The Start of the Year is Probably a Good Time for Force a Clean Inbox If You Need To

Say you have one of those inboxes with tens of thousands of emails in there. While you might still be a decently high-functioning email person, chances are slim. It’s probably an all-too-present sign of email being a problem for you.

My usual opinion is that you take steps toward fixing it. You’re probably subscribed to way too much stuff. You’ve probably got emails in there that literally just need to be archived. If there are ones that are important in there, you should chip away at answering them. My thesis is that good things happen through communicating with people and email is a particularly potent way of communicating.

But if that inbox number is, say, 20,000 or worse, that might just be untenable in your life. That doesn’t mean you’re stuck forever. “Email Bankruptcy” (just dump it all) isn’t my favorite choice, but if it gives you that mental relief you need to start fresh with better habits, I think it’s worth it.

Liz Gumbinner at Cool Mom Tech has documented the Gmail technique for Inbox Bankruptcy.

  1. Search for in: label:inbox (watch for a message that is something like “Select all conversationgs that match this search” or the like, so you can get them all not just one pagination worth)
  2. Create a new label like “Inbox 2021” and apply
  3. Archive them

Now you’ve got a historical marker that shows where you were at the end of the year, and a way to scope search if you’re looking for something you think is likely in there.

Now when the emails start pouring in again, take time to fight back. Find the unsubscribe link in them. Spam ’em if they really are spam. Do the organizational gymnastics you need to do to recluse yourself from receiving unnecessary emails. Change your app settings to what you really need. Chipping away at it can get the job done and then it’s easier to stay on top of.

Then when your inbox is clean, email can become… almost a pleasure. It’s generally where the biggest opportunities are.

40 One-Sentence Email Tips

Josh Spector published them. I’ll pluck out a few I like here:

3. If a message was truly urgent, it wouldn’t have been sent to you in an email.

13. You don’t always have to reply.

20. Emails are a terrible place for small talk.

24. Your inbox works for you — not the other way around.

29. The most important sentence in any email is the first one.

34. If you can write one great email, you can get whatever you want.

There are a bunch I disagree with, but I disagree with them in the context of myself. Most of them I get an eh, it depends feeling from. But clearly Josh thinks about this stuff and is sharing what works for him, and that’s the best thing you can do with anything productivity-related, email or otherwise.

What people like or hate about email

Lars Wirzenius rounded up some responses to an ask about what people like and dislike about email. Here’s the full list, but I’ll pluck off a few:


  • It’s not real time
  • It’s established
  • Seperation between discussions
  • Subject lines


  • Unreliable (no strong guarantee reciept gets it)
  • Spam
  • Quoting, specifically top-quoting
  • Organization is difficult

I think the whole list is fair, but the lists of strengths are really strong, and the list of dislikes feels solvable and not a problem for many/most. For example, I don’t really get much spam. I don’t have a problem searching. I don’t have a problem with deliverability. Email ain’t perfect, but it’s overwhelmingly good.

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.