I have written about using HEY email in 2024 and before that in 2023 and again in 2022. So here I am writing about HEY in 2025.
Many things can be true at the same time:
- Not too much has changed with HEY in that time. The Calendar is the biggest addition.
- It’s still opinionated.
- HEY is still not for everyone.
- HEY is still a great solution for many people.
As I have written before, HEY is like an Apple product: it works best when you just submit to whatever they want you to do with it. You either find this refreshing or insulting.
A lot of people don’t like the Imbox (sic) view because they read an email, and it goes into the pile below the “unread emails,” and they find it difficult to work with. This is because you are applying an old email habit to a product that wants you to act on messages at the time you see them. Either you read it and dismiss it, or, you read it and reply right then, or you “reply later” or “set it aside” where it goes into one of two other piles.
Some people don’t like how you can’t delete messages after you’re done with them. This is not how HEY thinks. It’s a real “let it flow” system akin to reading Tweets or Facebook Posts. You just let them fall off the bottom and trust that the system will process them out after a set time.
Some people don’t like that you only have an Inbox, Feed, or Paper Trail for sorting. They want more piles. That’s fair. But that’s not HEY (though you can create custom workflows with Kanban-style boards. I don’t use this feature much.)
My use case for HEY (for domains, so I can use my @justinharter.com email) works for me:
- It forces me to act on every email as I see it. I either move it, reply, or let is pass by.
- HEY forces me to keep on top of my “reply later” pile because if it gets too big, it becomes a little unwieldy.
- There are some features that work better in HEY than any alternative I’ve ever tried (including Spark, Sanebox, Outlook, and probably half a dozen others). Namely “Bubble Up”, which has the smarts to let me “snooze” an email if there is no reply. This is key. Sanebox, for instance, will resurface an email no matter what. I use this constantly to send a question to a client and, if they forget, I won’t because it’ll bubble up later. But if they reply before the reminder time, it won’t annoy me again. Nice!
- “Reply Later” and “Set Aside” are enough for me. A long email from a client goes to Reply Later. An email for a hotel about my check-in goes to Set Aside.
But there are also things that do not work for me:
- HEY Calendar has no interface to services like Calendly. I doubt it ever will.
- HEY Calendar still rotates the view to be “sideways”, which I hate.
- I like time blocking, and it’s nice to be able to “drag a block of time” on my calendar, then move them around like blocks. HEY Calendar does not support this at all. It’s a very fiddly series of menus that you have to toggle to set the name, date, time, etc. I find their “auto-formatting” poor. It never seems to get what I mean when I say, “Call with Chris at 8 am on Thursday.”
- HEY’s email editor encounters a weird bug where the cursor jumps around. I can’t quite figure that one out. But, I’ll be typing, and suddenly, it wants to jump to the frame that holds the prior email thread and deletes it. Maybe I’m hitting a weird keystroke. I can’t tell.
And then there’s the issue of HEY’s co-founder, David Hennemier Hanson (DHH). He’s opinionated on X and his blog, and, frankly, for a lot of people, when you know the views of the guy or woman behind a service, suddenly you might not like that service anymore. We all have those kinds of feelings about something somewhere. I won’t and have never eaten at Chic-Fil-A because they actively hate my marriage. For you, it might mean you never fly United because they lost your luggage once.
DHH’s views are his and he is certainly entitled to them. Sometimes I agree with him. Sometimes I do not. That’s okay! But it’s also a little weird I have to know what he thinks about employment policies or politics or whatever at all. A weird quirk of living in the 21st century I guess.
I have struggled with that like many people surely have for many services. You may feel that way about Amazon for being too big, Apple for being too opinionated about design, or Microsoft for being anything Microsoft. Google is another situation where people have strong privacy feelings.
I still use HEY in 2025 because it is the best email workflow for me. It fits my mental model of how I handle email, and how I would like to handle my email. It also fits my work model since I don’t need to do “corporate” stuff like sharing my calendar or delegating access or whatever.
I maintain that HEY’s biggest driver of churn is surely that when people enroll in HEY you can’t import anything. Your emails are trapped in your prior or existing system. For me, this was and is Fastmail. You can import an .ics feed into the calendar, but for most people this all means you have to maintain that prior service at least for a while. I’m still paying for Fastmail because it hosts my calendar and lets me use Fantastical (HEY and its calendar do not support any third-party apps at all; you get a webview. Period.) I use Fantastical because I like it and because it lets me drag and drop blocks of time on my calendar. I like that a lot. I’m visual like that.
But it also means I have the ability to switch back to Fastmail at a moment’s notice. From a business standpoint, this seems like a weak link in the chain. Like if when you switched to Verizon you had to maintain another line on AT&T because you can’t port your number. If HEY let people import more stuff, I have to wonder if the hosting costs would be more or less than the cost of having people always being a DNS settings change away from just “going back to their stuff”. Inertia is a powerful force. Clearly, they’ve decided it’s better to do it their way, so maybe it is.
New features in HEY
There are scant new features in HEY email. The biggest is their “Power Through New” where you can mark messages as read in bulk or see them in a list to reply through new messages. This is similar to their Reply Later “All” view, but I don’t use it much. It’s fine if you want to tap out small replies, but almost all my replies require me to send attachments. And you can’t attach anything in those views. So it’s functionally useless to me.
I stick to the one-at-a-time email model, which is another “perk”perk”: it forces you to only look at the one message. If more pop in while you’re writing, you don’t see them. I find this focusing. If I need to reference some other message, I can minimize the email draft and go navigate around and I find this functionality better than Fastmail’s. Fastmail is more of a “we save this as a draft and you can come back to this thread later” which requires more clicking around.
All this to say: HEY is still HEY. There are a few new features, but nothing dramatic. The value here is that it is a new workflow. If you can embrace that and it matches your mindset, you’ll like it. If you need all sorts of other stuff bolted on like you get with Outlook or a bunch of Gmail extensions, it’s not going to be for you.
