Task & Email Management – Inbox Zero!

A little over 2 weeks ago (writing this on September 21, 2019) I decided I needed a clean start with email. My inbox literally only had maybe 3 months worth of clutter because 3 months ago I tried to get a clean start back then. The problem the last time, and several similar attempts before that, was that I didn’t fundamentally change the way I was processing email. When I couldn’t or didn’t need to take immediate action on an email, I left it in my inbox so I knew I had to deal with it still. Other things I just didn’t know what to do with. They weren’t really a task, nor immediate if it was a task (like something to read or reference), so I just left them in the inbox marked as read so I could get to them when I needed to. Finally, for things that I absolutely needed to take action on, I might flag as well as mark unread so I knew I still needed to take action on it.

What a HORRIBLE freaking way to use email!!

I have read and watched countless videos on how to obtain inbox zero nirvana… but I never made the decision internally of how to deal with email and be consistent with it. I’ve read GTD by David Allen and many other blog articles and self-help productivity books and articles. But until you change they way you look at email and can compartmentalize it in your head quickly, you will most likely fall prey to a cluttered inbox like I have for decades. My physical desk is similar, and that’s something I still need to tackle.

What did I change?

I had to come up with a method to process my emails in a very simple and tidy fashion. This means that emails need to fall into one or more categories, and each category has a processing action associated with it. I’m not saying this methodology is perfect, and I expect it will morph as required while I use it and find inefficiencies. In fact, over the last couple weeks I have already made some changes. The categories and actions I am about to list are current as of September 21, 2019, but I started this out using Microsoft Todo as my task management solution, which I’ll explain later and why I switched. Where I list OmniFocus below (I use this on my Mac and iOS devices, but they recently released a cross-platform Web version too!), it could be whatever task management app you want to use.

Categories = Process Actions

• Immediate Action of less than 5 mins = Reply/Forward/Act-on as necessary
• Garbage/Don’t Need = Delete/Unsubscribe & Delete/@SaneBlackhole
• No action, but not trash = Archive
• Reference material = Save to Evernote (unstructured) or OneNote (structured) and Archive email
• Action item, but not immediate = If email related, forward to OmniFocus not changing anything in the subject line, then rename from within OmniFocus. If non-email related, forward to OmniFocus with appropriate task name as Subject Line
• Something to deal with later in email = Either use SaneBox Snooze folders to have the email reappear in my inbox at the appropriate time, or the iOS Outlook app “Schedule” feature to snooze email to return to inbox at appropriate time — SaneBox folders are universal across any email client —

How to start with a clean slate

Each person is going to have a different starting point/situation. The first ever time I tried to do this I had literally tens of thousands of emails in my combined inboxes. When you have something that massive, the only thing for it is creating a new folder in each email account labeled something like “Clean Slate” and dumping ALL inbox items into that folder. In this way you can start dealing with your inbox in an uncluttered way and follow the process you choose to deal with items. At the same time, you can go into that “Clean Slate” folder to start searching for things you may need to really deal with. If, like me, you have tried the clean slate approach before and only have a couple/few months of email in your inbox, you can use the method I used.

Sidebar: I have been using SaneBox for the last 4-5 years on all of my email accounts (the Dinner subscription is what it was called when I purchased it) to automatically filter unimportant email OUT of my inbox so I can deal with it later in batches. I get a daily digest every day around 4-5pm and opening that digest in a browser allows me to very quickly take action on those emails by seeing who they are from, the subject and a quick blurb of what’s in the email. From there I can chose to delete it (even delete many of the emails in one click), archive it, send it to my inbox just this one time, or train things to different folders (like maybe something should actually go to my inbox all the time, or maybe I want to Blackhole all future emails like this so I never see them again).

At first, you may think the cost of this service is expensive, but once you figure out just how amazingly useful and powerful it is, it is indispensable. It’s also universal, meaning it has nothing to do with any individual email application and is visible across all email applications as well! You can use Snooze Folders and create your own custom folders to do all sorts of things. I have some folders that filter stuff about hobbies and automatically forward all emails to Evernote where I can search for them later.

The link to SaneBox I am using is a special link that would put money towards my SaneBox account if you sign up for the free trial, so I’d appreciate you using my link if you decide to sign up. But even if you don’t, I’d still recommend you using this service.

While it will not completely solve your problems, nor get you to inbox zero, it definitely helps with inbox zero.

The first thing I did was filter my inbox for unread email, since these were things that I either literally never looked at or marked as unread because I needed to do something with them. I went through these very quickly and made decisions on how to deal with them based on the above categories/actions. Next, I filtered on flagged items and went through the same process. Finally, with only unfledged read items, I quickly scanned for anything that jumped out as important and processed those, and then selected ALL items and Archived.

Let’s Talk Task Management

While Inbox Zero has been working for email for over two weeks for me, I was worried that some tasks were getting missed. Using a tip from someone I respect that always has a clean inbox, I had started flagging emails with due dates and reminders. I was doing this in Outlook, which is what he uses… only on Windows, not a Mac. While I do like Outlook for Mac, it is NOT the same as on Windows and is missing one critical feature for this to work perfectly. That feature on Windows is the ability to have a task list below your calendar to see tasks that are either due or available to work on. I thought I had a solution, which was to use Microsoft Todo application, which is available for the Mac and iOS (and other platforms as well). This seemed to be working for the first week.

My work Exchange account seemed to be working fine with Todo, but my personal email accounts don’t seem to work with flagging and showing up in Todo. I believe it works with any Microsoft email account, like Outlook.com, but I have 4 other personal email accounts that aren’t these and there’s no way I am pushing all my email through my Outlook.com email (at this time anyway). What I started to realize was emails I was flagging to then show up in Todo and that I would not lose track of weren’t ever making it to Todo. That means Todo wasn’t my single source of truth!

