Going Paperless: Tools and Tips

I have kept a paperless office for nearly a decade. The technology has improved a lot since I started, making it pretty easy for anyone to reduce to eliminate paper from their daily life. In this post, I’ll share how I eliminated 95% of the paper from my home and office, and in the process, increased my productivity in a meaningful way.

My technology platform is exclusively Mac, iPad and iPhone. If you’re a Windows user, the software tools I recommend won’t be available — sorry.

Why I Went Paperless

• Reduce Clutter. I am one of those people who has to keep a neat desk and office clutter at a minimum to avoid distraction. The adage that a clean desk is an indication of a disorderly mind describes me well. When I see a mess of papers, it bothers me enough to interrupt my concentration. Before I went paperless, I hid all the squalor in stuffed filing cabinets and desk drawers. Now, all that paper is filed away digitally. Out of sight, out of mind, yet organized.
• Save Time. Having all my documents stored in an electronic and searchable format makes finding information when you need it much, must faster. Gone are the days of sifting through stacks of file folders, or waiting until I get to the office to retrieve an important document. Usually, anything I need can be retrieved on my iPhone wherever I am. Having near-instant access to all my files and documents is a real productivity boon.
• Increase Security. In my strategy job, I necessarily work with confidential information, usually about a potential acquisition of another company. Physical access to loose papers and files is far easier to snoop than hacking password-protected and encrypted digital files (though that’s still a risk).
• Help the Environment. There’s an environmental cost to all the paper that clutters our lives. By moving to mostly electronic means for office paperwork, home bills, note-taking and even the books I read, I’m doing my small part to save trees.
• Peace of Mind. Knowing I have complete access and control to all my information, both professionally and personally, is a real comfort to me. Important things like insurance policies, home repair dates and costs, school transcripts, and vital records — all available to me from my phone, tablet or computer — yet secured by password protection and two-factor authentication (more on this later).

A Paradoxical Love of Paper and Technology

My life has long revolved around paper. I’m a big reader and keep a private collection of treasured books. I still prize the heft of a leather-bound book in my hands: the texture of the pages on my fingertips, a faint smell of ancient cigar smoke left over from the previous owner many decades ago. I’m also an avid journal and note-taker, filling many journals and cheap spiral notebooks with my chicken scratch writing for all my adult life I still think more clearly with a pen and paper at hand.

Life as a certified public accountant in the 1980s and 1990s drummed into me the importance of paper: permanent files, work papers, ledgers, and forms filled the large audit case I carried to back and forth clients. There’s something damned satisfying about reviewing a well-organized client file with proper dividers and labels; the tactile feel of the paper, wired into the file through two holes punched at the top of the page (a vestige of accountants and attorneys), making me feel more like a Special Agent reviewing a top-secret file than a mere accountant. Ah, those were the days.

But I’ve also believed in the promise that technology can make me more productive, and I’ve dabbled in numerous emerging technologies over the years to help me, from the 20-years-too-early Timex Datalink (you could get radio alerts right on your wrist!), various models of Palm Pilot PDAs, and a couple of early eReaders that never quite took off.

The introduction of Amazon Kindle and Apple iPhone in 2007, and the iPad in 2010 paved the way for my current paperless environment. Technology finally caught up with human nature and needs, and I was able to piece together the basics of a paperless system that I still use today.

My Paperless System

Office and home paperwork and bills make up the bulk of the paper in my life. A good digital system needs to have an efficient collection and filing process, a fast and accurate retrieval method, and a comfortable way to consume the information.

Storage System

I use Apple’s iCloud cloud-based file storage system for 99% of my non-media storage. I switched from Dropbox after Apple’s solution became robust enough to handle my needs and benefited from better integration between my Mac and iPhone/iPad for file storage and retrieval. I spend about $40 a year to host my family’s files, photos, and device backups on iCloud, which was considerably less than I was paying for DropBox. And it’s a comfort to know that all the priceless photos on our iPhones are securely backed up each night.

File Organization

There are many schools of thought on digital file organization from do-it-yourself files and folder systems to cloud services like Evernote. I tried Evernote initially but became disenchanted with privacy breakdowns and the bizarre direction their various apps took to monetize their service. What clicked for me is a nested-folder system of broad categories at the highest level, with additional sub-folders beneath that. For example, I have a top-level folder called Receipts and Bills which includes a dozen additional folders for each type of expense (i.e. Car Costs, Travel, College, Utilities, etc.). I have a work folder with another dozen folders spanning the major responsibilities of my job. And I have top-level folders for each major interest or responsibility in my life. I rarely create additional folders below this one-level-down system. I find this organization scheme gives me a good balance of filing efficiency and information retrieval (more on this later).

