Organizational Chaos Followup

About a month ago I wrote about getting organized.  Since it is Sunday and I’m saving my big announcement blog entry for tomorrow morning <smile>, I thought I’d take a moment for a not-so-quick follow up.   

Two Philosophies Lead To A Unified Approach

Some years back I found myself with the strong conviction that what worked (for me) was this: “Don’t organize on the way in, search on the way out.”

Every time I forget this premise, and fall back into the habit of creating dozens of small categories in which to stash things away, I end up with lots of mis-filed papers and socks all over the floor.

[By the way, I have no idea if that was an original insight, or one that I swiped from Ed Belove, probably when he described Lotus Agenda. (So many of the good ideas I’ve heard over the past couple decades were actually Ed’s.)

Since I last wrote, I discovered what is probably the only popular self-help book I fpimd worth the cover price (though I still think it could have been edited down to a white paper):  Getting Things Done by David Allen.  Of course I’m not the first to discover GTD (as it is known); the book is a massive best seller (which I admit is often a bad sign).

More related than might appear at first, the essential message of GTD , at least as filtered through my brain, is:  “The more you keep in your head the less you can think about what you need to do so get absolutely everything you have to do or remember out of your head. The only way you can do that is if you have a system you trust 100%.  You must trust that the system won’t lose anything, and you must trust that the information will be there (proactively in my case) when you need it.  That is to say, you have to trust that the information will be stored more reliably and retrieved more reliably in the system than it would be in your head.

This apparently is a hurdle for a lot of folks, but I have absolutely no problem believing that a well designed system, properly backed up can do that. I’m reasonably convinced that silicon is faster and more reliable than meat.

Once I dump all my tasks, trivia, notes, things to remember and things I have to do but not yet into a sufficiently reliable system, I’m freed up to do what meat does much better than silicon: set priorities and make judgments.

Assembling the Right System

The time for writing my own system has passed. There are enough pieces out there that it is just a question of finding them and plugging them together. That took a little doing (and this real intention of this note is to save you the work of recreating that experience!)

For a while,  every “solution” created more problems than it solved.  But with a bit of refinement and a willingness to spend more money on applets than one would think possible, I believe I have found solutions that meet the specifications: they allow me to keep virtually nothing in my head that isn’t relevant to something immediately actionable, yet with total confidence that what I need will be immediately retrievable when needed. Even better, the system will alert me when that time arrives, and since I’m notoriously unaware of time passing that is a very good thing indeed (I asked my wife if it was lunch time yet, at 11pm just last week). 

Stringent Requirements:

For me to turn over so much responsibility to any system, I must have an enormously high level of confidence, and thus the system must meet the following outrageous set of requirements.

Information: Be able to save any bit of information that I receive or stumble upon in email, on the web, in conversation, in IM, on the phone, while driving, in short: any where at any time,  and store it 100% reliably and be able to retrieve it no mater where I am, with at least 95% fidelity,  in less than 3 seconds.

Responsibilities: Capture every task
, personal and work, instantly and then let me forget them until it is possible to take an action, and then alert me immediately that an action is both possible and necessary.  Allow me to set priorities and to aggregate tasks into projects, and to add these tasks from anywhere at any time and to be alerted to and to retrieve them no matter where I am.

Email: Manage the 3,000 email messages I get every day so that I spend no more than 20-30 minutes a day reading my email,  but see everything important and never miss a critical email and so that I can retrieve any email I need within 3 seconds.

I could certainly have treated E-Mail as just more Information but it was much more efficient to treat it separately.



I have to start by saying that I’ve built and bought at least a dozen systems that tried to meet the Information requirement. I believe it took the perfect storm of the Web, and massive advances in mobile phone technology to finally make this all work.  My solution here is centered around a single application: Evernote. The next image is Evernote running on Windows. I tend to throw just about every note into a single folder (cleverly named notes).  I make an exception for a few very obvious specialty notes such as business cards, passwords and my favorite: short term memory, the notebook in which I record my hotel room, where I left my car, etc.


