HEY… It’s Not Your Father’s Email

Email is indispensable in modern life… and inescapable… and the bane of existence for many of us.

There’s way too much of it, especially on our jobs. Before retiring I got over 400 emails a week at the office. Some people get that many in a day! Home is no escape either. I use email extensively with family, friends, political and volunteer activities, my blog, my website, doctors, insurance, accountants, attorneys, home projects, contractors, various service providers … everything! The volume of legitimate email is challenging enough, and then on top of it there’s junk and spam!

Years ago, I adopted the “Inbox Zero” philosophy advocated most prominently by David Allen.

As David Allen prescribes, even in retirement I like to completely clean out my email Inbox every day or two. That means handling what’s there — replying or taking some action or filing or just deleting. The idea is to not accumulate mountains of unread and unprocessed junk.

Many times I can’t or don’t want to act upon a given email in the moment I first see it, so I need to stage it some effective way for later action where I won’t forget. Most email systems don’t have a good way of accomplishing this. One way is to mark a message as “unread” again but that risks it becoming lost and forgotten amongst all the other unread messages.

For as far back as I can recall, I’ve been looking for a system that enables me to utilize and process email beyond simply reading and either filing it or deleting it.

Apple Mail (with MailSuite)

I exist entirely within the Apple ecosystem. For years I used Apple’s native Mail app that comes as part of the Mac and iOS operating systems. Apple Mail is a good, solid email application but it has been extremely slow to adopt new features and abilities. It’s pretty barebones.

Eventually, I discovered MailSuite, a set of plugins for Apple Mail developed by SmallCubed software. These plugins added all kinds of functionality to Apple Mail. I could assign tags to messages, add notes to myself, assign myself tasks and deadlines with notifications to prompt me when follow-up was needed, add links to things, and more. Unfortunately, the plugins could be clunky and they would break every time a new version of Apple Mail was released. Sometimes it took months before MailSuite was updated to work with the new version.

Finally, one day SmallCubed warned that Apple plans to eventually end support for plugins, at which point MailSuite will permanently cease to work. SmallCubed said they were developing their own email client that would include all the MailSuite functions built-in, but that was to be at least a year down the road. I decided it was time to move on.

Cost
Apple Mail is free
MailSuite is $80 to buy & $45 annually to renew

Spark Mail

After looking around at the alternatives I settled on Spark, a very impressive email client by a Ukrainian software firm, Readdle. Spark syncs seamlessly with iCloud so all your emails, folders, contacts, etc., are available. Spark’s power goes beyond Apple Mail by segregating your incoming email messages into three categories: People, Notifications and Newsletters. It also integrates seamlessly with other Mac applications like Things 3, OmniFocus, Evernote, Bear, OneNote, Dropbox, Google Drive and more.

I was very happy with Spark, and even happier when Readdle launched a new Mac version, Spark Desktop, in October 2022. Its beautifully redesigned UI visually enhances the segregation of People, Notifications and Newsletters. This video shows how it looks and works.

Unfortunately, despite its surface shine, the new Spark Desktop has many deficiencies. It lacks all the integrations that were in the previous Mac version and which are still in iOS — integrations I used often. When writing email messages to send out I found the formatting very subpar. I ended up using the old and new Mac apps side-by-side, which was annoying. Readdle has been promising to bring all the old Mac features into the new app but it’s going on 8 months and they still haven’t done it.

Despite my growing impatience with Spark, it was a significant improvement over Apple Mail. I had planned to hang in and wait for the promised upgrade — but then I learned about HEY.

Cost
Spark Mail is $60 a year

HEY Email

In March this year I heard about a radically-different email system called HEY. It was launched in 2020 by 37 Signals, the company that created Basecamp — an amazing application that deserves a whole separate post. I looked into HEY and was immediately intrigued, but decided against it due to the cost (more on this below). However a week or two later I came across a video about HEY by Peter Aikkes, a productivity coach I like very much. He does great videos on YouTube. His work mirrors David Allen’s “Getting Things Done” (GTD) methodology but Peter focuses heavily on how to use different technology tools for productivity.

