That Sync'ing Feeling

You know the situation. You might have a Classic-sized planner stuffed with D*I*Y Planner templates. You tote a Hipster PDA in your guidebag or purse. Somewhere, there's a Palm you sync with Outlook, online calendars or Palm Desktop. Then there's the array of Post-Its cluttering your monitor, the stack of index cards by the phone, a Moleskine yearning to be used, a notebook you tote to meetings, and so on. Slowly, as you come across neat ideas to boost your productivity, you take on more and more ways of doing things, your system begins to fracture, and your trusted system erodes. And the single most important plea, among all the lone voices crying in the night? -- "How do I make it all work together? How do I 'sync'?"

I've going to have a whirl here at addressing one of the most commonly asked questions posed of me in the past couple of years: how does one "synchronise" information between different sources, if you're going analog? In other words, how do you keep all your information up-to-date, whenever and wherever you need it, and still have it reliable enough to be trustworthy?

I've waited some time before writing this, for several reasons. First, every person using a hybrid system (i.e., one with multiple components, either analog or digital) presents a completely different set of variables. Second, the rapid changes underscoring digital time management, as well as productivity methods, makes it unrealistic to pin down an "average" way of doing things. And third, I wanted to make sure I fully understood and confronted the problem myself, and experimented until I had something I was happy with.

Let's talk a little about simplification first, since this is the core problem for most of us. We tend to love tinkering, and seizing upon ideas that hold some degree of hope for the chronically disorganised. Ironically, this just makes our organisational problems far worse. I've spoken before about the Beginner's Mind, and the need for simplification. If you have so many ways of "being productive" that it works against you, I want you to answer this question: "What, of all the materials that you play with or produce, do you actually need to use?" Being a pack-rat, and one that likes to experiment constantly, the first time I forced myself to actually answer that question was a real eye-opener. Oh, all the stuff I thought I needed.... If you haven't already read the Beginner's Mind article, please do so. Come up with a list of those things you actually need to track.

The next step is figuring out what environmental variables have to be considered. For example, do you need to share your calendar online with colleagues? Do you need access to thousands of contacts at a moment's notice for project management purposes? Do you need to take rapid notes or sketches when someone else is talking? Do you need to travel light, work in the dark, carry information to disperse, or be in a place where you might not have easy access to electricity? Answering these questions will help you decide upon the media type of your productivity aids (being planner, hPDA, Palm, laptop, online apps, etc.). What overlap is there between your tools? For example, do you really need to carry a notepad when you can write in your planner? Do you need to carry a Palm when the information can be synced to your cell phone? See if you can reduce your system to just two aids.

I hear your cry -- "But how will I do without all my favourite things?" Ask yourself this: pound for pound, ounce for ounce, what do you actually need to carry? By way of illustration, I know people that go backpacking lugging 150 lb sacks; mine rarely weigh more than 20 lb. Penalise yourself for carrying each ounce that you don't need, and your back will thank you. Small but efficient multi-use items will truly demonstrate their worth. They may be tech, or they may be analog. This reduction of devices is vitally important to staying on track.

Now that we're clearing ourselves of the clutter, it makes our synchronisation problem a little easier to deal with. So, now, let's talk about the hub. By "hub", I mean a centralised a priori archive of information that auxiliary aids can use. This way, the hub is the trusted source, and all other productivity devices can feed to and from it.

The key, I've found, is to create a trust for each type of information. For example, my main contact hub is digital: the Apple Address Book which syncs automatically with my Palm and iPod --I only write down the most important ones in my planner. In other words, my Apple Address Book "feeds" my planner. I make a digital change, and if it's an important contact, I mirror the new information on paper. There's only a few dozen contacts in my planner, and they change so rarely that this isn't hard at all.

On the other hand, the calendar and task lists in my Day Runner form an analog hub. If there's information that I need to put, say, online, then I'll block off the time there with skeleton details. In other words, all the important information, such as meeting location, attendees, driving directions, etc., are in the planner, and my online calendar just reads a three-hour block for "Off-site consultation meeting". Just copy what you need. You'd be surprised how little that is, most of the time.

Let's illustrate with another example: Projects. Now, you've probably noticed that the latest D*I*Y Planner templates encompass quite a number of project forms, and (hopefully) provide places to prompt you for all the information that you might otherwise have neglected to record. I use these forms to keep track of major projects, each in a different tab in my planner. "But how about email and meeting notes?" you cry. Ah, here's where we hit the fourth concept: distillation.

