Nick Douglas’ “How to Ask for Advice Over Email”

Great list:

  • Spend 95% of your time researching the person you’re emailing, and 5% writing the email.
  • Introduce yourself quickly but specifically, and ask specific questions.
  • Ask one or two questions. Not three! You’ll feel like adding a third because your email looks too short. It’s not.
  • Google your questions first.
  • Don’t offer to “hop on the phone” as a compromise. That’s not a compromise, it’s a threat.
  • Say “Even one sentence would be great.”
  • Novelist Tao Lin came up with this one: Tell the recipient it’s OK to ignore your email. Not just to say no, but to completely ignore it.
  • Say thank you.
  • As soon as you’re ready to send, find and delete at least one sentence.
  • Send and move on. Never “follow up.”

Email Statistics Report

This company The Radicati Group, Inc. produces “quantitative and qualitative research on email, security, instant messaging, social networking, information archiving, regulatory compliance, wireless technologies, web technologies, unified communications, and more.” Looks like one report will run ya about $7,500, but they publish summaries, including the email one. It has some interesting stuff in it:

In 2015, the number of worldwide email users will be nearly 2.6 billion. By the end of 2019, the number of worldwide email users will increase to over 2.9 billion. Over one-third of the worldwide population will be using email by year-end 2019.

Over the next four years, the average number of email accounts per user ratio will grow from an average of 1.7 accounts per user to an average of 1.9 accounts per user

As in, most people have 2 email addresses.

In 2015, the number of business emails sent and received per user per day totals 122 emails per day. This figure continues to show growth and is expected to average 126 messages sent and received per business user by the end of 2019.

They say “consumer email” continues to grow as well, but mostly because of stuff like notifications and not so much “interpersonal communication.”

“It’s going to get worse before it gets better.”

Quinn Norton for the Atlantic:

Email has changed since [the 1970s], but not much. Most of what’s changed in the last 45 years is email clients—the software we use to access email. They’ve clumsily bolted on new functionality onto the old email, without fixing any of the underlying protocols to support that functionality.

The article is mostly about the efail stuff and how it’s apparently inherently bad that email can be HTML because it brings the vulnerabilities of web browsers to email clients. Fair point. Pretty impressive that those protocols and such haven’t changed for half a century. What’s the HTTP/2 of emails going to be?

How much is email worth to you?

Fascinating little 10-minute podcast from Planet Money’s The Indicator that put a data-driven dollar value on some of the biggest internet services.

When economist Tim Harford was planning a trip to China, he realized he would not be able to access a lot of the online services he has come to rely on: no email, no maps, no internet search. He started to wonder what the value was for these services and he came across a study that look at just that: It put a dollar amount on how much these services are worth to us.

The least valuable to people? Social Media. The most? Search. Second place? Email.

Should I just get a new email address?

This seems like the nuclear option! Your email is so out of control that you literally give up and start over completely fresh. This might be fine for Beyoncé, but her success seems a little more locked in that yours or mine. 

This also seems awful dangerous to me. How many people are going to continue to send emails into the ether after you’ve made the switch? How many left hanging who already have? How many bills you’ve forgotten to pay lost in there?

Setting up an autoresponder telling people you’ve changed it is a possibility, but then what are you gaining by switching at all? 

The way I’ve seen it most commonly done is to essentially split your email. You create a new one that is your new squeaky clean email universe. Perhaps you email all the most important people in your life to tell them about it, and some small percentage of them notice and care. But then you also keep checking your old email address, because of course important stuff still pops up in there. The fix has become more work than the solution. 

Without having done any deep research here, I’d suggest not going nuclear with a new email. Fight that fight and clean up that existing email so it’s useful to you again. It’s a battle of unsubscribes and even filtering if necessary, but it can be done and you’re left with a stronger email history. Remember it doesn’t have to be done overnight.

It’s like a publication on the web. When they want to make big changes, they make big changes to the site they already have, they don’t get a new URL. Too much SEO value with the old one. 

GDPR Emails

Everybody is getting pounded with emails from apps that are changing their privacy policy or doing things like re-validating their marketing email lists. But I think I’ve read more joke tweets about it than actual emails!

MailPlane and Boxy for Inbox are Broken. Shift Working!

I’ve been using Mailplane for a long time. It’s just a wrapper for Gmail/Inbox, which is perfect. That’s what i like, web clients with native wrappers.

The Inbox tabs I use have been broken all morning. I figured it was something funky with my internet or VPN, but it turns out it’s straight up broken.

It looks like Google Inbox stopped working in browsers which don’t support a new technology called “Service Workers”. Feel free to let them know via their “Send feedback” functionality. The more reports they get the more likely it will get fixed, if it wasn’t by intention. We’ll try to find a way around it but we can’t make any promises yet. I’m sorry but in the meantime we can only suggest to either use Gmail in Mailplane or Google Inbox in your default browser.

So they use a browser rendering engine internally that doesn’t support Service Workers. I guess that’s a little scary since the support for Service Workers is pretty broad.

Boxy 2 is broken too, as it must use the same rendering engine.

Good news: Shift is also a native app Gmail wrapper, and is based on Chrome, so it’s working fine. Plus it supports extensions, so if you’re a fan of stuff like Grammarly, like me, that’s a big step up.

I’m hoping I love Shift because I’m switching right now.

Encrypted Email and Security Nihilism

Daniel Kahn Gillmor, reporting on the whole EFAIL thing (short story: even encrypted email isn’t truly safe):

Unfortunately, many of the responses to this report have been close to the line of “security nihilism:” Throwing your hands in the air and saying that because certain important security measures aren’t perfect, we should abandon them altogether. This is harsh and potentially damaging to the best efforts we currently have to protect email and risks leading people astray when it comes to securing their communications.

