Goodbye 'HEY'

As we are wont to do to this day, we were waiting on Jude.

But this time it was 2020 and we were in the hospital in that weird in between time from when you check in to when the baby is born. Julie’s contractions were close enough together for us to be in the delivery room, but not quite close enough to begin delivery.

We were pros, though. We knew the drill. Babies don’t come immediately. We were finishing up some work things, letting people know we were in the hospital, etc. etc. etc.

I was texting with a friend who said he had an invitation to the new email service– HEY– and asked if I wanted one. The username I wanted was open, so I signed up right there in the delivery room. I received my first HEY email before I received my second kid.

I always thought about that day each of the past three HEY renewals: it makes me happy to remember little details like this of Jude’s birth.

I never felt an affinity for HEY like some people did. It was a great idea and a great initial product. There was lot’s of promise, but I never feel like that promise was fully realized. The HEY of 2020 looks and feels very similar to the HEY of 2024.

So I’m cancelling HEY and migrating back to iCloud email– or more precisely, my email– for five main reasons:

HEY feels too heavy

This has improved in the past year or so, but it still feels like it takes ten clicks to do anything. I’m constantly waiting on the Mac’s electron app. There’s very little support for trackpad gestures on the Mac. Attachments feels like a chore to manage. For a service that prides itself on turning down the noise of email, it feels like not enough attention has been paid to managing the signal.

HEY feels stagnant

There’s been some improvement to the core ideas, but the pace of new features has crawled. Email may not need constant new features, but a subscription service like HEY does. That puts 37signals in a bind: if they iterate too much on email, it could collapse under itself. But not enough doesn’t feel worth the money. It’s not a great situation to be in.

HEY feels walled off

I get that the schtick of HEY is that while it’s built on an open protocol like email, it has so much special sauce that it’s impossible to import all your old email or work in third-party email clients. But with 37signals preference for and commitment to the web, it feels like HEY should be as open and integrate with as much as possible and it just doesn’t. 37signals wants me to use HEY for everything, but I like my other apps! What if I could connect my email to my Things today list or utilize the Drafts app for notes on an email?

When HEY Calendar launched with no intention of being able to manage existing calendars, it sealed the deal for me: it’s 37signals way or the highway. That’s not a bad thing if you’re going 37signals way, but there’s not much deviation allowed.

HEY doesn’t feel worth $100/year

I’m broadly supportive of this era of subscriptions: I think it’s the best way to ensure that developers can continue improving on an app or service. But the flip side of that is that once a service doesn’t feel worth it any more, it’s time to cancel. To pay for a commodified app/service like email, there has to be a lot of value added and I don’t feel like HEY offers enough to continue paying for it.

I’ve spent the past week back on the Apple mail apps and while there’s some things I’ve missed about HEY, the positives outweigh the negatives. All for the price of free.

I’m not optimistic about 37signals' relationship with Apple and commitment to embracing its new and future technologies

DHH doesn’t really bother me like he bothers most people. I really truly appreciate his contrarian views–even though I don’t agree with most of his recent ones. I truly do not think he needs to be a bridge builder, but I also truly think he does not need to be a bridge burner. He was dealt a bum hand by Apple and has every right to be incensed, but there’s an anger there that makes me hesitant that 37signals will adopt Apple’s current and future technologies to the extent that I want them to.

The straw that broke the camel’s back here is Apple Intelligence. I’m still working through my feelings on what was announced at WWDC, but I’m not confident that 37signals will allow HEY to integrate with any of this and I at least want the option.

Goodbye HEY. You are a great idea that no longer quite works for me.