My Personal Information Management System

The reason for writing this post is to share my current implementation of a system I use to simplify my digital life wishing to help others and hoping to offer a shortcut to the process of getting things done. The system may seem complicated, and indeed took me years to refine, but the methods are now second nature for me. I continue to evaluate the system and look for improvements and am curious what others are employing successfully in order to manage their daily dose of information.

Let me start with a bit of personal history before I go into the system itself. My first digital personal information management (PIM) tool was a Palm III, which I bought sometime in 1998 for around $399. The Palm platform served my very well for many years. To be able to have your contacts synced to your mobile, make calls, send emails, that was the future, and is today’s reality, with prolific smartphone markets and many free network services.

The Palm brought organization and clarity to calendaring, contacts, tasks and notes that previously were in the day planner. Those four areas are the cornerstone of the system I use, along with the concepts that were outlined in David Allen’s Getting Things Done (GTD) book.

My first accomplishment using Allen’s GTD concepts was to bring my email inbox down to zero messages. I have always kept my personal and work inboxes separate and it took me about a year to get down to the zero mark for both. In the beginning of my GTD practices the inbox would occasionally jump back up to several hundred messages. These setbacks would set things off track for a little while, but I stuck to the method of taking time to get things under control and  always managed to make  my way back to zero after the first time.

The discipline of getting my inbox to zero required practice, but this was the training I needed to begin seriously gaining control over the information flood. If I could manage data flow in one area, I knew I could repeat the process, thereby freeing up more of my time, which the true gold.

I’ve now spent over  a decade finding ways which I think increase my productivity, simplify my life, and help me stay more in balance. Simplifying things in your digital life has a high reward potential if you are willing to put in the work upfront.

After years of work keeping my inbox as close to zero as possible, the GTD practice has become rather effortless. Rarely do I have more than 25 emails in my work or personal inbox, and like a well-trained muscle, the process of purging is not painful, particularly since there is nothing “out of control”. I now enjoy being able to keep up on not getting behind and flexing new muscles on other problems.

In this post I will share the tools I am using today and how I leverage them to make GTD concepts work for me. This flowchart from Francis Heylighen and Clément Vidal’s, “Getting Things Done: The Science behind Stress-Free Productivity” research paper, elegantly illustrates the information capturing process.

Francis Heylighen and Clément Vidal’s GTD Flowchart

Here are the tools which I use to catch the many inputs in my life and get the streams organized as quickly as possible without becoming overwhelmed with data.

The Google Trifecta: Gmail/contacts, Gcal, Gdocs 

Google’s key concept for organization are views. Without sensible views into your data you have no organization. Views are similar to folders or containers, but the beauty of a view is that an object can live in more than one place at a time and that the view is virtual. For me the key to organizing my email is to have a simple, fairly flat, folder structure, which I can easily sort mail into, without thinking about very much.

As you’ll come to see my method for organizing data involves the hierarchical organization of the folders, views and groupings I’m using, which ease archival and retrieval of data. The structures have important differences to me, based on their application and context. By seeing my hierarchies perhaps you might be able to shortcut what has taken me multiple refactors and many years to perfect.


My high level email folder structure looks like this:

  • acquaintance
  • biz
  • diy
  • fam
  • friends
  • personal
  • spirit
  • sys

As a rule of thumb each contact or business I correspond with gets their own folder. I generally only have one level of sub folders in my email. This gives me all the flexibility I need to easily archive messages and find them when I need them later on.

I use Gmail keystroke features, it is easy to jump to folders using the “g+l” quick keys. In case you don’t use keystrokes, I recommend turning them on where possible and learning at a minimum how to bring up the help menu, so you can begin to replace your most used clicks with keystrokes. (add this as a task if you need to)


I use the following Google Calendar sharing setup to help me organize and separate the views for appointments and events in my life. When I talk about permissions, I am referring to the permission my spouse and I find work well for us. You likely have similar people in your life for which you can create a shared calendaring model to ease the burden of tracking time and appointments.

  • Main Calendar (read-only to spouse)
  • Spouse’s shared main calendar (read-only to me)
  • Joint calendar with my spouse (both can edit)
  • Well-being
  • Maintenance (both can edit)
  • Toodledo iCal (manually added iCal feed from Toodledo)
  • Contacts’ birthdays (added from Google special calendars)
  • Holidays (added from Google special calendars)
My Calendar(s)

My main calendar, syncs with my work outlook calendar using Google Calendar Sync. The well-being calendar records activities I like to track like exercise, meditation, journaling and things that are good for my well-being. The maintenance calendar is a place to put things that re-occur around the house, subscriptions, and yearly reminders.Given certain life circumstances I have some calendars come and go based on my tracking needs. It is great to be able to turn on and off any of the calendars, to see just the amount of information I need to see.