You might say, just use Tasks within the Outlook app! That would only work if I only used the desktop version of the app, because Outlook on mobile only contains email and calendar… not tasks. I even thought about using Reminders, but again, only flagged emails from my work Exchange email were showing up in Reminders… and while Reminders has its uses in my family (shared lists) it is NOT my go to task management app.

I thought that I may need to go back to OmniFocus, which at least now tracks email IDs correctly (meaning, within the task notes there is a hyperlink that opens your default email app to the correct email, EVEN if you archive it or move it to another folder – this works on iOS and macOS!), but in order to do that I can’t edit the subject line or it treats it as a new email thread and you don’t get back to the original email. Since the subject line becomes the task name, this means forwarding emails to be linked don’t have a very descriptive task name. Also, this means I couldn’t possibly automate parsing the subject line with due dates and projects, etc. All email ends up in the inbox of OmniFocus, so the ONLY way I can make that work is to religiously clean out my OF inbox too. Up to this point, my OF inbox has been much like my email inboxes used to be, so that means I need to come up with solutions to clean it up quickly with very few decisions, similar to how I am processing emails.

I abandoned Todo from Microsoft recently because the app isn’t flexible or automated enough. There is no single view that automatically populates with stuff I should work on today. There is a “My Day” view, but you have to manually choose what goes on that day, which is idiotic! There is no unfiltered view to be able to see everything on a single page… so I’m done with it. Pretty much, the ONLY nice thing about the app is that it automatically imports flagged emails, but only from my work account. Which means that it’s inconsistent, and I was flagging emails from my personal accounts thinking they would be in Todo, but they never show up and I forget about them. It’s better to always simply forward the email to OmniFocus and clean up the OF inbox on a daily basis. At least that is consistent, if not the perfect solution.

My gripe with OF is that I can’t change the subject line of an email if I want to be able to get back to the email from OF. Since the subject line becomes the task name, the subject of the email almost never matches up to what the task should be called. There also is no native way in OF to parse inbox tasks based on tags/keywords in the subject line anyway, and even though there are some scripting automation solutions that can parse emailed tasks, since changing the subject would break the email link it is not worth it.

This means that I have to take an extra step later by looking at the contents of the emailed task to determine what the task actually is. I suppose if I emailed the task to OF and immediately opened OF and changed the task name it would still be fresh in my mind, but I tend to batch process my OF inbox.

Finally, if the task doesn’t involve actually replying/forwarding the original email and is simply something I need to get done outside of an email app, then I CAN change the subject line to the actual task name when forwarding to OF… because I don’t need the task to link back to the original email. Again, though, this requires additional thought at the time of the forward and is less “automatic”, and still requires me to choose if it should be deferred/due on a specific day and if it’s simply something I merely want to do.

Cluttered Task Management

I have owned and been trying to use OmniFocus for many years now. David Sparks (MacSparky) has some incredible field guides/videos and blog posts around how best to use OmniFocus, but he can’t fix my/your brain to process items appropriately. I have purchased two versions of his OmniFocus field guides, and they really are amazing and super useful… I would recommend them to anyone, and I get nothing myself for saying that. They are that good. His latest version is amazing and easy to navigate thanks to his new training site. You can jump around the content to get to what you want, which is perfect for review/reference down the road.

One of my biggest failures with OmniFocus has been a very cluttered view… to the point that I had so many things I could be working on that I couldn’t figure out what to work on. This is in part because I was trying to use David Allen’s GTD method of a single inbox to empty your brain. My problem was everything I put in was “active” and therefore “available” to be worked on. I suppose you have to understand how OmniFocus works to better understand this, but some of these things are what make OmniFocus so powerful and customizable.

I started to try and “defer” things in OmniFocus, but I also used a lot of due dates arbitrarily so things didn’t get lost in the sea of available tasks. I also would flag things that I felt were important, but didn’t have a timeframe I needed to get them done… this was another way I ensured I didn’t lose things. It just kept the clutter and I’d still waste brain cycles looking at those items to decide I didn’t need to work on them.

Not EVERYTHING actually needs to get done

I read an article from an OmniFocus user a while back that was having the same issue as me. His solution was essentially to only have two major categories for tasks: either Want-to or Need-to. The concept is actually quite simple. Either you want to do something, but there is no real hard time limit/due date or even penalty if you don’t do it, or you need to do something, which means there is either a hard time limit/due date or a penalty if you don’t do it. With this, Want-to items relate to Someday/Maybe from the GTD principals, and can therefore be “paused” in OmniFocus, which means they do not show up as available tasks. Need-to items are active, and therefore available, but sometimes things need to wait or at least don’t need to be worked on right away. So you use “defer until” dates to make them only show up when they should be available to be worked on. Other times tasks literally need to be completed on/by a certain day. For those you actually set “due dates”. And, if something has a due date but doesn’t need to be started right away, you can also set a defer until.

Using these two major categories, most things will likely end up as Want-to and therefore won’t clutter your daily task list. But then you may worry that they will get forgotten. For this, you can either schedule review times for certain projects or simply go through the list occasionally to see if any tasks should be moved into something more active.

Get over FOMO (fear of missing out)

Almost my whole life I have suffered from fearing that I was going to miss out on, and this translated to my email and task management. I think it has only been recently that I decided this fear was counter productive and I needed to get over it. The bottom line is, if something truly needs to get done, you will figure it out even if you “pause” that thing or don’t have it in your face all of the time. This has been a relief on both my brain and stress levels. I am okay if things get missed because I had other more pressing matters to deal with. Not everything is a priority. Focus only on what truly matters the most… the rest you can do in your spare time.