Email penpals


Recently I’ve been sending novella-length emails back and forth with a few friends, and it’s been invigorating. I figured I could (should?) talk a bit about why, the way I’ve gone about it, and how it’s panned out.

Writing emails like its 1999

Kat Vellos’ We Should Get Together has been on my to-read list for a few months, and when I got to it I absolutely blew through it. Sometimes you’re in the right mood for a book and it’s less like reading and more like having a conversation in your head. The book itself is about building friendships as an adult, and one of the themes that comes through time and time again is the requirement that you and your new friend can just talk without a specific goal in mind.

Over the past year or so, I’ve found it harder and harder to have what I’ve mentally classified as “agendaless social interaction”. It’s a confluence of events - having moved out into the ‘burbs in a city that’s pretty split up, having recently had a kid, and of course the ever-looming threat of COVID-19 and its variants occasionally isolating households and turning every public outing into a quick back-of-the-envelope risk assessment. In the past, I’ve used social events as a way of turning colleages or acquaintances into friends, as well as keeping in touch with folks who I wouldn’t otherwise run into - so not really being able to have catch up has done a number on quite a few friendships.

Alongside all of this, I’ve had Cal Newport and Jenny Odell sitting in my mind - their books Digital Minimalism and How to Do Nothing both took their own approach to skewer social media and its impact on our lives. Specifically, Newport quotes MIT professor Sherry Turkle:

In her 2015 book, Reclaiming Conversation, Turkle draws a distinction between connection, her word for the low-bandwidth interactions that define our online social lives, and conversation, the much richer, high-bandwidth communication that defines real-world encounters between humans.

During an appearance on The Colbert Report, host Stephen Colbert asked Turkle a “profound” question that gets at the core of her argument: “Don’t all these little tweets, these little sips of online connection, add up to one big gulp of real conversation?” Turkle was clear in her answer: No, they do not.

Turkle specifically differentiates between online and in-person interaction - as does Newport. Specifically, Turkle identifies in-person interaction with high-bandwidth communication, subtlety of interaction and expression, and (as a result) nuanced communication and deeper relationships. In contrast, online interaction, limited to certain senses or even just text, is low bandwidth, not particularly nuanced, and proves a barrier to deepening connection.1

In general, I agree with their thesis: it definitely aligns with the feelings I’ve had using these tools over the years. But I think there’s a low-bandwidth medium that does provide the kind of deeper interaction that Turkle attributes to conversation. You might have guessed it, based on the title of this post and its central thesis: it’s email.

Email is a mode-shift

Email doesn’t feel like it fits into Turkle’s framework at all - in fact, if anything, it displays even less similarity to in-person conversation than the majority of modern online modes of communication. Email is asynchronous, it’s text-only by default…it’s decidedly disconnected and out-of-date when you compare it to pretty much every other social media channel. It’s super-low bandwidth. And yet email conversation - when you can get it going - feels richer than similar conversations over social media.

I have a theory about this, although I don’t feel I have a way to really prove it.

Instant messaging, and most social media messaging systems by extension, want to be analogues for conversation. Just consider the way they present themselves - with your messages and other parties’ represented by chat bubbles or ovals on either side of the box, using language like “conversation” and “chat”, and of course, by being synchronous, by giving us real-time feedback when people are typing, or letting them respond via emoji.

In contrast, email is an analogue for letter-writing. Consider how we start and end emails, how we often go through multiple drafts or rewrites for important or longer-form emails - even how typos in emails are construed.

Letter-writing is itself an art form that goes back centuries, and I would argue that it allows the sort of deep connection Turkle wants to see in conversation, just by different means. By giving each side of the exchange time - both time to write the letter, and time to read it - we can provide the extra bandwidth through word choice, pacing, sentence and paragraph construction, the same way that an author uses these tools to portray a richness and depth of writing even though they won’t exchange one word with you face-to-face. The same is true for email: just because I can send an email and have it delivered to the recipient instantaneously, there’s still mechanisms to slow to the cadence of the communication (no read notifications, a reliance on manually removing it from your inbox when you’re done).

And to me, that’s why email works as a medium separate from most other online interaction: because it’s not trying to be a conversation.

My plan

It would be a lie to say that all of this came into my head, I sat down and thought it out, and came up with a plan. What really happened was: life happened. Someone moved away. I found that with hybrid work and childcare, I was leaving my house less and less. I found myself holed up with a laptop of an evening, wishing I could just write something to someone but finding no one online I could really connect with (and really not keen on the, you know, interaction, just wanting to write). I finished up We Should Get Together and felt a pull to do something.

So the next time I could see someone about to vanish from my life due to changing circumstances, I asked if they wanted to collaborate on an experiment with me. And they did!

The experiment is still very small - I have one and a half folks on board2. But it’s finding its feet - I’ve sent a number of emails over about six months, and I’m starting to get some idea as to how it goes. So that’s not too bad.

The elements of good correspondence

So what makes a good exchange of letters (or, in this case, emails)? I don’t know! I’m also trying to work out. But here’s what I’m trying right now, based on minimal experience:

1. Correspondence must be two-way, at both the macro- and micro-level. At the macro-level, that means ensuring that your correspondence is an ongoing conversation - following up on previous topics, delving deeper on stuff that interests you. On the micro-level, this means ensuring your emails aren’t just screeds of your thoughts, but that you also ask questions and prompt your partner to respond. It’s also worth pointing out that different people have different demands on their time - you might find yourself writing two emails to your penpal’s one - and that’s fine, as long as both people are contributing. There’s no point you pouring your soul out into the ether, and you have to be ready for your partner to just not be able to return the favour, and let this one go.