Here are my high level correspondence contact groups. If you have two monitors you may find it handy to open another Gmail window and switch it to Contacts, and have this on your second monitor if you are working on updating contacts and need to also use your email window.

  • Acquaintance
  • Automated
  • Business
  • Family
  • Friends
  • Medical
  • Pastlife
  • Groups

Three of the above groups are further broken out, using the following naming conventions:

  • Friends + “Context” (e.g. FriendsWork, FriendsSoccer)
  • Family + “Location/Familyname”
  • Groups + “Groupname”

I use the “automated” category for account linked service email accounts (e.g. Evernote, Blogger, Toodledo) which create an entry when a message is sent to that inbox. The “pastlife” category is for contact information I want to hold onto, but don’t really plan on actively using. I could let these go if I really needed to, but there aren’t that many items in that folder.

Every now and again I import my Facebook contacts into my Gmail Contacts. To do so, you can Import your Facebook contacts into Yahoo, export from yahoo to CSV, and finally import this back into  to Google Contacts. It’s kind of a pain, but I don’t do it that often and allows me to keep address and phone information up-to-date, that I might not necessarily have otherwise.

It is good practice to perform maintenance on your contacts. Using the Google “merge contacts” feature and assigning new contacts into their correct folders are examples of what I do to keep things tidy. When you are done cleaning house, perform an export to get a backup of your contacts and store this file in an encrypted volume in the cloud — more on this below! By the way this is an example of a task I have in my maintenance calendar, which recurs each year.


Although I mostly use dropbox to store files in the cloud, Google Docs is ideal for collaborative work.

Task Management: Maximizing Toodledo for GTD

The key for managing my individual tasks is organizing them into contexts and folders and give them each a  status, priority and sometimes a due date. I add a Toodledo iCal feed to my Google Calendars, so any tasks with dates will show up. I like Toodledo, because it syncs well with smartphone application, Pocket Informant, which I have been using since the early days with my Palm Pilot. It is my favorite mobile app interface into my tasks and also combines the Gcal information into its interface.

Toodledo Tasks

My Toodledo contexts are as follows:

  • Communications
  • Home
  • Online
  • Out & About
  • Planning
  • Tracking
  • Work
  • Workshop
  • Yard

My Toodledo folders are fairly granular and include:

  • Various names of work projects
  • Things to checkout
  • Audio
  • Call
  • Email
  • Finance
  • Habits
  • Info
  • Letter
  • Maintenance
  • Medical
  • Blog
  • Music
  • Notes (I give my notes “-1 priority”, so they are not mixed in with actual tasks)
  • Personal
  • Reading
  • Remodeling
  • Spouse
  • Tech
  • Travel
  • Video

My Toodledo status fields, resemble classical GTD states:

  • Next Action
  • Active
  • Planning
  • Delegated
  • Waiting
  • Hold
  • Postponed
  • Someday
  • Canceled

I prefer to sort my tasks first by Context, then by folder, and finally using Toodledo’s “automatic” setting, which means dated items first, followed by priority. Sometimes I sort by Folder first, or Priority, ToodleDo makes it easy to change how you look at your data.

I also recommend turning on the create a task via email feature. To do so click on the “Tools” menu and select “More”. Then go into the “Email Import” section. Make sure the checkbox is checked, and then click the “Save Changes” button. This will enable email access to your account. Add this email address to your contacts and also save it as a auto-complete for your mobile phone so you can just type a few letters and the account will be automatically completed.

To add a task, send an email to your secret Toodledo email address with the task in the subject. In addition to the name of the task, you can also set the priority, due-date, folder, context and other values using a special syntax. For example:

Folder – To set the folder use the * symbol and then type the name of your folder.

Context – To set the context use the @ symbol and then type the name of your context.

That is all I do to customize Toodledo, and I just make sure things trickle into the structure from email, voice notes, and photos and are tagged at a minimum with Folder, Context and Status. As a side note I like to leave newly created tasks with no status, since they then appear on my mobile Pocket Informant in the inbox folder. New adds, which I’ve not yet categorized are also easier to find this way.

Paper & Mail

For all of my incoming paper and mail items, I carry around a plastic folder, with dividers, which I’ve used for many years.

My Mail and Paper Organizer 

It has the following categories, which I revise whenever I find one not being used and I need something new:

  • Inbox
  • Next Actions
  • Someday
  • To Scan
  • Waiting
  • Projects (several of these)
  • To Be Filed

I keep a separate file drawer at home, which I go through yearly to weed out old stuff. I’ve started to scan some things from my file drawer and organize those files into my Dropbox or Evernote folders. If it’s important I’ll put it into Dropbox, since I have more control over those files and can back them up, otherwise and Evernote article will work.


