It’s done: I’ve moved all of my e-mail over to Gmail. Folks at Google, please don’t let me down.

So how did I go about doing it? Let me tell you…

Step 1: Rationalize E-mails

I had almost 2GB of e-mail data and many thousands of e-mail messages in my Thunderbird Profile. I knew a lot of that was crap, redundant, and no longer needed so the first thing I did was whittle this down to about half a gigabyte of data and under 10k of e-mails.

The cool thing with Thunderbird is that you can sort your e-mails by attachment. That made it easy to find messages with big attachments and then either get rid the attachments while retaining the text or delete the e-mails outright.

I also deleted tonnes of other e-mails that I knew I wouldn’t need in the future. Indeed, as you may have gathered, I was brutal in my deletion criteria.

Step 2: Rationalize Contacts

Next, I exported all my contacts from Yahoo! Mail and Orkut and imported them into Thunderbird, which is my central contacts repository (I even have my old Outlook contacts in here) and is the easiest to mess around with. I then went through that list: updating, removing duplicates, and deleting old contacts.

I also went through my list of Facebook friends and, for those who weren’t already in my address book (only 3 or 4 of them), I added their e-mail information as well. 

I then exported that updated list into a CSV file. This file I imported into Gmail. For the heck of it — and to test how well it worked — I also imported that file into my Yahoo! Mail and Hotmail accounts. It worked just fine.

Step 3: Upload

Uploading thousands of e-mails to Gmail isn’t easy. There are two things you have to watch out for: First, it’s safer to upload e-mails (i.e. drag them from a local folder into a Gmail IMAP folder) in smaller batch sizes: ideally under 30 e-mails at a time. Second, don’t start uploading the next batch immediately after the first one has finished uploading: give it a few seconds. Why? Because the Gmail IMAP system has spam-blocking and load-controlling algorithms built into it. If you flood it with e-mail uploads — either too many or too fast — it locks you out for a short period of time, which is a real pain.

All of this makes uploading e-mails a long and somewhat tedious process though it’s not the end of the world. In fact, I did most of it in the background, which made it quite easy to do: I’d be working on other stuff and, every few minutes or so, I’d Alt-Tab to Thunderbird and upload another batch.

Step 4: Use

Now comes the fun part: actually using the new system (which I described in an earlier blog post). I now access all my e-mail either through Thunderbird (via IMAP) or a web browser (usually Firefox). Meanwhile, I’ve stopped Thunderbird from automatically checking my POP accounts. Instead, all those are POP-ed directly into Gmail, which has the additional benefit of drastically reducing the spam I get.

I still use Thunderbird when sending messages from my MBS account since I use a different e-mail signature for that but, otherwise, I’ve found it easier to move entirely to using Gmail’s web interface. Not having both an e-mail client and browser open all the time also consumes significantly fewer computing resources which, on my ancient laptop, is a real blessing.

What I do lose from not using an e-mail client are the event reminder pop-ups that I used get but I’ve found a workaround for that: I’ve configured my Google Calendar to send me a notification via e-mail and I’ve installed Gmail Notifier so I get a pop-up when that notification e-mail arrives. It’s not quite the same thing but, like I said, it’s a workaround.

Conclusion

All in all, I am very happy with my decision to move to Gmail and the way in which everything has worked out so far. Here’s hoping things continue to go this well in the future.

Oh, one last thing: When I do get a new laptop (tablet PC, actually), I might start using an e-mail client again. What I’ll do then is configure IMAP to maintain offline (i.e. local) copies of all my Gmail folders. That way, I’ll get the best of both worlds: e-mails available locally and in the cloud, both always synchronized. Also, you can never have too many backups, can you? :)

I truly am a geek. I am working on a new taxonomy for my e-mails (all of which I’m moving to Gmail, by the way) and…well, I’m having a really good time planning it all out!

The thing is: I’m a very nested-folders type of person so switching to the labels-and-search model is a little scary. Why is it scary? Because, other than the default folders (inbox, sent mail, etc.), I currently have 172 — yes, that’s one hundred and seventy-two — folders in Thunderbird. And I’m trying to cut that down to about 15.

The reason I can do this (quite easily, in fact) is that most of my existing folders are second-level folders: one for each mailing list that I subscribe to, one for each MBA course that I’m taking, etc. So really I have just 37 top-level folders. Actually, even that’s too many because, back in the day, I gave sites that I’m a paid member of their own top-level folder so those will now go. I also have a couple of temporary folders in there. I’ve been meaning to do a good folders rationalization for a couple of years now but I’ve just never gotten around to it. I guess this is my chance.

The good thing — which is making this move much less scary — is that, having used Google Web Search and Desktop Search for years now, I’m pretty confident that, even with 15 folders instead of 172, finding old e-mails shouldn’t be much of a problem.

The New Taxonomy

The key change I’m making to the taxonomy is that my labels will not be about who the e-mails are from — the taxonomy I’ve been following since the mid-90s that has served me well — but what the e-mails are about – the taxonomy I started to move to a few years ago (and which, obviously, I use for my blogs).

