I have been writing these Going Paperless posts for nearly a year now, and as you might imagine, I get asked the same questions over and over again. This was brought home to me last week, when I appeared on Lifehacker’s “Ask an Expert” feature as the “expert” for paperless living. It was brought up again later in the week when I did a Google Hangout with some folks from Evernote on going paperless. I got to thinking: while there are probably a fair number of people who return to this column week after week, there are also probably a fair number of new people who arrive here each week. And for newcomers and regulars alike, it might just be useful to have an FAQ available. Newcomers can use it as a kind of guide for getting started. Regulars can use it to answer questions they might get asked by others. In any case, I thought I’d present a list of some of the more frequently asked questions I get on going paperless.

1. What do I need to get started?

I think there are four basic tools for getting started with a paperless lifestyle:

1. An Evernote account. Evernote is like a second brain for me. It is where I store my paperless life. There are different types of accounts available, depending on your needs. Evernote provides a basic, free account, which allows you limited monthly uploads. You can get a premium account for $45/year, which increases that monthly upload to 1GB of data, and allows for larger note sizes. (I’ve had a premium account for more than 2 years.) Evernote also has a business account that may make sense if you plan on sharing notes across a business environment.

2. A good, reliable scanner (see the next question below).

3. A staple remover.

4. (Optional) A paper shredder.

2. What scanner do you recommend?

I currently use 2 different scanners. On my desk in my home office I have a Fujitsu Scansnap s1300i. This scanner is small, but does what I need it to do. It’s got a sheet feeder so I can scan multiple pages. It scan’s duplex in a single pass. And most importantly, for me, it scans directly into Evernote with the single press of a button.

In my messenger bag, I carry around an even smaller, Doxie One scanner. This scanner allows me to scan documents I might receive when I am away from my office. It’s small, lightweight, and easy-to-use.

There are lots of scanners out there, so look around for what works best for you. I’ve been very happy with the scanners I listed above.

3. What other tools do you use to go paperless?

For me, going paperless is a life style and so there are all kinds of tools that help in the effort. Here are some additional tools and software that I use that keep me paperless and make my paperless life a little easier. Note, I am primarily a Mac/iOS/Google Chrome person so that’s what I list below:

• Evernote Web Clipper (for Google Chrome). The browser plug-in allows me to capture just about anything I browse on the web and pull it into a note in Evernote. Including images and PDF files. I probably use this a dozen times a day.
• Evernote Clearly. This browser plug-in formats web pages in a nice, clean readable format and also allows you to highlight passages and then clip the resulting page to Evernote. You can read more about how I use Evernote Clipper and Clearly in my day-to-day work.
• Skitch. This is a image capturing tool that allows you to capture and annotate images and then sync them to Evernote. I use this constantly both here on the blog and in my day job as a software developer, capturing and annotating screenshots for software on which I am working.
• Penulimate. This tool has replaced the need for me to carry around a paper Moleskine notebook. When I want to scratch out an idea in longhand, I open up a notebook in Penultimate and jot it down. Penultimate syncs up with Evernote so I have everything in one place and it is all searchable.
• Kindle App for iPad. My preference for several years now, has been to do my reading in the Kindle App. My bookshelves are stuffed to the gills with books and there is simply no more space. Besides, for me, e-books hold many advantages over paper books, with only a few drawbacks.
• Zinio for iPad. Zinio is for magazines what Kindle is for books. I read New Scientist, Rolling Stone, Esquire and other magazines all inside Zinio. And I no longer have stacks of magazines cluttering my desk or my office.

4. This seems daunting! Where do I begin?

I tried to keep a few things in mind when I started going paperless:

1. Even if I stopped using paper, paper would still come into my life because other people still use it.
2. I had a filing cabinet full of paper, but I wasn’t going to touch it until I had a system in place for dealing with new paper

So I decided that the most important thing was to scan and get rid of any new paper coming into my life and worry about the old stuff later. I put together a process that worked well for me. I’d spend 10 minutes each evening dealing with any paper–and I’d do it right after I picked up the day’s mail. Here is what my process looked like:

Over time, this has gone from about 10 minutes each day to about 5 minutes each day. And guess what? I still haven’t gone back and scanned the paper in my filing cabinet. Why? Because in 2 years, I have never–not once–needed to go into that filing cabinet for anything. And if I don’t need it, why take the time to scan it. So if the thought of going paperless seems daunting and you are not sure where to start, I’d suggest the following:

1. Start with new paper only (your daily mail, for instance).
2. Do this each night, for a month and see how often you have to access old paper.
3. If you do need old paper, scan only those papers you actually use during the month.

