Leaving Google Mail

Google Mail is great. It’s probably the best combined mail-service-and-mail-app in the world. As soon as I think someone’s coming out with something that’s maybe-just-as-good, GMail kicks it up with something inimitable.

And, of course, their inimitable thing might be integration with a product that Google owns. After not-long, I was using my Google credentials to sign into apps. Then you had to sign into YouTube with your Google account. Then I was getting pop-ups and emails about Google+, a social network on which I’d never really found any of my friends.

However, as they say, if you aren’t paying for a product, then you are the product. Google’s goofy history of increasingly arbitrary decisions (decisions that never gave benefit to users, beyond giving Google more leverage with advertisers and thus paying for more years of GMail) finally got to me and I had to investigate alternatives.

Here’s what I learned:

You’re replacing your mail service and your mail app. I really like Google’s mail app, and I don’t really know all that much about mail services, so I knew I needed one that could ably replace both pieces of it. (And not necessarily the mobile apps and chat service and calendars and stuff, but we’ll get to that.) Your favorite feature of Google Mail (video chat, stars, all those apps that are built on top of GMail now) probably simply doesn’t exist elsewhere, and you have to suck it up and let go. (That’s how they get you.)

That sort of thing starts at a couple bucks a month. I didn’t really want to spend $10/month on email, when I already spend money on web hosting and owning my own domains. Fastmail has a great rep and fits the bill – because I wanted to use my own custom domain, I had to select one of their higher tiers, but

There’s a whole world of mail filtering I had no idea existed. I said that Google’s strengths aren’t matched elsewhere, but I’m having good luck with Fastmail’s spam filtering. But: do you set up mail rules to filter social, commercial, and pestering emails out of your inbox? One of Google’s inimitable features is that they will handle this for you. However, Fastmail supports something called Sieve which actually runs all mail through a script to determine where it should go. Look at this syntax:

if not header :contains ["X-Spam-known-sender"] "yes" {
    if allof(
      header :contains ["X-Backscatter"] "yes",
      not header :matches ["X-LinkName"] "*" 
      fileinto "INBOX.Junk Mail";
    if  header :value "ge" :comparator "i;ascii-numeric" ["X-Spam-score"] ["5"]  
      fileinto "INBOX.Junk Mail";

It’s not for amateurs (so there’s a GUI where a lot of this can be managed) but, for me, this is amazing. I keep a list of known noisemakers, commerce hounds, and social domains that makes filtering a breeze. (Actually, it’s not a breeze: maintaining the script and its data is a little obnoxious. But it’s mine, and it’s not written by Google, and it can’t be corrupted simply because advertisers have paid enough to defeat it.) I’m down to really truly inboxy stuff in my inbox, which is a huge deal.

It is a lot of work to change your email address. If you’re going to forward your old email to your new account, that’ll work, but I really wanted to be able to sunset my old email accounts and move forward with something that was new. (I’ve had my Google email address for 10 years, and my other main address for 16 years.) So I bit off everything at the same time: new address, new service, new app.

I watched my old addresses (which I still forwarded, naturally) and, one-by-one, went about the business of changing the email addresses by which they new me. From hardest to easiest:

  1. People. If you want to email a friend, how do you remember their email address? You might have a contact manager or you might just find an old email from them and reply to it. (Google Mail will suggest commonly used email addresses if you just start typing someone’s name.) None of these are updated automatically when I send out my “hey I got a new address” email. People are the worst.
  2. Companies who don’t give a crap. Lots of companies send email with no footer letting you get back to their site and edit your profile. All I could do was unsubscribe, and so I did. (Potential scope creep in any project: if the app should send an email, are you ready to think about every aspect of sending email, including allowing the editing of an email address?)
  3. Companies whose systems are tightly coupled to your email address. I have a number of accounts at places where editing one’s email never occurred to them. Apple was particularly bad. I’m still (eight months later) trying to convince iCloud who I am across all my devices. (How’d they not see that coming?)
  4. Companies who get it. I was actually pretty impressed by a lot of organizations who let me change my email no problem, so long as I clicked a link in an email to the new address, and almost all of them sent an email to my old email address just in case. Better yet were companies that had a concept of “membership” that would allow them to keep an array of email addresses. For a company like LinkedIn, that’s key: they want you findable by your “work email” no matter how many companies you work at over the years. But Microsoft has a similar system, and it’s really nice to be able to add a new email address without being logged out on all your other devices.

