Not a Big Deal

I had a conversation with a friend in tech the other day about email. It was refreshing to me, as they come at email in the same way I do: it’s not a big deal. Once you have your email under control, you just knock through it and it isn’t this huge burden. Even coming back from an extended stretch of totally checking out of email (a healthy vacation), you should be able to knock through hundreds (maybe a thousand) emails before lunch.

In fact, you come to love it, because of how effective of a communication method it is: it’s public, it’s async, it can hold files, it can be of any length, it’s threaded.

Tooling isn’t needed to “fix” email. Email clients these days, for the most part, are interchangeably good.

Now this story isn’t true of everyone. Very many people fall under the weight of email in various ways. I wanna keep digging into this from both sides. I wanna learn more about what makes email so burdensome for people, and I wanna learn more about what makes email so easy for some people. Hopefully this blog will be the home for that in years to come. I’ll still very much into thinking about email.

Golden Age of Email

Dvir Ben-Aroya for FastCompany:

There’s certainly a place for messaging, but email is still the centralized communication portfolio for many things that happen in our work and personal lives. When you want to reach out to a new client, you’ll use email. When you need to file your month-end expenses, you’ll find those receipts in your email. Email is still the focal point for containing our digital memories and footprint; and for most of our outbound, cross-organization communications.

I’d add a few dozen things to that list.

I’m not so sure we’re in a “golden age” of email so much as email has been incredibly useful for a long time, still is, and there is nothing anywhere close to unseating it.

Even the authors own thing isn’t trying to unseat email, just incorporate it into a new tool.

Not even realizing it’s a problem

We don’t get many comments around here, but when we do, they are good! Thanks Sara Hill.

One of the big problems I continually encounter surrounding email is that many people don’t think of it as an issue to “fix.”

That’s wild. I feel like all I ever see (anecdotally) is that trite “Ughck. Email. Right? The worst.” which to me insinuates that their inbox is a mess and they hate it. But it didn’t occur to me that people can be in that situation and not even realize it’s a problem to fix. And double so:

They don’t know they have a problem and are a problem to everyone else. 

Sarah also wrote she asks candidates what their inbox looks like and the answers can be telling. Wow. There ya have it. Your messy inbox might not just abstractly cost you opportunity, it might directly cost you opportunity.


They say design is like art with constraints. Even art can thrive under constraint. Constrained materials. Constrained space. Constrained time.

That last one is interesting. How can email benefit from constraint? What if you never sent an email longer than one paragraph? What if you could only answer 1 email each day? A more commonly-tried constraint: what if you limited your email time to 1 hour at the start and end of each day?

The Peculiar Rise of the Paid Email Newsletter

Nick Heer:

One of the hardest aspects of writing on the internet is developing a core audience of people who will make a daily task out of reading your website. Website feeds have long been a good way to alert subscribers of something new, but they need to be explained, so they aren’t great for reaching a wide audience of varying technical ability. For a brief moment, it seemed like automatic delivery of links through pages on Twitter and Facebook would be a good in-between answer, but their constant fiddling with feed contents based on unknown user metrics severely hampers reliable delivery to subscribers.

Email is a great lowest common denominator solution. It is an open standard that everyone already knows how to use. An email client is a feed reader without a learning curve.

I think paid newsletters are cool. It’s such a clear way to monetize an audience that finds value in what you have to say. I would think the tech is less fiddly than website paywalls as well. You pay, you’re on the list, you don’t pay, you’re not on the list. Websites need login systems which are non-trivial.

I haven’t gone down that road myself as so far I’ve monetized my writing career with advertising on the site that’s not behind a paywall, which is, of course, good for SEO. That’s mostly blogging, but I do also write an email newsletter (it’s a team-effort) directly on the site (and it gets sent out after being published on the site). I highly recommend that as having a URL for things you write is just a good idea. Then if you want to paywall in the future as well, that’s an option. I’ve also done that with some writing.

Whether it’s paywalling on-site content, or a paid email newsletter, I think it’s probably smart to 80/20 it. 80% free, 20% paid. Your true fans will pay you, and the 80% helps find new true fans. Maybe once you’re outright famous you can tilt the scale one way or another depending on how well things are going.

Core Tenets

The longer I have this site and nudge myself to write on it, the more clear my beliefs on what it takes to be good at email are getting. A short list:

  • Being good at email is far more about habits than tools.
  • You can’t fix a bad email situation overnight, you have to work at it.
  • Staying good at email means consistent effort and self-evaluation.

It’s a lot like diet and exercise. A flashy TV pill doesn’t help you lose weight and become healthy just like a fancy new client or email service doesn’t actually help you be good at email. Even if you find a tool helps you (in email or health!), that’s great, but it might be a burst of enthusiasm as much as it is the tool.

What helps you lose weight and become healthy is managing your diet and doing exercise… forever. What helps you get better at email is managing it… forever. Advice and coaching helps both.

Mark as Unread

I just noted that Slack released Mark as Unread. It’s just a form of moving a TODO list where you want it, which feels OK to me as long as your TODO management isn’t too disjointed. Should it be everywhere then?

For DM’s, I could see that being useful. I have one right now I know I need to respond to that I’m worried I’m going to forget about. I actually wish I could move it over to email easily. I can, by asking, but that’s not always desirable. When opportunity is coming to you, asking for context shifting doesn’t feel right.

Mark Unread (in Slack)

Mark Unread is a feature in some email clients that proves that people use their inbox as a TODO system. Mark Unread says: I have actually seen this, but I need to trick my future self into treating it like I haven’t so that they will deal with this in a way that I can’t right now. I don’t have any particular problem with at, unless it became a major crutch, because then I’d think you there would be a lot of time-savings to be had by only dealing with those emails once instead of multiple times.

Now Slack has the same feature, which is is being poked fun at:

I guess it just shows how powerful a concept “Unread” is. Theoretically, unread email doesn’t have any priority yet. Just because it is unread doesn’t make it important. But in practice, it does. Unread emails have the power to become the most attention-grabbing of all emails. Like a lottery scratch-off: will I win? Gotta play to know! Will this next email have some good news in it? Gotta read it to know! And so we exploit that feeling even to our future selves.

Leave Me Alone Leave Me Alone

I had on my list to check out Leave Me Alone, a service that purportedly helps unsubscribe you from newsletters and such. You give it access, and it, presumably, starts digging through your email finding newsletters it can help you unsubscribe from. Seems useful, if you trust a third-party reading your email. That’s a big leap for me, erroring on “no”.

I thought I’d just sign up and get as far as I could before it got creepy. This is where it got creepy:

There is a step here where you have to type in your Gmail password into their app. Nope. You never see this. Google has secure auth systems where the only place you type in your password in on a real secure Google URL. No way in hell am I coughing up a password like that to a third-party.

Remember, if your email is hacked, your entire life is hacked. The person with access to your email can reset your password anywhere else.

I have no idea if the company is credible or not, and to their credit, they tell you to turn on 2-factor auth before proceeding, but this just smells all kinds of fishy.