My thoughts on after using it for five months

This week, I stopped using Hey after being one of the folks that jumped in with both feet when it launched in June. I’ve imported my Hey messages into Apple Mail, which is what I used before, and set my address to forward to my custom domain. There are things I’ll miss for sure, but I just couldn’t do it any more.

The biggest benefit of Hey for me was that it, in its way, “fixed” email. I loved the Screener. I loved the Feed. And I loved the increased privacy. At times, I appreciated the ability to rename subject lines and combine messages together. I got used to the “Reply Later” and “Set Aside” functions and they became part of my new email flow. I no longer felt compelled to get Inbox Zero and that was a relief. I felt I could subscribe with abandon and screen out or skim past in the Feed. Email became less antagonistic, less burdensome, even a bit whimsical. I’ll miss all those things.

But there are issues that I never could integrate or feel okay about and that’s why I switched back. The first is the lack of being able to send from my professional email accounts. Some of you knew immediately that this would be a deal breaker, but I was more optimistic and thought they’d eventually add the feature. I emailed a month or so back and asked if/when they’d add it and they said they didn’t have it in on the list. This meant that for mailing lists I’m subscribed to through professional emails, I’d have to fire up Mail and send the email from there. This has meant that every week I’m in Mail sending emails to university-only email lists, for example.

But I’m in Mail more than that, anyway, because while DHH claims he never has to go back to search for old emails, I find that I do that all the time. And even if I could search for old emails in Hey, I wouldn’t want to because the search interface is terrible. Perhaps I’m not using it correctly, but my experience is that 1) there doesn’t seem to be logic to who appears first in your search results. When there are several people with the same first name, for example, people you emailed once for some random reason appear before people you email all the time. 2) When you find the person you’re searching for you, you have to click their name, scroll through the messages to find the one you want, and click on it to see something. 3) If that’s not the proper message you have to start over by searching for their name, navigating the false positives, clicking, scrolling through the list, and hunting and pecking for the next message.

There are also some pretty basic inadequacies that they should’ve fixed long ago. For example, if you set a message to “reply later” and someone else replies to it, it gets shuttled back to your Imbox and is no longer set to reply later. Also, if you have a thread going and several folks reply, you only see the last reply opened up when you click on the message, even though you haven’t seen the others (they’re collapsed for some reason). I also had at least one email that never made its way into Hey though it should have (this could’ve been on Google, but it seems unlikely). These are major violations of trust in my system and I feel I’ve traded my “inbox zero” obsession for a sort of constant vigilance to make sure I’m not missing something.

ALL THAT SAID… I’m hoping to take the best of Hey into my Mail habits. I’ve set Apple Mail inboxes to filter for unread (⌘L) which gives that same feel of emails going away once you’ve read them. I flag red for “Reply Later” (⌘+SHIFT+L) or gray for “Set Aside” and I’ve created smart folders that contain those messages. I also have Sanebox back up and running and have a smart folder looking at SaneLater and SaneNews across multiple accounts and putting them in a folder I’m calling “The Feed.” I also set them in order so ⌘1 gets me my inbox, ⌘2 The Feed, and so on sort of like in Hey.

It’s not as pretty, but it’s a heck of a lot more powerful. We’ll see where I am in another five months. :wink:

I’d be very interested in hearing from folks who are still using Hey and how they’re finding it. And also, as always, I reserve the right to be as fickle and change my mind three or four hundred times before all is said and done.


Thanks for the detailed look at how it worked out for you. I signed up, but don’t use it much as I wait for them to add support for custom domains, at which time I’ll see what the extra cost is and decide if it is worthwhile.

I currently have this odd workflow where I frequently read my mail (forwarded from my personal domain) in Hey, but jump over to my regular email client to respond. I do have Mailmate set up on the Mac to sort of replicate some of Hey’s features, and did the same the best I could in Spark on iOS.

If custom domains are priced OK, I’ll probably switch completely, although some of the cool features have lost their luster a little bit. For example, the Set Aside and Reply Later folders, while lean and functional in the beginning, can turn into just other folders where stuff starts to accumulate.


AFAIK, they don’t have any plans for custom domains. Here’s an email I received from support in October.


They changed their story then. It used to be that custom domains would definitely come as that had been announced as the service was launched.


They say they will for business accounts Q1 2021.


Well that support response was a bit misleading, wasn’t it? Thanks, John!


May I just bug you for two small questions: last time I checked, Hey did not support snoozing nor send later. Is it still the case?
Also, can you manually delete stuff from the feed?

