On Being An Unsuccessful Writer

Some reflections on my journey, one month out.

I want to avoid doing too much writing about writing in this space. It’s a subject that has the potential to be interesting, but it can also be a little navel-gazey, and it can bore readers who are uninterested in the ups and downs of trying to turn words into something you can exchange for food and beer. 

That said, we’re just about one month out from the launch of this newsletter, and while I won’t make this a habit, I do want to talk a little bit about what this has been like, and also take the opportunity to do a bit of housekeeping. 

The internet is rife with pieces about how to grow a readership or following. Some are interesting and helpful, most are rote and phoned-in, and some have the distinct musk of slimy get-rich-quick schemes. What almost all of them have in common though is that they are written by writers who, on some level, have already done it. They’re by people who are already raking in the bucks, and using their personal experience and personally-gained knowledge to offer a hand down to folks lower on the ladder.

That’s very useful. And experience is a pretty darn good basis for thinking you have the authority to speak on a subject. I’m going to take a slightly different angle here. I’m going to take this opportunity - and if things don’t go well for me, I’ll have many more like it - to talk about the view from this side of the fence. To talk about life as a writer who is not crushing it, who has not popped, and who is spending his days flailing around, trying to catch up, trying to see what works and what doesn’t, and trying to navigate a social media landscape that left him behind years ago in order to try and make the magic happen.

First the good news: I still like writing! That’s key. And that’s a victory, of sorts. I will continue to tweak how much content I offer here - more on this later - and continue trying to optimize what I share and what I don’t. But I started all this because I reasoned that I was doing a lot of writing anyway, and why not put it out there and see what happened? I was a bit worried that that would cause me to enjoy the pursuit less (as was the case when I tried my hand at stage acting). So far, that hasn’t happened. 

The part of this that has been less fun - and I was prepared for it, at least - has been the grind to find readers. I had a pretty awesome community on Facebook who nudged me along over the years with positive feedback on my work. Happily, most of those people became subscribers here, and some are even paying for the privilege.

But I always knew that once that inner circle of Facebook buddies was exhausted, it would be a hard march to get more eyes on my work. And it has been. Everywhere other than Facebook, I’m a social media neophyte. Not only are these platforms important for building a network of readers, they can now be quite lucratively monetized in their own right, and are thus, unwise to ignore. 

So I dedicate almost as much time to grinding for Twitter followers as I do actually writing and that, I do not enjoy. I’ve read that at a certain tipping point, the algorithm should start doing some of my work for me, and I hope that’s the case. But I spent years avoiding the time-suck of non-Facebook social media. Now that success in my new enterprise is dependent upon non-Facebook social media, I feel kind of like a dope. Nothing like being almost 40 and trying to figure out how to get people to like you on Instagram.

But hey, it’s something to do. And I’m glad I’m doing it. If you’re reading this, thanks for helping out!

A few things to expect in the coming weeks. Comments always welcome:

*I’m probably going to scale back the volume of newsletter content. I’ve been aiming to post three times a week, mostly just for discipline, but I think that’s a lot of strain on the inbox. I subscribe to a huge number of newsletters myself, so I’m aware of the diminishing returns associated with email-bombing people.    

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I’m going to be changing up the podcast. Because I’m new to any kind of broadcasting, but not new to acting, I’ve been recording the podcast as a narration of my newsletter, and treating my entries like a script. It was useful to do this for a while. I was within my comfort zone, and it gave me time to learn some of the ins and outs of audio recording. It also made the podcast - what’s the word? - suck. 

I want to start experimenting with more authentic, off-the-cuff commentary. I think it’ll be better in the long term, but I also think it may be worse in the short term. So if you’re not loving the new format, do let me know. I’m starting to see why so many podcasts are co-hosted, or feature interviews. Talking into the ether is a lot scarier than talking to another human, but for now, the ether is all I’ve got.

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I’m going to start offering content that is only for paid subscribers. This will be a slow trickle at first. I want to continue building a subscriber base, and I want the experience here to continue to be mostly free. But more of you than I thought were generous enough to sign up, right off the bat, for paid subscriptions, and it’s only right that I begin to reward that. So starting soon, some posts will be paywalled, and I’ll be trying out a longer version of the podcast for paying customers. There will still be a free version too, so no worries if you’re liking it, but you may have to start shelling out if you want to ride the full ride! 

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I’m going to start trying to diversify my online presence. I’ve been setting up a Youtube channel which, like the podcast, is going to be pretty bare-bones for a while. I’m going to start looking for ways to get active on other social media platforms (hope you like pictures of Thailand, Instagrammers!) Hey, on that score, if you read this, and you’re on one of these platforms, throw me a follow! 

Unless and until you try to do this for money, you have no idea the psychological and emotional reward that comes from learning you picked up a new follower, or a new subscriber, overnight. For real. I hope to get to the point where I’m not still watching my follower count ratchet up in 1s or 2s, but I am not at that point now!

I think that’s about it. Once things beef up, a natural next step will be looking to broaden my connections and collaborate with other content creators. Substack - and this is more good news - has a pretty awesome format for that, and when I’m ready, I mean to take full advantage.   

I’ll close with this. My day job is as an educator, and one of the most enduring lessons I’ve found in that field is this: the best way to learn something is to teach it. That’s what this is really about. It’s also worth remembering that however new I am to this, somebody’s even newer. Maybe this post will end up before a reader who’s only a week into their Substack journey instead of a month, and if you are that reader, I hope you find this either helpful, encouraging, or both.