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A lengthy review of how HEY email has changed my relationship to email

Update: There is a 2023 HEY review because I am indecisive and like to try things a lot. And, uh, another for 2024.

Update, May 2022: I’ve included an update at the end on my interaction with Hey over several months and why I switched back.

This original post was first published in November 2021.

I’ve done lots of tricks over the years to control email. Like most people, I have a few different inboxes for a few different responsibilities and organizations and, like most people, I have them all funnel into one app or service. For me it’s historically been Apple Mail. The result has always been a native service that lists email with a dozen or so emails in my inbox at any one time. HEY from the same people who brought us Basecamp, has changed my interaction with email in one crucial one: I now routinely maintain inbox zero.

To be clear, I don’t have and never had a huge problem with spam or email from places or people I didn’t want to hear from. I was always conservative with handing over my email and maintained a separate info@ address for stuff I knew would likely fling junk at me.

Following the belief an inbox should not be a glorified to-do list, I worked hard to keep threads and messages limited in two ways:

  1. Moving things to do to my to do list. This has usually been Basecamp. I always appreciated how Basecamp’s “flat fee for as many users as you want” worked. It’s helped me automate messages to clients without having to do anything or pay extra for them, like Trello requires.
  2. Eliminating email hot potato where I just try to fling messages back and forth in hopes of getting them off my plate long enough I can breathe. I want it one-and-done.

HEY email vs Sanebox

HEY email’s “Screener” is probably the secret sauce no one has tried to replicate. I’ve seen guides where people try to build this into Fastmail using rules and labels, and Fastmail is good—it’s what I used for years. But I never used or liked Fastmail’s app or web app. I don’t like web apps at all. I make websites and spend a ton of time in my browser on my Mac. As such, tabs get lost and I never wanted another pinned or loose tab floating around. I want a big freaking icon in my dock that’s always there.

The Screener is what it sounds like: a special purgatory where every first-time email sender goes. Give it a thumbs up or down to approve messages from that address.

There are limits and one place Fastmail was superior is in the granularity of its filtering. For instance, I get notifications from services and websites that come from something like, noreply@website.com or wordpress@organization.com. The HEY screener applies one-by-one to that specific address, not the domain. So if you screen in noreply@website.com you can still screen out newsletters@website.com and it’ll figure it out.

The problem is many, if not most, places have one or two email addresses for these sorts of things. It would be great if everyone used info@website.com for notifications, noreply@website.com for receipts, and newsletters@website.com for everything else, but they don’t. So I often find myself saying, “Well, I want or need emails that’s likely to come from this address, so I guess I’ll screen it in and just deal with the fluff in The Feed.”

Fastmail enabled me to say, “Take every email from wordpress@website.com that has this specific Subject Line and delete them.” This was a handy way to get rid of those automated “Some plugins have failed to update” emails I get every freaking morning. “Yes, I know, you can’t auto update that plugin. But I’m not checking this every day. You’re just going to have another update tomorrow. Go away and I’ll notice you from time to time when I login to the site.” HEY can’t do that, so off to The Feed they go.

HEY could fix this by enabling slightly more advanced filtering based on a subject line. This is tricky, but surely they themselves have the same problem.

One solution I’ve used in the past to try and fix this is SaneBox. SaneBox is cheap and lets you tack itself on to any existing Gmail, Outlook, or IMAP service. It’s basically universal and creates a special set of folders like the “Black Hole” where you can just drop an email and it’ll auto-filter it out forever. Like HEY, SaneBox also gives you a special inbox for newsletters and receipts and emails to deal with “Later”.

I’ve always thought SaneBox had too many inboxes. Maybe my email volume is too low, but it just introduced more clicking around to check what amounted to 3-4 more inboxes. HEY defaults to 3: an inbox, newsletters and such, and receipts and delivery confirmations. [Update, May 2022: I’ve come to spend more time with Sanebox and have changed my mind on some of this by embracing custom folders and just springing for the slightly higher priced plans. I was being cheap on a month-to-month basis, but when bought bi-annually, the price is comparable. More on that below.]

None of these solutions accurately fixes the manual problem that comes from a place like Amazon. Amazon sends me shipping notifications that I want in the Feed, receipts I want in the Paper Trail, and other stuff that goes in the Feed, I guess. The other day I got an email from noreply@amazon.com saying a credit was applied to my account due to a mistake on their end. I had selected “No Rush” shipping and they noticed they hadn’t applied the $1 credit to my account. But they also send me promotional crap I don’t want from noreply@amazon.com. I don’t have a lot of ways of dealing with that except to just take it and dump it in the Feed. SaneBox doesn’t really solve this problem, either.

It’s a lot harder to screen out people than you think because you’ll always wonder, “Wait…if I have to get a password reset email from this place, where will it come from?” You just don’t know. And yes, you can go back and change it, but in the case of my Amazon credit, how would you know it ever came? That’s a low-stakes example, but you can imagine situations that might come up you know exist but can’t foresee.