I can retrieve this information (or enter new notes) instantly on the Web,


or, even better, right on my phone:


EverNote provides a clipping application that allows me to grab any highlighted text anywhere and just add it, or drag and drop into evernote, but my favorite feature is that I can take a picture and Evernote indexes the words in the picture, which I can then search for.  Hmmm…. I know we stopped at a good place to eat in Brewster on the cape; didn’t I take a shot of it for Yelp? Let me search…

brewster coffee

In less than a second it finds my picture and while the red arrow is mine the highlighting is provided by Evernote.  Very nice.


image Be able to save any bit of information that I receive or stumble upon in email, on the web, in conversation, in IM, on the phone, while driving, in short: any where at any time,

image store it 100% reliably

image be able to retrieve it no mater where I am,  

image in less than 3 seconds.

[I’m going to table the issue of adding notes from the car for the moment, but see my discussion of Jott below)


This is the hard one. I recently tweeted that working for Microsoft is like learning to juggle a dozen razor sharp plates a dozen razor sharp plates, while riding a unicycle on an escalator”

I’m told that many people feel that their memory leaks a bit, mine seems to leak a bit more than usual.


Young man kayaking down waterfall

Keeping track of my myriad projects, deadlines and responsibilities is critical to meeting the expectations of my bosses, peers, clients (that would be you) and myself. But I’m happy to say that David Allen says that trying is a losing strategy. Once again, the right answer is to turn it over to a system you trust. So I set off to find a 100% reliable system. 

I’ll spare you the details; the solution I found uses a back end web-based service with a phone-based front end, augmented by a call-in transcription service.

The backbone; the engine that makes it go and makes it available from everywhere at all times, is the unfortunately named Toodledo. The Toodledo interface is not simple, but it is powerful and it supports everything I need and then some. In fact, I switched from Remmeber the Milk (which I very much liked) to Toodledo because the latter was a much better fit with GTD and with the approach I as formulating.



Toodledo has three key features:

  1. It understands projects and sub-projects
  2. It works and plays well with the ToDo application that I use on my phone
  3. It is more than happy to sync with and to notify you of upcoming events by SMS, its own iPhone app, email, fireFox, twitter, Google, iCal, netVibes, pageFlakes, rss, jott, tSheets, outlook, VistaGadgets or Android. Pretty good


Toodledo is almost enough, but I need something much more immediate. To accomplish that, I added to vital pieces of software. First: ToDo:



Appigo’s ToDo is a wonderful iPhone application for ToDo lists and project management, and is especially rewarding if you follow the GTD method as it understands projects, sub-projects, priorites, and most important Context (where you must be to act on a problem – no point seeing that you need to update the blog if you’re not near a computer.

I take it back, most important is that if you assign a due date and time ToDo will notify you. My one feature request would be to add a reminder date/time that is not the same as the Due date/time, but that is just a quibble.


The same set of tasks seen on the ToodleDo, looks like this on ToDo



Almost There, but What About Ideas and Tasks that come to you on the highway?

The one missing piece in all of this is the requirement that I  be able to capture data and tasks any time, any where.  For a long time, it went like this: someone would ask me to do something (during a call) or I’d think of something important and then I’d face an interesting dilemma: which was the better choice:

  1. Wait until I could get off the highway to write it into my software by which time I was certain to have forgotten at least one important detail if not the entire reason I’d gotten off the highway in the first place

iStock_ Shrugging Man Medium

The second choice is to try to enter the information into my phone while driving 65 miles per hour among Massachusetts drivers



The answer is Jott. . Jott is a dictation service that lets you call in (or send a message from their phone app or their desktop app).They then transcribe your message and send it to whomever you like, including Evernote or Toodledo. Tweter, Outlook or any of your contacts.



There are limitations to Jott’s voice recognition (see this article) but all in all it is just great. I can say “Jott ToDo” and add to my todo list while driving, such as “Jott Todo, pay speeding ticket”

GTD Bliss

Together, ToDo, Toodledo and Jott make a system that completely meets the GTD requirement: I can put every task, big or small, into the system with 100% assurance that I won’t lose it, miss it or have to think about it until it is time to think about it.


image Capture every task, personal and work, instantly

image let me forget them until it is possible to take an action

image alert me immediately when  an action is both possible and necessary 

image Allow me to set priorities

image and to aggregate tasks into projects,

image and to add these tasks from anywhere at any time

image and to be alerted to and to retrieve them no matter where I am.