This lends itself well to the whole labels concept because an e-mail can be about more than one subject. So, for example, an e-mail sent from my sister about an Internet meme will get the ‘Funny & Forwards’ label. However, if she also wrote some family stuff in that e-mail, I’ll also attach the ‘Family & Friends’ label to it. Neat, huh?

The challenge, of course, is in coming up with those few, most useful labels. Here’s what I’ve come up with so far:

1. Friends & Family — e-mails about (you guessed it) friends and family
2. Funny & Forwards — jokes, forwards, memes, etc.
3. Life Admin — e-mails from banks, utilities, ISPs, etc.
4. Lists & Sites – e-mails from mailing lists and sites I am a member of
5. LUMS — old e-mails from my undergrad days as well as current alumni-related e-mails
6. MBS — all course, admin, alumni, etc. e-mails
7. Music — old and, in the future, new band-related e-mails
8. Nadia — a whole separate label for my wife since she is, after all, more than just a friend or family member
9. Saved Stuff — stuff I want to keep for future reference that is not a funny or a forward (i.e. articles and the like)
10. Sites & Projects — stuff about non-work websites I maintain or about various projects that come up
11. Temp Bukkit — e-mails that I’ll catch up on the weekend but want out of my inbox for now
12. Work — all work-related e-mail (I presume I’ll be maintaining another taxonomy in my work e-mail account)

Just twelve?! Not bad, eh? :)

Of course, as with any taxonomy, I expect this one to evolve over time. So far, though, I think it’s an accurate representation of all the e-mails I currently have in Thunderbird. And if it isn’t, I’ll probably tweak it as I upload my e-mail to Gmail (either that or I’ll delete the e-mails instead!). Meanwhile, I’m quite pleased with this list. Now…let the uploading begin!

For the two people who read this blog: what taxonomy do you use for your e-mails?

I have three primary e-mail accounts: Melbourne Business School, Yahoo! Mail Plus, and insanityWORKS.org. I also have three secondary ones: The University of Melbourne, Gmail, and Hotmail. I forward UniMelb to MBS, Gmail to Yahoo!, and I check Hotmail via a browser periodically. I POP mail from my primary accounts to my laptop and I use Mozilla Thunderbird as my e-mail client. That is:

When I’m away from my laptop, however, I usually only check my primary accounts. To do that, I use the MBS webmail interface, Yahoo!’s excellent webmail interface, and I POP my insanityWORKS mail into Yahoo!. That is:

This system has worked well for the last seven years because I’ve always had one primary computer to work on (which, for the last four years, has been my laptop). Now things are starting to change and I’m tempted to (a) move all my e-mail online and (b) move to one primary e-mail account (Gmail) and five secondary ones (all the rest). That is:

Here’s why…

Three Major Changes

First, I’ve become a lot more mobile and I increasingly want access to all my old e-mails (and some of my data) regardless of where I am and which computer I’m working on. This wouldn’t be a problem if I was to carry my laptop (and, therefore, all my e-mail and data) with me everywhere I went, but that’s not something I want to do all the time. Also, in the future I want to use my phone to access my e-mail and I simply can’t do that with my current setup.

Second, cloud computing has come a long way over the last couple of years and Yahoo!, which is by far my preferred e-mail provider, lacks a number of cloud computing features that I really want. For example, Google Reader is much better than Yahoo!’s RSS reader and Microsoft’s SkyDrive is much better than Yahoo! Briefcase. I also prefer Google’s Calendar to Yahoo!’s, I really like Gmail’s labelling mechanism, and Microsoft’s Live Mesh sounds very exciting as well. In other words, I want to start using cloud computing-like services and Yahoo! alone isn’t giving them to me.

Third, we live in an increasingly connected world. My current system of downloading all my e-mail to my laptop works well because it assumes that I’ll be doing a lot of e-mailing (and, in general, computing) offline and from one computer. Increasingly, that is not the case. Instead, I now use communication tools like Facebook and Twitter for which you need to be constantly online, I don’t limit my e-mail usage to just my laptop, and I even access the ‘net and my e-mail through my mobile phone (though I don’t do much of that right now because it’s really expensive on my current phone plan!).

Two Implications

This means two things. First, I am seriously considering moving all my e-mail to the ‘cloud’. I want this for seamless and synchronized e-mail access across multiple computers and devices. And since I am frequently online (or at least in mobile phone signal range) not being able to access my e-mail because I don’t have an Internet (or mobile phone) connection is no longer an issue.

For this to work, though, I will need an IMAP-based e-mail solution and not a POP-based one. IMAP will not only let me sync my e-mail across multiple computers and devices, it will let me work offline (before re-syncing) as well. 

Second, because of that IMAP requirement, I am seriously considering making Gmail my sole primary e-mail account. In fact, I’ll start to POP e-mail from all my other accounts into this one as well (see diagram above).