HEY and my inbox zero

Perhaps the reason I stick with HEY most is because it has subtly changed my relationship with my inbox in an unusual way I hadn’t predicted.

HEY doesn’t make it easy to “Delete” or “Archive” emails. It takes some getting used to, especially for neat freaks like me. But it is liberating if you follow their model and treat emails like a stream of Tweets or news updates. They just stack on top and old stuff moves down the pile.

Like most email, most of it’s never going to be seen again. And in the few cases where you do need to refer back to an email, most of us most of the time turn to search to find it no matter what service we use.

As an aside, some people have complained that HEY’s search is lousy, and while I won’t say they’re better than Gmail or Fastmail, it strikes me as no better or worse than Apple Mail’s. It’s a low bar, but I’ve not been frustrated with it (yet).

When an email arrives in your inbox, you open it and read it. In most apps the email now just sits there, waiting for you to file it. HEY nudges it down from an “Unread” section to “Read” where they just stack up in one of its three processed filters (Inbox, Feed, and Paper Trail).

You can mark an email as unread again, or “Reply Later” or “Set Aside”, all very easily. And I’ve discovered that because this UI nudges things just out of my attention enough, I’m much more likely to do what people should really do with email all along: handle it at the time of receipt.

I used to load Apple Mail, read some messages, maybe reply to one or two, and leave the rest for later. This was stressful without me noticing it. I always had “that email I need to reply to” stuck in the back of my brain.

With HEY I sit down, read some email and process each one. “This one gets a reply”, “This one gets processed into my to do lists in Basecamp”, “This one I can move on from”, etc.

If we’re being honest with ourselves, checking email should be done a few times a day. Handling email should be a block of time on your calendar where you spend 20-30 minutes just dealing with it. About like checking the physical mail from the USPS, you go to the box, you pick it up, and you open the things you need to open, trash the stuff you don’t, and make reminders in your to do list of what bills need paid and so forth.

Email should be the same way and I’ve always been close to achieving that ideal. HEY has pushed me into that because I know what’s in my inbox is work I need to do and not just a treadmill where I know “Another email is just going to plop in”. Because the Feed takes a lot of that away, my inbox is truly more like an inbox. It’s somehow better than I was ever able to achieve with SaneBox and Fastmail filters, while powerful, can’t be applied from inside Apple Mail. And Apple Mail’s native filters don’t sync across iOS and Macs.

HEY’s app resource usage is fine

The developers behind HEY have a pretty good record of making powerful web apps, but they are still just web apps. It’s a write-once-run-everywhere approach that drives me and picky developers nutty. I get it, I understand this is where we are, but it worries me. I don’t like Slack or other Electron apps running on my Mac. The resource usage is just higher than a native app.

I ran HEY and Apple Mail side-by-side for a while during a trial period, managing both inboxes simultaneously by forwarding a copy of all mail from Fastmail to Hey. It’s a useful way of trying HEY without committing to it by redirecting your MX records. Apple Mail and HEY were basically equally, consuming about 7-20% of my processor during some actions and running around 100-200MB of memory in the background. For comparison, this put HEY at around the same resource usage as Fantastical and slightly heavier than Paste, Tot, Spotlight, and Bartender 4, all of which I use frequently.

I just didn’t notice a slow down or hogging of my system resources. What I do notice is the iOS app has more menus that are easier to find and use than the Mac/desktop version, and when you hit the “X” to close the window it pretty much closes the app. It will still run, but clicking it from the dock is basically a hard refresh after a minute or so and it’s noticeably slower than Apple Mail at launching and showing messages. iOS does not have this problem.

I find that using the Hide command (CMD+H) on HEY’s window does what the “X” does in Apple Mail: go away, but be ready to show up real fast when I want you back.

Other limitations to HEY I hope they resolve

Aside from the slow click-to-launch-from-the-Dock, I’ve run into a few other odd problems:

  • There is no out of office or auto response feature. This seems table stakes for most anyone. I’m doing a light week this week because of the holiday, and, well, no one knows that.
  • It’s strangely impossible to reply to an email that goes in the Feed. For those “If you need anything or have questions, just reply to this confirmation message” kind of message, you have to go into the sender’s info and a series of clicks to reply. I find it easier to just start a new message and copy in their email address.
  • Starting a new message is sometimes cumbersome and I can’t quite figure out how or why sometimes my messages start in the window and sometimes start in a new window. HEY, like Basecamp, really likes to be in a one-window-does-all interface, which can be focusing but limiting.
  • The aforementioned filters are a slight problem, insofar as I wish I could apply them at least to the Screener by subject lines or keywords.
  • Send later should be a feature. I’ve thought long and hard about this and why such a “power user” feature might not be high up their list, but it should be because it helps reduce email. For instance, I’ve been working on a project and finished it up just before Christmas. I needed to ask one last question related to shipping details, but I didn’t want to do it over Christmas. It wasn’t that important, but it’s taking up room in my head. I have to remember to send the email after the holiday. If I sent it, it’d be out of my head and into the recipient’s, which isn’t great for business and is mean to them. The solution is my being able to schedule the email for after the holiday. It gets it out of my head, keeps it from appearing in theirs, and lets us all have a break. Sending messages on a schedule should be a feature.

