On Avoiding Email: Second, Consider the Tool

Last week, I addressed avoiding email with the fundamental question of motivation. Specifically, are you using the easy stuff to avoid doing the hard stuff?

Despite its widespread use, email is not an efficient tool for all types of communication. We’ve overlooked its limitations in our attempt to make it do everything. It’s time we acknowledge that email is often the wrong tool for the job.

Numerous approaches to team communication can free you from the constant need to check your email. While these methods require some initial investment of time and thought, they can ultimately save you hours that would otherwise be spent on lengthy email threads.

For example, I have a scheduled weekly call with my editor where we talk about existing projects for about an hour. During that hour, we get everything handled for the week. Throughout the rest of the week, we keep notes for each other on individual project pages in Notion. Any question that doesn’t fit with a specific project goes on a separate page called “Open Questions.” Then, about a half hour before our weekly call, I go through all open loops and open questions so we can get on the phone and move through them. That one hour every week saves us multiple hours of messages and emails. With a bigger team, that saved time grows exponentially. Additionally, the back-and-forth nature of a phone call often yields better results.

If you are working with a team on a project, a setup like this is way easier than constant email chains with multiple people on it. This gives you one source of truth and one place to go to. It’ll take a little convincing with your team, but once you establish it, they will see the wisdom of it.

Also, try to schedule an in-person meeting regularly to review any open loops. When I was an attorney, every day at 4 PM, my paralegal and secretary could come in and ask me any questions they had. But it was understood they would not pepper me with emails or questions throughout the day.

Finally, there is an ancient bit of technology called the telephone. I put effort into my relationships with coworkers to make them understand that if they have something urgent, they can call me, but it better be urgent. I also make sure they understand that if they email me with something urgent, they will not get a timely response; I’m not your email monkey.

Many other tools are therefore better suited to team communications than email threads. Use your creativity to find a few that can work with your team. Only then can you loosen the grip email can have on your focus.

Avoiding Email: Do the Hard Stuff Instead

I recently heard from a listener asking me how to check email less often. I often get email like this. Indeed, I get this question so frequently that I’d like to answer it with a short series of posts on avoiding email. I have some expertise in dealing with email precisely because I’ve made all the mistakes myself.

One of the initial things you must consider with email is whether you’re using it to avoid doing the hard stuff.

Email is ever-present and it multiplies!. The more email you send, the more you get back. It can become a hamster wheel that never stops. In the abstract, we think of that as a bad thing, but what if getting off the wheel means you’ll be faced with some really hard work? Isn’t it easier just to keep running on the wheel and dreaming of cheese?

We like to complain about email, but it’s easier than many other things. The stakes are usually pretty low, and you can spend days and weeks on it without having to confront the hard stuff. I’m not saying you’d do this intentionally, but the easy path is so much less work.

You can check your email, maybe send a few replies, and feel like you’re getting something done while finding a great excuse to skip the hard work. You need to be honest with yourself about that, particularly if you find yourself checking frequently without good reason. It’s a one way that rebellious organ between your ears avoids doing more work. In that case, you’ll need to take steps. The blissful misery of email is not going to make a difference for you. It’s not going to get you the promotion, close the deal, or make progress on you big thing. The hard stuff, while difficult, is what matters.

Setting Up MailMate (MacSparky Labs)

As part of my Rethinking Email series, I’ve installed MailMate on my Mac again. MailMate is the powerful (and nerdy) email solution for the Mac. Here’s a video showing what I’ve done after a few hours of setup, including some custom Key Bindings. There is more to come on this, but here are some early impressions for the Early Access Members…

This post is for MacSparky Labs Tier 3 (Early Access) Members only. Care to join? Or perhaps do you need to sign in?

Rethinking Email – Inbox Serenity (MacSparky Labs)

I’m behind on my email, which made me rethink my email practices and how I can improve them. This is no less than my quest for email serenity. I’ve decided to do this as a series for the MacSparky Labs. Here’s the first entry talking about the problem, potential solutions, and some trouble areas where a specific email can gum up the works. I also share diagrams of some of my email workflows…

This is a post for MacSparky Labs Level 3 (Early Access) and Level 2 (Backstage) Members only. Care to join? Or perhaps do you need to sign in?

Will MailKit Save Mail.app?

One of the announcements to come out of WWDC this year is a new framework for third parties to create plugins for Apple’s Mail.app called MailKit. Mail.app has been stagnant for a long time. While the app continues to get support for email rendering and improvements to its basic functions (like search), that’s about it.

Most who use it day-to-day have gotten somewhat accustomed to how dated it feels. Making a stable, feature-rich email application isn’t easy. Most third-party developers seem to fall down on the “stability” part. Apple nails that but seems uninterested in the “feature-rich” part.

