Why I switched from Gmail to HEY

I was in the middle of writing this piece when, last week, Ezra Klein published ‘Happy 20th Anniversary, Gmail. I’m Sorry I’m Leaving You’ in which he shares his experience switching from Gmail to HEY Email, focused on the intentionality of using HEY. I loved the way he described feeling overwhelmed by a frictionless, unintentional world of software, and so I finished this piece to give my technologist perspective on HEY Email and how I want to see more technology designed with opinionated defaults.

When I was running my last company, I had a mountain of emails every day. My friends told me to use Superhuman, an email client built by ex-Runescape intern Rahul Vohra, which touted a philosophy of GET TO INBOX ZERO at superhuman speed. My friends loved it, saying “getting through my emails is so fast!”

When I heard that, I thought it was cool but figured I was fine “getting through” my inbox already—I didn’t really need a ‘faster horse’ to help me do it quicker.

When I wound down my last company and stopped getting as many emails, I suddenly realized that most emails I was receiving now were not from actual people. I’d get notifications on my phone for things like ‘New StreetEasy Listings,’ and I’d be disappointed that I broke my focus just to look at that.

But then one day, I saw a video of Jason Fried (CEO of 37Signals, the company that made HEY) talking about the Screener in HEY Email, which keeps out unwanted emails. And instead of Superhuman’s ‘get to inbox zero ASAP,’ I felt that HEY was saying to me: ‘just stay at inbox zero in the first place.’ That felt fundamentally different to me. Was it really possible? I tried the HEY free trial and found out it was.

There are three defaults of HEY that made this a reality for me.

The core default that changed the fundamental email paradigm for me is the Screener. It forces me to make a choice every time I get an email from a new email address. HEY asks if I want to get emails from them. If I say no, none of their emails ever touch my inbox. No more new Vercel product updates, TurboTax reminders, or political campaign donation requests. I used to have a separate email just for signing up for crap I knew would spam me (you probably have one too!). Now I just screen it out. This is completely different from the current email paradigm of ‘anyone who has your email address can email you.’ Gmail lets you block senders, but that’s once they’re already in your inbox.

The next default reframes the concept of an inbox. Instead of one inbox, HEY has 3 inboxes already set up for you: Imbox, Feed, Paper Trail. You decide what goes where. I’m sure Gmail lets you make labels and you can somehow set up filters and rules for your emails to go into different buckets but I was too lazy to do so.

    The first is the Imbox. Not a typo. (The HEY team felt so strongly about naming it this, that they literally made itsnotatypo.com). The Imbox is for “IMportant, IMmediate emails.” For me, these are emails from real people that I’m conversing with over email. Like my family email thread where my uncle shares his photos of baby elephants (pics at end). This makes it really easy to track down real conversations I should be participating in.

    The second is The Feed. This is for all my newsletters and ‘announcements’ (Young the Giant is dropping a new album!). The Feed is specially designed so I can just browse headlines as if I’m scrolling, well, a feed, and click into the ones I want to read. I don’t use the Substack app anymore because I can just browse all my newsletters here.

    Finally, the most mundane inbox: The Paper Trail. All of my receipts and confirmations are routed here. These are actually the bulk of my email these days. So it’s nice to have them in one spot but not in the way.

The final default is extremely opinionated: no one should take your attention away. HEY does this by not having ANY push notifications for ANY emails by default.

This one made a huge difference in my life, and took a lot of adjustment. Before HEY, I was constantly checking my phone because a Gmail notification would pop up. It’d just be a new newsletter post, some confirmation email, or a promotion. Nothing important, but it broke my focus and split my attention. I missed some important emails early on because of this, but because of this default, I realized almost no emails are actually that urgent. And I’ve since turned on notifications from specific senders that are important. Sure, you could turn off notifications in Gmail, but that takes work. Defaults are powerful!

There are a lot of other great features of HEY, but these 3 things are how HEY helps me engage with email differently. It’s an opinionated alternative to Gmail and Superhuman, focusing on email being a clean, intentional space that I come to. It’s clean because it keeps emails out on my terms. It’s intentional because I have a goal: “Let me talk to X. Let me catch up on news. Let me pull up that receipt.” It’s a space I come to because there are no push notifications; I am consciously choosing to check it. The defaults in HEY all drive this home. Whereas Superhuman seems like the ‘faster horse’ of the current email paradigm with amazing speed and efficiency; HEY has fundamentally shifted my experience of email because of its defaults.

Email used to give me anxiety, new push notifs for every little thing, a heap of unsorted outreach from strangers, key info and conversations with my family buried in the mess. I now love checking my email, talking with my family, seeing if there’s any new goodies in there, choosing what comes in and out, catching up on my newsletters, easily finding my flight confirmations.

A lot of people dunk on HEY because it doesn’t look super minimalist or have buttery smooth animations. People often laud the “clean” feeling in products like Superhuman. This is awesome, and I’m so glad that software can be an artisanal craft that inspires beauty and aesthetic.

But I don’t mind that HEY is a little slow or a little clunky. Because philosophically, it’s redefining my relationship to email in the way that I want. And I think a lot more software can and will be built like this.

I believe people will want to use commodity software (think website builder, email client, todo list) that is 1) opinionated about how to use it, and 2) aligns with how they want to engage with technology. As Ezra Klein says about HEY, it is “software that insists that I make choices rather than whispers that none are needed.” I’ve used other great examples of this like mmm.page, which doesn’t make building a nice professional website easier/faster but rather redefines ‘building a website’ as playing on the internet’s canvas. How refreshing is that? There’s other opinionated tech like Light Phone, a phone company whose slogan is ‘designed to be used as little as possible,’ and provides you core phone apps (call, text, maps) on a simple Kindle-like device. I personally don’t use a Light Phone—and that’s okay! Opinionated tech means some people won’t align with it and won’t use it. I think this is why opinionated tech is rarely funded by venture capitalists / is rarely built by venture-backed companies (VCs want your business to appeal to as many people as possible, like Gmail does).

Just as music has its top 40 and alt-rock, I believe we should have more ‘alternative’ software. With AI making software smithing even easier, I’m excited to see an emergence of opinionated ‘alternative’ technology that emerges as digital native generations with a highly fragmented culture and diverse set of values builds tools and experiences that align with the way they want to engage with technology.

One of my uncle's baby elephant photos