October 14, 2019

The Newsletter That Almost Was

Fun fact: this blog was almost turned into a newsletter a few weeks ago.

It was beginning to seem like a great idea. After all, if you want your writing to reach people, you either invite them to come to you (blogging, RSS, etc.) or you go to them. To the one place we all inhabit in some fashion: the inbox.

Newsletter startups are blooming in every corner of the garden, and their pitch is compelling—email is the oldest, sturdiest, and most diversely populated social network in existence.

All of that is true, but it’s also true that building an audience has more to do with what you do than where you do it.

The Allure of Email

There are more ways to put words on the web today than ever before, but it’s more difficult than ever before to have those words reach people.

This really hit home for me after a recent conversation with my wife, who pointed out that she doesn’t follow indie blogs—not because the content isn’t good, but because it’s kind of a pain to keep up with all of them. I’ve always thought of RSS as this beautiful connective tissue holding the indie web together…but for her it’s just another feed to scroll through, and she has enough of those in her life already.

Each of these feeds—Twitter, Instagram, RSS, etc.—is also a silo, catering to a particular subset of the total audience. Users of one won’t be users of another.

But all of them use email.

For all its imperfections, email is ubiquitous, proven, and personal. And it’s the only timeline that hasn’t become algorithmic.

Yet email isn’t a magical solution. It just happens to be the latest cool thing that Silicon Valley has latched onto and pretended to re-invent.

The decentralized nature of email also brought up the question of online identity, and whether it was a good thing or a bad thing that a post wouldn’t have a canonical copy, but be distributed across thousands of inboxes instead.

Personal Sites and Identity

I have always appreciated the value of having my own personal website, of owning my identity on the web, even as I traversed and explored the landscape of platforms both centralized and not.

Still, when I migrated the blog to Medium in 2016, I wrote:

…any “personal brand” I have must be durable enough to assert itself anywhere. It should live in the content, not the platform.

Over time, even as I moved away from Medium because of its alienating changes to the publication system, I’ve become more and more convinced of this.

We all accept that “owning our online identity” is important, but what does that mean? A particular visual representation of my ideas? A domain name? A style choice?

Too often in these discussions I feel as though people are treading on the fine line between identity and vanity.

Is the content more mine if I put it on a website that I hand coded instead of on a managed platform? How much of the stack do I need to own before I’ve sufficiently established my identity? I can own the code that contains the words, but I only rent the server that hosts it and the domain that you access it from.

I’m taking it to an extreme, but my point is this: it’s just words and pictures. If there’s one thing I’ve learned from moving back and forth across all sorts of places over the years, it’s that this stuff is really portable.

And so are mailing lists, with the added advantage that email is inherently decentralized. Whatever platform or system I use to deliver it, it ends up in all kinds of inboxes, endlessly archived across tens of different platforms.

But I couldn’t help wondering: do readers care about any of this, or is it just another thought spiral that keeps writers awake at night?

Building an Audience

Ultimately, that was the show-stopping question, though it didn’t hit me until after I’d already set up a Substack and gotten ready to migrate everything over.

You may have heard of them; they’re the current darlings of the indie newsletter space. Substack is built by a small team with progressive ideas about what comes after the ad-supported web.

They’ve effectively erased the boundary between blog and newsletter. Even though each entry can be an email, it’s also simultaneously a blog post on the web. Posts can be email only, or web only, or both. My existing RSS subscribers could continue to get new posts the same way they always have, and anyone could choose to subscribe via email instead.

Unfortunately, Substack and its newsletter brethren don’t solve the problem I’m facing, which is that building an audience with writing—let alone allowing that audience to support you financially—is immensely difficult.

And while it’s easy to look at some of the success stories out there and glumly conclude that they managed because they got in early, the truth is less comforting: even if their timing was better than yours, that’s not why they found success. They didn’t find success because of luck, or because they used a new platform, or a particular method of distribution.

They found success because they put in the hours. They did the work, and they kept doing it, staring down the spectre of self-doubt, enduring the emptiness of a small audience, and weathering the changing seasons of technology.

It’s a very long game of earning trust, providing value, and being approachable in a way that gives people a reason to gather around your content and help you make more of it.

All my hand-wringing about platform and distribution was ultimately just a lazy deflection, I just didn’t see it at first.

Doing the Work

My job isn’t to decide what my readers want or how they should access my work. My job is to do the work, and provide all the options I reasonably can to allow people to read, share, and support what I do.

Over the past year, I’ve been encouraging people to reach out to me directly, and the result has been a better connection with my readers than I’ve ever had before. Chatting with readers helps me understand what they’re drawn to, what they’re interested in seeing more and less of, and what I can do to make their experience better.

I learned, for instance, that while some love the idea of getting posts in their inbox, others hate email newsletters and would never follow my work if that was the only way to access it. I now know that if I offer email subscription, it should be just another option, not the main point of interaction. I heard from others that they’re much more likely to read a piece if I share it on Twitter instead of just relying on RSS, and I’m happy to oblige.

My friends, who I discussed this idea with candidly, said the same thing: all that matters is the content.

So instead of transforming the blog into a newsletter or switching platforms again, I just sat down and wrote more—you may have noticed that there have been more posts than usual. You can expect that to continue as I double down on doing this blogging thing that I love so very much.

And you know what? Traffic is up, I’m reaching new readers, and people are beginning to support me. Go figure.

Turns out that the only true path to success as a writer is one that transcends platform and genre: just keep writing.


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