I get about 3,000 emails a day and that is enough to treat Email separately.  Just a little analysis shows that my email breaks down (roughly) as follows:

  • About 2/3 comes from valuable lists but is not directed to me and is not immediately actionable
  • About 80% of what is left have me in the To or CC list but are not really to me specifically. I need to read them but most are FYI and while important to someone are not critical to me
  • We’re now down to 20% of 1/3 or a select 200 of the 3,000 daily messages. These 200 look important but only 1 in 10 really are. But those 20 message  must not be missed!
On any given day the proportions will change, unpredictably, but I strongly suspect that overall there is a normal distribution,  and further, what I’ve described is well within one standard deviation. What’s more, I’m wiling to bet, based solely on experience that this describes the contents of most corporate email inboxes.


The Best Laid Plans of Mice and Men

You may remember that my first approach was to have just 5 mailboxes:

  • Inbox
  • Act  (take action on this email)
  • Waiting  (pending someone else’s action)
  • Reference  (hold for future blos or videos)
  • Archive (can’t do anything with this now, hold on to it)

This lasted less than a fortnight. . There was just too much email to sustain it. 

I then created “rules” in Outlook to separate out the newsgroup emails and other chaff that I knew I could defer.  Worked fine until I found I had missed some pretty important emails. 

I’ll save you all the interim steps, and skip to the solution that is now working quite well.

Email Working…

Step 1, I created a small but vital second contacts list called VIP.  In it, I put the v-cards for anyone who I work for, work with or who is associated with a project I’m working on. Then I added anyone else whose mail I must not miss.  I will not be publishing this list 🙂

Step 2: I created these mailboxes:

  • Inbox
  • VIP
  • VIP Urgent
  • Probably Not Urgent
  • Reference
  • Read
  • Discussions (under which are any number of mailboxes for each discussion area)

Every single message that arrives is copied to read and marked as read, and thus I can count on having a copy. 

Each of the following rules has an Except clause that reads: Except if my name is in the to or cc field or the sender is in the VIP list. 

There are then a series of rules, with that except clause that copies mail for discussions to the appropriate discussion and out of the inbox.


There is an additional rule that essentially says that if it is not for a discussion and doesn’t meet the exception criteria, put it in the “probably not urgent” folder.

Finally there are two vip rules, anything that is from someone on the VIP list that is marked urgent goes to the VIP urgent list and a template is used to send an SMS to my phone.  Anything that is from a VIP but is not urgent goes to the VIP folder. And then anything to me or cc to me but not vip stays in the inbox.

I can now read my messages in just the order I want, deleting as I go safe that a copy of everything is already in “Read”

1. ViP Urgent and VIP – never miss a message from a VIP again
2. Inbox  – read everything addressed to me
3. As time allows skim Probably not urgent and the discussions

Save anything I might want to come back to in reference and/or copy it to Evernote (discussed below) and/or make an entry in ToDo (discussed below).

All of this is supplemented by Copernic, an extraordinary search engine that is able to retrieve the messages I need in the specified amount of time, along with any matching files, contacts, images and so forth,


Email: Manage the 3,000 email messages I get every day so that I spend no more than 20-30 minutes a day reading my email,  but see everything important and never miss a critical email and so that I can retrieve any email I need within 3 seconds


image Manage the 3,000 email messages I get every day

image I spend no more than 20-30 minutes a day reading my email

image I see everything important

image I never miss a critical email 

image I can retrieve any email I need within 3 seconds,


An Evolving Story

I’m quite sure that this is not the final chapter, but there does come a point where organizing becomes a major distraction in and of itself, and as a friend once said, “How many frogs do you want to kiss to find an even-more-handsome prince?” 

I look forward to your comments and can only promise to be returning to matters of more immediate substance very soon.

About Jesse Liberty

Jesse Liberty has three decades of experience writing and delivering software projects and is the author of 2 dozen books and a couple dozen Pluralsight & LinkedIn Learning courses. He was a Senior Technical Evangelist for Microsoft, a Distinguished Software Engineer for AT&T, a VP for Information Services for Citibank and a Software Architect for PBS. He is a Xamarin Certified Mobile Developer and a Xamarin MVP and a Microsoft MVP.
This entry was posted in z Silverlight Archives. Bookmark the permalink.