The Email Tortoise

Whether I like it or not, email is a big part of my job. (And I’d guess this statement holds true for you, as well.)

In the past, the biggest email innovation that I had experienced was the ability to use keyboard shortcuts in my mail app to quickly read and sort emails into folders.

As the saying goes, though, first you use the tool and then the tool begins to use you: processing email quickly, via keyboard shortcuts, only made me want to process email more quickly. Whenever I entered my inbox, I measured the quality of my engagement by using a quantity-based metric. In short, a good email session meant that I removed emails quickly.

As I worked to increase my processing speed, every email session felt like a sprint, my digital lungs burning as I lapped the digital track.

And then I maxed out and, frankly, burned out. At a certain point, I couldn’t go faster. Measuring quality as quantity meant that I was as good as I was ever going to be. Which is when my mail app, serendipitously, crashed.

A colleague advised me to use the web version of email while the app sorted itself out. He assured me that everything would return to normal in a day or two. The backend, as is sometimes the case, was out of whack.

As I started using the web version of email, I was forced to work very slowly. I didn’t know my way around the interface. My old tricks — for speeding up the process — didn’t work.

Working slowly, something strange happened. My joy for the medium returned. My intentionality turned up a notch — and then another notch. I was slower, yes, but I found myself asking questions like:

  • Is this the best time to send this email, or should I schedule it?
  • Would the contents of this email be interesting or informative to someone other than the primary recipient?
  • If I send this email, is it going to generate another email? And would that be a good thing?
  • Should I save that email I just wrote in case I have to use parts of it again in a different venue or in a separate message?
  • Should I just walk down the hall or pick up the phone?
  • If I reply to this email right now, quickly, will I be training this recipient to expect quick replies from me from here on out? Do I want to be beholden to that expectation?

Another thing that happened during my slow emailing is that, ironically, deeply so, I reached “inbox zero” for the first time in three years. Tortoise-like, I beat the hare I had been.

By moving slowly, I found that I never — okay, rarely — needed to pass over an email to solve it later. Solving later, it turns out, is only a problem for someone trying to move very quickly in the moment. In my old system, emails that would take four minutes to process were massive roadblocks. Four minutes was an eternity to someone who prided himself on crushing emails in mere seconds. As a result, they remained “unread” which meant I glanced at them again and again — and passed on them again and again.

The new me, emailing slowly and steadily, sees email as an opportunity to be connected to others, to be responsive, to demonstrate engagement, and to sound like a human being. I give each email the time that it deserves. I still favor short responses — one word if the message permits — but that has more to do with my acknowledgment, regained in slowness, that there’s a colleague or friend on the other end of the send button. And their time is important. My old way of emailing was designed as a response to a more selfish instinct — my time is important. Both are true, but the former is more true in a communication exchange for which I am responsible.

Machines are built for speed. That’s one of the things that they do best. Humans are built for context and nuance and connection. As a human emailer emulating a machine, my upside was limited in that I would only ever be able to increase my speed up to a certain point. This meant that every time I entered my inbox I was destined to fail; worse, in some corner of my mind, I know now that I was keeping score and worn down by losing a run here, a run there. On the other hand, as a human emailer emulating a human, my upside is unlimited because I can always connect with others more deeply, more thoughtfully, more intentionally; I can always raise my awareness of context and tone and the needs of others.

To round out the story, I won’t be returning to the mail app I was using, even though it resolved itself and seems to be working perfectly fine again. I’m sticking with the web-based version of email for a simple reason — as a toolkit, it amplifies and extends aspect of my personality and ability that I want to amplify and extend. I can still email quickly, but speed is now a choice rather than a default. (I choose to email quickly when I’m sitting at the center of a bottleneck and my input, via email, is the only thing that can allow work to flow.)

Best of all, when I open my email now, I don’t see it as a mountain to crush; I see it as a mountain that, climbed slowly and steadily, will offer up the joy of human connection . . . and a great view. It’s not a grind anymore. It’s an interesting daily ramble.

Today I learned . . .

The most common way to get from San Francisco to Stanford is to take the Caltrain from San Francisco Station (@700 4th St, intersects with King St) to Palo Alto Station, which takes 45-65 mins depending on the type of service (bullet/limited/full).

Downtown Palo Alto is a nice area to take a quick walk around if you haven’t seen it before.

To get to Stanford’s campus, you can either walk ~25 mins or take Stanford’s Marguerite Shuttle (weekend service limited to every 60 mins via the SE Shopping Express).

And finally: Stanford is huge and a walking tour can take anywhere from 1-5 hours based on what you want to see.

