Tuesday, October 29, 2024

Thoughts on Hey Email and Fastmail

 


Introduction


Early this year I was seduced by Hey’s fresh take on email, so I decided to switch to it from Gmail, which I had used for well over a decade. I had toyed with Hey email in the past, but initially there was no way to use an email address on your own domain with the service (you had to use an @hey.com address), so it was a non-starter for me, since my primary email address is on my own domain. Later on, Hey began allowing the use of aliases on other domains, and later still they came out with “Hey for Domains,” which is when I decided to take the plunge. On January 20th, 2024, I changed my domain’s DNS settings to route all of my email to Hey, and began using the service in earnest.


TLDR: After using Hey for nine months, I switched to Fastmail a week ago.


Here’s why.



The Allure of Hey


Hey is a proudly opinionated email system. Its attitude is, hey (pun intended), we found a better way to do email. So I’ll  begin by describing some of Hey’s most touted features, and how they worked for me in practice.



The Screener

Whenever you receive an email from a new sender, Hey places the email in a sort of waiting room, “The Screener”, where you go to tell Hey whether or not you'd like to receive emails from that sender. This is an interesting idea, but, in practice, after the first week or so, most of what ends up there is spam. Good spam filters, like those in Gmail and Fastmail, achieve the same objective in a less fiddly manner.


Imbox, The Feed, Paper Trail

Hey divides your inbox into three categories, "Imbox" ("important" inbox), "The Feed" and "Paper Trail." The idea is to have newsletters, announcements, etc. delivered to The Feed and receipts and such to Paper Trail, so that the only email delivered to your Imbox is "important." You achieve this by manually assigning senders to either The Feed or Paper Trail (you can do this directly from The Screener, or at any other time), and email from allowed senders not assigned to either goes to the Imbox. As I began receiving email to my new Hey account, I dutifully assigned senders accordingly, and after a week or so most emails were properly directed.

The objective of this system (similar, of course, to what Gmail has been doing for years with its “Primary,” “Promotions,” “Social” and “Updates” inbox sections and Apple just began doing in their email clients) is for you to check The Feed and Paper Trail occasionally, and focus on the Imbox. In practice, though, I mostly checked all three when I checked my email, partly from fear that something would be miss-classified, but also because there could be truly important things in the other mailboxes, particularly in Paper Trail, for example notification of a suspicious credit card charge. When I transitioned to Fastmail and went back to one inbox, I found it much simpler to triage all of the items (using Fastmail's keyboard shortcuts, particularly the "archive and next" one) than to have, in essence, three inboxes to check.

People who like to receive their newsletters via email may benefit from The Feed component of Hey's system. In my particular case, though, I've set up my newsletters to arrive via RSS feed, so that benefit didn't apply to me. Bottom line: Hey's Inbox-The Feed- Paper Trail system added unwelcome cognitive load and complexity, and a simple inbox works much better for me.

Additionally, if you really like your mail to be pre-classified into buckets, you can achieve that using Gmail or Fastmail's powerful rule systems, with which you could recreate Hey's buckets, or tailor something similar but specific to your own needs.


"New" vs. "Previously Seen"

Hey eschews traditional folders and labels, and instead presents you with a continuous stream of emails, only dividing them by whether you've read them or not. You can even place a "screen" over your previously seen emails, so that all you see in your Imbox are the new ones. So when you read an email, unless you take any other action, the email stays in your Imbox but is now in the "previously seen" section. You can also reply to the email right away, send it to the "Reply Later" pile, set it aside (the "Reply Later" and "Set Aside" piles are both pinned to the bottom of your Imbox), set it to "Bubble Up" later (what other email systems call "snooze") or take other actions, such as request notifications specifically for that thread, or share the thread via a public URL.

There are some good ideas here, but most of what Hey's mechanic enables can be achieved in traditional email systems using folders or labels. And, as with the incoming mail buckets, with Gmail or Fastmail you can craft a workflow specific to your needs instead of having to abide by Hey's particular takes.


"Read Together" and "Focus & Reply"

Instead of opening each of your "new" emails, you can click on "Read Together," and they will be presented as a feed, where you can take action on them individually. But if you choose to reply to one of them immediately, you leave the "Read Together" interface to craft your reply, so in the end this mechanic works similarly to using Gmail or Fastmail's "archive and next" keyboard shortcut.

If you have more than one email in the "Reply Later" pile, you can click on "Focus & Reply" to put all of such emails in a sort of feed, where you can reply to them individually without leaving the feed. This interface works well for terse answers but is not suitable for crafting longer, more thoughtful replies, and you can only "reply to all," so if you want to reply just to the sender and not to the others copied on the email, you need to exit the "Focus & Reply" stream and reply individually. I tried both “Read Together” and “Focus & Reply,” but neither really clicked with me.


Other features

Hey provides other innovative features, such as adding personal sticky notes to emails, a "Speakeasy Code" that allows a new sender to bypass The Screener, saving frequently used text snippets to easily insert into emails as you compose them, and selective notifications for specific contacts or threads. The only one of these features that became important to me while using Hey was the selective notifications, and Fastmail boasts that exact functionality.



Why Fastmail


When I decided to switch away from Hey, I decided to try Fastmail instead of going back to Gmail. One of my overall themes this year has been to try to use indie apps and services instead of those offered by tech giants, and although Fastmail is by no means a small company, it offers email as a paid subscription and not a free service in exchange for personal data, which I prefer. Also, unlike Gmail, Fastmail is strict about complying with JMAP,  IMAP, CardDAV and CalDAV standards, so in the event I’d like to use third-party clients, things would work flawlessly. (Hey only works with its own web app and mobile apps and is not compatible with third-party clients at all.)

It’s difficult to explain exactly why, but going from Hey to Fastmail has felt like I've shaken off a huge burden. Hey’s gaudy interface never really agreed with me, and its opinionated takes came off as arrogant and restrictive. 

More on the tangible side of things, in addition to the benefits I address above in the context of Hey’s “allures,” Fastmail adds a host of features not found in Hey. For example, Fastmail has an excellent migration tool, which Hey lacks, so I brought all of my email from Gmail and Hey to Fastmail. I’m back to having all of my historic email available to search within my current email client, as I did when I used Gmail but I missed during my time with Hey.

Lastly, there has been much debate among email nerds regarding which is a better method to organize email, folders or labels. There are advantages and disadvantages to each, for example, an email can exist only in one folder while it can have more than one label applied to it, so labels are more flexible organization tools, but, on the other hand, third-party IMAP clients have difficulty dealing with labels. Guess what: with Fastmail, you can switch between folders and labels on the fly, at any time, as many times as you want! Just awesome.


Bottom Line


I’m glad I spent the better part of a year with Hey. It is indeed, as they tout, a fresh take on email. I’m sure there are many people who enjoy its quirkiness, and others that greatly benefit from its features. For me personally, though, Hey’s features were either easy to recreate with traditional email systems or not useful to me at all. Once I decided to switch away from Hey, Fastmail (which I had previously used as a backup email provider and a historic email repository) seemed an obvious choice. So far, my experience with Fastmail has been fantastic, and I wouldn’t hesitate to recommend it to any technically-inclined user.