My Envelope Organizational System

This post is more than 3 years old.

I have tried and dismissed a number of personal organizational systems over time, but none of them has lasted as long or served me as well as my current system: my life and all of its to-do lists are managed on the back of used envelopes.

Before I tell you more about how it works, let me first assure you that I've tried the alternatives:

Past Solutions

  • I have carried a Franklin Covey Day Planner around, and it wasn't too bad. Plenty of space to keep track of events and to look into the future. But it felt like a waste of paper, and I felt silly buying filler replacement kits every year. I also noted that as my todo lists grew more complex and with varying priorities and deadlines, it was much harder to get the big picture of what to be working on.
  • I have carried around a Palm Pilot PDA, and it's probably the closest I've come to finding a solution that involves an electronic device. Manage calendar items and todo lists on my desktop computer, sync it with my Palm, manage them there, sync them back, and presto. But I didn't like the awkward geek factor I felt in busting it out at meetings and in public places - especially since I used the optional portable unfolding keyboard - despite (or maybe because of) the fact that I geek out in plenty of other ways. I also found that even though it was pretty small and convenient to transport, it was still an expensive thing that I had to remember to carry around with me all the time, and I felt a bit tethered by it. Subconsciously, I think I want to know that at any minute I can jump in a lake and not have not to worry about what devices I'm ruining.
  • The sense of tethering was probably why I thought the Timex Ironman Data Link Watch would be such a good solution. This puppy was straight out of a James Bond movie or something like that, at least back in 1999 when I had it. You could manage your events, contacts and todo items on a computer, and then synchronize it to this wristwatch just by holding the watch up to your computer screen! Yeah, I know. You could even add some stuff to the watch while you were away from the computer and then sync it back later, though the interface for typing was limited to the four or five buttons it had. I *thought* it was cool and it was a conversation starter at parties, but somehow those conversations never went very far, and looking back, I think people were just humoring me while they planned the most direct route to the punchbowl. Stupid parties.
  • I have tried Getting Things Done (GTD), mostly in the form of various software packages for the Mac, and so far, I can't say that I like it. I probably started out with a predisposition to dislike it because of all of the hype it received, but even so I just didn't find it to be that revolutionary, and in some cases, found the structure it imposed to be too much. I'm glad it's working so well for so many, but it didn't stick for me, at least not in the form of a software tool.
  • I've tried using my cell phone as a PDA, and it worked okay for a while. It was a lot harder in the days when the synchronizing involved manual copying and/or fumbling with cables, but now that Bluetooth is pretty standard, I can get my calendar, contacts and notes synced up pretty quickly. The problem is that I just hate having to type anything using a cell phone keypad...some people have that down, but I am NOT a fast texter. I also notice that the screens on most cell phones are too small for meaningful interfacing with, say, a week or month calendar view.
  • I use a Powerbook laptop for most all of my computing needs, and it's a logical choice to have as a single organizational gadget. It's where I maintain my primary calendar and addressbook, and there are myriad todo-list managers out there. But I come back to the same distaste for having to carry a computer with me just to be on top of all the stuff I want to be doing. It works sometimes, but there are still meetings, trips, walks, etc. where lugging a laptop along is too much.


Okay, so you see that I've experimented quite a bit...this hasn't been cheap, either. Between the gadget prices (only part of which were ever recovered on eBay) and the significant time spent, this has certainly been an exercise in poor return on investment. I'll also take a moment to say that I fully recognize that a life and culture requiring such ridiculous mechanisms just to have a smooth daily existence is probably in need of some serious examination.

But, I hope you'll believe me when I say that this isn't the result of some dysfunctional lack of self-discipline or self-created artificial busyness just so I can feel important. I take on a lot of stuff, and I like to leave as much of my brain as possible available for creative fun stuff instead of "administrivia." So I like to have stuff written down, externalized, discretely managed.

The Envelope System

And so it's writing down that I do. On plain white 9 1/2" by 4 1/8" envelopes that have been sent to me and opened, their contents long gone but their utility still very much intact.

My main envelope is usually divided into four quadrants, denoted by folding the envelope in half the long way and then orienting it vertically, one column of items in each quadrant. Each quadrant is devoted to a major part of how I spend my time...for some time now, three of them have been devoted to Summersault and one of them to personal projects.

Until recently, I was using that last column for both personal items ("pick up some soy milk") and organizational items ("review the minutes from the board meeting"), but organizations now have their own envelope, also in quadrants.

If a quadrant has so many items in it that they don't fit in the single column, then I know I have laid out too many things to do in the near future; tasks that won't REALLY require my immediate attention then go into other organizational structures for later retrieval (whiteboards, software ticketing systems, etc.)

