about how to protect documents with passwords, disk images, and for Mac: File Vault 2. I’ve heard about using Disk Images, but this is the first time I’ve understood how it works and how to set it up.


If you’re spending all this time organizing your digital life, it should go without saying you MUST back-up. I don’t like throwing around the word, “must!” willy-nilly people, but this is key! Just as I prescribe, Brooks advocates at minimum a two-tiered backup system, here he goes in detail describing the main four types of backup.

Suggested Workflow and My Workflow

I find this section appealing because I’m visual and it gives you a number of flow charts showing you just how this whole paper to scanner to file system can work in a number of possibilities.

Creating a Habit

How do you make all this stick? Practical advice on developing this specific habit.

Action Item Roundup

At each chapter, there are suggested actions to move your forward in your goal of organizing digital products, this brings them all together so you can knock it out checklist style!

The Extras

There’s three different packages available and they all include bonuses beyond the guide. Brooks is generously giving you the chance to win the Platinum package: which has it all: audio interviews with his readers, lawyers, and professional organizers (including yours truly), videos and screencasts and a huge archive of his course The Paperless Action Plan with its own worksheets and audio. In short, everything and more to whip your digital life into shape.

Paperless Document Organization Guide Platinum Edition Giveaway

To enter to win the big enchilada package sign up for the Bos Organization list below and reply to my welcome email with a one sentence description of your current greatest digital organizing challenge. One email reply will randomly be drawn as the winner.

Giveaway ends Friday May 15, 2015 at 5:00 pm PST.

Update: The giveaway is over, but the guides are available for purchase by clicking on this link.

Note: Affiliate links used in this post.

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  • repoman

    Hi Bos, I believe there is an incorrect link under ‘Worlds best document scanner’. It goes to Amazon but not to a scanner. I had to read through the whole page to make sure I didn’t miss the joke but there was no joke. Lol. Click on the link and you’ll understand.

    • Aw man, thank you! Fixed! Of all the incorrect Amazon links that was a doozy although I suppose it could always be worse. I’m trying to think if I was somehow the victim of a weird internet practical joke where you put in your affiliate link and you always get that link in return…but I don’t know. Thanks again!

  • Thanks for this Deron! I guess my only question is: in both the picture and the video, which one am I?

  • Julie Bestry

    This summary-come-review is ideal. It’s the best of both words, and you guys are the best at what you do. Take it from the Best-ry. (I know. Boo. Groan.)