Personal email addresses are weird and a pain in the ass.

I used a raw gmail address for years for my personal email, while keeping my professional consulting work separate using our consultancy’s domain. Hey excited me not only because of their opinionated manifesto about email, but because the idea of having a @hey.com email address for my personal email was super tantilizing.

Email addresses inherently mark a person as belonging to whatever the domain happens to be. Have an @gmail.com address? You’re a gmail user. Have a @aol.com address? You’re about twenty years behind the times. @hey.com was neat: it didn’t feel like it represented a product or service. It was almost like an independent concept. Hey! Personal!

But this whole implied belongingness of email addresses is a pain in the ass because when your @whatever is tied up with a specific provider, you are all tied up to that specific provider. So when Basecamp releases a new opinionated manifesto about things that have already been covered in great detail on Twitter and are fundamentally at odds with my own values and expectations, it means that I’m left with the question of “Do I want to continue to demonstrate my belongingness to the values represented by my personal email address?”

I already changed my personal email address everywhere once. Doing it again is gonna be a huge pain in the ass.

Which reinforces that I really should just have a personal email address that’s my own, independent from any given email provider, so that I can change providers at any time and absolutely nobody cares and I don’t have to go through this whole pain in the ass.

The brilliant thing is email lets you do this. Anyone can take a domain they own and give themselves an email address, and suddenly, who gives a hoot who’s actually providing it?

But boy, email addresses, by which I mean domain names for email addresses, are a gigantic pain in the ass. I already don’t use my professional email as my personal email. I have my own domain for my personal slash professional life, quinnkeast.com, but it’s super weird to use as an email address. See, email addresses have a built-in affordance for the whole idea of person at whatsit dot whatever.

Let’s say I use my personal domain for my personal email address. quinn@quinnkeast.com is accurate but also feels very strange. hey@quinnkeast.com, hello@quinnkeast.com, et cetera aren’t bad but they’re weird, like you’re sending a note to a robot or a form or something instead of the person at whatsit dot whatever.

So let’s instead suppose I want to get a whole fresh new domain specifically to use for my personal email. Well, that’s a pain in the ass too.

There’re pretty much no domains available for any kind of sensible TLD. And the new generic TLDs are fun to think about, like quinn@enormous.pizza, but the vast majority of these TLDs don’t afford whatsoever that they make up a domain. I gotta write this email out by hand on forms and stuff and in other languages—not just on the web—and I gotta feel confident people always, 100% of the time, know that my email address is quinn@enormous.pizza and not assume it’s just a bad joke and it’s actually quinn@enormous.com or quinn@enormous.pizza.com. I don’t need that kind of stress and second-guessing about why I haven’t received important emails from whatever important paper-driven specialist profession I’m waiting to hear back from.

And even if I do find a good .com domain and set myself up with a personal email address like quinn@enormous.com, well, then I have to deal with the pain in the ass of implying that I belong to or represent a company called Enormous, and it ultimately just doesn’t feel like a personal email address.

I don’t really have a solution to this. I don’t think there’s a product opportunity here, frankly, because the vast majority of users fundamentally don’t really care what their email’s domain is. Maybe I care too much about what my email address is.

And yet—like it or not—my personal email address represents me, as a person, and I wish it wasn’t such a pain in the ass.