Staying Organized in a Digital World

I am very anal when it comes to staying organized.  I obsess over very small things and I am constantly making to-do lists, or managing things on a calendar.  I offload as many standard things I would otherwise have to remember, such as bill due dates, onto a calendar system.  I find my day to day life is much more enjoyable when I can put my faith into other systems for remembering when things are due.  If you can trust your calendar to remind you when a bill is due, that leaves your brain open to focus on other, more important things.

My biggest issue with staying organized has always been related to the world of computers, however.  As much as they help, they tend to make an obsessive person such as myself want to have access to everything from everywhere, since something like a calendar is only useful when you have access to it.  I am going to try to describe my digital world, and how I have it set up to keep me organized.  My system has many flaws but it might be able to help others in similar situations as myself overcome their daily mess.  I would love to see some comments and suggestions though, in case anyone has a better way to do the things I attempt to do.

My digital world consists of 3 facets, Work, Home, and On-the-go.

Work:

Work Issued Laptop
Work Issued Blackberry
Access to work, from home.

Organizing my world of work is easy.  I have a laptop and a blackberry both of which tie into each other seamlessly.  All of my unix accounts and home directories are synchronized and shared.  I have access to my work calendar and emails from anywhere thanks to my blackberry and I can log into my work VPN from anywhere I can get internet access.

Home and Mobile:

I make no effort to integrate my work world into my home world, since there is no real need to.  The blackberry pretty much takes care of having everything I need for work at home and on the go.

So lets take work out of the mix and focus on at home and on the go; this is where things get complicated.

Currently my girlfriend and I have between us:

• 3 Desktop Computers
• 2 Laptops
• 2 iPhones
• 2 Web Servers
• 1 Digital Camera
• 1 Collection of Photos
• 1 Collection of MP3s

Most of this, of course, is mine, but we try to keep everything centralized and in-sync.  We both want access to all of the music, photos, and calendars.

On a regular basis I use my Windows Vista x64 desktop and my Macbook Pro.  Both my girlfriends PC and Laptop are Windows XP Pro.  The 3rd Desktop PC is a Dell e521 running Leopard which I simply use to experiment with.

I have several things which I need to remain consistent:

• Bookmarks
• Calendars
• Contacts
• Email
• Instant Messaging
• Music
• Notes and Lists
• Photos

Bookmarks used to be really easy.  Using Firefox across all of my systems, Google Browser Sync made having all of the same web bookmarks everywhere, very easy, even on my work PC.  Now that it is not supported on Firefox 3, I have switched to Safari full time on my mac and I use Del.icio.us to organize my bookmarks.  It takes a bit more discipline to use, but it gets the job done.  I know there are other options for syncing bookmarks but I actually have grown quite fond of del.icio.us.

Calendars is a bit tricky, but we have a setup which works quite well.  My girlfriend and I both have google accounts and use google calendar.  We both create calendars and privately share them across to each other using full access so we can both essentially manage one calendar which we both share but each maintain our own separate accounts with google.  If you share a calendar with full access, and both maintain the same list of calendars you are basically both looking at, and have full access to, the same exact calendar.  On my end, I sync my google calendar with iCal by simply subscribing with one-way access to it.  I do not usually update my calendar very often, but she does.  She uses Microsoft Outlook.  After much searching and trial and error I greatly recommend using gSyncit for 2-way access to your google calendars within outlook.  It is the best solution I was able to find.  Using this solution she can manage our calendars from the web, outlook, or her iphone.  I can then use iCal, the Web, or my iPhone to view the calendars.  Giving us both access to all of our bills and appointments across all of our devices.

Contacts I am still working on getting a firm grip on this.  Having an up to date list of addresses for all of your friends is still unfortunately a highly manual process.  I simply try to keep my macs address book up to date as best I can.  FacebookSync is a neat little took to help you do some of the work.  Apple address book can also sync with google contacts, but this provided me with highly undesirable results.  Basically google contacts keeps a list of every email address you use, and when you sync your address book to that you get a ton of garbage.  I sync my contacts with my iPhone which keeps things pretty normalized.

Email is helped through the graces of webmail and IMAP as I have many email accounts.  My domain email addresses recently switched from self hosted email, which I got sick of taking care of, to google apps for domains.  So basically I have a couple gmail accounts all cross-pollenating to each other, and my domain emails are also essentially on gmail as well.  Whenever I check email on any device which is not my home computer I use webmail or IMAP.  On my phone I use IMAP, at work I use webmail, and when I get home each day I clear out the inboxes using Thunderbird to pull everything down on POP.  This allows me access to all of my email from everywhere while still having a long-lasting record of it kept on my home PC which has every email I have received for the past 10 years on it.

Instant Messaging is pretty much a no brainer.  Across all of my accounts I use Digsby on my windows platforms, and Adium on my Macs.  This makes everything stay consistent buddy list wise and keeps all my accounts manageable under one client.  I really don’t understand how anyone can communicate using multiple IM services and individual clients for each one.

Music is done very manually.  I maintain my entire 60GB music collection on my PC.  This is where I sync my iPhone for music.  All of my other devices such as my Xbox, Playstation, Laptops, and Girlfriends computers access my collection using my home network.  I also regularly back up this data to my linux server just in case I have a hard drive issue.

Notes and Lists are managed by a fantastic program not many people know about:  Google notebook.  They are basically like portable post-it notes which I use religiously.

Photos are sort of a pain having only one digital camera.  I maintain all the photos on my primary PC, and we do a similar thing as is done with the music.  The problem is making sure that all the photos we take wind up on my PC first.  If we are out and about and need to clear off the memory card and plug the phone into one of our laptops we need to be conscious of getting those photos onto my PC later.  It also prevents me from really being able to use things like iPhoto since it takes control of how your collection is organized.  Having my main photo repository on my laptop, via iPhoto, does not promote me having good access to the photos on my Windows based machines.  I have been making more of an effort to use Flickr in an attempt to centralize my access to photos a bit, but I am weary of putting ALL of my photos online.  Since I have my own server I attempted to use Gallery for a bit, but I didn’t like the feel of it.  My Facebook profile is linked to flickr so I don’t have to worry about posting photos for my friends to see in 15 different places.  I also sync selected galleries to my iPhone using my PC.

So as you can see I go to great lengths to remain organized in my life, and being a regular user of several different computers definitely complicates this matter.  The main two pain points are the photos and music collections.  I wish there was a better way to maintain these in a manner which is not only accessible from anywhere, but also easy to keep in sync with various devices.

The iPhone does have one major shortcoming which I would like to mention here as well.  It is a sync only device, and on top of that, it can only sync with one other device.  This means that for me, I have to choose what items sync to which computer, and stick with it.  You cannot manually copy music, photos, or anything directly on or off of it.  I have my contacts, email, and calendars set to sync with my Mac, and my photos and music set to sync with my PC.  Ideally, if I could sync my phone with both my PC and laptop it would bridge the gap and allow me access to everything, on both.  Instead it leaves me slightly more fragmented.  I cannot sync my contacts to my laptop and PC, which means my PC loses access to my contacts, and I cannot sync my music and photos with my mac, which means I must manually copy that stuff to my mac from my PC.

In closing, I feel the internet has come a long way as far as helping us stay organized goes, but I also think there is still a major convergence issue.  Even with all of the above efforts to keep my life as organized as I can, it still feels like everything is scattered about.  I think the future is bright, but we aren’t quite there yet.  If you have any tips for me, they would be very welcomed!