I’ve just recently added Evernote to my bag of tricks and have not settled in yet on how I will use it. For now it has been a handy way to take pictures from my smartphone, dictate using Dragon Dictate and capture information via email, or record audio clips, which all of syncs to all of the systems I use.

I’ve begun storing my dream journal in Evernote and it seems like a good platform for capturing multimedia rich thought streams. I go through my Evernote notebook to process items I’ve captured much like I do for email. Some things I do just leave in Evernote, since it has nice organization capabilities.

I’m not ready to put my important data files into Evernote, since I like to have those in their raw data format for security and backup purposes. Although you can do a backup of your Evernote notebooks, you’d have to restore it back into Evernote and can’t get directly at the files within. My Evernote setup will likely be used to get media rich information on all of my systems, which I can then properly file into a more traditional file based location (like my dropbox folders).

I’d also recommend using your Evernote email account if you like submitting things from your mobile. I have the account added to my contacts and an auto-complete for it on my mobile phone, so when I type “je” the address is auto-propagated.

1. Select a destination notebook for your email by adding @[notebook name] to the end of the subject line.

2. Add tags to your note by typing  #[tag name] at the end of the subject line. This feature works with existing tags in your account.

3. To designate a destination notebook and add tags, be sure to list the notebook name before the tags.

An example subject:

Fwd: Recipe for Bouillabaisse @Recipes #soup #fish #french

My Evernote Notebook


I use dropbox to organize my smaller files. I have a Western Digital My Book to store larger personal files.

Here are the folders for my Dropbox accounts, which I try to keep fairly flat and unnested:

  • _safe (contains the following TrueCrypt encrypted volumes:,,,
  • astrology
  • carving
  • consulting
  • cygwin
  • fitness
  • for sale
  • genealogy
  • shopping
  • insurance
  • jobsearch
  • letters
  • lists
  • network
  • recipes
  • papers
  • programming
  • spiritual
  • templates-forms-spreadsheets
  • travel
  • web
  • work

Encryption is important to me for the safety of my data. I keep a large TrueCrypt volume with data that rarely changes since the entire volume has to sync if you make a change. Within the “_safe” folder I have a small volume, which contains spreadsheets with passwords and so forth.  A third TrueCrypt volume is used for private journals.

To use TrueCrypt in with Dropbox it is important to change the TrueCrypt setting to allow the synchronization of a volume, which will never change its byte size, but will have a new date. The change you need to make is to uncheck “preserve modification timestamp of file containers” preference.

And here are my WD MyBook folders, which have pretty deep nesting and many sub-categories for fine grained separation of a lot of material. By the way the WD MyBook is a network appliance which I can access from all the systems behind my wireless router. I have a reminder in my maintenance calendar to make a backup of this data quarterly, along with what I store in the cloud.

My large volume folders on my personal network share quickly go from broad to specific topics and I’ve made great effort to continually reduce categories to the minimum needed and creating additional  sub-folders where I want a better delineation of topics.

  • audio
  • binaries
  • print-media
  • videos


As I like to take in a lot of information on the web, it is important that I organize and update my bookmarks. I use Xmarks for bookmark synchronization across all multiple systems, platforms and browsers. I primarily employ Chrome for browsing, IE for a few banking sites, and Firefox for its bookmark syncing application that runs on my mobile device.

Another thing I like to do is sort all of my bookmarks. I do this in Firefox using Andy Halford’s sort places add-on.

I keep my bookmarks within a hierarchy on the bookmarks toolbar. Here is what that that top-level hierarchy looks like:


For storing my code, I use two services, which offer free versioning services.

Mobile Tools

These are the tools I use on my iPhone to look into the world above as well as channel information into the tools I’ve mentioned thus far. The only things I can’t get to at the moment, are my TrueCrypt encrypted volumes.

  • Pocket Informant (Toodledo + Gcal)
  • Evernote
  • Dropbox
  • FastContacts (better than the default iPhone contacts)
  • Documents To Go (useful for working with docs in Gdocs)
  • GoodReader
    • access/download docs from Dropbox, Gdocs, Windows shares, FTP and the web
  • Dragon Dictate
    • Create iPhone abbreviations, to your automated email addresses for services like Toodledo, Evernote, and Gmail, as well as your personal email. That way you can dictate and send to those addresses fairly easily. (I don’t have Siri!)
  • Firefox Home (This allows me to get to my latest bookmarks. You can set this app to use Safari as the default browser.)

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