Long term, I’m really happy I did this. It’s not without effort or expense, but it’s where I am right now: too concerned with being sold to advertisers to sit comfortably with an ad-based service, and not wanting to run a mail server in my house.

An Outlook Mystery

I think it’s the case that a lot of developers spend as much time in Outlook as they do in Visual Studio (or their IDE of choice). As a matter of fact, I’m fairly sure that there are more Java developers stuck using Outlook than there are MS developers who are on a different business email platform. (Because what’s the other business email platform?)

I’m writing this up because I just found a bug (in my workflow, if not in Outlook), and it had certainly bitten me a few times before. But, before I share what I found, I’d like to share a couple of Outlook observations.

  1. It looks like Outlook’s gone away in Windows 8, but that’s not true at all. People open up their Windows 8 machines and fire up all of the full-screen, touch-friendly, formerly-known-as-Metro Mail client, and find that they can’t really do as much as they could in Outlook. Well, Mail is free like Solitaire was, and Outlook costs $100. So there’s your answer. I think they still expect you to install Outlook if you need it, and you do.
  2. Outlook plug-ins are to be avoided. I don’t know if it’s Outlook’s API/SDK, or if QA is harder with integrated software like Outlook plug-ins, but I’ve had really bad luck with them, even if they come from Microsoft. (One exception would be the Evernote plugin, which does exactly one thing – save what’s on the screen to Evernote.)
  3. Folders are for the weak. If I see you fishing through a mess of folders (per project, per sender, per month) it makes me sad. Old emails are empty husks or shells: they contain information, and your job is (probably) to get the information out of there and put it somewhere useful. (Not a folder.) I did a lot of this, too, until Google Mail trained me to search instead of sift.
  4. Make only as many changes to Outlook as you will remember if you wipe it out and start again. It is frustrating and confusing that Outlook does not remember your email signature (this is an application setting) when you switch from one computer to another. Properly configured, it remembers every email you’ve sent and received for a decade, but if you deck out the customizable ribbons (y’know, like they made them customizable) that’s something you have to back up and restore yourself. I generally live pretty close to software defaults anyway, but this is one area where I’ve had my heart broken enough and it’s not worth it.
  5. Archive, don’t delete. Speaking of Google Mail and customizations, I also got trained to get everything out of my Inbox and into an Archive folder. This is one of the rare modifications I’ll do to a new Outlook setup. True garbage goes into Trash, but everything else should be in the Archive for searching. (Because sometimes you need to refer back to the empty husks of email to refresh your memory.)
  6. One weird email trick to save your career. My other must-have modification is to set a one-minute delay on every email I send out. 60 seconds to reconsider that snap answer, reword an argument, or recant the response to a meeting invite can make a huge difference. Follow these mail delivery delay instructions, probably, and you’ll thank me at least four times in the next year.

So what’s the hiccup? My problem has been with the last item: delayed delivery. Outlook implements this (client-side, frustratingly) by setting a “sent” time that’s one minute in the future. So it sits there in the Outbox, waiting for its sent time to arrive, and you can “unsend” it by simply opening it. When it’s opened, that unsets the “send” flag. (When you send it again, it sends without delay, so don’t count on getting another 60 seconds to change your mind.) And I was noticing that more than a few of the emails I would send would be stuck in the Outbox, not leaving. This has been going on for years.

And what’d I just figure out? It happens when you combine wicked search skillz with that delayed delivery. A search for an old email (about “teapots” let’s say) will pull up a list of everything in Outlook’s influence that contains that word, so Inbox items, Archive items, and even Drafts and Outbox items (and, arguably, it shouldn’t). And, like I said, opening or viewing an Outbox item unsets its “send” flag. What was happening was that the search window’s live preview was “opening” my just-sent email, ostensibly assuming I might edit it, I guess? And it didn’t happen all the time because I generally don’t send emails that match the search I have open in the background, but it happened often enough that I knew it was a problem.

I don’t have an answer for that problem (I’ll probably just stop leaving search windows open for so long), but I did get a blog post out of the deal.