10 min read

HEY vs Fastmail: One year on



For all the social media, messaging, and productivity apps I have installed, my digital communication is still dominated by email. Sure I use WhatsApp, iMessage, Slack, Basecamp, Twitter, Instagram… but email is the constant that I can’t do without, at work or at home.

I’ve been using Fastmail for around 7 years, and before that I used Gmail. When HEY launched just over a year ago I signed up as soon as I could. Not because Fastmail had flaws, but because I quite like new shiny things, I love Ruby on Rails, and I’m intrigued by the products that Basecamp create. I don’t think Basecamp have the slickest products on the market by any means (they really don’t), but they create a narrative around their products and I found the promotion around HEY quite compelling.

I’ve used HEY for almost a year now, so it feels like the right time to reflect on the product. I should admit that I haven’t use HEY exclusively over this time. I did try forwarding all my email into it for a few weeks, but I found it something of a trial by fire and I quickly reverted. Instead I started to move different cohorts of email over to it (newsletters, GitHub notifications, receipts), enough to give me a solid experience of it without committing full time.

I wrote a popular post last year that has had thousands of views, and I think all those first impressions still stand today. What follows is a breakdown of what works for me with HEY, what doesn’t, and why I’ve ultimately decided it’s not for me.

What worked for me with HEY

Let’s start with the obvious. I lucked out with a choice email address: olly@hey.com.

The HEY apps are really good. I’ve used them on iOS, iPadOS and macOS and they work well. They’re fast, responsive, and I’ve not really encountered any problem with them. That said, I do actually still use Apple Mail sometimes (I love the embedding photos functionality, where I can choose what size I want the image to be), so the fact that HEY is a closed system does bother me a little. I can live with this limitation (and I do think it’s a limitation) but in the back of my mind I can’t shake the fact I’ve handed over complete control to the Basecamp team.

The specific workflow HEY forces upon you actually works for me, mostly. Directing receipts into Paper Trail is nice, and I like The Feed (the concept, not the UX as much). Set Aside and Reply Later are nice ideas.

I really like the Files area. An at-a-glance, and searchable, view of all the attachments. This is nice, although when people embed images in their signatures these also show up in the Files area which is pretty irritating as they can quickly dominate the list.

HEY World is fantastic. Nobody expected a blogging feature, but it makes total sense and the simplicity of execution is excellent. If you don’t want to run a static site for your blog, you’ll probably have to pay for a blogging app so bundling one into your email which you’re paying for anyway is a nice touch. However, let people use a custom domain!

Things that didn’t work for me

Unfortunately, for me, the cons outweigh the pros by quite a margin. I really want to like HEY, but there are just too many things on this list that bug me and will probably never change. What followsm might sound like a hatchet job, but it’s not intended to be. It’s more like death by a thousand cuts.

Much as I love the @hey.com email address (which, as I understand it, is now mine forever since I paid for HEY for a year), I still want to use a custom domain. Owning your own domain is brilliant. It costs around $1/mo and it gives you the freedom to switch email providers at your leisure without enduring the major hassle of updating your email address everywhere. My email address is in hundreds of online accounts (419 according to 1Password, OMG!), and the thought of changing them all is too much. Of course I could choose to forward mail into HEY, but I’d rather do it the other way around. Unfortunately, Basecamp backtracked on their promise about custom domains (which they have publicly regretted), choosing to rebrand HEY for Work as both a work and custom domain solution. This isn’t good enough for me. I already have a HEY account, why make me sign up for another one just to map a domain? It’s half-assed and a cop out.

HEY is based on principles and you’re expected to conform to them. There are some areas where this is particularly irritating, such as notifications. By default, there are no notifications in HEY at all. The HEY website, however, states:

Instead of getting push notified for everything, you decide which senders or threads are important enough to warrant notifications. You’re in control.

Except you’re not in control! Want to be notified when there are new message in The Feed? Nope. Want an unread badge on the app icon? Nope. If I’m in control, let me choose! They did relent somewhat and allow push notifications for all new mail, but they steadfastly refuse to add a badge count. I think this is obstinate. The Feed should have some sort of notification. Not necessarily push notifications, but some sort of indication in the Imbox that there is something new to read in there. Instead I have to compulsively check it just to see on the off-chance if there’s something new to read. This is anti-productivity.

The keyboard shortcuts generally work ok, but they’re not enough. I found there was a constant need to click on the avatar with the mouse to select one or more mails, and then take an action. I’d much rather cycle through them with keyboard shortcuts as I can with Fastmail.