Why? Not only is Gmail the only one that offers IMAP (which is why it should be my only e-mail interface), it’s free and it gives me tonnes of storage, great calendar integration, and excellent e-mail search capabilities. It is also reliable, universally accessible, and, once I switch, I won’t have to take regular backups of my e-mail folders any more.

I could, of course, use other (paid) IMAP services, but I think I’d be better off using Gmail for all the additional benefits I get from it.

One Decision

So I have a big decision to make. Do I move all 2.1GB of e-mail archives off my laptop, out of my direct control, and into the cloud? Some people have done that and are happy with it. Others didn’t have such a great time. Until I try it myself, I don’t know how things will turn out for me. What might be useful, though, is if I was to do a bit of e-mail housekeeping before uploading everything to Gmail. Doing that would be a pain up-front, but it would make life a lot easier going forward.

Actually, maybe the bigger issue is this: should I commit myself to using only Gmail (via IMAP) from this point on? I guess another way to think of this is to ask myself whether this is better than the status quo. That is: should I commit myself to using only my laptop (with occasional backups) to store all my e-mail? Or, to get the best of both worlds, does it make more sense to store my e-mail both on Gmail and to maintain a local copy of all that e-mail in Thunderbird as well? The answer, in theory, is pretty obvious. Naturally, it’s much harder to go ahead and actually implement the solution.

I think I’ll start off with a baby step: I’ll activate IMAP on my Gmail account and will start using that with Thunderbird. I’ll even try uploading copies of some of my old e-mails into Gmail to see how it goes. If that goes well, I’ll spend the next few weeks moving all my folders over one-by-one. Before I know it, I’ll be good to go. Let’s just hope things go as smoothly as I’ve just made them sound!

Want a deeper and most awesome analysis of the recent WGA strike? Read Matt Prager’s essay on Lawrence Lessig’s blog.

Or is it a debacle only when, say, Microsoft does it but a minor PR issue when Apple does it? Whatever.

I’ve been meaning to write about this for a while now, but haven’t gotten around to it (the last week of my MBA starts today! Yaay!). Meanwhile, Paul Thurrott’s gone and said pretty much what I wanted to say in his article: Apple lofts middle finger at PC users, PC users thank Apple for acknowledging them. Of course, he says it much better than I ever could (and with a lot more authority, being a tech journalist and all) but that’s okay.

Peter Gabriel, one of my all-time favourite musicians, continues to be at the forefront of technology usage — particularly when it comes to technology for music and human rights:

• Back in 1993 he launched Xplora, the first music and multimedia CD-ROM created by a musician
• In 1999 he helped set up OD2, which was one of the first online music download services (and is now owned by Nokia)
• This year he is MIDEM’s 2008 Personality of the Year (more on PG & MIDEM from Reuters)

On the human rights side:

• In 1992 he co-founded WITNESS, “an international human rights organization that uses video and online technologies to open the eyes of the world to human rights violations”
• In 1999 he started TheElders.org, which is a “new gathering of world leaders who [have] come together to guide and support our ‘global village’”.

So it’s no surprise that he is involved in recent areas of music technology as well:

• First there’s we7, which is a free, ad-supported music download community
• Then there’s TheFilter.com, which is a music, video, literature, and news discovery service (more in this CNET article by Greg Sandoval)

Both sound really interesting and I’ll write more about them once I’ve played around with them a little more.

[More PG: Wikipedia, Last.fm, Real World Records, WOMAD]

Inspired by the hard-core science fiction of Arthur C. Clarke that eventually became real science, awesome article in Popular Mechanics on The 10 Most Prophetic Sci-Fi Movies Ever.

I’d heard a couple of Jonathan Coulton songs before but, thanks to this episode of TWiT, I went and explored more of his music…and I love it!

If you’re a geek and you love good music with fun lyrics, be sure to check him out. I mean, who couldn’t love these lyrics:

Heya Tom, it’s Bob from the office down the hall
Good to see you buddy, how’ve you been?
Thing have been OK for me except that I’m a zombie now
I really wish you’d let us in
I think I speak for all of us when I say I understand
Why you folks might hesitate to submit to our demand
But here’s an FYI: you’re all gonna die screaming

All we want to do is eat your brains
We’re not unreasonable, I mean, no one’s gonna eat your eyes
All we want to do is eat your brains
We’re at an impasse here, maybe we should compromise:
If you open up the doors
We’ll all come inside and eat your brains

[From Re: Your Brains]

:)

Both Gotta Be Mobile and Tablet PC Review have recently published their reviews of the Toshiba M700 tablet PC:

• GBM InkShow: Toshiba M700 Tablet PC Overview — Matt Faulkner
• Toshiba Portege M700 Tablet PC Review — Tiffany Boggs

Both are positive and both have reinforced my decision to buy the M700 as soon I can afford it. Things may, of course, change over the next few months but I doubt any manufacturer will come out with a machine that tops the power, versatility, and customisation options of the M700.

Naturally, Hinckley has a day #13 in his Twelve Days of InkSeine series of posts!