All of the above came from a local. I copied it into a blog post (a) so I can find it if and when I need it and (b) as a spur to your own explorations, should you find yourself in San Francisco with some time to kill.

“The technology was backward, but the system worked.”*

As a daily habit, I read — or at least glance at — Pitchfork’s music reviews. Sometimes, in the process, a news item catches my eye, and today that happened.

Being a fan of the Elephant 6 collective, a headline about an Elephant 6 documentary triggered a nostalgia response in me. As I read about it, I was delighted to see that the marketing and distribution plan is as stubbornly, backwardly innovative as the bands in the original collective.

Filmmaker Chad Stockfleth has spent the last ten years on the documentary, and instead of opting for a traditional release, he decided to distribute flyers advertising the documentary at coffee shops and record stores in Chicago, New York, Atlanta, Portland, Athens, Los Angeles, and more.

The flyers promote an organization called the Elephant 6 Video “Rental” Club, and feature pull tabs at the bottom with a phone number. When the number is dialed, a pre-recorded voice message reportedly prompts the caller with different instructions. Eventually, the caller will receive a VHS tape in the mail, as well as a “library card” to sign when the tape is mailed back. The VHS case also includes a fresh flyer for the renter to hang in their own neighborhood.


*The title for this blog post comes from, which I used to check the meaning of “backwardly” when I wrote it in the second block of text above.

Reduce the Cognitive Load

By the end of this week, the school year will be underway for me. I will have oriented new teachers, attended a 6 hour retreat, and run a 6 hour retreat.

One of my goals is to learn as much as I can about cognitive load theory, and to reduce cognitive load for others when possible. It’s not that I want the people around me to work less hard; I just want them to work less frantically and more efficiently. As a leader, I want to leave greater focus in my wake.

On this front, I’ve been pondering an article for about a week, ever since Morgan Housel tweeted about it. It contains quotes like:

[Most] geniuses—especially those who lead others—prosper not by deconstructing intricate complexities but by exploiting unrecognized simplicities.


[Geometry] doesn’t have bad days. 

And, yes, it’s about football. Even if you’re not a fan, if you read Refreshing Wednesday, there’s something in this short piece for you.

The Impulse to Beauty

Tony Cuneo passed away earlier this week. He was a friend and colleague and one of the top three most masterful teachers I have known / observed / learned from / aspired to be like.

Here’s his Artist’s Statement, updated in July, when he was in the middle of his illness. In addition to my list above, Tony was a great artist (and father and baseball fan and . . .).

I don’t put a lot of faith in artist statements. 

Describing what I do as “work” has a slightly bitter, puritanical aftertaste to me; I like slopping paint around. It’s the reason I wanted to be an artist as a kid, and I think it’s still a fine reason to paint. I’m very comfortable with a perpetually unfinished process. I go (after much reflection) in whatever direction the painting takes me. Having too clearly defined a concept for a body of work (and this is just me) gives me claustrophobia.

I pray I never get to the point where I’m making product and not art.
Beyond that, I’m a fan of uncertainty. Not knowing you’re doing it right is a good thing. It makes you stop and think. When I paint, I’m playing as much as I’m working. I’m asking questions.

However having said that, the complex, charged tension between apparent opposites — chaos and order, emotion and intellect, creation and decay, high and low, representional and non-objective — is the text of my current painting; also, how the impulse to beauty wrestles with the desire for truth.  
Art is one of the most natural things in the world, fundamentally useless, but hugely pleasurable, very important, and deeply satisfying. 

Source & R.I.P.:

Teaching Now

Today, I recorded a podcast for Nabeel Ahmad, Partner at Rose Rock Dynamics, planned a Webinar for alumni at Teacher’s College, Columbia University, and booked an in-person workshop for independent school Trustees. Though each lesson will be similar — focused on the teaching mindset documented in Make Yourself Clear — each classroom is very different.

Which means that, in each classroom, if I want to teach well, I have to ask myself some simple questions:

In the time and place that I’m meeting with these particular students, what can only happen then and there and in the way in which we’re assembled? What affordances exist in each context, and how can I make full use of them?

Obviously, the answer is very different if I’m doing a Webinar that will only serve a live audience vs. a Webinar that will serve both a live audience and an audience that listens to the recording at a later time. And the answer will again by different if I’m working with a face-to-face group. Or teaching with Reshan Richards, which happens to be the case for all the scenarios described in the first paragraph of this post.

Teaching now is amazing in that it happens in so many places and ways — it’s been untethered from its brick and mortar origins. But for the teacher who really wants each class to be special, there’s a lot (more) to consider. I like this challenge . . . or I guess I wouldn’t still be teaching as much as I do.