TL;DR - I used HEY for five months, gave it a fair trial I think, had no huge complaints, but I've gone back to Gmail. For the details, read on.
I was excited when Basecamp (formerly 37 Signals) announced their HEY email. I asked for and eventually received an invitation. I’ve been a long time Gmail user, from back when you needed an invitation. Back in the days when Google’s motto was “do no evil”. They’ve since replaced that motto with “get all the money”. Which doesn’t make me comfortable giving them all my email.
Basecamp has a good record of supporting old products. (I still hold a grudge over Google Reader.) And they are more privacy minded than Google. I didn't have a problem paying for the service. Paying customers are often treated better than the users of "free" services.
I like a lot of the HEY features - screening emails, spy blocking, reply later, set aside, paper trail, feed, etc.
One thing that bothered me was that it was a closed walled garden. Traditionally, email has been built on standards (like SMTP, POP, and IMAP). You can use Thunderbird to access your Gmail, use Apple Mail to access your Hotmail, etc. HEY lets you forward mail in or out, but that's as open as it gets. You can't access your HEY email from another client, and you can't use the HEY client to access other email accounts. Their explanation for this is that their special features aren't interoperable. I'm not sure I totally buy that. It seems like a more believable reason is that it simplifies what is undoubtedly a large challenge. And of course, the HEY software itself is not open source. I prefer open solutions, but I use other walled gardens, like the Apple ecosystem.
It was easy to redirect my Gmail and start using HEY. It was easy to learn and use. I was quite happy with it, and I must admit, a bit excited to be in on the beginning of something. Like when I first started using Gmail. But it wasn't long before I started running into annoyances.
On the positive side, it was nice being able to report an issue and actually get a response from what appeared to be a human. (Hard to tell with some of the bots these days.) Good luck with trying to report a problem to Gmail.
One of my big frustrations was not being able to view attachments. You could argue that's not really the responsibility of an email client. But I was accustomed to being able to view pdf's (e.g. resumes on job applications) with a single click. That single click in HEY just took me to a file save dialog. So I could download it (cluttering up my download folder and taking up storage) then find the downloaded file and then open it in a separate file. No more quick glance at the contents of an attachment. That was using the standalone Mac app. If I accessed HEY from my browser it was a little better (if I can convince Firefox I don't want to download it). The funny part was that HEY displays a thumbnail, and on iOS you can zoom in and read it. So obviously they were already interpreting the content, they weren't just treating them as opaque blobs. I told myself this was a minor issue but it continued to bug me.
There were quite a lot of bugs at first. In some ways that's not surprising for a new ambitious project. But I have to admit I was initially a little disappointed. I guess I've drunk a little too much of the Basecamp/David/Jason kool-aid and had high expectations. I told myself they would fix them, give them time. And some did get fixed. But others didn't. For example, the touted Feed uses infinite scrolling, except when it needs to load more content there's a noticeable pause and afterwards the view is messed up. You lose your scroll position and all the items are doubled. Not exactly a great experience. I can imagine most of the testing happened without enough data to hit that. They even mentioned it in a job posting as the kind of thing you might work on.
Then I listened to a podcast with David where he talked about how hard they'd worked to fix bugs after the release. But that they'd had to put that aside to work on their promised HEY for Work. Great, too busy adding features to fix bugs. Heard that story before. Then he went on to talk about how bugs are overrated, they're not really a big deal. You shouldn't feel bad about your bugs, they're "normal". They should have been playing "Don't worry, be happy". I'm exaggerating, I understand where he's coming from. And I agree there's a big difference between cosmetic bugs and functional bugs. And bugs that affect a minority of users versus ones that affect the majority. But it's a slippery slope. Where does that Feed issue fit? Is that a "cosmetic" issue to be shelved? To me it was a major problem, but I realize that's a judgement call.
To me, telling programmers not to worry about bugs is just asking for a bug filled product. And once you have a lot of bugs, it starts to feel pointless to fix them. Personally, I'm ok with feeling a little bad about my bugs. Not to the point of flagellation, but enough to make me e.g. write more tests next time.
I also found I'd (not surprisingly) grown accustomed, if not dependent, on a whole assortment of Gmail features. I screwed up and sent an email to the wrong recipient, which I would have caught with Gmail's undo feature. I was used to typing a few characters of a contact and having Gmail suggest the right person, whereas HEY constantly suggested contacts I never used. The Feed is a nice idea, but it's (currently) a pretty minimal feed reader. It doesn't keep track of what you've read, and if you get interrupted, there's no way to pick up where you left off. You have to scroll down and try to remember what you've read. I've switched to using Gmail filters to forward feed type material to my Feedly. Filters are another feature missing (or omitted) from HEY.
I'm not writing HEY off. I have my account and I don't mind having paid for it. I think they're trying to do something worthwhile and I don't mind supporting that. I'll keep an eye on it for potential future use.
I'm not completely happy going back to Gmail. I don't have anything particular to hide, but I'm not a fan of surveillance capitalism - of companies like Google making their profits from selling my private information, or the ugly things done with that information by the companies that buy it.
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