Hypothesis: The Personal Email Newsletter is the Modern Replacement for Letterwriting

Letterwriting is nearly dead, along with all of its personal (and societal) benefits. Is there a realistic, sustainable way to get some of that back?

My grandfather (called Gumps) used to tell me about the importance of letterwriting. He had books of correspondence between historical figures he admired and he would read them to me when I "couldn't sleep"/just wanted to hang out with him. I was always struck by how beautifully these letters were written. Incredible prose with personality, sharp wit, and flourish, intended for one person who may not receive it for weeks.

Letters are responsible for the existence of the historical record, and yet it's a practice that's been completely lost today.

But we're so much more connected now. We know what's going on in the lives of people we went to high school with.

— People on Facebook

Sort of? I would argue that modern social media is an entirely new (and often shitty) way of being connected, and that it doesn't replace what's been lost in letterwriting even a little bit. It's sort of like replacing all the red fruits and vegetables you eat with Twizzlers. Certainly Twizzlers are red and "edible," but that's where any similarities end. Seeing pictures of people's kids and food and knowing what they're politically upset about, while nice (I enjoy all of those things, for the record), does not begin to replace the benefits of letterwriting.

The greatest benefit to letterwriting is to the writer herself. It is in the process of writing that ideas actually take form, where paths are carved between disparate localities in an individual's unique experience, where beliefs are questioned and strengthened. A letter sent by Abraham Lincoln isn't just a record of some thoughts he had one day that a donkey took far too long to deliver. The letter is actually the documentation of Lincoln's thinking process, of his ideas and decisions as they formed.

So why don't we all start writing letters again? This has been an unmet personal goal of mine for many years. Even though I've set up all the infrastructure to do this (I've got all of the stamps, cool stationery and envelopes, typewriters and antique typing paper a guy could want), there is one really devastating barrier: I don't have time to write letters to all of the people I want to write letters to. 😦 And then there's a larger-scale problem: None of them have time to respond. That's not a problem for me. It's a problem for them.

A thoughtful letter sent through the mail today is so countercultural that, no matter how many disclaimers I can attach ("I'm not expecting a letter in return"), in the hands of the recipient, it tends to transform into an unfulfilled obligation, and no one needs more of those. On top of the already-impassable mountain range of too much work, too much email, not calling mom enough, not being attentive-enough parents, and whatever the fuck else we all should be feeling guilty about, delight is unfortunately not the only emotion associated with receiving a letter. We're all too busy, for many reasons both real and dumb. We don't have extra time to stare at the wall, or write letters, that we used to (this is a much bigger problem than the loss of letterwriting, and is outside the scope of this essay).

Like it or not, letterwriting is a two-way street. If moving culture forward to letters again is even possible, it will require some pretty big intermediate jogs.

So how can we get the benefits of letterwriting in a sustainable way that reaches more of the people we care about: family, friends we've made (and friends we'd like to make), and even business relationships, without creating unfulfilled obligations for others, keeping the relationships we care about warm for serendipitous connections and occasional, low-pressure engagements?

I think the answer is in the Personal Email Newsletter (PEN).

You're very likely thinking "Oh no, I hate email newsletters."

I'm not talking about the dickbaggery sent by most companies "just so you'll keep them top of mind!" I'm talking about something a lot more like a personal letter, where you share the ideas you're noodling on, helpful summaries and links to books and articles and films you've found interesting, a quick tip that you find yourself giving out a lot.

To do this type of personal newsletter, you don't need to be a brand. You don't need to be selling something. You don't need to stay in any lane. This kind of newsletter is just you, synthesizing your experience, and offering the ideas you think are the most valuable to the people most valuable to you. And maybe, sometimes, when they feel like it, someone will send you a response, or an idea, or a note on your work, or an offer of help. Or just a "Hey, great to hear from you." Those are nice, too.

Does it replace everything lost with letterwriting? Of course not. The biggest thing it fails to replace is the sheer volume of words and ideas that used to be sorted out on the page by the average person. A place for everyone to slow down, consider what's important to them, which ideas make sense, and which are just noise.

But perhaps it could replace a lot of it, for me.

I'm going to try this, and if you want to hear about how it goes, you're very welcome to sign up here.

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I'm looking for others like me. My newsletter is the best way to connect.