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Taming My Inbox

I’ve been on a big push lately to eliminate the time I waste on email. David Sparks’s book Email - A Macsparky Field Guide was an incredible overview but focused a lot of attention on some tool solutions that I wasn’t necessarily interested in1. I feel like I’ve hit a sense of equilibrium with managing the deluge of emails across many different accounts and figured it was time to share.

For quite a while, my tools of choice were and SpamSieve running on a Mac Mini. I would access email on my iPhone with Dispatch and, since SpamSieve was doing such an admirable job keeping my Inbox free of garbage, I rarely was bothered by unwanted emails while working remotely. The messages that hit my Inbox were the truly important emails.

Recently, a major downside to this method started to develop. The incoming emails would hit the Inbox of the Mac Mini but would still trigger an inbox notification on my iPhone before they could get moved to the Spam folder. The last thing I want interrupting me is spam. I’m not sure what changed with the timing between the two servers but it was starting to really bother me – my phone would buzz, I’d check it and not only was the message spam, but it was also not there anymore. That sucked (times two).

Around that time, Mailmate entered my life and it was innovative and flexible enough that I’d be able to build a decent workflow around it. My first task was to solve the spam issue and to do that I had to remove the Mac Mini/ parts of the equation.

First, I turned off on the Mac Mini. As expected, I was bombarded by spam no longer being trapped by the intelligent Bayes database of SpamSieve so I looked to Fastmail’s spam filtering to save me. In order for Fastmail’s user-driven Bayes database algorithms to work well, it needs a reasonable sample of “good” and “spam” emails for analysis so it took a few days of training to get to the thresholds required2.

Problem remained and they were three-fold:

  • Fastmail’s spam filtering wasn’t as good as SpamSieve even after a week or more of training. Email that I had marked as spam multiple times were still making it through. I was spending the first part of my morning wiping out spam, training a Bayes filter, and looking for a better way.
  • I had trained my SpamSieve with over 8000 emails over the course of its employment. That’s a lot of knowledge to expect Fastmail to pick up quickly but it still wasn’t happening fast enough to keep me sane.
  • Dispatch, my iOS email client of choice, didn’t give me access to all of my IMAP folders. I couldn’t effectively train for both good and bad emails. I could map a shortcut in Dispatch to either “TrainGood” or “TrainSpam”, but not both.

The first step to solving this issue was to start using an iOS client that my friend Scott told me about – Boxer. Boxer is pretty good. It lacks some polish and feels a little too shoulder-to-shoulder with partners like for my liking but it does have some nice features that put it in the same league as Dispatch.

  • It allows access to your entire IMAP directory.
  • It has a rudimentary To-Do feature.
  • It is fast and has background updates and notifications
  • It “integrates” with Sanebox (although how exactly I have yet figure out)
  • It has some interesting and configurable shortcut gestures

There is one big downside – it doesn’t report message counts in folders anywhere that I can see. This makes using Sanebox difficult since you never know if there are emails that require your attention in the many folders it sets up for specific purposes. It is a good app though; probably the best iOS email client I’ve used so far. It isn’t exactly ugly, but it focuses on form over function and there’s a lot of room for improvement. I can live with that. I wish Sanebox integration actually did something helpful. More on that in a second.

So, speaking of Sanebox3

As I mentioned, Fastmail’s spam filtering wasn’t cutting it. A tweet by Collin Donnell and David Sparks’s mention of Sanebox in his book piqued my interest and I decided to give it a try.4

The gist of Sanebox, for those of you unfamiliar, is that it looks at your email and siphons it into a set of helpful IMAP folders, leaving the truly important email in your Inbox. +SaneLater is the default folder into which it siphons things that are less of a priority. Given the somewhat subjective nature of what it is accomplishing (and with very little training), it is doing an amazing job knowing what I will find important. My Inbox and my iOS client have become unobtrusive and useful again.

With the right kind of account (I subscribed to the middle “Lunch” tier which gives you Dropbox attachment handling, five special-function folders and other features), you can send messages into more useful places. There are folders like +SaneBulk which saves things like receipts and order entries, +SaneNews which collects things like mailing lists or news emails and +SaneBlackhole which does things to your email which are as bad as it sounds5.

Once your emails are sorted into these trainable buckets, you can deal with them as you wish and at your leisure. You can delete them, train them as spam, “blackhole” them, tell Sanebox they are actually important and other handy things.

On really busy days, when you don’t have time to even peek at email beyond your Inbox, Sanebox will email you a digest of its folder activity. You can process the emails from the digest or at least skim it to know you’re not missing anything. I thought Sanebox was going to be a lot of hype but I am loving the service so far and I’m more than happy to pay for something that works this well.

As I mentioned above, Boxer supports Sanebox but I have no idea what that means. I ticked the feature in Boxer’s settings but nothing really changed in the app that I can see. There are some options that read “Setting up…” in my action palette so maybe they will become something useful soon? Who knows but here’s to hoping.

Overall, my email flow looks like this these days:

I do occassional triage on my iPhone using Boxer. I get two Sanebox digests a day - one at 6AM and one at 6PM - to let me know what got moved to my +SaneLater folder etc. When I have time, I sit down at my Mac and use Mailmate to process email quickly. It has hotkeys to shoot email to different folders and the Mailmate’s SmartFolders keep me aware of the big picture. I love writing email in Markdown using Mailmate so that’s another plus. It also has the ability to send email “to-dos” straight to OmniFocus which is a feature I find I’m using with increasing frequency.

Due to Sanebox, I only really see the important email in my Inbox and that makes it easy to keep my Inbox count at zero (like a gentleman). I’m happy with my current setup. Even though the parts that comprise it are disparate, they avoid Google entirely and are paid services and apps which hopefully means I’m helping build a sustainable service that won’t go away or get sold (to Google). Each part of the workflow serves a specific and useful function and they all work together to keep the email tidal wave looking more like a calm night at sea.

  1. I don’t use and I have moved away from Gmail which are big focuses in David’s book. He does touch briefly on Mailmate and goes in depth with Sanebox though. Go buy his book. It’s great. 

  2. I pressed my SpamSieve “TrainGood” and “TrainSpam” server folders into use for this purpose and they worked fine. 

  3. Affiliate links, ahoy. 

  4. It has some very influential spokesmen. “Legends” and people who use both a day phone and a night phone. Impressive. 

  5. It unsubscribes from email lists for you or forever banishes emails from a given sender. It is the nuclear option and it is awesome