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.

“Email lists grow slowly, but their growth is sturdier than social networks.”

Robin Rendle, who writes the email newsletter for CSS-Tricks and has a email newsletter of his own called Adventures in Typography, quotes a bit from Robin Sloan’s book How to Make a Book:

Of all the followings you can accrue—on Facebook, Instagram, Twitter, and platforms yet to be invented—one is more important than the rest by an order of magnitude. It’s the group of people who have given you their old-fashioned email addresses and agreed that they would, from time to time, like to hear from you. Even if no one quite loves their inbox, everyone has one. Across generations and geography, through digital fads and fascinations, email is the common denominator, the magic key.

Email lists grow slowly, but their growth is sturdier than social networks. It’s exciting to see the sharp little bursts of attention on the social networks when something you write takes off. But it’s easy come, easy go; as quickly as attention finds you, it moves on, eager for the next thing. Email lists are sturdier and stickier. There is a real sense, you’ll find, of building them one person at a time.

Robin (Rendle) goes on to say about email:

After an email goes out there’s often nothing but radio silence from the other side and then I begin to worry for half a second whether anybody is reading them at all. I probably just have to remember that every social network has been training me as a writer, for the better part of a decade now, to be dependent on those likes and faves and retweets for my emotional well-being.

It’s pretty much radio silence. Once in a while, people respond to the newsletter with something they’d like to share or some little anecdote. I should do a better job at passing those along to the team, but Robin’s point stands, it’s nothing like the engagement feedback you get on other platforms, which is weirdly at odds with the fact that the actual engagement is likely much higher.

Spam vs. Junk

I really think you should be unsubscribing a lot. An inbox full of only things that matter is a good place to be.

But when you’re doing that unsubscribing, what you’re unsubscribing from is junk not spam. Spam, hopefully, is a very small problem for you. Perhaps a few spam emails leak into your inbox a week and you click the button to mark them as spam. Junk is the real problem. Junk is real email that you just don’t care about.

An inbox full of junk is the #1 contributor to email overload that people experience. Their inbox has 2,874 unread emails, because 2,764 of them are junk. That feels like an extraordinary amount of work to come back from. My advice is to chip away at it over time.

What you shouldn’t do is tediously click and delete each one at a time. Just deleting them is a very temporary solution. They’ll be back. Chipping away at it means opening one, hitting that unsubscribe link and following through with that on the web (they’ll try to trick you six ways to Sunday to stay subscribed), and then deleting the email. Don’t worry about them not honoring your unsubscribe or making you a target for more email you don’t want. There are literal laws against that and unsubscribing is effective.

Sometimes it does take a while though.


“Ugjkadgk. I’m terrible at email.”

It’s like a catchphrase these days. Everybody trying to one-up each other about how bad at email they are. You don’t fit in at dinner parties unless you “like all music except country and rap” and “haven’t looked at my inbox in a month.”

It downright scares me when I hear this from otherwise successful people. It’s straight up saying “I’m unreliable” which is a truly bizarre thing to announce, even if it’s true. They’ll gleefully tell you how they just archive massive swathes of emails in an effort to start fresh. A worthy goal, surely, but how many people were just left hanging? Nothing good is going to come from that.

I quite literally don’t want to work with someone, in any capacity, who I can’t expect email responses from. It’s unreliable and unprofessional.

I don’t wanna stress you out, but there is a better way than giving up on your inbox. You can chip away at it. You can be more vigilant at unsubscribing. You can create filters to programmatically remove things. Maybe you can even outsource it to an assistant if you have the means.

Perhaps over time on this blog we’ll gather up as many strategies as we can to fight an unruly inbox.

Emailing Yourself

I email myself. A lot. I’m still trying to figure out if it’s a bad habit or not. It’s a tough call.

By doing it, it’s effectively making my inbox my to-do list. That feels a slightly problematic because it’s a to-do list that isn’t entirely of my own making. It’s letting the world control my to-do list. Not to mention that I already use another app for my to-do list (I like Things).

But somehow it doesn’t bother me that much. It’s just a little reminder to myself to deal with it later. I often end up moving it to my more official to do lists. Or I just deal with the thing right away. Or it was just a link to something interesting anyway so it goes into my separate workflow for that. Emails to myself never seem to feel like a burden.

I’d say 50% of the email I sent to myself is simply a subject line with enough to remember why I’m doing it. For example, I spot a typo in a blog post and can’t fix it right then, so I write an email to myself quick that says “Typo: applience” or whatever the word was.

The other 50% is from Mail To Self, which adds a quick sharing button that blasts whatever I’m looking at on my iPhone to my email.

How often do you email yourself?

Drip Campaigns

Drip emails are those emails you get after creating an account on a website that come after certain periods of time.

Drip, drip, drip, like a leaky faucet, and sometimes just as unwelcome.

But email is such a strong way to talk to users, and companies know it. A well-done drip campaign can educate users and re-engage them. Possibly getting these users to upgrade or lose less of them to churn. I recently signed up for You Need A Budget (YNAB) and actually quite liked their drip emails.

Useful, and hopefully effective drip emails is exactly what we were hoping to do in a recent stab at that at CodePen. But it’s likely we went a little too far, and have reeled it back a little. We’re still trying to figure it out.

Listen to me and my co-workers Jake Albaugh and Marie Mosley talk all about drip email campaigns over on the CodePen Radio podcast.

Unsubscribing

Sometimes I’ll go on an unsubscribing tear. It’ll happen around some fake holiday like Black Friday or Cyber Monday when even the laziest of marketers manage to pull together a DEALS DEALS DEALS email.

I’m sure we’ll all experienced this. Your inbox will fill up with marketing emails from companies you haven’t heard from in ages. Email overload sets in harder than it normally does. So unlike a normal day, where I might just archive a marketing email to be done with it, the overload pushes me into action and I start unsubscribing en masse. I almost can’t wait for another one to show up so I can get myself off that list.

No barricade is too high. I’ll reset my damn password to your app so I can log in and manually adjust my email preferences – a hoop jumping that normally makes my blood boil. 

But lately, I’ve extended this unsubscribing vigor throughout the year. My unsubscribing finger is a hair trigger.

The vigilance feels like it has paid off in that my inbox feels clean and full of only important and relevant things. It’s work, though. I probably unsubscribe from 2-4 things a day. That sounds unreal as I type it, but it’s true. I shop for things online. I buy tickets. I subscribe to services. I test stuff out. I end up on a lot of email lists and it requires constant scrubbing.

It’s like keeping a house clean, isn’t it? To really keep a house clean, you work at it constantly. You do the dishes and sink every day. You sweep up after yourself. You leave rooms a little cleaner than you found them. Then you do bigger cleaning jobs weekly and monthly. You don’t let it become completely filthy and become overwhelmed by the thought of cleaning at all.

You can start today. Unsubscribe from something. Even if you do one a day, you’ll see progress.

Unsubscribing is also a good baby step toward better email productivity in general. If you can’t be bothered to unsubscribe from junk, it’s likely going to be hard to get the rest of that house in order. If you can, you’re already building momentum.