Yeah, that lack of cohesion doesn’t reflect well on their support or company.

That’s right.

You can.


FWIW, this page about custom domains still says it will come to personal accounts:

I’m not sure when this page was last updated though.

Thank you! I am almost tempted but no send later is a bummer. However, the reply later pile is intriguing and could probably emulate the same idea.

I would really need to give it a serious try.

Federico Viticci talked at length¹ about his experience using Hey on yesterday’s Connected

¹ The total conversation about Hey is split into two chapters in the episode, the first being 27m47s and the second being 22m36s, for a total of just over 50 minutes.

I can’t remember the last time they talked about any app or service that long. But if you’re interested in Hey there’s plenty of content for you.


Great Post! Any thoughts you can share about Protonmail? Thank you

Hey’s value proposition seems pretty low to me.

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Thank you for posting your thoughts.

In my humble view (and I have written in detail about this), Hey’s biggest feature is also its biggest problem.

Hey is not flexible and if the way HEY works is in line with how you work with email, than its a match made in heaven (assuming you don’t change your ways). Basecamp made Hey the way they want to use email.

This inflexibility and close platform doesnt work for me. You can use any open system and set it up like Hey (to almost 80%) and be on your way. Like you have done with Apple mail and any imap service of choice.

The other big problem is that I still have to go back to my previous service for my emails. I refer back to my emails all the time. For Hey to assume, I wont ever need them is crazy. They still have yet to give a single reason why there is no option to users to import their mail into the 100gb storage they provide. Something that almost every paid service does. Hell, even the free ones will import all your mail.

The other main issue is the value proposition of $99 a year. With Fastmail at $50, I cant see getting twice as much value out of Hey as I get from Fastmail. Not logical thinking but I have limited resources like everyone else on this planet and I do not mind paying more if I get value out of it. Right now, I do not see the value.


To be fair, emulating Hey completely would require a Sanebox subscription on the side, for automatic filtering. You can achieve the same result with filters of course, but it’s constant work, unless you’re very conservative with your subscriptions.

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Good point. it depends on your use case. I do everything on fastmail with their rules and filters. That is sufficient for me. I took inspiration from Hey and set up Set Aside and The Feed folders (drag and drop and rules). Using a flexible system allows me to take inspiration from others. Hey wouldn’t allow me to take inspiration from someone else. Its their way or the highway (my dad used to say this a lot, and now I am saying this… i am getting older lol)


One thing in particular to note is that Federico evidently has early access to Hey for Business (which he is using with the MacStories domain) so anyone specifically interested in those aspects might want to give Connected a listen.


Applying the habits you picked up with Hey to your own system is super smart. Thanks for sharing this.

I have always wanted a way to defer acting on an email within the native, so I created a “Reply Later” folder and modified this AppleScript to move a message into it and set a reminder with a single hotkey. Perfectly nerdy way to spend a early morning on Thanksgiving Weekend :slight_smile:


Nice writeup!

Context: the primary use of personal email, for me, is conversational threads with friends and family. I don’t run business out of it and I don’t subscribe to a ton of newsletters.

Hey’s working out quite well for me. It’s just my personal email at this point, so I don’t think about it as often as I used to. I actually don’t think about email in general as much as I used to, because Hey reduced a bunch of problems for me, in a way that requires zero maintenance, and it also replaced my old solutions that had been running for ~15 years in Gmail without my having to deal with cruft anymore. More time to figure out to-do organization. :wink: I also really like the aesthetic though understand that’s subjective.

It seems like one difference between me and everyone else in the thread is that I actually like having the new email address, i.e. I’m not just handing out my old email address and processing in Hey.

My biggest issue was handling huge threads that go on for days or weeks, which I’ve written about elsewhere on MPU. I love these email threads because some of my best friends keep up with each other this way. It took a few months, but they finally implemented a solution that makes it easy to stay caught up with them without loading the whole thread. That eliminated my biggest concern about sticking with Hey.

My second biggest issue is search. You’re right about all its limitations although, for me, the way it surfaces files mitigates that as it’s saved me time a few times. The most annoying search term I’ve found is “D&D” - it can’t find my D&D threads! Support has acknowledged it needs improvement but not given a timeline.

The third biggest problem is the performance of the Mac app–hopefully electron support for Apple Silicon trickles down into production apps quickly. In the meantime, I just use the browser. The iOS app is much better and the bulk of my usage.

So, again, nice writeup, totally agree, and at the same time, I would hate to give up the saved time, peace of mind, and fun I’m having since the email address switch.