As of this writing, I have five active email addresses. That I can recall. There are quite possibly more I’m not remembering at the moment.
That’s a lot. It’s entirely too many.
The thing is, I didn’t mean for that to happen, the list just kind of naturally grew as things changed and came up.
Now I’m trying to change that as a long-term fix. I don’t know that there can ever only be one, but fewer would be great. But that’s turning out to be an unexpected, maddening challenge.
When I left Gmail shortly before Covid hit North American shores, I was looking for an email service that was focused on digital privacy and security, which I had read up on and had come to highly value. Google does a great job with security, but privacy with its Gmail service is simply non-existent. Quite the opposite, actually. Google readily says it scans users’ email (better known as data mining) in order to collect extensive, sometimes disturbingly granular information on people, which they then package and sell to advertisers wishing to target ads to people of specific, for instance, ages or incomes or political leanings or religions, etc.
For those who haven’t looked into it, Google long ago stopped primarily being an internet search engine and became what may be the world’s largest advertising entity. An estimated 80-90% of Google’s income (US$348 billion in 2024) is from selling access to user data to advertisers, which it then gets money from again to show said advertisements to said targeted users.
I wanted the hell out of that system.
I went to what, for simplicity’s sake, I’ll call Service B, which is a European email service — the EU is the tip of the spear for user data and privacy rights — that is still widely regarded as one of the best in the world. I let every one of my contacts know about the official email change, and proceeded to swap over all of my business contacts and online subscriptions to the new email address, from newsletters to streaming services.
My only regret with that change, as I soon found, was that Service B was not a short company name, so paired with my full, unusual name to start with, the whole thing became quite a mouthful to relay verbally and was riddled for possibilities of mishearing, both of which happened a lot over the following several years, particularly after March of 2020 came and brought Covid to North America. Not only was it a lengthy email address (with objectively weird spellings of both my first and last name), but having to relay it by phone or, eventually, through a mask and from behind a plastic shield while cashing out at stores that used email addresses, it got to be a real pain.
I had come to accept all that and settled into its use until earlier this year, when the Service B CEO put his foot in his mouth by praising… let’s just call it “a highly controversial political party”. That got my attention anyway, but it was only made worse when he tried to gaslight those who took him to task over it, and then outright removed his and the company’s account from Mastodon, the one social media platform I’m on and where he had longtime frequently active account. There was no reprimand that was made by the company, that we know of, despite plenty of calls for everything from an apology to his being fired outright. Instead, the company seemed to ignore the issue entirely and in a tonedeaf statement, maintain that they’re bipartisan.
The original comment itself was concerning and disagreeable enough to me, but even that aside, I couldn’t stand by and watch the company seemingly take zero action or responsibility for what he had done, so along with seemingly a lot of other users, I left.
Service C was the runner-up when I was originally choosing a security and privacy-minded email service, so I immediately went there. Once again, I let all my contacts know about my new email address change. Then changed the address on… almost all of my subscriptions and websites I need to sign in to. I readily admit this was done in spurts and starts and not in any systematic way, and remains unfinished even now. I held onto Service B’s login details because there are some websites and services that accomplish an email address change by contacting your previous address on file to verify confirmation that it’s okay to make the change to the newly requested email address. So I’ve at times had to log into Service B to confirm that yes, I’m now changing my address to service C.
On the one hand, I learned my lesson from Service B and made my new email address at Service C short and sweet, which was a decided win for spelling it out to people. On the other hand, I wasn’t exhaustive in my changing over of everything everywhere, so literally months after changing email addresses, I’m still now coming across little-used websites that have Service B’s email information. So there’s still a bit of whack-a-mole happening there.
Everything started off well with Service C, but I started noticing some small issues with the service early, and then over the last several months have noticed more and more. And some weren’t just little preferential things, but fundamentally large issues that directly affected my inability to use the service at times, either for what I needed it to do, or wholesale when recurring connection issues kept cropping up. Issues that, last I knew, haven’t been fixed.
Those problems recently added up enough for me to want to change to a service that I could just use with fewer (ideally no, but I’d take fewer) issues, especially prohibitive ones.
I didn’t want to widely announce a change to my email service again. I understood how relatively often I had done it to family, friends, and other contacts, and I know such things are pretty trivial in the greater scheme, but I was getting tired of doing it and it was something I didn’t want to have to do again, let alone keep doing to others if/when this newer email services had issues as well and I ended up changing again.
With Service C still active, I quietly searched around for another email service, and found one — Service D — that seemed to check all the right boxes. It’s based in the EU, privacy and security focused, widely reviewed as being solid… great, I’ll call that my new address. I sent out a few test emails to a few people, because that was one of the big issues I was finding with Service C (which in all fairness is something they couldn’t control, but was still an issue for me): My emails were triggering peoples’ spam filters and so were too often getting erroneously put into spam folders. This created issues ranging from family and friends and others just not getting my email, all the way to my possibly having lost a chance at a new job over it, because the hiring company didn’t realize my application had gone into their spam folder until I called to ask about it a couple of weeks after I applied, which was after their window for the interview short-list had already closed and stayed closed despite their own system having made the error.