2. Give it time to breathe. And not just so you can think of interesting and well-thought-out responses. A gap of time between emails allows life to happen, and the things you experience, the conversations you have, will then feed into your next email.

3. Go deep slowly. The great thing about a long written text is that you’re able to address a subject at much greater length than you might be able to in instant messaging, or even in spoken conversation. That’s not to say you should start here - you want to spend time building trust until that kind of conversation feels natural. But it’s a great endpoint, and it takes advantage of the medium.

The step-by-step

So how’ve I been implementing this? It looks like the following:

Step 1. I find people I want to email with. This started with one person who was changing jobs, who I didn’t see socially, but whom I wanted to keep in touch with. For you, it could look different. Maybe you want to make a list of your friends whom you’ve fallen out of touch with, or whom you want to know better. I’d recommend introducing penpals one at a time, or you’ll find yourself overwhelmed.

Step 2. Get them to sign up to the scheme. It can feel intimidating to say to someone, “Hey, do you want to be email penpals?” - if you want, you could always frame it as “Hey, I’m trying this new thing, want to help?” Either way, you want to make sure the other party is on board. (Some particularly good people don’t have the kind of life that allows them to write long emails, and know it - and will tell you straight up. That’s a great way to avoid several emails’ worth of work for little gain.)

Step 3. Send your first email. This bit is tricky, because you don’t just want it to be you broadcasting what’s happening in your life - you want to provide hooks for deeper conversation. Going back to the top of this post, We Should Get Together has some great conversation-starting questions you can weave into your email. Failing that, you can always ask what people have been reading/watching recently.

Step 4. Wait. This is perhaps the hardest bit. (Or the easiest bit, depending on your life!) Other people’s lives are just as busy as yours, and it’s unlikely people will be as invested in this scheme as you are (after all, you’re the one who’s reading two thousand words on email penpals, and the one who initiated the whole thing). You need to have faith that your penpal will read your email, will respond.

Step 4a. And then one day, nestled amongst sale brochures and notifications of changes to terms of service, you’ll see an email written especially for you from your friend! Go on, open it and read it. Now I said step 4 was the hardest bit, but it’s not, because it’s actually…

Step 5. Wait (again). Don’t respond immediately! Instantly responding means you burn out all the energy you’ve built up, and you barely have anything to write about. So sleep on that email. Let it sit in your inbox for a few weeks. Wait until things start happening in your life and you go “Oh, that passage I read really speaks to what we’ve been discussing”, or “Oh, I know how to answer that question!”. And then, once a few weeks have passed…

Step 6. Start writing a response. Don’t feel like you have to write it in one sitting. I often start mine with a date and time and where I am, and finish them the same way. If it takes you a couple of weeks to write your email, that’s OK! If you’re feeling picky, you can always do a quick go-over and edit at the end to tidy it up. But also, your friend won’t mind if it’s a bit rambly. It’s not like you’re going to publish it.

Step 7. And you’re back to Step 4! Keep going, and watch your stack of correspondence build up.

But what about…

What if my penpal doesn’t respond?

Be patient! People have lives, those lives are hectic.

It’s a real tough job not to follow up after a couple of weeks to go “Hey did you get my email are you replying?” Every time I get that urge, I tamp it down immediately - if the person wants to respond, they’ll know it’s on their list, and you want this to be a pleasure for them, not a chore.

Some people will want to email you - and will probably be happy to try this experiment out - but will then find they don’t actually have the time to email you back. That’s fine too! You’ll find out soon enough, even if you send a couple of emails with no response. You might have to look at other ways of keeping in touch with them.

What do I talk about?

This is a question whose answer varies greatly depending on you, your penpal, and your relationship. But to start off:

  • What interests do you have in common? If you used to hang out in-person, what would you do when you hung out?
  • What parts of your life have they shown an interest in previously?
  • What parts of their life are you interested in? (This can be good for throwing them conversation prompts to help them out.)

Hopefully as you’ll go along you’ll be able to address other subjects that come up - respond to elements of their previous email, follow up on themes which have emerged, and so on.

But I talk to my penpal outside of emails!

This is a fun one to deal with - I’m often Facebook friends with my penpals anyway, and that provides a really obvious medium for quickly checking up with them (or sending them photos of our kid doing silly stuff, or what-have-you). There’s nothing wrong with communicating over multiple media, but it can feel like the more frequent medium will suck the life out of the others. I’ve been trying to keep Facebook messages to quick and light-touch stuff, and in some cases I’ve actually told people I’m saving subjects for my regular emails.

What’s the future?

Right now, I’m still working this out. I hope that over the course of 2023 I can build my emailing muscles a bit more, and work out how this whole thing can work long-term - and then perhaps when another good friend shifts jobs, or moves city, I can use this as an opportunity to spread the project a bit wider.

It definitely feels like a slow burn - this isn’t a product of a world that’s interested in 10x scaling, or exponential growth. But it feels like something that - if done right - I could be doing decades from now, and I’d love to see if that’s the case.

  1. However, this low-bandwidth communication may still scratch our itch for acknowledgement and connection - kind of like a “junk food” equivalent to in-person communication and a potential evolutionary mismatch that social media companies love to exploit. 

  2. Like many good things in life, I suspect this project won’t scale too much anyway. There’s the point where it’s a joy and a privilege to write someone an email, and then there’s the point where you have to get an email written every week or you’re falling behind.