What Will Happen to Our Email and Digital Correspondence?

I’ve been reading a collection of Hunter S. Thompson letters called The Proud Highway: Saga of a Desperate Southern Gentleman, 1955–1967 (The Fear and Loathing Letters, Vol. 1).

Released in the late 90's, Hunter was already a famous writer by the time it hit shelves, and in place of a proper memoir, it’s perhaps the best record of what he was thinking when he was still fairly young, struggling to find his footing in both life and in the larger world of journalism/writing/whatever.

I’ve often told people that in place of a diary, the best written record of their life is probably their email. As it stands now, my own gmail inbox dates back nearly to when I signed up for it, some time in 2005, and I’ll likely never clean it out.

Occasionally, when I want to take a trip down memory lane, I glance back at past years and look at the things I was writing to people. Long emails, play-by-plays of this thing or that thing, how I was feeling, moods, etc. Short of keeping a journal, this is the best thing I can think of. Some of the correspondence I can even remember writing.

A couple weeks ago, I visited a discussion board that I wrote on a lot in the early 2000's. For a solid 6 years, I wote at least a few posts a week, replied to people and generally looked at it every day, multiple times. At one point, I even served as the moderator, a stint which lasted a few years.

In the process of looking back at it, I was able to attain a record of the first post I ever wrote, way back in the fall of 2000. I was 18-years-old at the time, and had just entered college. By looking at it, I could see this young, inquisitive kid, hungry to learn about whatever it was I was asking about. I was stupid, but thirsty.

By and by, as I went through the posts, month after month, year after year, I could see a progression. I could see differences in how I was replying, topics I wanted to discuss. By reading these posts, I could see my thinking change. I could see myself growing up.

Unlike Hunter S. Thompson, I didn’t write these things in the hopes that they would be published one day, and frankly a lot of it I hope never gets discovered, not because I’m ashamed of it, but because nobody needs to see some tossed off reply that I wrote one lonely night under a pseudonym.

But reading his book of collected letters, I did get to thinking about letter writing and correspondence, and how we might collect these things moving forward, when the ability to write is so instantaneous and fluid.

I don’t mean to suggest that the frivolity and casual nature of email — its convenience, essentially — lends itself to shorter and less meaningful correspondence, but when I think of a lot of email, particularly in recent memory, it feels like something that is kind of tossed off and not really done with much care.

I was watching someone compose an email last night and it was interesting to see how they did not capitalize anything and barely looked over how they were saying what they were saying. It was all so breezy. It had no value beyond the point of just getting the message from point A to be point B.

Obviously, all email is not like that, but in recent years I’ve found that I receive less weighty correspondence from people, either because they’re inundated with text in their day to day life, or perhaps more illustrative, they’re glued to a smartphone, where they don’t really have the ability to play the phone’s touchscreen like a piano.

In looking back at the discussion board as well, one thing that really struck me was the breadth and depth of the commentary, of the subject matter and replies. This was still the dial-up era, and I can’t help but think that because of that, we all took a little more time to make sure we were saying things more carefully.

What mostly comes to me when I’m reading this collection of Hunter S. Thompson letters is that it would be increasingly difficult to do this, to collect these records of correspondence, in modern times. We might have easier access to it, and a greater means of searching through the records, but there might also be far less interesting stuff inside, shorter and less thought out.

For example, if I want to get a snapshot of how I might have been thinking in 2009, I can go look at my tweets from then. But even those, they’re pointed at nobody in particular — followers! — and there are so many of them that I can’t tell when I was being serious or when I was just messing around because I was a 27-year-old with a phone in my hand.

What is the point of all this? Like most things I write here, I don’t know. I just think it’s cool that you can look back at printed things and sort of piece together a rough framework of someone’s life. And I think that it’s a lot harder to do now, when the casual, tossed-off nature of the digital written word makes writing — which is data, after all — such a big, giant mess.

Written by

Wrote for the New York Times, New York Magazine, Esquire, Rolling Stone, Vice, Fader, Vibe, XXL, MTV News, many other places.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store