Rethinking my entire digital/paper sytem

For various reasons, I'm starting to rethink my entire digital/paper organizing system. Right now I use a combination of hardware/software/paper that's partly functional, partly leftover from previous systems, partly mandated by work. I would really like to streamline while at the same time increase functionality. Here's what I use and what I use it for:

Paper: I have a zip-to-close Classic sized case that holds a ring-bound set of pages. Right now I am using Covey monthly pages so I can see big-scale planning; two-page-for-a-week pages for more scheduling detail and short to-do lists at the bottom of each day; lined paper for note-taking; pocket at the back for holding notes until I file them at work or at home. In the front of the case is a pocket that holds my Palm device. This works pretty well except that I occasionally forget to write things in this calendar because they are on my electronic calendar.

Palm device: I used to use for everything. Now I just use it for Calorie King (food and exercise tracker) and Pocket Quicken. Both of these are must-have apps for me; I use them constantly, they work really well, and I have no desire to change them.

Home computer (Sony VAIO): I used to use for lots of things but because it is 6 years old, is having some memory problems, and has Windows ME I cannot update/install software for my digital camera or my Pocket PC. I cannot use this computer for email or internet access any more; it has too many problems for that. I canceled my home ISP since I don't have a computer that works well any more. Any downloading I do at work where we have a super fast connection and I can do over lunch.

Pocket PC/cell phone combo: I use for contact list, schedule, simple games to distract me while waiting for dd13 to get out of various activities, a little MP3 playing, phone use. I sync this to my work computer.

Work computer: PC, MS Office based. I have to use MS Office, including Outlook for email and calendar.

Sony Memory Stick music player: I used to use every day. This is a 5-year old device that uses only older memory sticks so I end up carrying a case of them around with me when I'm using it for an entire day so I can swap out music.

Here are my issues:

1. Too many things that are single function resulting in too many things to carry around.
2. I occasionally forget to put things on both calendars (paper and Outlook). There may be no equipment/tool work-around for this.
3. Home computer with limited use - needs to be replaced.
4. Taking music with me is a hassle. I can rip music to Windows Media on my work computer and sync in onto my Pocket PC/cell phone but if I'm at home I can't change music. Unless I buy additional memory cards and carry them around with me. In which case I could just use the Sony device I have but which means carrying around one more item.
5. Music in different formats on different computers means wasting time ripping stuff multiple times. The Sony music player will only play music converted into a Sony-only format. I have a couple of hundred cd's converted on my hard drive at home but am willing to abandon them for a new solution - like an ipod. Having music in two different formats (Sony and mp3 means carrying around two different kinds of memory cards.
6. I can't sync my PocketPC at home (Windows ME won't handle the Pocket PC software) so my home computer is totally useless for any scheduling.
7. I can purchase Pocket Quicken for my PocketPC. Calorie King does not have a PocketPC version although there are similar apps out there.

So, it's pretty clear to me that I need to buy a new home computer. I've never used an Apple computer and I know there are dual processor versions now. I have no reason really to switch from PC but it is an option that I am willing to consider.

Right now I'm thinking if I buy a new PC and an ipod then the music problem of carrying around multiple memory sticks/memory cards is pretty much solved. Except that I don't have internet access at home so using iTunes at home will be pretty limited. I don't want to keep my personal music collecton on my work computer and sync my ipod there. I could, though, use the wireless connection at work on my lunch break for my personal PC if my new PC is a laptop with a wireless card and not a desktop.

With a new PC I could sync my PocketPC to my home computer and my work computer. I'll also have to purchase Pocket Quicken (in Windows Mobile platform) and new diet and exercise tracker (in Windows Mobile platform) in order to ditch the Palm device.

If I went with an Apple computer could I sync a PocketPC to it and keep home and work calendars up to date? Or is that totally not possible?

If I did all of the above I would be carrying and updating one less thing. Instead of binder, Palm device, PocketPC, music player I would be carrying binder, PocketPC, ipod.

Comments? Things I haven't thought of? Thanks.

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Initial observation

It seems that all the "issues" are on the digital side. Many of them concern music. A few concern data sync.
"I think the surest sign that there is intelligent life out there in the universe is that none of it has tried to contact us." (Calvin and Hobbes/Bill Waterson)

One approach...

