How the Moleskine Rocked My World

It's so weird how a small black book and a nice pen can change things. Since graduating from college I have increasingly gone "all digital". No more paper, vacuum tubes, tapes etc etc. However, in this process I have tried to cram the needs of my life into a set of rather restrictive tools, at least when compared to paper. While Getting Things Done has really helped me to manage my life using digital tools, I feel that I've arbitrarily limited my own success because I never even allowed myself to consider paper as a tool for helping me. Kind of short sighted looking back.


When I first red Steve's post about the 21st century PDA it really made me think. In school I used to take lots of notes, I mean lots. That is how I learned. Since then I use the computer for everything. I have owned a few PDAs over the years, and looking back on my experiences I can't say that any single one has really done a better job than paper can do for some core things. I think the PDA was initially attractive to me because I could have my contacts and calendar everywhere I go. However, now my phone provides that functionality, as well as e-mail and wireless synchronization to our corporate exchange servers. Whether it's Smartphone or Pocket PC Phone Edition, they both do this well. However, the Smartphone is to much of a read only device, and the Pocket PC is to clunky for taking notes. To this day, I have yet to find a better note taking experience then paper. The Apple Newton came dammed close, and since then no one has bothered. My Tablet PC and OneNote has an amazing writing experience but my laptop is to big, heavy, and runs on batteries making it non ideal for note taking. Until there is a small slate like device that can capture ink like the Tablet PC, I will probably never feel that it's suitable for the kinds of things my Mokeskines are.

So, what does a guy who has a SmartPhone, Tablet PC, OneNote, and 3 computers need a Moleskine for? A lot of things, and I'll explain them based on the notebooks I purchased.

Moleskine Large Ruled Notebook

I use this notebook exclusively at home for taking notes when I read computer books, photography books etc. Basically anything where I am learning something that I want to commit to memory, as well as have available for reference later. This was basically how I worked in school, so why not in life? I also check a lot of books out of our library at work, and once I return them I pretty much lose whatever I didn't commit to my brain. Cuddling up with a book and my 5 pound tablet with 3 hours of battery life ain't going to suffice in these cases.

Moleskine Pocket Ruled Notebook

This notebook goes everywhere with me. I've obviously read all the Hacks out there, and have taken some and applied them to my notebook. This notebook is primarily for my "Life" since I use my PC so heavily at Work, and use the Outlook Task list for my Actions. I've organized the notebook into 4 sections. I divide the book in half and I place the first  Avery Write-On Tabs there. The first section of the notebook is for Next Actions. In the Next Actions section I label pages with Contexts like @Calls, @Home etc. From the middle and for the next 10 pages I have Projects, then Someday List, then Reference. In the Someday section I have a page for my Wish List and then my Blog Post list. In the Reference section I place any reference info like the Caltrain schedule, our Microsoft shuttle schedule, a map of the Redmond Campus, Flight info etc.

Then I turn the notebook horizontally and vertically and that is where I write my generic Notes or where I dump stuff. Things I would normally write on a post it and then lose track of later. So think of it like this:

  1. (1 - 96) : Next Actions

    1. A page each for @Calls, @Errands, @Home etc. I use one page per context, and then I move to the next free page when it's filled.

  2. (97 - 107) : Projects

    1. For a list of all my active projects.

  3. (107 - 117) : Someday

    1. A page for my Wish List
    2. A page for my Blog Posts list

  4. (192 - 127) : Notes/Dump

    1. this section starts from the back of the notebook and works it's way in.

I can't tell you how amazing it is to just have this thing around to immediately write things down. It gives me a lot of control in my life and makes it quite fun. I use a Fisher Space Pen Bullet in Matte with a Clip.


I keep the pen strapped to the top of my notebook. I also keep a Bart card, a New York metro card, some stamps and a $20 bill in my secret hidden Moleskine pocket.

Moleskine Large Squared Notebook

I keep this at work and use it for meetings where I don't want my laptop, for my weekly One on One's with my direct reports, and for an ideas that I have. It's divided into 3 sections:

  1. (1 - 120) : General Notes, Meeting Notes etc
  2. (120 - 130) : Projects
  3. (130 - 240) : People

    1. This is for any One on Ones, Interviews or an discussions I have with people.


At first I was worried that I would have a hard time integrating analog and digital. However, what I have found (like Brian Johnson) was that I became a better OneNote user. I love OneNote, but because it was so easy to create sections, pages and the like my Notebook had this crazy complicated taxonomy that I could never figure out myself.

When you start using paper again, you are limited by some fairly basic things. One you write you can't erase, when a page is full it can't be moved, and you can't search your notes with a computer. However, this isn't so bad, as this is how I did things for most of my life and it tended to work fine. Digital has introduced so many options that I never knew how to use them. Some of the things I have noticed doing the past few days are:

  • I like taking notes in my Moleskine at work. I am not distracted by Outlook, and I can focus on the meeting rather than bury my head in my laptop.
  • I transfer important work items like next actions to Outlook at some point, and then cross them off.
  • When I am using OneNote to take notes, I mark Next Actions using the Todo flag, and when the meeting is done, or I am finished taking notes, I send these tasks to Outlook from OneNote. 
  • I take all notes from my One on Ones in my Large Moleskine.
  • I keep the number of sections and folders in OneNote to a minimum.
  • I separate a Work and Personal section in OneNote.
  • My personal stuff is mostly in my Pocket Moleskine since that's what I have the easiest access to at home, on the weekends etc. It doesn't run out of batteries and doesn't require that I boot it up.

