Long emails

I have a confession to make: I write long emails. I don’t write them frequently, but when the topic is right, I’ve been known to expound in paragraphs at a time. I compose in stream of consciousness, and go back to edit, restructure, and make cuts. But no matter how much I rewrite and excise the junk, I still end up with hundreds of words.

This is seen as a nuisance by many, and discourse on email best practices often makes me feel guilty for pressing send. Yet in our new tl;dr normal — mobile connectivity, short-form communication, and constant distractions — there’s something deeply refreshing about a long email dialogue. So I will no longer be apologetic about my habit.

How could long email ever be refreshing? Let me count the ways:

The Ladder of Inference

  1. Completeness. You present the whole picture of relevant detail all at once. This encourages consideration of a topic holistically, and systemic thinking before analysis.
  2. Data. You travel down the “ladder of inference” and present not only your conclusions, but the underlying data and assumptions that guided you. Opening up your data allows for reinterpretation, and we can identify differences in perspective on the same observations.
  3. Logic. Writing long-form thoughts activates your reasoning, which helps you to organize complex information, eliminate senseless connections, and achieve greater understanding in the process.
  4. Quality. Taking your time forces you to think deeply, and encourages solitude. Receiving a long email changes expectations around synchronicity, and allows the recipient to sleep on it.
  5. Revision. Stepping away and rereading your email yields edits, reconsideration, and simplification. It also encourages perspective-taking, which in turn helps you better understand your recipient’s point of view.

Even beyond these useful properties, long email reveals something beautiful: your passion. When you have the instinct to write an essay-length message, it’s a direct indication of how deeply you care about the topic. For example, I’ve recently uncovered my intense excitement about disruptive fintech startups by sending long-form thoughts to several founders. I wouldn’t have realized how much I love this area if I had cut my ideas short.

In the process of speeding up our communication, we’ve somehow managed to discourage our passionate thoughtfulness. Brevity and rapid, informal tone is now interpreted as a signal of confidence, rather than of superficiality. Attention span is limited to thirty seconds or less.

Of course, for the majority of email, these heuristics make sense. We focus on getting things done, and use the email inbox as a task list. But this task-orientation makes email glib. For example, the Times recently suggested: “Make one point per e-mail. If you have more than one point, send separate e-mails.” And there’s a whole email charter that asks us to avoid open-ended questions and send only short, actionable messages.

So I propose a more nuanced view: that there is a place for long email in our communication toolbox. Sure, it’s not the hammer or the screwdriver, and shouldn’t be used as frequently. It’s more like that hex key you’ve been saving from your last Ikea trip. Not useful in most situations, but when the right opportunity arises, you’ll be happy you kept it around.

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5 thoughts on “Long emails

  1. Good post. I was actually thinking of writing an app called Correspondence that was meant for exactly that: long, well-thought out emails back and forth. The problem is that there’s an assumption with email that you’re going to respond quickly. So people don’t like sending long emails back and forth because it feels like a big responsibility / time suck. The point of Correspondence would be that it’s understood that the latency between messages is longer (1-2 weeks) but they’re much more details. Sort of like Twitter but on the opposite end of the spectrum.

  2. […] in sending meaningless token gifts. Though many favor brevity over the art of communication, I send long emails when I’m passionate about a topic. And I don’t like coffee, so when people think they […]

  3. Connor Theilmann says:

    Great points, Jesse. Agree with your points and I enjoyed reading this one!

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