Fujitsu ScanSnap Scanner and Scanner Pro

I have kept a Fujitsu ScanSnap S1500 document scanner on my desk from the beginning of my paperless system. After eight full years of service, I replaced this original scanner because its 32-bit software would no longer be compatible with Catalina, Apple’s newest Mac OS. Fujitsu offered a $200 credit to upgrade as compensation for the soon to be out of service scanner which I sold on eBay. The new scanner, the ScanSnap IX1500, tears through scanning jobs even faster than its predecessor, and sports a touch screen interface which allows easier and wireless scanning. The resulting scans are saved in PDF format with OCR capabilities which means I can search for information within the document, not just its title.

For mobile scans and anything that can’t be fed through the ScanSnap sheet feeder, I use an iPhone app called Scanner Pro. This inexpensive app includes OCR technology and provides more advanced document workflow management to allow me to process these scans into the same paperless system as my desktop scanner.

More and more documents are available digitally (electronic statements, owner’s manuals available for download, etc), and phone apps like Scanner Pro are quite powerful, eliminating the need for a dedicated desktop scanner for most people. I’m sure I scan less paper today than I did five years ago. And while I like having a robust scanner on my desk, it’s more of a luxury than a necessity.

File Storage and Hazel Automation

Files come into my system one of four ways: (i) computer or iPad generated documents; (ii) email and email attachments; (iii) web page downloads; and (iv) via desktop or iPhone scanner.

Files I create on my Mac or iPad and emails are filed away using a simple “Save As” command to the appropriate place in my system. Apple’s relatively new Files App on the iPad is now powerful enough to save files pretty easily, putting it almost in an equal footing with the Mac and its Finder tool.

For web downloads and scanned documents, I use a Mac automation app called Hazel to help me properly name and file away routine documents like bank statements, credit card statements, utility bills, etc. This ingenious little program watches for any new PDFs that I’ve scanned or downloaded from the web. I have roughly 50 Hazel “Rules” I’ve created to help me name and store these routine files in the proper nested folder.

For example, I download a credit card statement from my utility company every month with the unhelpful name of ViewFullPdfBill.pdf. I have a rule in Hazel that looks for any PDF with contents that include “Puget Sound Energy” (my utility company) and my specific 10-digit account number. Hazel then searches within the document for the statement date, renames the file to Puget Sound Energy (2019-08-29).pdf, and finally moves it to my Utilities folder within Receipts and Bills. These Hazel rules take care of the mind-numbing and soul-sucking drudgery of routine file naming and storage for the vast majority of file intake in my system. I wouldn’t have been able to keep up a paperless system without a tool like Hazel to help me.

Finding Information

For a paperless system to work, finding and retrieving files must be fast and accurate.

On the Mac, I have replaced the built-in Spotlight search tool with Alfred, a very handy freemium utility from Running with Crayons Ltd. To find a file, press CMD-Space and start typing. Here’s a search result where I’m looking for my most recent utility bill:

While I could use Spotlight, the Mac’s built-in search tool, Alfred is consistently better at locating the files I need. Alfred has many other features, including more advanced workflow automation, clipboard manager, and application launcher, but its ability to quickly retrieve the information is why I became a Mega Supporter of Alfred a couple of years ago as a way to give thanks for the boost in productivity this app gives me.

On iPad and iPhone, the built-in Spotlight search tool works really well. A one-finger swipe down from the home screen brings up a search box you can use to find apps, search the web, email messages, or files in iCloud.

Consuming and Reviewing Information

Most of my files are stored in PDF format these days. On the Mac and iPad, I use PDF Expert to read, review, and annotate PDFs. I have a 27” 5K Retina iMac in my office, but given a choice, I prefer to read these documents on my iPad Pro because of the small form factor, the bright screen and Apple Pencil. I use PDF Expert because I like its simple user interface, solid annotation tools, and seamless cloud integration between the iPad and Mac. Like many software developers, PDF Expert has recently moved to a subscription platform. I haven’t subscribed yet as my paid-for version does everything I need.

I rarely print out a document ahead of a business meeting these days. Armed with an iPad and Apple Pencil, I can follow the conversation with the materials in PDF Expert, jotting notes in the margin, and flipping around the document as needed. I am not alone in this: at a strategy retreat last week, only two people out of eighteen participants chose to bring paper copies of the discussion materials. This is good progress.

