Overcoming Email Aggravation With Inbox Zero, Gmail and Mailplane

The Techie Scheky series offers tips and tactics for being more productive and creative through technology (especially with a Mac).

After last week’s “Perfect Computer” post, it occurred to me that I’m yet to talk about the thing that started me off on this whole geeky trajectory: email. A while back, after consistently being told I have a social media problem, I decided to install RescueTime on my machine. The application essentially spies on you and tells you how you are spending, or wasting, your time. It was brutal, but informative. I quickly found that I didn’t have nearly the social media problem that everyone thought, but boy was I spending way too much of my time in email.

Dear Email, I don’t care for you much…

Email was and still continues to be the bane of my existence. As a naturally disorganized human, it has always proven to be a challenge. Staying on top of it, organizing it, getting away from it. Let’s just say I have a hate/hate relationship with the stuff. Beyond being inherently bad at it, I also had a terrible setup. At the time, my email was running on our office’s 2003 Microsoft Exchange server alongside what I believe is probably the single worst application ever created for the Mac, Microsoft Entourage (essentially a second-rate, half-assed version Outlook). These were dark days.

While complaining about it sure is fun, eventually I had to do something…

After talking it over with a few friends (read: other geeks), I was introduced to a video that would indelibly make me a lot geekier: Merlin Mann’s Inbox Zero talk. Now if you’ve been following the site, you know I’m borderline obsessed with Merlin’s work. Beyond the fact that he’s hilarious, he also is someone who has put a lot of thought and technology into his workflows to overcome his ADD and focus issues. In other words, I can relate. Inbox Zero gave me a framework that I could use to start tackling the email best and his two Mac Power users episodes helped me find many of the tools that I use today.

Inbox Zero, boiled down to point of being rude…

Let me start by giving you the 30,000-foot view of Inbox Zero. While it stands on its own two feet, it’s essentially a focused and tactical implementation of GTD for handling your email. At its core, it is treating your inbox as what it was meant to be, an INBOX. Not a to-do list, not a filing cabinet, not an action box. A place for email to arrive, not a place for it to remain. You really need to hear it from the source, but essentially you process your email inbox to zero periodically throughout the day (trying to process as little as possible). As you process there are five main steps: delete (my favorite), delegate, respond (if it takes less than 2 minutes), defer or do1. The end goal is to either get rid of something or convert it into an action.

Why I use Gmail, even though it’s probably reading my messages…

After listening to Merlin’s first workflows episode on the aforementioned Mac Power Users, something became crystal clear: I needed to get off of our dated Exchange Server, off of Microsoft Entourage and onto Gmail and Google Apps. Why? Several reasons:

  • The 25GB of space that comes with each business account was a major upgrade from my previous 2GB maximum.
  • It has a fantastic spam filter which only seems to get better with time.
  • The keyboard shortcuts seem geared towards executing the ideas of Inbox Zero.
  • You can make it so all of your various email accounts come to one inbox and respond as if they are coming from the correct account.
  • As it turns out, Google is actually pretty darn good at search. So good, in fact, that I was able to essentially eliminate the traditional email folders system that was just never going to work for me.

Right, but my work is still on an exchange server…

So how did I go about this? Well it is going to take a $50 investment on your part and you are likely going to need a friend in IT. Request to set up a Google Apps pilot program for your office. This lets your office keep their Exchange Server intact, but lets you send and receive all of your work email from Gmail. From there, you just need to decide how you want to use it. Do you want to use the web interface through your browser, an application like Mail.app or Sparrow or do you opt for the best of both worlds, as I do, with Mailplane?

