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I still want to switch, but haven't gotten around to it yet. Thinking either Proton Mail or Gmail with a custom domain.

@IsaacKing you'd also get the sexy @pm.me address

@wasabipesto 40% off during Proton's black friday sale: https://proton.me/mail/black-friday

@IsaacKing The only thing I would note here is the importance of being able to communicate it clearly in-person or over the phone. is@ac-ki.ng may be easy to type, but I've found that longer emails with whole words are easier to communicate. Something like isaacking.org or isaacking.email would give you a legible primary domain and plenty of subdomains/addresses to pay with.

@IsaacKing If you're on the paid version, you can also use a catch-all address. I've found this super helpful for isolating/quarantining spam, or just having multiple accounts per site. Just sign up for facebook with facebook@isaacking.email and if facebook gets hacked and leaks your email, just set up a protonmail filter to send anything from that address directly to spam. It's a lot more robust than something like isaac+facebook@gmail.com (though proton can do that too!)

@IsaacKing https://www.hey.com/features/ lists the features hey has; there's not much point in me diving into each of them. That said, the overall point in my opinion isn't the specific features, though some are quite useful. It's that Hey has a somewhat opinionated view on how best to interact with email, which is what allows them to build a better-than-normal email client. Rather than being everything for everyone, Hey focuses on making a smooth experience for those willing to adopt its way of thinking about email.

For anyone who already has strong opinions about how to manage email, Hey might not be the best fit. But if your email is a bit of a mess, and you want an opinionated framework for working with email, that's when I'd say Hey is worth it. But it's definitely not for everyone.

The other big advantage of Hey is that insofar as you're paying for it you're the customer, and I feel like I can trust that far more than I can something free. If, heaven forbid, something happens to my Google account, I know I'd been in for a heck of a time navigating the byzantine hellscape of Google's support channels. Hey has very good customer support, with actual people answering you quickly and helpfully.

They're not the only ones with good customer support, of course, but I'm pretty sure that you'll only be able to find that level of support for a product you're paying for. Email is a pretty darn important part of your digital life, so all in all I'd prefer to be paying for it. That not exclusively a reason to use Hey, but that is a reason to not just default to a free service.

@benjaminfox Does Hey offer anything particularly useful for the price it charges?

"The only people that can read your emails are you and Google — that's because Superhuman operates on top of Gmail accounts."

https://blog.superhuman.com/superhuman-soc-2-compliant-data-privacy

Also doesn't support custom domain names even on the paid plan. Seems almost strictly worse than Gmail for my purposes unfortunately.

ProtonMail looks pretty good, but the free plan likely won't have enough storage for me, so I'll need to get the paid one. That's not a dealbreaker though.

I'll probably be doing this; this'll be convenient for a number of reasons. The only issue is that some providers don't let me use my own domain name, or only let me use it with a paid plan.

I'm a little uncomfortable with Google's track record of surveillance. I'd like my emails to actually be private.

note that many emails will be with gmail accounts.

so benefits are a bit limited

I bidded this up because I think that it the "rational", superior option, on account of its better privacy, which the OP claims to value. Going line by line:

> I'd like my emails to actually be private.

Tick. They get you because normally your counterparty uses something like gmail, but Protonmail does well on your side. But if you're doing something illegal in your jurisdiction, maybe use XMPP (<https://en.wikipedia.org/wiki/XMPP>) instead.

> I know there are various privacy-focused services, but I also value good UIs, feature richness, and overall ease of use.

> I'm guessing many of them are worse at this than Gmail, though I haven't checked yet.

Protonmail has good UI, is relatively feature rich, and most importantly, I'd expect to improve on this in the future. Say maybe 90% of the polish of gmail

> I also don't want to pick a service that's going to stop existing or change significantly a few years down the line; transferring everything over is going to be a pain and I don't want to have to do it twice.

Not a concern for Protonmail.

Oh, I also don't want it to require 2FA, as that tends to result in me getting locked out of important things.

@IsaacKing at gandi.net it is optional

@IsaacKing note that there could be 2FA not tied to phone number

@stone for example:

ac-king.com or c-king.com, so your adres can be: isa@c-king.com or maybe there's a .ng top level domain, New Guinea maybe?

Then you could buy:

is@ac-ki.ng

@stone you can then combine that domain with any provider you choose.

Additionally, importing from gmail is easy. Did it a few months ago, & don't regret it.

https://proton.me/support/switch-from-gmail-to-proton

I’m subsidizing people suggesting alternatives! Also the status quo is powerful.

@wasabipesto They have a much better track record of privacy than most other services, plus the ability to bring your own domain. The UI is pretty nice, plus it has its own calendar and drive alternate.

Yeah, I'd actually like to look at this market. I use gmail, but I have similar questions.