Personally, I’ve never bothered with encrypted email. As a Gmail user, I’m pretty meh about the fact that Google “reads” it to deliver me contextual ads. I own zero tin foil hats. If you’d like to use me as anecdotal evidence, I’m a decade and a half in and nothing weird/bad has ever happened to my Gmail account.

But I am bullish on general security best practices. You really should have 2FA turned on if you can and have a very secure email password that you change somewhat regularly. If someone gets into your email account, that’s extraordinarily bad. It’s like they have access to every single service you use (that doesn’t use 2FA).  

The Search for the Perfect Email Client

Ars Technica published Inbox zero and the search for the perfect email client, a staff-roundup article all about email preferences. Here’s some choice quotes.

… as anyone who sits through several hours of meetings a day surely knows, staying on top of one’s email becomes a welcome diversion during the many boring bits.

Jonathan Gitlin

Probably not a good sign that a meeting is so un-engaging that you’re literally checking your email during it. But I get it. I stay on top of email everywhere. On the couch, in the line at the grocery, even in bed. How good of an idea that is is debatable, but hey my inbox is usually pretty clean.

I occasionally use both the Outlook and Gmail browser applications to set up filters. The Outlook website is easy to use and looks great, while I’ve always found the Gmail website to be a confusing mess—Gmail.com doesn’t even let you delete messages with your keyboard’s delete key. I prefer non-browser applications, so this isn’t a big deal.

Jon Brodkin

What I find interesting here is that a lot of us have a primary email application we use, but hop around a bit too. We might like a desktop app, but hop over to the web app for some tasks or situations. And use an entirely different app on mobile. Using a service like Gmail or Outlook enables that jumping around. That’s why Google Reader was so nice! It was home base for RSS but we could jump around third-party reader apps easily.

Email, in short, is to be avoided. Unfortunately, email cannot be avoided. My policy is the following: work emails from students and people I know personally get replied to within two working days. Emails from Ars Technica staff are treated much the same, and email from readers is read (but not necessarily responded to) within two days. Emails from family members get replied to within a year. Everyone else can go whistle.

Chris Lee

Chris represents to me the most common email type. Doesn’t like email. Must do email. Fights with himself about email.

I was a huge fan of Sparrow as an email client, and then Google bought it and killed it, which was powerfully disappointing. Inbox by Gmail, the thing that Google sort of made out of Sparrow’s parts, has none of Sparrow’s grace and functionality.


In Sparrow’s absence, I’ve shifted to using Airmail on the desktop for my personal accounts. The interface is an evolution of Sparrow’s (which in turn was an evolution of Tweetie’s). It does everything I want and doesn’t make me angry, and that’s about the best one can say about an email application.

Lee Hutchinson

Almost everyone in this article has mentioned Airmail. No absolutely glowing reviews, but plenty of “this seems to be the best thing out there” sentiments.

I average close to 7000 emails a week now. I’ve taken to using MailSpring, an open-source mail client that I use on Linux (my preferred desktop environment for a number of reasons) to cope with multiple webmail accounts, and I have aggresive spam filtering. I tend to keep emails either in my inbox or in archive so that I can search them for contacts I’ve had on specific topics. I have learned to stop worrying and love my “unread” number.

Sean Gallagher

My god. I wonder if that 7000 is entirely non-Junk and non-Spam. If it is, that seems pretty unreal. Like if Beyonce had a public email address. (Uhm, she doesn’t, and the one she does have changes every week.) I’d really like to talk to a guy like Sean sometime and dig into this is tenable at all.

I try to read every email as it comes in. If I can deal with it immediately—by writing a one- or two-sentence response or by ignoring it entirely—I’ll do so. If it’s something that will take a few minutes and I’m busy with something else, I’ll mark it as unread and come back to it later in the day. If an email requires me to do something that will take more than a few minutes, I’ll make an entry in my to-do list and come back to it later.

Tim Lee

I’d say that sounds mostly healthy, particularly if email is the vast majority of Tim’s job.

Inbox has really good search functions—like, better than Gmail’s traditional interface. It groups related travel emails, for example, automatically pairing flight and hotel information, without any other input from me.

Cyrus Farivar

In my personal email usage, I try to avoid services like Gmail that capitalize on my data these days.

Samuel Axon

There are 159 comments on the post, as I write, so if you’re really into reading about people’s email client preferences, there is plenty to dig into.

AI/Machine Learning and Email

Seems like a natural fit, right? What better data set than decades of email complete with meta data?

I would think that spam filtering may have been one of mankinds first foray’s into machine learning. My Google-based email has been saving me from spam for a decade. We know that spam evolves to fight the machines that keep it down, and yet the machines seem to be winning. Certainly that’s some form of machine learning and not entirely human hand written filters.

We also have some evidence in the form of Gmail’s tabs (the Promo Tab, et al) which attempt to sort your email by type. And Inbox’s bundles which attempt to intelligently group your email types. That reeks of machine learning. Anthony Dm. has done some home-grown work in this area as well.

Today I wondered what would happen if I grabbed a bunch of unlabeled emails, put them all together in one black box and let a machine figure out what to do with them.

Google outright tells us this is the technology they employ. Although this research paper is about more fancy things like improving email search using actual behavior:

we leverage implicit feedback (namely clicks) provided by the users themselves. Using click logs as training data in a learning-to-rank setting is intriguing, since there is a vast and continuous supply of fresh training data.

There is even a company that is focusing on this entirely! Knowmail.

We’ve heard you hate email, so we fixed it!
Personalized artificial intelligence to help you focus on things that matter most, do more with less effort, and balance work and life.

Fascinating stuff.