This Service C test run was a bit iffy at first, but ultimately everyone got the test emails I sent.
Great!
But then, an issue.
I was posting on Mastodon, and to a couple of experienced family and friends, about how frustrating it was changing email services this often, and did they have any suggested solutions for how to work around it.
One suggestion from one of my step-sisters (who made websites in a previous life and so I thought could offer some insight into best practices) was to maybe look at getting a new domain name and then pipe email to it through whatever email service I chose at the time but without ever needing to change that email address again. I’d heard of the idea before but hadn’t thought about using it for myself — nor did I have any clue about how to make that happen — but the idea is a solid one: I choose and register a domain name (i.e. a URL/website address, like coolestguyever.com) to set up an email address for myself using that domain name (such as reay@coolestguyever.com), and then tell any email service I’m using from one month or one year to the next to receive emails to that unchanged email address into this other service’s inbox.
The huge benefit of doing that is that no matter how often I want to/have to change email services, my email address that everyone has remains the same.
I learned a lot of that info after the fact, when data security and privacy advocates and forum feedback backed up the step-sis’s same suggestion as probably the simplest way to handle it.
So great, thought I, I’ve got a solid course of action. All I have to do is pick a new domain name, register it, and get Service D to handle the email. It could be the last time I ever need to change my email address anywhere, and the last time anyone else will have to change it on their end to contact me.
But then, another problem.
Service D, as I found out, simply doesn’t handle custom domains (the term for a third party email service handling a domain name of your choosing). So the otherwise solid place I’d chosen for my new email base of operations couldn’t do this one critical thing I needed it to do.
I had to move on.
So begat my scouring more websites and reviews and deep dives, trying to find another service that ticked all my preferred boxes for an email service but now also ticked the big one of handling custom domains.
I found one and asked them before I even signed up, and they confirmed that yes, they handle custom domains.
Great! While it was a bit minimal on slick interface, it would I guess suffice. Service E was alive and kicking.
… but then I found another service that checked all the boxes, including handling custom domains, and that had all that Service E did plus the user interface was notably better. If I was going through all this hassle, I figured I might as well use an email service that worked and was more aesthetically appealing to boot.
So I dropped Service E and moved over to this newest one, Service F.
As an added bonus, I came up with a logical, systematic way to actually change all my email accounts everywhere, in one (hopefully fast) sweep.
God willing, that email service is where I’ll be for a while, because this has all taken a lot of time and effort on my part. You’ve only been reading this far into all this process. Imagine this taking up the bulk of your scant free time for weeks, maybe now edging into months.
And kindly spare a moment of sympathy for my wife and teen, who have both had to endure hearing even the hugely truncated bits of my experience with all of this when I’ve wanted to share updates or interesting new things I discovered along the way. Because there’s been nothing that so plainly demonstrates to me that “interesting” is entirely subjective, as all of this mess has. We’ll be approaching two decades of marriage soon, and I’ve never seen my wife’s eyes glaze over at all, let alone as quickly or fully as when I start telling her about the technical side of what European email services offer or don’t, or my confusion over why one German company would differ in what they say they can offer compared to another one when both area referencing German data privacy laws.
Really, I can’t blame her.
But anyway, good. Settled on an email service that offers everything I need. So now I’m good to go, right?
Well… no.
Remember, getting the lauded, data privacy and security-focused email service in the EU that met my other criteria, and that would handle custom domains, was only half of the total task. The other half was coming up with a new domain name and registering it, to then channel my new, customized email address through to said new email service.
And good lord, that’s been a deep rabbit hole in its own right.
A brief history on that score: I have spent what is probably an extremely unusual amount of my waking hours of my life coming up with names for many things. In early grade school I went through a few nicknames that I gave myself. I know that giving one’s self nicknames is highly uncool, but I objectively wasn’t a cool kid, so that tracks. What I find a bit odd about it in retrospect is that I don’t know that I ever told anyone almost any of them. I recall once asking one friend to call me one of them, and I don’t think he ever did, which was frankly fair enough. I used a couple of them on notes to my parents that I found in later years, but that seemed to be the full extent of uses of coming up with cool-sounding nicknames.
Then there were the number of name changes of a basement band I was in with first one and then numerous friends, whose name, as I recall changed a little more often than the lineup of members as said friends gradually joined.
There were aliases back in the early, spreading new world of “the internet” and one needed a handle to use when interacting with people on BBSes — Bulletin Board Systems… kids: Think a version of Facebook or Twitter/X but where you could only leave plain text messages for others, and where only one person at a time could connect by literally dialing up to connect with the BBS’s phone number, although very popular BBSes run by people with money to spare would sometimes have more than one phone line to connect with, which was crazy advanced stuff… yes, I’m a hundred years old — and those chosen names had to last you a while so people got to know who was connected to what name without one changing it all the time.
All that while, I was of course coming up with names for the short stories, and eventually the screenplays, that I was writing.
