Email Explained from First Principles

I need to take some time to closely read this insanely detailed article from Kaspar Etter. It’s not my goal necessarily to understand every detail of how email works, as I’m more interested in how managing it well is an ingredient to business success, but understanding how things work is always enlightening.

Sometimes digging into the how things work of it all can be useful as well. Kinda like how reading a CSS spec can make me a little better at CSS sometimes, even if they are dense and not necessarily for authors directly. If nothing else, it can be fun. Check out this post on how internal combustion engines work and tell me you didn’t learn something.

Why don’t Vikings like to send emails?

They prefer to use Norse code!

This stupid joke had me searching for when the first email ever sent was (I’m, uh, well aware there is a significant time gap between Vikings and Computers). Turns up as:

Sometime in late 1971, a computer engineer named Ray Tomlinson sent the first e-mail message. “I sent a number of test messages to myself from one machine to the other,” he recalls now. “The test messages were entirely forgettable. . . . Most likely the first message was QWERTYIOP or something similar.”

Email Clients Should Offer to Hide Autoresponders

You can filter for autoresponders and archive them, to some degree, with elbow grease. But it’s that time of year where we start seeing a ton of autoresponders and it’s got me thinking about it again. Personally, I don’t care to see them ever. I literally don’t care in any context. Hit me back when you hit me back, I’m not going to read what your autoresponder says anyway.

This is the kind of innovation I want to see in email clients. Not reinventing the entire concept of email, just helping me see less junk I don’t want to see, without me having to work so hard.

Email Tracking Embarrassment

Most people are anti-email open tracking because, ya know, it’s a violation of privacy that the recipient didn’t opt in to and it’s weird and creepy (literally everyone I know turns off read receipts on text messages). Extra creepy when it tries to geolocate the open.

But hey it can also be embarrassing to show the sender how absolutely immediately you open the email…

… and then how many times after.

Don’t judge me I just have to read an email 15 times before I can respond to it.

Inbox Context

There is a bunch of funny ones in the thread. Black Friday emails next to Black Lives Matters emails.

An email inbox is a weird place to be. Emails try to play to your emotions and deliver emotions, but those emotions can be extremely opposite. Serious and silly sit right next to each other. But they always want something from you.


News from back in August: Automattic Invests $30M in Titan, a Business Email Startup. That’s the kind of news that perks my head up as…

  • I’m kind of a fan of Automattic and the WordPress universe.
  • I, uh, have a blog about email.
  • I think the name Titan is cool
  • Apparently .email is a TLD and now I want one.

Titan looks a lot like Front. Front has been husslin’ since 2014 building a “shared inbox” tool. We use Front at CodePen and it’s honestly indispensable, so I’m actually surprised there aren’t more companies trying to replicate and innovate past them. Front has also taken quite a bit of money and apparently used it well, as around a year ago one researcher valued them at 1.3B and that was before at least one other round.

I agree with what Jan-Erik Asplund says there:

But there’s another company that—albeit growing more slowly—may have a much higher ceiling than the intra-team chat app.

Front is like Slack for your email, except instead of creating another distracting, noisy, always-on tool, Front allows users to spin up ephemeral chats within email threads themselves.

Instead of forwarding an email to a colleague or going into Slack to ask them a question that relates to a customer question or request, you can tag them into the thread and have a quick chat right in the context that’s most useful.

Email is just darn useful context. It can be messy, but that’s where technology can come in and be helpful.

Best of luck to both Titan and Front here. Email has been notoriously hard to build actually useful new tooling around, and these companies both seem to be actually doing it.

The Email TODO List

Personally, my inbox is my TODO list. One of them, anyway. I also use Things as my TODO machine. That seems messy, doesn’t it? But it seems to work for me.

The reason is that my TODO list isn’t all email-related things. It could be “buy a gift for my nephew’s birthday” or “make an appointment to get a new driver’s license”. That’s my master list where nearly every important TODO ultimately makes it.

But the emails sitting in my inbox are often essentially TODOs as well. In the form of “edit this article so I can respond with next steps” or “answer this person’s question but also write a draft blog post on it because it was interesting”. Those things are worthy of being on the master TODO list, but they don’t always make it there. Usually, they feel fine sitting in the inbox for a while, because I know I’ll get to them there as well. Moving them feels like unnecessary busy work. It doesn’t always feel messy to me, it feels like a working system.

But sometimes I will yank long-sitting emails off the inbox. I’ll write them up, like the examples above, and plop them into the master list. Sometimes I just feel like hitting “Inbox Zero”, and I know it’s going to take me a little while (days, weeks) to get to that thing and that is too long to sit in an inbox for me. That busy work of moving TODOs from one place to another is exactly what I don’t like about real Inbox Zero.

I don’t mind alternate TODO lists. For me, for now, it’s fine.


It’s been six months since Mailplane threw in the towel, saying Google is going to destroy the ability for users to log in in apps like Mailplane. I keep an eye on this saga a bit as I’m a big Mailplane user. I like having a dedicated app for email, but I actually like the default web experience of Gmail, and I like having separate tabs for separate accounts.

So if Mailplane really were to die, that’d be a little sad for me, but I’d move on and find something else I like. It won’t destroy my email productivity.

I’d probably give Mimestream a real shot. It’s clearly macOS-y in a way that I usually like, and clearly entirely focused on Gmail support (which would be much harder for me to switch away from):

But this isn’t a wrapper around the web experience for Gmail, this is making Gmail more like Apple Mail or Sparkmail. As of yet, I’ve never got into this style of email client, but I’d try it before switching back to using my actual browser for email. Jason Snell was in the same boat as me:

I went through the stages, as you do. I tried to run Gmail in a single-site browser. It didn’t really take. I opened Apple Mail and… nope. It doesn’t work the way I want my email to work, and it’s inconsistent and slow in just too many ways. I’m not going back to that relationship.

If Mimestream can convince a fellow Mac dude who seemingly feels the same way about email as I do, that’s certainly worth something.