We experience thousands of pieces of significant information a day, and we'd be fools to track it all. We'd spend so much time recording that we'd never get anything done, and woe to us if we needed to find something. For example, think about your email. For all the text that you actually receive in a message, there may be one important point that needs to be recorded and acted upon. The idea here is to filter out the crud and select those things which are absolutely necessary. Sure, you can save that email in one of your mailboxes, along with the thousands of others, but take your primary points and note them in your hub. I remember an eight-hour meeting where I took some forty pages of notes. Out of that, I distilled the information into one page of significant bullet points, which were then copied into my planner's project tab and the relevant portions of my calendar.

So spend a little time to distill your mountain of data into relevant points, and synchronise these into your hub. What an amazing exercise it is --gaining that overview and perspective-- and so beneficial to productivity!

And lastly, we have to remember to synchronise regularly. I liken it to a garden. A few minutes a day of weeding keeps your plants and soil clear. Leave it for a few weeks, and not only will your flowers and vegetables suffer, but you'll have to spend a back-breaking day on your hands and knees. And guess what? We'll never make time for that, because we're so busy otherwise. The longer we go without synchronising, the further our system breaks down, to the point we can't rely upon it. If you can't sync right away, pair it with your daily review, and force yourself to keep on track.

So, to review the best way of streamlining the synchronisation of our productivity aids:

  1. Simplify the information to be sync'ed
  2. Reduce your aids to the minimum you actually need
  3. Choose a trusted hub for each type of information
  4. Distill your mountains of data into relevant points and tasks
  5. Synchronise regularly, else you lose your trusted system

It's not that difficult to keep your information timely and accurately across different aids or devices, but it requires some planning and just a little effort on your part. While every situation is undoubtedly different, the above process should still offer a glimpse of hope to the chronically disorganised, whether one's main tools are digital or paper, or both.

I'm eager to hear from others who keep multiple tools working together in an efficient manner. Any other tips? Please leave them below.

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I actually sat down on my

I actually sat down on my couch last night with my Moleskine (just began using one a few weeks ago) and started mapping out how to get organized with all the tools I have. So, this is a very timely post for me. After a few years of using a PDA, I really only use it to have information (contacts, calendar, notes synched with Outlook) at my disposal wherever I am... if I carry it. I rarely actively use it to input information and interact with it from day to day but I mostly use it as a reference. I just bought a 30 GB Video iPod which I'm sure will accomplish those things for me. I should be able to sync notes, contacts, and my calendar with it to have with me when I'm away from the computer. I'd hate to carry a PDA, iPod, and a moleskine around with me all the time. Most often, the PDA gets left at home which pretty much defeats the purpose of having it.

Thanks for the great ideas. It's a big help at this stage in the process. I'd be interested to hear how others are using their iPods in these situations.

It's all abou the hub...

"I rarely actively use it to input information and interact with it from day to day but I mostly use it as a reference."

This could've been me talking. :)
My PDA has become simply a pocketable reference book for needed information.

This article is a very good analysis of the problem of combining a digital and analog system. Lots to think about. I think the "hub" is a particularly key concept.

With work it's best to just start.

Apps that Print to Hipster?

Good suggestions!

I'm looking for a way to format and print from an electronic calendar/contact/task application. There are a few scripts and tricks to get something out that will fit in a Hipster. I'd really like to get a Hipster formatted page of the daily summary type screens Korganizer, Outlook, etc.. offer.

Maybe if an application can generate content, various CSS could be created for for individual's Hipster/Planner format.

This is exactly the problem

This is exactly the problem I'm wrestling with now. I have my accounting system in one binder--an invoice book, timesheet book, deposit slips and slash pockets for open invoices, paid invoices, deposits to be made, etc. Then I also want to journal every thing I do that I may need to refer to later, and I also want a calendar that will have the week on one page, vertical. And I'd like to combine the accounting binder, calendar, and journal so I could carry them all together in my purse. In a lightweight analog solution that won't break my back. Probably impossible.

But thanks for opening up this subject. I was feeling really stupid for not having solved this problem. It's good to know I'm not alone.


Great article. My biggest problem right now is how to keep all my passwords with me, encrypted yet instantly available? If I could find a way besides my pda/laptop to keep them, I could lose one more piece of "stuff" that I have to carry around with me.

Can an iPod store things like this?

Yes, but...

Yes, but...

I can subscribe to every word you wrote. Meanwhile, I've reduced the stuff I carry around to a Palm Treo, a smartphone which doubles as a phone AND a PDA. Just need this for storing the approx. 1,200 contacts I might need any time. And a small notebook which fits in my jacket pocket, yes, for taking notes.