The speed of HEY is really pretty good considering it’s all server-side rendering, and I’m delighted they open-sourced Hotwire which is a game changer, but looking at it objectively, Fastmail is much quicker. Fastmail is insanely fast on both iOS and web. Once you become accustomed to using Fastmail’s web interface and their powerful keyboard shortcuts, nothing will come close.

No swipe to delete on mobile. Maybe the idea is that I shouldn’t be deleting mail, but I genuinely don’t want those GitHub notifications once I’ve dealt with them, ever. Rather than being able to swipe to bin them, I am forced to click on the avatar, click the More button and then trash. Too much effort, especially when you have multiple mails. I tried bundling email, but I didn’t get on with that either.

I couldn’t shake the feeling that I was being locked in, and there’s no denying that you are. Sure eventually I can leave and forward my HEY email somewhere else. I can export my mail, but if I have been diligently labelling all my email in HEY, exporting my emails results in a single .mbox file and all my label history is gone. This needs to be fixed by offering multiple .mbox files, one per label.

No snooze. I think this is such an important feature of Fastmail and Gmail and it’s a glaring omission from HEY. Sure I can set aside and reply later, but there are too many occasions where I want to set something aside for a few weeks, months even. With HEY, my only option is Set Aside but then the email is staring me in the face constantly, demanding my attention. With Fastmail, I can snooze for a month and have it reappear in my inbox when I need to deal with it, allowing me to forget all about it until then. This is liberating, but with HEY it feels regressive.

Cover art. This feels like a poor excuse for an Archive folder. Some people (🙋) really don’t want to see the ‘previously seen’ list every time they view their inbox. HEY acknowledges this by allowing you to cover these emails up with an image. I get the intention here, of course, but maybe the feature customers really want is to be able to archive their email from the inbox (sorry, Imbox)?

What impact has HEY had?

I think it’s pretty clear that HEY isn’t working for me, but has it changed the way I use email?

I still use the Basecamp workflow labels in Fastmail (Set Aside, Paper Trail) as I wrote about in my original post. I find Set Aside works for me to some degree, but I tend to use snooze more than set aside. I don’t think Reply Later really works for me because I can’t help but leave mails that need attention in my inbox, and archive the rest! Inbox Zero for me isn’t a religion, it’s a productive workflow. The inbox is a todo list.

One of HEY’s principles was a fresh start where you don’t need all that old email baggage. I took this to heart somewhat. I have loads of folders of archived email, well over 20 years of it. I would agree that the majority of this is baggage so I’ve gone ahead and remove a tonne of it. I didn’t delete it entirely, I exported the folders to my local macOS Mail and deleted them from Fastmail. So I still have it and can search it if I really needed to find something, but I have far fewer folders in Fastmail now.

What next?

My HEY account is up for renewal soon and while I’m tempted to cancel, I am still intrigued to see how it develops over the next year so I’ll probably pay for one more year (I’m fortunate enough to be able to cover the cost, which I appreciate is a luxury).

I understand now that I’m not their target market. You might say I’m an email ‘power user’ which isn’t a good fit. I’m too high maintenance feature-wise, looking for specific export options and a more flexible custom domain implementation.

I have a feeling churn will hit HEY badly in 2021 as excited early adopters are faced with renewal (never mind the additional impact of the recent Basecamp policy debacle). Following my first blog post, I’ve had a few HEY customers get in touch and ask what I’m thinking now, and most of them are not convinced by HEY, especially the custom domains, and are going to ditch it.

Final reflections

I wholeheartedly recommend Fastmail but I want to stress a big caveat. Only use it with a custom domain. Fastmail have a policy of recycling email addresses when customers stop paying, which I can’t help but think is a security disaster. As an example, my Fastmail username was previously used by someone else and I still get some of their emails, including active online shopping receipts complete with their name, address, phone number… this is crazy! 🤯. Both Gmail and HEY strictly never reuse email addresses, and I honestly can’t see understand Fastmail’s position on this. So tread with caution here.

Ultimately, the Fastmail service is just too good to leave behind. Not only is the UI insanely fast and intuitive, the product is very reliable, it has superb custom domain support, a powerful calendar, human customer support (albeit not as responsive or friendly as HEY), and you get all this for half the price of HEY if you pay annually. It’s a great deal and I would argue still the best email offering on the planet.

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