I am currently (work in progress) using a digital/analog hybrid. 1) I use Palm Desktop on my work PC for scheduling appointments, recording contacts, and other digital tidbits of info. I use it for both personal and work scheduling.
2) I sync it with a Palm PDA that I also sync with Mac Palm Desktop on my home Macintosh. Windows based PDAs can be synced with Macs, but only with third-party software.
3) From Palm Desktop, I print monthly calendars on paper (2-up layout) for cutting and smurfing. That results in 1/2 letter size pages. You could probably do this from Outlook.
4) The smurfed calendar printouts go into a Circa junior notebook with medium Circa rings for notetaking and logging new appointments and action items. That goes with me most everywhere and is usually sufficient.
5) If I need to have my list of contacts and current and historical appointments with me, I'll also take my PDA along. Can't beat a PDA for that.
6) I have an iPod Nano that I use for music, podcasts and a few photos (syncs on either PC or Mac). If you use a Mac, you could sync your iCal calendar and Address book to your iPod and perhaps skip on the PDA (a bigger iPod would probably work better for that).

It ain't perfect, because I haven't fully "implemented" a system yet, but it seems to be working fairly well so far.

Yeah, I recommend Macs. I've used them for years, and have used PCs too. It's work on a PC, it's a pleasure on a Mac. What can I say. Wish they'd let me have a Mac at work. Oh yeah, I have Windows Office at work, and Mac Office at home. Document exchange is pretty near transparent and I sometimes take work home on a flashdrive and work on my Mac. And, if you gotta run a Windows program, you can do so on the Intel-based Macs.

Hope that gives you some ideas.


Remember, no matter where you go, there you are.
B. Banzai

or... an iPhone?

Apple's soon to be released iPhone may be the perfect convergance device to replace the PDA/iPod. No, it won't do everything a PDA can, but it sure comes close to doing all of the essential tasks of a portable digital device - cell phone, email, contacts, calendar, music, and photos, plus video, web, etc.

Would sure like one... :-)


Remember, no matter where you go, there you are.
B. Banzai

I'd love one, but...

the price makes me flinch, first of all. Second, I am uncomfortable with the idea of one gizmo covering all that functionality. If it goes, it all goes.

Another cost factor to consider is service fee. In the US, data plans for cell phone type devices cost a lot. More than I might be willing to pay. My cell phone can "do" e-mail and web surfing, but I do not have those features on my service.

For portable use (what we can carrys in our pocketses...) I have reduced myself to a cell phone, an iPod and a hipster. My iPod currently only has music and audiobooks on it, but I am planning to put contact info and notes on it. My cell phone has many capabilities, but all I use it for are phone calls and a few pictures.

Beyond that, all I (use/plan to use) is my home 'puter and a classic size DIY planner.
"I think the surest sign that there is intelligent life out there in the universe is that none of it has tried to contact us." (Calvin and Hobbes/Bill Waterson)

Yup, cost is a real issue

Even though the initial cost of the iPhone is high, the accompanying data/phone service plan cost will overtake that easily within a year. I have a cell phone that can access the web, but I never bought the data plan. That's a real concern. And, those service plans are where the wireless companies make their money. Yowza.

Although I'm really interested in the iPhone, largely because it looks like it has a superior user interface, I'm planning to wait until the initial feeding frenzy dies down and evaluate it then. I have a Cingular phone, but I hate it's interface. Would be happy to replace it with something better. :-)

re: "If it goes, it all goes." Actually, that's why I originally switched from an all paper planner to a PDA. The PDA you could at least back up by syncing to a computer. If you lost the paper planner, there was no backup. That was scary. Now I use a hybrid system. Part digital, part paper.


Remember, no matter where you go, there you are.
B. Banzai

Suggestion for music issues

It sounds like you are trying to use the best format for each place you play music.

Is there a single format that will work everyplace ? If so, use it. I think you will find less overall inconvenience.

I love audiobooks and I have an iPod, but my kids have MP3-CD players, so I encode all my audiobooks to MP3 so that the kids can share. MP3 is not, according to some, the best format to use on an iPod, but it is a format that works everyplace I need to use it.

Just a suggestion. Good luck.
"I think the surest sign that there is intelligent life out there in the universe is that none of it has tried to contact us." (Calvin and Hobbes/Bill Waterson)

Simplification ?

Consider this:
For a moment, ignore the phone and the music player.
Everything else can be handled by paper and desktop computers.

This is the direction I find myself moving toward. My setup is simpler than yours as I do not sync between work and home. My work is such that I cannot bring it home and I am finding that to be more a blessing than a problem.