The main envelope usually only lasts about 1-2 weeks before it needs to be replaced. Fortunately, used plain white envelopes are plentiful and free.

The benefits are clear:

  • I can pretty much take the envelopes with me wherever I go, and I can update their contents at any time without being self-conscious of using an electronic device inappropriately.
  • The system doesn't require any financial investment beyond being the recipient of postal mail.
  • Depending on what kind of ink I use, I can probably jump into a lake and be okay.
  • Re-using existing resources!

Some drawbacks:

  • I still can't schedule future events in real time unless I have my laptop with me too.
  • I tend not to make backups of the envelopes, so if I lose them (which happens rarely), I'll have to count on things being important enough to make their way back to my mental list so that I can then re-record them on paper.
  • People who have been using paper to manage their todo lists forever can laugh at me for thinking this system is anything new.

So, that's what I've got. I put it out there in part to see if anyone wants to improve upon it (please, resist the urge to tell me to get an iPhone), but for now the simplicity and reliability is hard to beat.

5 thoughts on “My Envelope Organizational System

  1. Have you ever seen PocketMod? It sounds a lot like what you're doing!

    I'm in a similar boat to you -- I've tried (and still have) a PDA (it's sitting on my work desk). No money invested, fortunately. Outlook's calendar feature is my LIFEBLOOD here at work, but I find lugging around the PDA to just be an inconvenience and I never used it when I was out.

    At work, I have two ways of organizing things:
    - Legal Pads: I have a stack of legal pads. Anytime I go to an appointment / meeting, I bring the pad and take notes. I don't have any fancy dating system or anything, I just write stuff and expect to be able to figure it out later. It's worked so far. *shrug*
    - Manila Folders: There's a stack of Manila Folders next to my desk, rotated 90 degrees to the "tab"/opening is facing to the right. Each folder has a project name / topic written on it, and they are stacked in order of priority -- highest priority on top. All relevant materials related to the task get stuck in the folder, so that they're always handy. (Frequently, pages from the Legal Pads™ get torn out and stuffed into the Manila Folders™)

    I know it's weird to be a tech-nerd and yet be so averse to techie devices -- but I just really like tactile-based tools, and so far no gadget has been faster to use than either of these things.

    Check out Pocket Mod though -- it sounds a lot like your Envelope Organizer™.

  2. Great post Chris.

    I've struggled with myriad organizational schemes over the years in a strikingly similar fashion. I started off with an old Phillips Nino PDA, one of the earliest Windows CE models featuring a 4-shades-of-gray screen and a clip-on modem, used it for a while and gave up.

    A couple years later I tried again with a Toshiba Windows PDA with all sorts of cool features like wi-fi, but eventually it too fell into disuse.

    The problem for me is always in the synchronizing. I could never handle having to try and keep things in sync, and it seemed like every few months something would hiccup and I would have to restore the PDA, which meant I couldn't really only rely on the PDA and never sync it.

    Within the last few months I think I've finally come upon a workable solution. And yes, mine does involve a fair amount of geeky-techie stuff.

    I got a blackberry curve back in June and I've found that using it in conjunction with Google Calendar and Remember the Milk I'm able to have my calendar and to-do lists easily accessible wherever I've got my phone, on my laptop, or on anybody else's computer, should I ever need to access it elsewhere.

    Unfortunately the blackberry probably wouldn't pass your jump-in-the-lake test, but even if I did jump in the lake at least my data would survive.

    I think this may call for a blog post of my own ... thanks for the inspiration!

  3. I like to use the back of the faculty meeting agenda packet pages. Lots and lots of pages. Lots of space. And if I use them during the meeting? Lots and lots and lots of time, too.

  4. i've been taking my laptop with me more and more, especially now that i feel comfortable biking with it. but i really like being free of that too.
    so my cell phone has taken the place of writing on my hand - i set reminders in my phone for a time i think i'll be online (or able to get online) to enter something into google calendar. the main drawback of this system is that i have learned to dread the sound of the reminders going off. the second is that the reminder only plays for an hour, so if i'm away from my phone for that crucial hour, the reminder is gone forever and i probably won't think to go looking for it.
    sometimes i still write on my hand.

  5. Folks got too much splintered stuff goin on!

    For years I've managed to rid myself of (or never adopt): corporate job, bedside clock/alarm, watches, PDAs, laptops, cell phones, iPods, thumbdrives, pagers, GPSs, navigation systems, and other digital deadweight...

    I bought a used minivan last year, and cringed at having to carry the remote control fob... That and big brother's IPass tollroad transponder...


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