The Wikipedia disambiguation page for “synchronicity” lists one of the meanings as “A goal or result of synchronization.” I mention this just so you aren’t expecting me to talk about anything exciting here, like Jungian psychoanalysis … This is just a boring post about how I’ve figured out ways of syncing my laptop and my new iMac in my office without purchasing an expensive .Mac subscription. Having a second computer is a blessing of sorts – I don’t need to cary a laptop on my bike everyday, but it also creates new challenges with data being created on two systems. If you don’t have this problem, go read something a little more interesting.

What do I need to sync? Most important is e-mail, followed by my iCal calendars, AddressBook, to-do lists, web browser and rss reader content, my internet passwords, and any files I happen to be working on at the moment. Here’s how I’m handling each of these challenges:

(NOTE: Although I mentioned an iMac, many of these solutions are cross platform. I’ve highlighted those solutions which are Mac-only)

1. E-mail. That’s easy. I use IMAP instead of POP. My IMAP server of choice is Luxsci, which has never let me down in all the year’s I’ve been using it. Tech support has always been reliable and nearly instant. Fastmail.fm is cheaper, and has a nicer webmail interface, but I’m happy with Lusxsci and don’t want to mess with a good thing.

2. For my iCal calendars I have a two part solution. First, I have a WebDav drive courtesy of my lifetime account with TextDrive. Second, I use a neat tool called iSynCal [Mac-Only] to synchronize my calendars with my WebDav drive. So far I’ve encountered a few hiccups setting it up, but it seems to work well and the developer is very responsive.

3. For my AddressBook I use Plaxo which I’ve been quite happy with.

4. For to-do lists there are lots of choices these days. I could just use iCal’s to-do lists, but I need some more flexibility. Up till now I’ve been considering Kinkless GTD [Mac-Only], but that isn’t very good for syncing between computers. I also don’t see any other reason to fork out money for OmniOutliner Pro [Mac-Only] when I already have the basic version. [NOTE: Omni is working on a dedicated GTD solution which should be quite nice when it comes out.] I could save it on my WebDav or JungleDisc (see below), but I’m also not crazy about how Kinkless requires constant manual syncing. A better solution seems to be something online. Zenlist.com looks great, but the software it uses is still lacking a lot of features, like hierarchical to-do lists which I consider a must. I also don’t drink the GTD kool-aid, especially since the very concept of “contexts” is nearly useless when you are always in front of your computer. The best option right now looks like Tasks from Alex King. I prefer desktop applications to online ones, but until Omni releases their dedicated task management program Tasks looks like the best bet.

5. Google Browser Sync for Firefox is very reliable for keeping my open web pages, bookmarks, cookies, etc. in sync. But for some reason it always ignores the fact that I have Gmail open! Del.icio.us is also very useful when browsing on multiple computers and browsers – especially now that you can keep some things private. The Del.icio.us Firefox extension is pretty good, but I’ve recently started using WebNoteHappy [Mac-Only] which is looking very promising.

6. NetNewsWire [Mac-Only] now offers excellent synchronization features via NewsGator.

7. I’m still stuck looking for a good password syncing solution. I use PasswordWallet [Mac-Only] for my important stuff, like bank accounts, and Password Maker for less important stuff – but neither seems well suited for synchronization across computers. (Although PasswordWallet does sync well with my Treo.) I guess synchronization doesn’t mix well with security concerns.

8. For the rest of my stuff, like files I’m working on on both computers, I use Jungle Disk. This could potentially solve some problems with syncing other things, like my to-do list and my passwords, but the added step of syncing between local and remote drives does make life more complicated and I’m trying to simplify. Several new online tools also allow you to work on the same document from multiple locations. I’m particularly fond of Writely, which I’ve been using a lot lately – but I think it is mostly useful for collaborative projects.

That’s my list. If you have any other tips or tricks for achieving true synchronicity, let me know!

UPDATE: iSynCal is just too complex and resource intensive for me. I paid for it, and the devleoper is great, but I think I’ll do something simpler: create a single calendar on my office computer which I subscribe to at home, and subscribe to all the rest of my calendars at my office. I’ve done that before and it works pretty well. Plaxo is planning to include iCal sync for OS X at some future date, and I’ll revisit the issue then.

For all my daily files: notebooks, citations, documents I’m working on, etc. I’ve decided the best solution is a USB drive. Uploading to Jungle Disk is just too slow on my home DSL connection. I also discovered a great application which allows me to specify folders I wish to keep in sync between my computer and my USB drive. It is called CronoSync and it is very easy to use. For instance, I can create a single folder full of aliases to files & folders I want to sync and it will include them. I can also mark items I don’t want to sync with a “label” in the finder.

Finally, Password Maker doesn’t offer two-way sync, but you can manually upload and download to a WebDav or FTP server pretty well.

It has all taken some work to figure out what I needed – but most of this seems to work pretty well without thinking once you’ve set it all up.

UPDATE: For the rest of my files I gave up on the Chrono-sync + USB Drive solution since having to sync twice was both annoying and prone to trouble. I figured out how to connect to my office computer directly from home over the network, but found Chrono-sync was too slow for that. However, I then discovered Unison which is great. It is a command-line tool, so it isn’t for everyone (there is a GUI but it doesn’t much help if you don’t understand the command-line). Still, Unison is basically rsync on steroids. Here are some links to how-to guides for Unison.

UPDATE: A few months later, I’d like to report that Unison is still working great. I no longer use NetNewsWire, having switched to Google Reader, and there seems to be a new option on the horizon for iCal. (And regarding IMAP, I’m glad I stuck with Luxsci, as Fastmail seems to have had some issues this year.) I should also point out that Writely is now Google Docs.