Again, just my suggestion. Good luck.
"I think the surest sign that there is intelligent life out there in the universe is that none of it has tried to contact us." (Calvin and Hobbes/Bill Waterson)

Music on the Palm

Depending on the model of Palm you have, you can listen to music through the pTunes app. I bought a 2GB SD card and filled it up with my favorite songs (in MP3 format) after my iPod died. Now I have one less thing to carry, and the 2GB card was only $27 at Best Buy if I need more space.

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does it sound ok?

I've never had an iPod, but my Palm has a slot for an SD card and software for music playing (I think it's Real Player).

I've thought about getting a card, but haven't gotten a round to it.


Well, you probably don't want to listen with the built-in speaker -- it's not very loud, or really made for music -- but with headphones or a car adapter it sounds excellent. (I have one of those iPod car adapters that broadcasts over my car stereo; I can plug it into my Palm's headphone jack and it works exactly the same as the iPod. I highly recommend it.)

Surprisingly, music doesn't drain the Palm battery very fast at all. You can get several hours' worth of listening, because pTunes (and probably your software too) turns off the screen when it's not in use. And the screen is what sucks up most of the battery power.

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great comments

Great comments. A lot of the trouble is on the digital end. I have avoided some paper troubles by trying to keep some things digital - task list for example that I would really prefer in paper. Right now I have my tasks in Outlook and printed out on paper that I carry around in a bag but haven't gotten to punching yet to include in my binder. I like them digitally because I can sort by context (a la GTD) and I like them in print because I can just pull them out and look at the list without turning on a machine, launching the app, scrolling up and down a list to see the whole thing, etc.


It seems to me that some of your problem stems from the fact that you have some old, faithful, and once-useful tech that you are trying to continue using. Maybe dumping some of that redundancy is enough. I don't know...

Now, to that 6 yr old computer. I have a really off-the-wall suggestion--Ubuntu. I've got a 7 yr old Apple Powerbook (affectionately known as the "Pismo" amongst Mac heads--Doug also has one) which is my main brain, and has been since I bought it new 7 yrs ago. About a week ago, for kicks, I threw Ubuntu onto an extra hard drive I have lying around, and have been amazed at 1. how easy it was to install--at least in comparison to Windows! 2. how easy it was to configure, and 3. how fast it was, and 4. how easy it was in comparison to Windows, to use. You might find that this free OS/office combo (It comes with will add new life to your laptop--and even undo some of the memory problems you've been having.

Next, for your PocketPC, Maybe get a Treo 650. It is a capable Palm device, and phone combo. It can also play MP3s as has been noted. While, like you, I've been a long-time opponent to all-in-one devices, I've slowly come around, and am waiting the time I can buy myself a Treo.

In line with that, I would recommend keeping your "hard landscape" items in electronic format only, rather than on paper. There are several reasons for this--ease of moving/syncing between multiple computers/devices, the ability to alarm and alert yourself ot upcoming items (primary reason, IMO), and ability to search for past or upcoming, as well as different views without the redudancy of rewriting, and its potential mistakes. Furthermore, you can print out calendars if you need a hard copy.

Second change I would make--an analog (paper) "inbox"--a place to write all incoming data, including meetings, tasks, project items, etc. Personally, since I gave up my Newton, I have discovered that paper is the best place for all this stuff, rather than a Palm or computer. Because it's on paper, it's easy and quick to make adjustments, glance at it, or whatnot. I use Circa to hold everything together, but any format you are comfortable with is sufficient.

So, to summarize--I'm not offering "advice" here, just suggestions. ;-)

1. Try Ubuntu (
2. Move your handheld devices to a Treo (Palms sync fine with Ubuntu--it's built in!)
3. Move your hard landscape items, such as meetings to electronic.
4. Move your inbox, tasks, projects, etc. to paper.

If Ubuntu works for you, you can buy an extra year from your old computer, and use the money saved to get a decent Treo, and dump all the incompatible hardware you are currently using.

I can't say that Ubuntu will work for you. I'm not using it for my main OS, my Pismo is running the latest Mac OS just fine--albeit slowly, but the day I get a newer Mac, Ubuntu is going full-time onto my Pismo! If I were a Windows-user, however, I would have dumped Windows for Ubuntu. I like Ubuntu that much. :-)

So, have fun trying to figure this stuff all out.



I've never heard of Ubuntu; I'll have to check it out post haste. Great suggestions. I think you're right on about which things to move to paper. I've tried so many different combos of which things to have digital, which things on paper, that it's easy to get lost in the muddle. Thanks for the perspective.