And names were also something I’ve mulled over a number of times when registering business names (which nothing ultimately ever came out of, but one of course couldn’t know that in advance). That was still happening as of earlier this year, for the record.
… and now we’re way into the digital age, where anyone who’s connected to the internet has the means to connect with others and can often do so by email or social media, using, yes, a chosen screen name. Those with even modest means are able to purchase (okay, rent, really) a domain name of their own choosing. And with a bit more more technical knowhow and money, they can connect that name to a website of their own and have it do and say basically anything they’d like it to.
All of which is to say, these days a domain name is the face and so may offer a first impression of your business. Or, probably more often for anyone doing anything personal or independently professional that they’d like to share, of yourself.
And thus, while not something that most people ever consider, a domain name is not something to be taken too lightly.
But I’ve also got to keep in mind that I do… I wouldn’t call it “obsess” about names (though others may say that), but I certainly spend a lot of time coming up with them and weighing a lot of their pros and cons as I do. I’m also someone who likes certain visual and aural aesthetics; I like the way certain words sound and evoke and feel. Words have always mattered to me (says the English degree holder and published, award-winning writer), and so picking a name for a new website — even if it’s only serving as a landing page that a) redirects you here, to my home site, and b) is a location to redirect email from — genuinely matters to me as well. After all, this will, if everything continues to play well together, be my email address for the foreseeable future. That’s not nothing.
This has caused a whole new vector of needed thinking, of course:
- I’d like the domain name to be easy to spell and relay vocally. Ideally one that’s also easy to remember, but that’s not as big a deal, because of course once someone has it down properly once, their email system will remember it forever.
- If possible, I’d like the domain name to be relevant to me. It doesn’t have to have my name in it. In fact, far better that neither of my first or last name, both rife with misspelling opportunities, aren’t included. It could perhaps speak to an interest, either widely known or more private. It would be nice to have a cool-sounding word, or combination of words. But again, still one easy to spell and speak.
- I’d like it to be evergreen, meaning I want to avoid current trends or lingo. I’m reminded of seeing a car’s licence plate that said ON FLEEK. Yeah, that phrase aged well. I’d even like to avoid song titles or lyrics that I currently like, because that may not mean much to me a year or ten or twenty or fifty from now (yes, I plan to be a brain in a jar and still emailing when I’m 103, aren’t you?)
- But I’d like it to not be such a cool name or blend of words that I’d want to use it for a story or game title at some point in the future. This isn’t a huge concern, but there have been a few examples of stuff that I’ve come up with in the last few weeks that have been pretty evocative and started springing settings and characters and plot ideas in my head. I’d rather avoid an email address being forever connected to one thing I write or gets published produced. That’s a much lower issue on the food chain of important things, but still something to consider.
- I’d like it to not stand out so much that it draws undue attention to itself (or at least not negative or judgey attention). One can of course never be sure of how anything will be received by others, but I think we can all agree that if I went with the previously mentioned coolestguyever.com, it would be difficult for others to ever take me seriously. Which is totally fine (hell, encouraged) at times, but less so when I’m, say, trying to apply for a legitimate job. There will also be some assumptions made if I were to use the likes of darkdesires.com or hotandheavy.com or whatever. Again, words matter.
But… and here’s the tricky part… while ideally hitting all of those checklist items (already a tall order), it also has to be a domain name that’s currently available. That alone has been a huge obstacle.
I recall seeing a Saturday Night Live episode that has to be 20+ years ago at this point, where in a skit there was a very serious, straight-laced board meeting happening for maybe a law firm called Smith & Partners, or somesuch, and one of the men said that he had finally registered a company domain name, which was penisclownfart.com. It was, the man went on, the only domain name that hadn’t already been taken.
That was decades ago, and was funny even back then in part because of how true it was. If you guessed that domain names have only gotten way more widely bought up since then, you’d be right. I’ve come up with probably a few dozen that hit all of the above bullet-pointed criteria, and only eight of those were available to register. Of those eight, I really like two the best. One is a bit quippy but relevant to me, if only as something of an inside joke. The other is a truncated line from a recent book I read that hit me so hard that I literally couldn’t tell you what any character’s name is in that book, but I’ll probably remember that line for the rest of my life. But… while it’s pretty easily spoken and so would be conveyed with confidence it’ll be properly spelled, it is a bit wordy and lengthy to type. And maybe a bit literary, gothy eyeroll-inducing. And of course, it’s something I like right now. Will I still like it as much if I’m saddled with it as my email address for coming decades?
Then I get on myself for of course not being able to know what I others will or won’t think of it in the future, and knowing damn well that no one else is nearly as interested in you as you are in yourself, and so please just try to stop overthinking it (overthinker.com is taken) and refocus (refocus.com is taken) and just hurry up and pick something. Not quite anything, but geez, something.
I unintentionally came up with four more domain name possibilities this morning.
Three are taken, including one I really liked.
The one available one is… just okay.
Welcome to my world. (.com is taken…)