I’m Declaring Email Bankruptcy

I’ve known that email is broken for a long time, but I was hoping, when I started researching this week’s newsletter, that I’d find some piece of software that would just fix my email problems—a magic bullet of an email client, setup to handle multiple email addresses seamlessly, while keeping me from missing important messages from my contacts, all without requiring a bunch of tedious daily maintenance. If AI is worth anything as a technology, shouldn’t someone be able to create a client that’s smart enough to notify me about messages that are important and never bother me about messages that aren’t?

After testing a bunch of different clients and services that I found (and that folks recommended), I’m sad to say that I didn’t find a magic bullet. There’s no easy fix for this problem, and that’s a problem for me. That’s why I’m going to declare email bankruptcy and just start over. Again.

The Problem

Part of my email problem is admittedly self-created. My main email, the one that I’ve been using for 20+ years and the one where important messages get lost constantly, is just my name at Gmail. I have a famous name, which didn’t seem like an issue when I set up the account but has become a major problem. (Thousands of people a week are confronted with forms that require an email address to show them something they want to see. And before they get their car insurance quote, free estimate for pest control, prepaid cellular phone bill, or the sticker price on a car they’re interested in, many of them put my email address into that field.) I don’t feel that bad for not anticipating that this would be an issue in 2004.

But when I talk to other people this is an almost universal problem. If you’re using the same email address for all of your personal and business and household communication, it’s almost impossible to keep it off the spam rolls. If you make one mistake, and hand your address to a company that sells their mailing lists, you’re doomed. And even if you don’t, a breach will release your address and the next thing you know, you’re on the dark web and well on your way to spam city.

This is damn near a universal problem. We all get a range of messages of wildly varying importance via email every single day—bills that need paying, notes from my kid’s teachers, doctor’s appointment reminders, important stuff from work, all the crap that you have to take care of as an adult immediately, messages from friends I haven’t talked to in a decade, and more.

I also get another few hundred emails every day that sneak past my provider’s spam filters. And those messages range in relative maliciousness from “We want to sell you some bootleg sneakers that will suck if we even bother to ship them” to “If you click on this link, we’ll empty your bank account and end up owning your home”.

The enormous gap between these two extremes means that the simple act of checking email creates an enormous cognitive load for almost everyone who uses email on the reg. There was a time, in the distant past before I got mortgage and tax missives via email, that I looked forward to the little ding of a new email message. Hell, in 1998 Tom Hanks, Meg Ryan, and Nora Ephron even made a romantic comedy about how great getting emails from random strangers was. It was about someone who definitely wasn’t Jeff Bezos dating an independent bookstore owner over email. They even play modem noises and AOL’s email sound!

The other big problem with email is that big tech has already mined all the value that they can out of electronic mail. The level of investment in email from Google, Apple, Microsoft, venture capitalists, and the rest has slowed to a trickle, at least when compared to the early, heady days of Gmail, when people were constantly building exciting new products on top of email. The TLDR is that we have to find our own solutions to these problems—email isn’t profitable enough to wait for the giant tech companies to save us.

The Solution

I said there wasn’t an easy solution up top, and there really isn’t. Once the spammers have your email address there’s not much you can do. So I’m starting over, moving all of my important communication off of my ancient Gmail account and into a place that it’s more manageable.

The first thing that I had to do is let go of the unitary inbox. In the current spam and ham climate, I don’t think it’s realistic to have one email address that will work with everything—although there are services that make it easy to have one place to check your emails. More on that in a moment.

I actually started this migration several years ago, when a malicious actor started attacking accounts attached to my email with a famous username. The process of migrating my accounts was pretty straightforward, because I’ve been a dedicated password manager user for a long time. I just opened up 1Password and searched for the email address, which gave me a convenient, auto-updating list of the sites I needed to change. Then visited the important sites one by one and updated my contact email address.

I’ve setup different email addresses for personal communications, transactions and businesses I’m buying stuff from, and public-facing emails that I have to be able to post on the web and social media. I also have a standalone address for talking to potential employers, to ensure I don’t miss any important emails.

I made sure to name the public-facing email address something that was easily identified as mine (it’s [email protected] if you want to send me an email). It’s also the only email address attached to that domain, as spammers tend to attack common name variants once they find an active mail server.

The private facing addresses are more circumscript. For the address that I hook my services up to, I chose a random username that’s just a few memorable words jammed together. (There’s a convenient username generator that’s free to use on 1Password’s site.) This has been highly effective at limiting third-party spam—my account that handles these transactions gets virtually no spam after years of use.

For my personal correspondence, I chose an email that’s just will-private at a domain I own. I don’t want to have to update this on the reg, because getting friends and family members to update their address books will be a hassle, so I want to avoid spillover from spammers brute forcing attacks on my server by using a common email format like firstname-lastname or firstinitial-lastname.

Obviously, this approach demands some level of care, lest I accidentally use my personal correspondence email address to sign up for Spammers’R’Us. But there are a handful of tools that can help you along the way.

Private Relay Emails

When you’re signing up for a new service, instead of using your one good email address, you can use a private relay email—essentially a one-off email that is created on-demand for each signup. Apple gives you the option of automating this when you’re an iCloud+ subscriber and are filling out a form on your phone, tablet, or Mac or buying something with Apple Pay. There are other services that will handle this for non-iPhone users, as well as a few manual ways to get the same effect.

In Gmail, you can create one-off addresses by adding a +keyword to your username. Gmail will deliver the email to your account, but you can filter or just see who is selling your address by tracking the +identifier. So if your email address is [email protected], and you want to sign up for an account at your local Wingstop, you’d tell Wingstop that your email [email protected]. (Please don’t email Ptoledo. I’m sure he’s a nice person). Wingstop will send you emails, Gmail will deliver them, and you’ll get some middling wings delivered to your house along with the peace of mind that the fine folks at Wingstop haven’t sold your email address. The only downside of this approach is that some services know Google’s trick, and won’t allow you to add a + to an email address.

SimpleLogin and AnonAddy provide platform-agnostic email address anonymization services similar to the Apple’s Hide My Email. Rather than hosting your email, they’ll let you create one-off aliases and then forward all of the messages that come to that address to an email address of your choice. Both services provide browser extensions to make it easy and fast to generate new aliases, but you should be aware that by using these services you’re giving them access to the emails that cross their servers. Knowing that, I’d avoid using these services for critical accounts and limit your use of them accordingly.

Fastmail, which is a fantastic dedicated replacement for your email host, has a few really clever solutions for this, but they only work if you’re using their service to host your email. Masked email lets you create as many unique address as you need—one for each account—just like Apple’s solution. If you use 1Password, you can even directly connect it to Fastmail so that when you create new logins, it will auto-generate a masked email for you. Additionally, you can setup Fastmail with a general rule like Gmail’s + modifier. With Fastmail, if you Ptoledo has the email address [email protected] and he wants to create a Wingstop account, he can tell Wingstop his email is [email protected] and Fastmail will deliver it to his inbox with a filterable address of [email protected] attached to it. Switching to Fastmail is a bit of a process, but we’ll talk about that more in the future.

What’s Next?

This week is the launch for the newsletter, so I’m going to be listening to you! Drop me an email or hit me on Bluesky and let me know what you like here and what you’d like to see more of. After working on this for a few months, I’m excited to show it to a broader audience and can’t wait to hear what you think!

As always, if you like the newsletter, please hit the Sign Up button! I try to keep them short enough that you can read them in a few minutes, and I promise that they’ll always be full of information that’s useful if you feel like your computers aren’t working for you as much as they used to.