I hope that this new MailKit will allow third-party developers to pick up that slack. There is already a rich ecosystem of Apple Mail plugins, but I’ve become increasingly leary about using and recommending them during recent years. My concern was that Apple could, at any point, pull the plug on Apple Mail plugins.
A few years ago, I talked to an Apple engineer at WWDC who explained that mail plugins, historically at least, represented a security vulnerability, and Apple is very much interested in removing any security holes. The good news is that the announcement of MailKit means Apple is not pulling the plug on plugins but instead found a safe way for them to continue while keeping the platform secure.

This new sense that mail plugins have a future path and will continue to exist makes it easier for me to use them. I hope this also encourages other developers to get off the sidelines and explore developing new and helpful Mail.app plugins. Hopefully, another benefit will be that in future updates to macOS, plugin developers won’t have to re-invent the wheel every year. One of my favorite plugins is SmallCubed’s MailSuite, but every year I have to turn it off on beta machines and often for the first few months after a macOS update releases.

Unfortunately, MailKit is only for the Mac, leaving Apple’s Mail app on the iPhone and iPad sad and lonely, still without even the dignity of a sharing button. I’d love to see MailKit also make its way to iOS and iPad OS, but I’m not holding my breath.

Hey Email Gets Multi-Account Support and Hey for Work Released

The Hey team has been hard at work with several updates for Hey Email released today:

1. HEY for Work is now released. I’ve been trying it with one of my accounts and I’m impressed with its collaboration tools. Thread sharing with people on your team without hitting that damn BCC button is a massive improvement to team email. You can also move your work domain into Hey for Work as part of the setup. Another nice features is that the labels (tags) work everywhere and are consistent. That is not an easy nut to crack with other Mac email solutions.

2. Multi-account support. If you have multiple Hey accounts (e.g., work and personal) you can now see all that email at the same time or filter by account.

3. Revamped Forwarding + SMTP send-as support. There is better SMTP support so you can reply using alternative domain email addresses rather than your @hey.com address (partially depending on your alternative email host).

One of the big questions when Hey first arrived was whether it was going to be sustainable enough to merit continued support and development. It looks like that is no longer a worry. I’m impressed with the service, but I still don’t like the icon.

AppleScript to Link to Apple Mail Message

I’ve always like the way OmniFocus can create links to Apple Mail messages when saving an email as a task. With help from listener Jacob (@evansio), I’ve now got a script that can do that anywhere via a text expander snippet. Here’s the AppleScript:

  Returns a link to the first selected Apple Mail message
tell application "Mail"
  set _msgs to selected messages of message viewer 0
  if (_msgs is not equal to missing value) then
    set _msg to first item of _msgs
    set _msgID to do shell script "/usr/bin/python -c 'import sys, urllib; print urllib.quote(sys.argv[1])' " & (message id of _msg)
    return "message://%3C" & (_msgID) & "%3E"
  end if
end tell

Here is that script embedded in a TextExpander Snippet. I’m using the abbreviation “elink”

Screen Shot 2019-02-05 at 7.19.58 AM.png

That’s it. Once you’ve installed it, just type “elink” in any app that can take a URL and you create a link to the currently selected email message. I use it all the time in Notes and Calendar note fields but it really works anywhere. Here’s a short explanatory video.

A Case Study in Phishing

A few days ago I received this email. I thought it was an excellent example of a phishing attack. If you’ve never heard of it before, phishing is a process where a bad guy sends you an email that looks legitimate in hopes that you’ll click on the link and give information to him that he can use to somehow screw you over or steal your money.

Here’s the email. Click to enlarge.

In this case, they’ve created an email that looks a lot like it came directly from Apple. It’s got the Apple Logo and the YouTube logo and, on first glance, looks official. It informs me that I’ve subscribed to YouTube Red for $149.99/month and it gives me a handy link to unsubscribe. There be the dragons. If I were to click on that link–I didn’t–it would ask me for my iTunes login or my credit card (or both), and then the bad guys would have my information. Game over.

The first tool you need in fighting Spam is common sense. YouTube Red does not cost $149.99/month, and a simple search will tell you that. If there is any question, also take a closer look at the details. The sender lists their name as “App Store” but disclosing the actual email address; it’s “noreply11@fillappealform.com”. Does that really sound like an address Apple would send you to confirm a subscription? Also, it lists “Payment Method” as “By Card”, not the usual xxxx-xxxx-1234 you usually see. It also creates this sense of urgency, explaining I’m on a free trial but I will be charged $150 in just two days if I don’t act. While I can see how this email may fool some people, on the barest scrutiny, it starts looking shady.

Screen Shot 2018-02-28 at 9.27.27 AM.png

If you ever find yourself tempted to click on any link in an email that involves a problem or access to any of your online accounts, stop and think for a moment. Then go to the source website itself and check. In this case, logging onto my iTunes account would show that I have not, nor have I ever, signed up for a YouTube Red subscription.

Finally, there’s nothing wrong with proving yourself wrong on this stuff. I recently got a “credit card expired” email from Squarespace. Rather than clicking on the link, I went and logged into my account and discovered that my credit card had, in fact, expired. Better safe than sorry.

Want to learn more? I wrote a book about email.