At the end of the month, you will have a nice collection of useful scanned documents, as well as a better sense of what you’ll need going forward.

5. How should I organize my notes?

Organizing notes various by your requirements. So my first suggestion is to consider why you are going paperless. What is it you are trying to achieve? Once you have a better idea of your requirements, you’ll have a better idea of how to organize your notes. Here are some general suggestions I’d make regarding organization:

1. Some information, like created date and modified date are captured automatically. The create date in particular is useful because it allows you to build a natural timeline of all of your notes.
2. When I scan a document, I will change the create date to match the date on the document. This prevents me from having to come up with a title that embeds the date and makes it more difficult to search. If I have a bank statement dated 1/31/13, and I change the create date to match the statement date, it is much easier to find.
3. Give the simplest possible title to the note. I’m not big on complex titles. I just try to be consistent. So, for instance, my bank statement note titles might read something like “[Bank Name] Monthly Statement.” Yes, I’ll have 20 notes with that same name, but they are distinguished by the create date.
4. Use tags only when you have to and have specific purposes in mind. For instance, I generally use tags to help produce lists (like novels I’ve read, or story submissions I’ve made). I also use tags to identify to whom the note pertains (i.e., this note is tagged with my daughter’s name; that note is tagged with my wife’s name, etc.)
5. Use notebooks to partition vastly different sets of notes. I organize my notebook stacks into the areas of my life: Work, Writing, Home Life, and then have a couple of additional stacks, like Diary and Reference for things that cut across all areas.
6. I recommend keeping once piece of information per note. Discrete notes allow you much more functionality down the road. What I mean here is: don’t cram all of your bank statement PDFs into a single note; have one note for each statement. That way you can take advantage of the meta data for each note. Unlike limited space in a filing cabinet, you are not under the same constraints with notes.

I’ve written in more detail about how I organize my notes:

• A Closer Look at How I Organize My Notes in Evernote
• My Annotated Notebook and Tag Structure in Evernote

6. Are you concerned about security? What precautions should I take?

Like note organization, security is a personal decision and based entirely on your comfort level. Evernote goes to great lengths to protect your data. If you haven’t read Evernote’s Three Laws of Data Protection, you should check out that post.

One of the big advantages of Evernote is that it makes your notes available to you from virtually anywhere. This is because the notes are stored in the cloud. Some people are not comfortable with this, and that is, of course, understandable. Evernote does provide the ability for you to create “local” notebooks, which are not stored in the cloud, but are stored locally on your computer. The downside to these local notes is that they are only available on the machine on which they are stored.

A subset of the “are you concerned about security” question is often this: What if Evernote goes away? What happens to all of your notes?

I don’t anticipate this, but as part of good personal data protection practices, I do backup my entire library of Evernote notes monthly, by exporting them to an EXEN file. This file is essentially an XML file that contains all of my notes and attachments. It can be easily imported back into the Evernote application, and even into a local notebook. In the very unlikely event that Evernote went away or became unavailable, all of my data is still accessible.

The truth is that having my data in Evernote has saved my bacon on more than one occasion. I’ve been able to pull up data that I would otherwise not have been able to access, and I’ve been very glad that I’ve had it available to me.

Again, each person has to judge for themselves what they are willing to store in Evernote. Find what you are comfortable with and go from there.

7. What are some of the benefits of going paperless?

For me, there have been three big benefits to going paperless:

1. I can find just about anything I need no matter where I am, within just a few seconds.
2. I save a fair amount of time each day because I don’t have to go hunting for a document.
3. I can automate a lot of processes thanks to Evernote’s integration capabilities with other products and systems.

There are probably lots more. You can feel better organized. You can reduce clutter and waste.

If you have a suggestion for a future Going Paperless post, I’d love to hear it. Drop me a line at feedback [at] jamietoddrubin.com. As always, this post and all of my Going Paperless posts are also available on Pinterest.