I email myself all the time. A half dozen times a week at least. Looking at my sent items box now, I did one this weekend when I ran across a neat hike I wanted to do from a Reddit post. I actually have a place I keep stuff like this (a special project in Things) but I didn’t feel like putting it there right then. I wanted to email my wife about it too, and who knows, maybe look into it a bit more first. That’s for future-self to deal with.

In that case, it’s sort of like my email is my TODO list, but it’s more like a “deal with this later” list. That’s distinctly different to me. My TODO list items are specific tasks with context. An email, to me, isn’t a TODO list, it’s a “deal with this soon” list.

Notice I had to look in my sent items box to find that email about the hike, not my inbox. That’s because (probably just hours later) I did what I wanted to do with it (read the article on a larger screen, emailed wife, put on my real TODO list of places I want to go in proper context).


I had one of those days last week where I had to go to war with my email. There were a lot in there and I wasn’t making good headway. It was a slog to get through and I don’t think I was doing my best work.

My general philosophy is that email shouldn’t be a slog. That if you manage it well, at worst, email is boring, and at best, it’s productive and fun. But never something that gets you down and feels like a waste of time. So this was a nice reminder in how that can feel.

The thing was: it wasn’t the email. That was misdirection. It was all the work I had to do in order to answer those emails. For example, editing an article that was super rough shape, so I could move it along in an editing schedule. That slog was about the sloppy article, not about the email. Fixing that slog is harder. It means saying no more to articles in that shape. It means adjusting our workflows to share that load. It means being more clear upfront about expectations. It’s people stuff, not so much email stuff.

Public vs Private

When you post something to the internet, like a comment on a blog post or a social media post, there is this expectation that what you are doing is public. If your identity is tied to it, it becomes this permanent reflection of who you are, and in general, people act accordingly.

Email has no such public component. Even though an email might become public in some capacity, it general doesn’t, and people act accordingly. There is a lot more yelling, a lot more serect-divulging, and lot more bad behavior over email.

I’m not sure what I think of that.

Part of me thinks it’s nice we have these different communication channels that can be used differently.

Part of me thinks it’s best to behave in such a way that it doesn’t matter if email is public or private. It might as well be public because you treat people well no matter what.

Physical Mail to Email Service

I wanted to sign up for one of those services that gives you a physical address, but then allows you to scan whatever it gets for you. My situation was that:

  1. I was moving offices, and while I could have changed the address to the new office, it somehow felt better to move the address to an address that theoretically would never change.
  2. 80% percent of physical mail I get becomes a little chore in which I need to scan the contents and file it in a Dropbox folder. If the mail was already scanned, that saves a step.
  3. I could hand over control over this service to someone else someday if I needed to.

I had never used a service like this before. After asking around, I landed on Anytime Mailbox. People seemed to like it. There was a good amount of hoop-jumping to activate the account, including a virtual video call with a notary. One reason I picked Anytime Mailbox is that they had physical locations in my small town (Bend, Oregon). That’s good because if I get a package or something, I could still go get it. (Most packages, like from Amazon, I still have come right to the new office.)

Turns out the physical location is one of those “ship whatever” stores that isn’t like an official USPS, FedEx, or UPS store, but is an affiliate or something and can still ship stuff, as well as sell greeting cards, empty boxes, and Mountain Dew. So Anytime Mailbox probably accounts for 1% of their overall business (I don’t know, it just feels like that), which does worry me a smidge about the longevity of that physical address. I imagine they have have boxes for all these type of services.

Now that I’ve been using the service for a bit, I think I like it. As soon as I’m completely out of the old office, it means I’ll never have to physically go check the mail again just to see if something has come. Now, every single item that comes generates an email. I didn’t quite realize that until now, but it makes sense. So far I’m not annoyed by it as it seems like the time saved is higher than the time spent. Although the fact that I can’t “unsubscribe” from physical mail very easily is slightly concerning.

When I get a new bit of physical mail, I choose to…

  • Open & Scan it
  • Shred it
  • Recycle it
  • Save it for pickup

Already twice I’ve had to save something for pickup and go get it (a physical check, and some confirmation letter I wanted to really see). That’s nice that I can do it, but I have to get in my truck and drive over there, which is definitely a net loss on time, not to mention not terribly pandemic friendly. But I suspect I’ll have to do that pretty rarely going forward.

Ideally I’d like to set up some kind of automation so that if I choose “Open & Scan”, it just ends up in the Dropbox Folder I want it to, rather than me manually doing that step. I don’t know if it’s even possible, but hey, baby steps.


Bad/Junk emails don’t take much time. You just unsubscribe from them or delete them. Maybe a quick-but-nice “no” if it’s warrented.

Good emails don’t take much time either. You’re excited. You want to write them or reply to them because they mean something good. They don’t feel like a time sink, they feel like accomplishment.

It’s all the emails in the middle that are the slog. Emails that need attention, but they aren’t exciting. They require work, but work that really doesn’t amount to much. There is some satisfaction to getting through them all, but it’s unfortunate that that bulk of work is ultimately going to be worth so little.

It’s worth strategizing how to slim those medium emails. Either demote more of them to bad and shooing them away, or promoting them (shaping them) to a more exciting place.

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?