I'm not happy with the calendar solution. I have this stored in my Treo, of course, but I feel I lack a paper planner to visualize my time planning. Needless to say I don't want to carry around something heavy like my filofax of old. But what else could address this need?

For the moment, I'm using the great idea of pocketmod (, having a folded piece of paper in my shirt pocket which I replace on a weekly basis (the paper, not the shirt) and which contains my appointments, to-do-things etc. for this week. However, this won't work for next week, or next month.

So, some combination of notebook and calendar might be useful. And it has to fit in my pocket. Still looking for something I like...

A single cipher

I once knew a very smart gentleman who used a single complex cipher for most of his passwords, he only needed to keep a copy of the cipher on him becuase the password was always an cipered version of some key fact about that site (I think it was IP, but it was a long time ago).

As every school boy knows...

Sarah why not try writing your passwords in cypher?

40something, the D*I*Y Hipster or its calendar combined with a notebook may suit your needs better than a Treo.

Sardonios, I don't feel like

Sardonios, I don't feel like writing 1,200 address sets into a hipster... also, I like to have a backup. What should I do, copy the stack of cards?

hPDA Calendars

I could be wrong (I often am), but I think Sardonios was actually referring to the Hipster PDA Edition calendar templates for keeping track of appointments, meetings, etc., and not the contacts. Unless your days are really jam-packed with meetings, one "flip" card for each month should suffice. Fuller days might necessitate the weekly or even daily cards.

I keep my uber-contact-list as digital too, and only write the most important ones in my planner or hPDA.

all my best,

T'is true...

You are right Doug, I just threw a couple of quick replies together before going to bed. Hmmm, bed-time again. History is repeating on me. :O

Writing them in cipher...

You mean something simple that I can calculate in my head as I go? Hmmm I've got several hundred passwords... some quite complex.

A password system

Yes, I mean that your passwords do need to be unique, but they don't need to be unrelated, as long as the realtion is non-obvious. It is also handy to key them to site features so that you can quickly determine what this passoword is:
For example say I start with a # for all sites that involve fitness then a simple alpha-numberic ciper of the first three letters of the URL then the TLD backwards (or something of the like)
It works for casual use site, but you need something more sophiscated for a site that demands regular changes
(no I don't actually use this system)


Yeah, I'm not talking about website passwords, I can usually just remember those. I'm talking about root and administrator passwords for major systems. Don't want those lying about on sticky notes... or easily discernible.

Cyphers, keys and hints

Back in my Cornucopia of Planner Tips #1, under the section "Vaguely Insane Tips", is a couple of ideas. One that might make sense, especially if your passwords are very random, is using a "key" that you keep in your wallet. Whenever you forget a password, use the key strip to decode your password. It shouldn't happen too often that this becomes a nuisance.

all my best,

I don't know how much use this would be to others

but as a child I was required to memorize poems for an elocution class. Believe it or not, I can still recite those poems -- word perfect -- decades later. So I use them to generate my passwords. :)

I have 'assigned' a particular poem to each category of passwords, for instance "Casey at the Bat" might be used for anything to do with financial matters, while "Ozymandius" could be for work matters, and "Lilacs Once Grew" for store sites. I translate the first three letters of the 'significant' part of the web page name into numbers using the old a=1, b=2, c=3 system which will point to that that number word in the poem.

Then I pick a pair of random two-digit numbers. I use a simple mathematical method of converting one two-digit number into a different two digit number which I won't bother to explain -- there's got to be a zillion ways of doing that, any will work.

All that I have to write down on paper is enough to ID the page in my memory plus the two random numbers.

Suppose I had an account at Dutch National Bank. The written entry on my password card might read: Dutch Nat. 34-22

To recreate my password I translate DUT into 4-21-20, mentally recite my 'financial' poem while counting on my fingers to find the 4th, 21st, and 20th words. The password is:

[the first two letters of word 4] [the number '34' converts to] [the first two letters of word 21] [the number '22' converts to] [the first two letters of the 20th word.]

It may sound complex, but it takes only a few seconds to recreate the password, and without knowing the exact poem I'm using, I defy anyone to get from DUT 34-22 to, hmmm, th19sa75aa

Oh -- and to simplify life, I use a single 'junk' password on all sites where I really don't think anyone would bother to hijack my account or it wouldn't matter if they did. I mean, do I really NEED to protect my account at a freebie game site?

And on the pedestal, these words appear:...

This is very similar to the system I use Susan. However I cannot claim credit for it, it was used by British intelligence during the second world war. The historian M. R. D. Foot wrote a piece about it but I cannot find a link. I can say that anyone who has tried to decipher one of my e-mail will testify to its effectiveness. ;)