Tell me more about this Mailplane you speak of…

Mailplane is an application that essentially wraps the Gmail web interface in a free-standing application, while adding additional features. There are tons of things to like about Mailplane, but there are four that stand out for me:

  1. Break out of the browser: I’m an idiot and when I use a browser to access email, I almost always accidentally close the email window every single time I jump into another tab to do a little research. By letting your email stand on its own, I manage to avoid this inevitability.
  2. Plays nice with Evernote: One of the biggest reasons my inbox used to be a mess was the need for reference. I may want to quickly find a passage from a previous email or an attachment. Mailplane includes a handy button that quickly sends highlighted text, an entire email or even an attachment directly to Evernote. Evernote also creates a link back to the original email in Mailplane, making it easy to find and respond when necessary.
  3. Plug it into Omnifocus: As my addiction to Omnifocus continues to grow, so does my appreciation for this plugin that makes it easy to create tasks from specific email messages. This is how I “defer” a message. If something is going to take longer than two minutes or would be better handled at a later date, I simply hit a keyboard shortcut that makes it easy to create and add a task to any project or just add it to my Omnifocus inbox.
  4. No offline access: Some are going to see this as a negative, but the fact that I need to be online to handle email is one of the reasons I love Mailplane. Anything essential has already been added into Evernote or Omnifocus, so this is rarely a problem (and when it is there is always the iPhone or iPad). The lack of offline access to email has forced me to marginalize its importance, keeping me focused on what I really want to do, rather than whatever distraction sits at the top of my inbox.

Inbox Zero is a great starting place if you are a disorganized mess…

Chances are, if you’re a struggling with productivity, the problem starts at email. While there are tons of suggestions, solutions and tactics out there, I’ve found that Merlin’s approach is the best way to get the job done. It’s full of common sense, it’s fairly intuitive and the learning curve is slight. It’s also a great, targeted way to start getting your act together. If, like me, you’ve found figuring out how to get more organized to be impossible, it’s a great way to ease into the pool. Over the years, I’ve tried plenty of full-blown systems, including GTD. They were just too overwhelming. Inbox Zero let me focus on one thing: email. It gave me a straightforward path for overcoming my challenges and it started me down a road that lead me to implement so many of the changes I’ve shared in this series. So thanks for that Merlin!

Geeky Quick Tip

As I mentioned earlier, I’ve essentially abandoned folders, using Gmail’s Archive option to send all completed messages to a single folder. As it stands, you hit send on a message and then can click the Archive button. Gmail Labs offers an optional button that allows you to Send & Archive at the same time. It may seem like a little thing, but it saves you time and lets you seamlessly get the messages you’ve completed out of your sight. Enabling this also activates the keyboard shortcut of Command-Shift-D, making it faster and easier to plow through your inbox.

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  1. Although in my execution of it, defer and do have really become one and the same.  

12 Responses to Overcoming Email Aggravation With Inbox Zero, Gmail and Mailplane

  1. I have 37,265 unread emails in my Gmail inbox. Three years ago, I had deleted all. We’re not even talking about my email accounts for spam. Enuff said?

    I haven’t checked my corporate email accounts in five years. I may have three or four of those. [shrug]

    Ironically, my past corporate email accounts were only for clients, but since clients were getting hit by malware and spyware all the time (porn sucks that way), the spam mounted beyond imagination. From here to the moon. And like you said, Google deals with spam a bit better than anything else.

    Recently on my blog: A Fan Letter to Penelope Trunk and her farmer http://wp.me/pbg0R-qQ

    • Wow, that would bring my blood pressure up to a proportional number. At some point you’ve just got to go nuclear on that thing or just abandon email altogether (which I’m sensing is what you’ve sort of done…).

    • The real one? No way, I’m just trying to come up with something to yell out on Twitter :) It is kind of sad (read: super sad) to see something so useful turned into something so ridiculous.

      Feeling’s very mutual!

  2. […] Get Out Of Your Inbox – You’re likely already familiar with this, probably because you’ve seen someone tweet out #INBOXZERO! the one time they burned through all of the messages in their inbox. While processing all of your email is one of the core tenants of Merlin Mann’s Inbox Zero, it’s often mistaken as the central theme. The real idea is getting your work and more importantly yourself out of your inbox, to determine what is truly important rather than constantly jumping into your email. If you find yourself living your life in Outlook or Gmail, give Merlin’s seminal talk to the team at Google a shot. If you’re already familiar and need a few ideas on how to implement Inbox Zero, I’ve got you covered. […]

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