So the bottom line is that I use a mix of my Large Moleskine and OneNote at work. I like to think on paper, and take notes in some meetings (the ones where I am learning new stuff), and use it for ideas. Stuff that is actionable I move to Outlook later. I use OneNote for all my other Meeting Notes, as well as putting small snippets of reference data and such.

Here is what my OneNote looks like:

  • Side Notes - screen clippings, etc
  • Inbox - dumping ground for all unprocessed stuff
  • Personal

    • House - House related notes
    • Journal - Journal for when I travel
    • Notes - General notes, dump, ideas
    • Programming - Stuff I learn about programming
    • Reference - General reference info
    • Restricted - Password protected for personal notes

  • Work

    • Lists - my GTD lists that I manually transfer to Outlook later

      • Next Actions - things I can think of before I move them to Outlook via OneNote.
      • Projects - A list of all my active work projects

    • Meetings - a place for all my meeting notes that I don't use the Moleskine for
    • Notes - General notes, dump, ideas etc
    • Classes - for classes I take at work

As you can see my work Section has Lists for my GTD stuff, but all my personal Lists are in my Moleskine Pocket notebook. I've found that this is just the right balance of digital and analog to make me more productive. My work notebook is more temporal/transitive in nature, where my pocket notebook is not as in many cases it's the primary life task list.

I'm still tweaking the system, but so far I like it.

If you are interested in any relevant links that I find as I learn more you can read or subscribe to my link blog.

Comments (18)

  1. Mike Rohde says:

    Hey Omar!

    Congrats on finding Moleskines as good tools for your life management. I’ve been a fan for a little over a year now, and have similar experiences.

    Because I’m a designer, I add in the sketching aspect (separate journal) but it seems to mirror yours to a degree. It is interesting to see others finding balance between analog and digital.

    Anyway, just wanted to say hello from an old MS Outlook Express user who still remembers you when you ran the Mac email site. Glad yo hear you are doing well at Microsoft. 🙂

    Kind regards,


  2. Fred says:

    Hello Mr. Shahine,

    As I can see it’s the MoleskineOMania on the blogsphere!

    Then there is a link that you would probably like to read:

    There exist a community of bloggers that are fascinated and that talk about them. I think that I can say that the core of this community is present there:

    So enjoy the reading and welcome back in the old world of paper!



  3. Brian says:

    Check out the web site called 43Folders

    and the related Google Group. They have been discussing these very same subjects for months, in great detail.

  4. skrike says:

    Its odd how the internet has a niche for everything. Having grown up in a small suburb I was usually alone in any computer/design/reading/music interests, so it never ceases to amaze me as Iget older and I come into contact more and more with people who have the same interests and solutions that Ive had to come up with on my own.

    I recently was given a moleskine as a white elephaqnt christmas gift. I had never seen one or heard of it before, but Ive carried it with me for the last month solid and have been using it to get organized and keep notes. Imagine my surprise when I recently found 43folders online and was opened into this huge world of GTD, social bookmarking, and above all, moleskines. Ive been tyring to think of ways to organize my moleskine more effectively lately, and I think this is a great starting point for me. Thanks for the great insights!


  5. Office 2003 XML Reference Schemas Schemas as used in MS Office 2003 (categories: development standards xml microsoft office) How…

  6. mamamusings says:

    The relative quiet around here hasn’t been a sign of malaise. Instead, it’s been an indication that I’ve been deeply engaged in activities that take me away from the blogosphere…and for good reason. At the beginning of the year, I think I tripped an internal circuit breaker on clutter—in my office, in my house, in my brain. I didn’t make any resolutions, per se, but I started looking seriously at how I could find a way to reduce clutter and the stress that it causes. For dealing with household clutter and disorganization, I started with FlyLady. But while the basic…

  7. Kevin says:

    I have never touched one of these, but the DigiMemo A501 pad sounds like exactly the sort of writable pad you mentioned wishing for.

    It supposedly doesn’t need special paper. I did try out some of the earlier similar ideas a few years ago and didn’t think they were worth the money, but this one looks interesting…



  8. It is intriguing how most people miss the main point of the moleskin: it has the same size than old Toshiba Libretto, thus it is the biggest area notebook still fitinh in a coat pocket. no more, no less.

  9. Anonymous says:

    a million monkeys typing » “Paper? Ain’t that extinct?”

  10. Generally, I’m not the kind of person who just has to have the hot new thing that everyone is carrying around or playing with. I try to remain apart from the mass consumerism that dominates our culture. I TRY, I…

  11. Generally, I’m not the kind of person who just has to have the hot new thing that everyone is carrying around or playing with. I try to remain apart from the mass consumerism that dominates our culture. I TRY, I…

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