Mid-2022 update: I switched back to Fastmail and away from HEY

Much of what I wrote above is still true and some things have been resolved. “Send later” came to the service in early 2022 and search definitely got better. But I started noticing more problems with the Mac app that drove me bonkers.

The most glaring was how often I’d hit Cmd+W to close the window, go do something else, and come back relatively quickly by Cmd+Tab or clicking the Dock icon. You’d think it would load the Imbox, but it would stubbornly insist on opening to the “New Message” window. Try as I might I could find no way to get this to go away. It was like a web browser trying to restore the last opened tab, but it forgot which page to load. Since there was no other way to navigate, I’d have to force quit two or three times to get it to flush its cache and load the Imbox. This happened a lot.

While the overall resource usage of HEY was fine, Apple Mail was still far better and despite its many problems, never failed to load to the same trust starting point each time I switched to it. If you do use HEY, I recommend getting in the habit of using CMD+H to just hide the window. Closing or quitting the app will always take a few seconds to load. HEY was always noticeably slow to “start up”.

HEY changed my relationship with email, but I get nervous getting locked into things. I’m like Don Draper—I don’t want to be tied to really anything, ever. It’s why I’m highly unemployable I guess.

Using Sanebox + any mail app

I switched to using Sanebox alongside Fastmail. I like this setup, too, after I did the tweaking to make it more like HEY. This enables me maximum flexibility in using whatever app I like, whether that’s Fastmail in the browser (which I never use), Apple Mail (which I use primarily), or Spark email (which I sometimes like but find it struggles with attachments in an Exchange inbox I have.)

This was partly because I do have other email inboxes I have to manage, so I was always running Apple Mail anyway to get at them.

My Sanebox configuration works nicely as a flexible HEY alternative:

  • I renamed the initial Sane Later folder to “The Screener”, changed the Sane News folder to “The Feed” and made a custom folder named “Paper Trail” for receipts.
  • You could call them anything, but I got used to this naming convention with HEY. I left Sane Blackhole as just “Blackhole”. It’s effectively “the screened out” folder from HEY.
  • That was kinda it. The Sane News/The Feed folder was basically the same as HEY’s, and the Sane Later already worked like HEY’s Screener folder.
  • In Apple Mail, or really any mail app, you can set some top-level favorite folders in the sidebar to serve as quick access to these folders. Or, hide them entirely and just focus on your Inbox/Imbox.

It took me about ten minutes to configure Sanebox and it was re-trained in about a week or two to do what I wanted, just as HEY was. The benefit is I get to use any email app I want. And the cost at $144 bi-yearly worked out to about the same as HEY when combined with $60/year with Fastmail. Technically I pay $132/year, or $11 a month instead of $9.99.

This might be overkill for you because if you don’t mind HEY’s apps, you’re probably fine. Me? I rely on a Mac app because my browser is full of tabs. I do not want another tab running. I have never used email in a web browser tab because I always lose it, even if it’s pinned. I just want a dang Dock icon to Cmd+Tab to that works. I also really missed the ability to drag and drop attachments into Apple Mail on my Mac. Often, HEY’s app would treat it like a browser would and just render a JPG over everything in the window.

Saving files out of HEY’s emails was like downloading from a browser, but it always defaulted to the Downloads folder. When clients send me a random document or whatever, I almost always want it temporarily and seriously, who ever remembers to clean their Downloads folder? I keep my Downloads folder tidy by just saving each file I do download into an appropriate spot (or a “Temp” folder I keep on my desktop) as they come up. HEY was absolutely ruining this workflow for me.

Likewise if you typically use HEY or your email from a phone. The HEY iOS app is fine, but I spend a fraction of time in iOS compared to my Mac.

One difference is I rarely maintain Inbox Zero with Apple Mail. HEY sorta forces you into it, but only because I was tucking so many things into the “Reply Later” or “Seen” area. Truth be told, “Reply Later” was sort of an out of sight-out-of-mind space for me that did sometimes prompt me to take action on some emails sooner than later. “Seen” gave me a lot of anxiety because I was always trying to remember something was somewhere in there.

HEY’s system wasn’t perfect because sometimes a client puts me into a thread that just behaves like people do: slow, imperfect, and somewhat messy. I do, however, maintain a stable inbox in Apple Mail with Fastmail and Sanebox. My inbox right now has about 8 or 9 email threads in it.

If you’d like to try Sanebox, use my referral link and we both get some kickback. You get $5 off and I get a free month: https://www.sanebox.com/signup/ea7300de90/c. They’ve always had a generous free trial period and are easy to cancel. It’ll also handily restore your inbox as it always was or would have been if and when you decide to cancel.

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Justin has been around the Internet long enough to remember when people started saying “content is king”.

He has worked for some of Indiana’s largest companies, state government, taught college-level courses, and about 1.1M people see his work every year.

You’ll probably see him around Indianapolis on a bicycle.

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