Respecting Peter as I do, his enthusiastic recommendation inspired me to sign up for HEY’s free 14-day trial — and then wow! Using HEY in practice was a revelation. It’s unlike anything else. It literally reinvents email from the ground up.

It is hard to overstate the gigantic leap forward this application represents. I’ve looked at and used at a lot of different email applications — Apple Mail, Post Box, Spark, Airmail, AOL, Gmail, Yahoo, Outlook, Proton — and with the possible exception of Spark, all these applications are variations on the same old stale theme.

Features

HEY boasts 36 distinct features, many of which are groundbreaking. I describe a few here, but you might want skip past this and jump straight to videos below. It’s really best to just see it.

• • No one — I mean no one — reaches your Inbox without your explicit permission. The very first time any person or organization sends you an email, they land in a special place called ‘The Screener.’ There you decide whether you want to to receive email from them or screen them out — permanently. If you say no, you’ll never be bothered by that sender again. Their messages will still come in but will be sent quietly to a special section you never have to look at unless you want to double-check your decisions or change your mind and allow someone back in.
    .
    Although the Screener will save you enormous time and bother in the long run, when you first start out with HEY every email sender is arriving for the very first time, so everything will end up in the Screener. Once you get past this initial start up, the Screener is a godsend.
    .
  • When you agree to accept emails from a sender, you tell HEY where you want that person’s messages to go. From then on, all messages from that sender will go to place you have designated. You can always  change your mind later. There are 3 boxes you can direct messages to:
    .
    1. Imbox.  This is like your typical Inbox, but HEY calls it the “Imbox” because this is where your important messages go. These are the things and people you need to see.  
       .
    2. The Feed.  This is where you send newsletters, promotional emails, and similar messages that you want to see but are not urgent. It doesn’t really matter if you read them today, tomorrow, the next day, or maybe not at all. What’s really great about The Feed is that all emails are open and readable simply by scrolling down like we do on Facebook and other social media. Quick & easy! 
       .
    3. Paper Trail. This is where you send receipts, order confirmations, shipping updates, bank statements, credit card statements and other official emails of record. They don’t clutter your Imbox. They remain permanently, and are of course searchable.  
       .
  • HEY starts out with all notifications disabled. You will get zero notification of new mail unless you designate specific senders that you want to be alerted to. I’ve designated just 5 people that I want to be alerted immediately when they’ve written me, otherwise HEY doesn’t bother me. Silence is golden!
    .  
  • When going through your Imbox, you can do several things:
    • Simply read a message and move on. You can delete the message, or otherwise the read message will drop to a section below that’s titled “Previously Seen.”
    • You can reply right away.
    • You can mark a message “Reply Later.” It’ll be held in a special bucket at the bottom of the screen.
    • You can mark a message “Review Later.” It’ll be held in a second bucket at the bottom of the screen.  
    • You can snooze a message to “bubble up” later as new in your Imbox. You decide when.
      .
  • HEY allows instant searching for any attachment that you’ve ever received or sent. There’s no need to know which email contained it, and you don’t have to dig through old emails to try and find it. You can pull up all attachments, or just all PDFs, or just all images, or all PDFs sent by John Doe, or all images sent by John Doe last year, etc. When you find the attachment you want, you can also click to the message or thread that contained the attachment if you need to see that too.  
    .
  • HEY automatically creates a separate Contact page for every person or organization that has ever sent you an email, or you have sent them an email, or was a participant in a group thread. Each person’s Contact page is divided into sections. You’ll find all the emails that ever involved that person. You’ll also find all attachments from any email that person was part of.  You can update how you screened the person initially, turn on or turn off notifications for that person, assign automatic labels to their emails, etc.
    .
  • HEY’s spam filter is nearly airtight. I’ve been using HEY for a month now and have only seen three spam messages — all of which only made it as far as The Screener, of course. I reported them as spam and poof. Gone forever. Spam is retained, however, in a special section you can check if you ever feel the need.