Ubuntu: not just an operating system

OK, I went to and got the the World Forum of Civil Society Networks. I got popped over immediately to A worthy looking organization, and one I'll explore more, especially in how they are addressing the Millenium Development Goals which I have an interest in through a couple of other organizations I'm involved with. But, I didn't see any mention of an operating system there. I went to handy google and found Voila. I'm really happy about the .org site though and am psyched to find another organization dealing with critical global social issues.

Forgot to mention

On Ubuntu, its default email is Evolution, which is Microsoft Office compatible, including the calendaring/scheduling, as well as "Exchange"? compat. You might find that useful--or not. Just wanted to mention it.



Ubuntu is wonderful. It's my main OS...

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Ubuntu as main o.s.

What? You mean the shiny new Windows Vista isn't the solution to all of our o.s. problems? I'm shocked, shocked I tell you. :-)

Using Ubuntu

Can one install Windows-based software on Ubuntu? For example, I have Quicken (that I sync with Pocket Quicken on my Palm device) on my laptop. If I used Ubuntu as my o.s., could I install Quicken? What about my digital camera? Would I still be able to connect my camera to my laptop with Ubuntu? Trying to find out the implications before I take a big scary leap like taking on a new o.s.


On Intel computers, there are solutions to run some/much Windows software without actually loading Windows. Wine is, I believe, just one of them. However, what these "solutions" do is emulate Windows APIs without actually installing Windows. If a program works outside those, it won't run. However, some have done extra yeoman's work in that they also cover some of these glitches as well, enabling things like Office to run. Since I'm a Mac-only dude, I know nothing on how this stuff will work with Quicken or other specific apps. I did some looking HERE, specifically HERE and it looks like Quicken may not run too well. You will need to do some digging.

However, there is at least one Palm app that does online banking, and there's always MoneyDance that also does online banking for Linux (costs $30) Also, I'm not sure what support the Ubuntu Palm tools have for financial apps. I've been thinking about reloading my Ubuntu hard drive into my computer this evening just to see how the Palm support goes, so I will look into that for you while I'm at it.

As to digital cameras, from all I've seen, support is just about a given, but it would be wise to try it. If you have an extra hard drive, or can partition your drive, it would be worth trying an install. Beyond that, Ubuntu has a live CD you can play wit, just to see how well your camera is recognized, and how easy it is to set it up.

BTW, I'm facing almost the same issues--financial software and photography. Oh, and iTunes... could I live without iTunes? ;-) I've already un-DRMed most of my purchases, but still... the videos won't work in any case... oh well... Maybe we should start a new thread for Ubuntu in the proper section (digital), as it may not be of general interest, yet worthy of garnering interest. ;-)


Palm and Linux

Palm support on Linux is crap. I back my Palm up about once a week under a WinXP partition. That's the only solution I've been able to come up with. I hate it, but I want to be able to use all the cool Palm tools...

Camera work great, though. No drivers needed, usually.

[ web site ]

12-step for organizers

Over-Planners Anonymous

Over-Planners Anonymous

OPA, Where do I sign up????

"Astronomers say the universe is finite, which is a comforting
thought for those people who can't remember where they leave things."


Is OPA a subgroup of d.i.y.-ers? What are the 12 steps? Do any of them include index cards?

Memory issues

Home computer (Sony VAIO): I used to use for lots of things but because it is 6 years old, is having some memory problems, ...
... I have a couple of hundred cd's converted on my hard drive at home but am willing to abandon them for a new solution - like an ipod.
I'm guessing that the memory problems may have something to do with the massive number of music files you have on your home computer. It sounds to me like you may need an external backup for your computer files rather than just a new computer. Even with a new computer with a large memory you could find that keeping that many CDs on it could give it troubles.

I can't sync my PocketPC at home (Windows ME won't handle the Pocket PC software) so my home computer is totally useless for any scheduling. .... I can purchase Pocket Quicken for my PocketPC. Calorie King does not have a PocketPC version although there are similar apps out there.
Can your Palm talk to your home computer and your Pocket PC? If it can, then perhaps you can use it as a linking device to your work computer (I'm assuming that you can't use your Palm at work).

Alternatively, buy the new software for your Pocket PC and use it instead of your Palm. Is it that important to sinc the Pocket PC to your home computer right now? Or is it more important that it can talk to your work computer?

Or maybe even print out the schedule at work.

I suggest that before you buy any more hardware that you try leaving most of your devices at home for a day or three. Just try taking to work the few things you actually need for work. Then think about what else you need for your music and private files. You might be surprised at the compromises that come to mind once you've thought about it.