April 19, 2021

One Year of Hey

It’s time for me to leave this innovative but frustrating new take on email behind

It was my fault—I knew from the start that Hey wasn’t for me.

Still, I soldiered on because I was excited by the first real re-think of email since its inception; I wanted to make sure I gave it a proper try. I did my best to adapt, to use it as it’s designed to be used…but it’s been nearly a year now and I’m afraid I have to throw in the towel.

For all of its benefits—and there are several important ones—Hey turned my seamless experience with email into a slow, frustrating, opaque mess that I haven’t been able to get used to and that has negatively impacted my productivity and email efficiency for months. I won’t go into too much detail around why because I covered the majority of the reasoning in my initial pieces about it.

Instead, I want to discuss what the process of migrating away from Hey was like.

A Middle Ground

At first, I thought I should try to adapt my usage of Hey to something less fragmented by using only the Imbox and pretending the Feed and Paper Trail don’t exist.

After all, one of my core complaints was that the cognitive load of deciding which bucket” to put email into (and seeing when there are new messages in each) is heavier than the load of simply dealing with email in a traditional inbox zero fashion as I’d done for years. About two days into my attempt to consolidate existing messages into the Imbox, I gave up on this middle ground.

Hey actively fights against non-standard usage. There is no way to select all messages in any given list, so something as basic as moving all messages from the Feed to the Imbox is a tedious nightmare. To make matters more complicated, I wanted to ensure that no messages go into the Feed in the future, which meant opening each message, going to its sender’s contact page, switching delivery to Imbox, and then backing out and moving on to the next message in the list.

One by one.

Mercifully, if you have multiple messages from a contact in a given bucket (common for newsletters and other bulk mail), they do get moved together when you make this change. Even so, that still left me with hundreds of messages to process.

After finally clearing The Feed, I moved on to the Paper Trail—only to realize that it would be even more tedious because there are fewer repeat senders in there. Worse, when you move messages from the Paper Trail to the Imbox, they get placed into your unread pile at the top, leaving you with the additional step of visiting the Imbox, clicking Read Together, scrolling all the way to the bottom, and clicking a button to mark them all as seen.

Adding insult to injury, messages moved into the Imbox don’t respect their original chronological placement; they all get added to the top of the pile. So now, all of my recent email in the Imbox is buried under months of ancient and irrelevant correspondence.

I recognize that what I was attempting to do is not something that normal users would encounter, but this default behaviour is so hostile and off-putting that I couldn’t bear to finish plowing through the rest of the Paper Trail. It’s a reflection of Hey’s youth more than anything else; as a product matures, it gains the ability to accommodate more kinds of users harmoniously. Hey isn’t yet at that stage, and that’s perfectly fair.

Since changing this usage pattern in the midst of your experience is so painful, I’d like to see a future update to the Hey onboarding experience where you get to choose whether you use the three buckets or just one. Ideally, choosing the latter option would then hide the other two entirely.

In the end, I wanted to stay with Hey, but their intended workflow neither works nor flows for me.

Export and Forwarding

Suffice it to say, the middle ground option didn’t work out.

Hey prides itself on providing an industry-standard MBOX export should you want to leave the service, so I took advantage of that. My worry was that it wouldn’t respect the basic structure of messages so that, for example, sent messages from Hey wouldn’t be filed into the Sent label in Gmail.

I imported the Hey MBOX file into Apple Mail and ended up with a local copy of all my Hey messages, with threads and attachments intact. I then connected my Gmail account to Apple Mail and simply dragged the local MBOX emails into Gmail’s Archive folder.

In the end, the emails made it safely into Gmail, but sent messages were not placed into Gmail’s sent folder. Not the end of the world, but something to be aware of. Everything remains easily and immediately accessible via search, so I don’t mind.

Separately, I asked support to clarify how Hey’s forwarding works when you’re pointing email away from Hey to an outside service. My hope was that it would bypass the screener and spam filtering, essentially acting as a completely neutral redirect. I was keen to avoid a situation where I’d have to keep checking in with Hey periodically to rescue messages trapped in the Screener.

Here again, I was glad to see that the feature worked as I hoped: once you set up mail forwarding out of Hey, it will funnel all incoming messages to the destination address, letting you deal with them downstream. Perfect!

One thing to note is that Hey retains its copy of incoming mail, and that includes keeping things flowing through the Screener, so if you check back in with Hey and notice a bunch of email stuck in there, don’t worry—those messages have been forwarded to your other address. Hey essentially operates in parallel while forwarding, so you can always return if you change your mind.


Leaving Hey behind isn’t all positive, of course. I will miss its privacy-first architecture and the concept of the Screener. I will miss being able to rename and merge threads effortlessly.

On the other hand, I won’t miss the core email tools, all of which remain inferior to Gmail’s for my needs and preferences. Attachments are handled bizarrely, Reply Later and Set Aside are functionally identical to me and basically black holes where emails go to be forgotten, there’s no undo send, no scheduled send, and I won’t even bother discussing the shortcomings of the search experience.

With the final transfer out of the way, I’m left with a cool email address that’s mine to use forever, and I’m back to handling email through Gmail. I can’t express how relieved I am to be back to the simplicity of my previous email system. It feels like a veil has been lifted.

My experience with Hey just goes to show that you shouldn’t try to solve a problem you don’t have, even if the solution seems cool—email was a totally solved problem for me, and I suppose I expected Hey to make it even better…but of course that turned out not to be the case.

I’m glad to be back to an ecosystem that offers me the flexibility to choose my approach to email, and the tools I use to access it. After all, Hey will always look like Hey and be accessible only via the interface they decide to give us. Gmail and Outlook and the others I can access through apps that really transform the experience in interesting ways, or that simply provide beautiful native access to the core Gmail experience.

Problem Solved

I don’t want this to come off as a polemic against Hey; the problem was with me trying to fit a round peg into a square hole.

Most of the folks I know who switched to Hey have remained there and are very happy with the service. Crucially though, it was people who weren’t previously satisfied with their email for one reason or another. I completely understand how certain kinds of email users will come to Hey and feel like everything is suddenly more sensible and easier to manage.

I suppose my story is just a cautionary tale for the rest of us who had a perfectly functional and satisfying system before Hey came along. If you’re in that boat and are considering the switch, make sure you really explore the workflow during your 14-day trial so you don’t end up frustrated like I did.

Hey remains an excellent service with progressive ideas that I will continue to follow and may even return to one day if it evolves into something that better fits my needs.

technology productivity

Did You Find This Post Helpful?

Previous Post
Amazon Finally Allows Book Covers to be Displayed on the Lock Screen → A long-standing feature request is granted at last
Next Post
Keeping Wanderlust at Bay With Alba: A Wildlife Adventure Revisiting my childhood through a charming journey of wildlife rescue, friendship, discovery, and nature conservation on Apple Arcade