The Email Do Over


I’ve had an email address since 1992, so for 27 years now. Golly.

As you can imagine, in that time the volume and nature of the messages I receive have changed a bit. But the way I use email hasn’t really changed very much at all…until today!

I am declaring a colossal email do-over. Email bankruptcy. This is not an impulsive decision, I’ve been thinking it over for months. Still it is an uncharacteristically irreversible decision, and it’s happening — oh yes it’s happening — later today.

Here are my four steps to email liberation!

Step #1: Delete Everything

WHAT?!? All!?! Yes, all. Though for CYA reasons I had to archive all my work emails, and for personal reasons I exported some as text files to a local backup drive first. But then I’m still flat-out deleting every single email that you or anyone else has ever sent me. Every email message I’ve ever written, every reply I’ve ever sent, it’s now going to be as gone as an email can ever be.

Why would I do this? Because it was eating up my life, that’s why. 27 years was enough. No more! I just couldn’t keep doing it the same way for the next 27 years, y’know?

Are you too young to remember before there was such a thing as email? Don’t worry, I’m not about to get all nostalgic about the 1980s. But do note that actual work did still manage to get done without it. As much as email sped up certain things about our world, it totally bogged down other parts. The bottleneck simply moved upstream. I was the bottleneck.

There is an assumption that emails are to be read — or at least skimmed. I mean, that’s ostensibly why we send them.

Sure, two decades ago it was probably true that we read our emails. Today, not so much. Bots read our emails and decide if/how we should look at them or not. Being that over half of all emails are spam, this tends to mostly work out. But then when things that I want go into Spam (as is inevitable), I’m left with a permanent sense of insecurity. And there’s all these bots reading and cataloging and indexing all my email, a thought I’m becoming less and less fond of.

Even the basic idea that I should read something just because it was sent to me is a flawed one. That would mean that I don’t control how much time I spend reading email, you do. And that you don’t control how much time you spend on email, I do. That sounds backwards because it is.

I think I’ve struck upon a better idea: change the defaults.

Step #2: Automated Self-Distruct

I’m not proud of the way my email got handled in the last year. I’ve had a ton of system failures on my computers, my other local devices, at server level, with the Googles, my router, basically everything technical that could break did in 2019. As a result, I outright missed many emails. How many? I’ll never know. But some were the really important kind. In most cases, though, people just emailed me back again later to check up on why I hadn’t responded. This got me thinking…

So I’m writing up a little script to ensure that every email I receive will self-destruct within 72hrs — whether I’ve checked it or not. I’m now considering if a little warning auto-response will go out to everyone who emails me, linking back to this post. That’s up for discussion, and I’d love it if you used the comments below for that ;)

Drastic? Yes. But honest. And I will honestly make every attempt to read and respond to every little individual message as appropriate. There are specific appointments on my calendar 1-3 times daily, exclusively dedicated to handling email & phonecalls. They’re short windows, but they’re there.

But at the same time, I’m not worried about reading anything. If someone sends me something and doesn’t hear back in a day or two, they’ll know they won’t unless they message me again. That’s kinda how it works with everyone nowadays anyway, amiright?

But what about spam? Won’t the auto-responder tell the spam-bots where to find me? That’s what steps #3 and #4 are for.

Step #3: Divide then Multiply

I now have different email addresses than before, and I’m not telling you what they are. This goes for my personal email, music biz email, learning biz email, all of it. Those that worked for the last decade or two may still work for now, but they are actively being transitioned and depreciated in favor of the new. New rule: if you want to email me, you can to call me and ask me for my email address.

Millennials may be shocked to learn this, but once upon a time the whole world really did used to work that way. We had to call to make sure faxes went through, too. And faxes were…oh, nevermind ;) Suffice it to say that I’m not worried about spam, I’m only worried about who is messaging me.

Here’s my public phone number if you want it: +1-415-508-7627 (that’s 415-508-SNAP!). FYI, I don’t pick up for calls this line, which is why I can give it out freely. Anyone can call, and anyone does. Mostly robocalls and people I’d rather not talk to. But you? I’d love it if you would leave me a message! Preferrably an intelligible one less than 2min in length.

Depending on who you are and how I interact with you, I’ll give you a different email address. Ever had one email “just for signups”? Yeah, it’s a little like that.

But what about how this changes over time? What if word gets out about my super-private-friends-only-email address?

Step #4: Anti-Legacy

My email address now changes at the first every year. So come 1/1/2021, it will change again. And it won’t change in any automated or predictable way, either. No address for me. I’m more, uh, artistic than that!

Also, once a year — and ONLY once a year — I’ll look at all the emails I received, decide what’s working for me and what isn’t, and send a “contact update” message to everyone I want to have that year’s email. For instance, I just sent that out last night. Everyone else who sends to the old address will soon get a gentle “call me” auto-response.

I’m not trying to be a jerk here, I’m trying to keep my interactions with the world on a real, human level. Kind, generous, and clear messages are possible when we make it an objective. Personal messages like that make our lives better, and more…well, personal.

If you know me, then you know I’m not the kind of guy to tell you what you want to hear just to make you feel good and then go delete your email or mark it as spam. I respect you, and I believe you deserve to know what I’m up to! Likewise, I think it’s reasonable to ask for your honesty about what you are actually up to. So tell me when you call.

Added bonus: this automatically removes all the AI-generated emails that I could ever receive. AI can try and call me to get my email address, but I’ve got some AI bots of my own listening and transcribing to text every phonecall to my publicly listed number. So…good luck with that, oh ye clever little bots!

There’s a lot that I love about AI, really I do. But not for email. Sorry all ye robots! Go human or go home.

I believe we can all stand to be more a little more human with each other. This is simply one of my attempts to do that.

Will this method work? I don’t know. But I’m willing to try it and find out. Sign up to my RSS feed or — ahem, my email list — if you’re interested future updates on the results of this grand experiment. I’ll also be posting about my new direct messaging strategy for social media soon.

What about you? Wanna try this with me? Use the comments box below to say if so. Or you can use it to rant and rave or whatever too :)

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