Security and Backup

Unlike loose paper on a desk or stowed away in folders within a metal filing cabinet, the information I need in my paperless system is locked away pretty tight. The Wild West days of early cloud storage security breaches are hopefully behind us. Even so, I take security very seriously and employ these best practices:

1. Unique and strong password. The password I use for my iCloud system is a long string of meaningless letters, numbers, and symbols that my password manager 1Password generated. I don’t use this password anywhere else, and I change it once a year. Using the same password on multiple online services because it’s easy to remember is the fastest way to get hacked. Don’t do it!
2. Two-factor authentication. I also use iCloud’s two-factor authentication which provides an additional layer of security. If a new computer or device logs into my iCloud account, even with the correct password, trusted devices on the account are notified, and a secret code must be entered to allow access.
3. FaceID and Passcodes. Both my iPhone and iPad have FaceID technology which effectively the device from prying eyes or if one of the devices is ever lost or stolen.
4. Paper Shredder. I use an Amazon Basics Shredder to destroy sensitive paper documents once scanned. I had to replace the first one after about five years, but the cost is low enough that I think of these as disposable.

Even with all these strong security measures, there are files and information in my system I still won’t save to iCloud. These include any documents with my bank or investment accounts, social security numbers, income tax records, and certain will/trust documents. As a result, I can’t access these unless I’m physically at my office desktop Mac. It’s just too great of a gamble to have these sensitive documents in the cloud, even with the strong security measures I have in place.

Finally, it’s critical to have a backup strategy for a paperless system in the event of a catastrophic event or system issue. I use the following belt and suspenders approach:

1. The files I save to iCloud are automatically backed up to Apple’s servers as well as being stored on my local Mac hard drive.
2. Every file on my hard drive is backed up continually using Apple’s Time Machine backup system. I have a 3TB hard drive on the network to process these backups.
3. I store a complete copy of my Mac’s hard drive every week on a series of four rotating external USB drives using program SuperDuper. I keep three of these drives in a fireproof safe. One is stored at an offsite location. These copies are “bootable,” meaning I could plug one into a brand new Mac and boot up my system using the external drive.
4. I keep critical paper documents like wills, passports, vital records, titles, etc. in the fireproof safe along with the backup drive.

Conclusion: Some Tips for Going Paperless

So there you have it: my paperless system from stem to stern. It’s been a multi-year process of tinkering with software tools and automation to get this right, so I hope you picked up a few tips and ideas on how to improve or expand your own paperless environment.

I’ll leave you with a few tips I wish I had known when I was starting down the path of a paperless system.

• Don’t Scan Old Unnecessary Documents. As I was setting up my paperless system, I had to sift through drawers and drawers of old paper documents stuffed in my filing cabinets. I recall a moment of despair as I considered how long it would take to scan and organize such a mess. I realized that just because I had saved all these documents, I didn’t have to keep them forever. For example, I had utility bills going back to the 1990s from a home we no longer own. I decided to limit my scans to the three most recent years of invoices and statements. That decision reduced my initial scanning project by at least 75%. I kept the old documents in bankers boxes in storage for two years but never found a need to hunt through them and finally destroyed the whole lot.
• Search before You Scan. I had a large number of operating manuals for equipment we own stored away in filing cabinets. A lot of these are bound books that would be difficult to scan through a scanner’s sheet-feeder without destroying the binding. Luckily, 95% of these manuals were available as PDF downloads from the manufacturer on their website. Do a Google search of the make and model to see if you can find it online.
• Sign Up for Paperless Statements. Look at all the bills you pay and monthly statements you receive and see if a paperless option exists. In my case, just two of my normal monthly bills don’t offer paperless billing. Every other bill is downloaded from a password-protected website and stored automatically using Hazel. I keep a list of these bills and statements I need to download in an Apple Notes file, so I don’t forget.
• Pace Yourself and Have Fun. Getting over the initial hump of dealing with an office full of paper can be a challenge. Rome wasn’t built in a day, and you don’t have to tackle every stack of paper all at once. Find some time to tinker with a program like Hazel to learn how a few simple automation rules and a capable scanner can devour stacks and stacks of documents without any mental energy. Once built, these tools keep working for you while you focus your talents on more productive (or fun) tasks.

Thanks for reading this paperless office manifesto. As always, let me know if you have questions or comments in the section below. Cheers!