I find all this mind blowing and I’ve barely scratched the surface. Check out these next videos. To really understand HEY, you need to see it.

The Videos

1️⃣ Peter Aikkes’ video that inspired me to give HEY a try (8 minutes).

2️⃣ “Hey Email – Why It’s a Game Changer” by 6 Months Later (8 minutes).

3️⃣ “Take a Tour of HEY” with Jason Fried, Founder and CEO of 37 Signals that created HEY. This comprehensive overview and demonstration runs 37 minutes, so you might want to grab a cup of coffee.

Due Diligence

Now a few warnings because HEY has characteristics that some people might find problematic.

• To start, it’s expensive! HEY costs $99 a year. That’s $40 more than Spark Mail, not to mention $99 more than Apple Mail and GMail, both of which are free. At first blush, I ruled out HEY for this reason. But after experiencing HEY in action I thought about all the shortcomings in Apple Mail, and even Spark Mail for which I was happily paying. For just $40 above what I paid Spark, I get the near-perfect email experience I’ve been seeking for years. Amortized over 365 days I decided it’s worth it to me.
  .
• HEY is its own ecosystem. It doesn’t support IMAP and you can’t import your old mail from your previous system. You can set up HEY to send & receive using your existing email addresses, but only from the point you join HEY and thereafter. For old email prior to HEY you’ll have to go back to your old email client. The idea behind HEY is getting a fresh start. I decided I like this. I’ve gone back to my old email a few times for this or that, but it takes just a moment. I’m now using my new HEY email address universally.
  .
• You can only use HEY’s own apps or its web portal via browser, but HEY has native apps for all platforms: Mac, iOS, Linux, Windows and Android. The apps are all free, and everything looks and works the same everywhere.
  .
• HEY also doesn’t sync with your existing contacts. You can import them as a snapshot the day you do so, but they won’t sync thereafter. At first this bothered me, but I’ve come to I prefer it. I took the time set up the 80 or so contacts I want in HEY. I have a lot of old junk and defunct email addresses in my main contacts at iCloud. I like having HEY slim, current and clean. Like I said, HEY is about a getting a fresh start.
  .
• HEY doesn’t accommodate a folder system beyond the Imbox, Feed and Paper Trail. This has been my biggest hurdle in deciding personally whether to adopt HEY. I am an extremely heavy user of folders and subfolders, and then subfolders to the subfolders! HEY requires that I give this up. Yikes! I may discover in time that I can’t handle this, but HEY offers ways of organizing messages through labels, collections and other means. It also has superior search capability. I used to spend an enormous amount of time filing emails! Now I don’t. It is fantastic!
  .
• For those like me who adhere to the ‘Inbox Zero’ philosophy, HEY’s Imbox might feel jarring. There are no folders as I’ve said, so everything remains forever in the Imbox (except the Feed or Paper Trail). To me this doesn’t matter. As you saw in the videos, the Imbox has two sections: ‘New for You’ at the top and ‘Previously Seen’ below. As I see it, if ‘New for You’ is empty then I’ve achieved ‘Inbox Zero.’

‘The HEY Way Manifesto’

I’m finding in blogs and on YouTube that HEY inspires a lot of passion, much of it positive but also negative too. I’ve never seen anything quite like this with software, certainly not over something as mundane as email. Yet here I am inspired to prepare this post! I’m obviously passionate too.

This unusual passion comes straight from the creators of HEY who have actually written The HEY Way Manifesto. A manifesto! Is this crazy, or what?

Along with the manifesto, CEO Jason Fried has posted this letter introducing HEY to the world:

The title image background is a photo by Christin Hume on Unsplash.

Note to Email Subscribers: Thank you for your interest and support! The email notifications you receive omit some elements and others don’t display properly. To see this post as designed and intended, please click on the post title to view it in your web browser.

A Request to my Facebook Friends: If you have a comment I encourage you to enter it below instead of on Facebook. This way everyone can participate in the conversation!

A Request to Everyone: All opinions are welcome. I only ask that we remain civil and respectful of one another.