Fuck You, Pay Me #15: Why You Should Have a Newsletter
This is part 15 of “Fuck You, Pay Me,” an ongoing series of posts on writing, editing, and publishing. Read the rest of the series: Part 1: How To Become a Writer in 12 Easy Steps, Part 2: The Pros and Cons of Traditional vs. Indie Publishing, Part 3: Scenes From My Life Writing a Porn Novel, Part 4: Why I Hate Memoirs (but Wrote One Anyway), Part 5: 19 Ways to Make Money as a Writer, Part 6: Letters From Johns Revisited, Part 7: Some of My Favorite Things I’ve Ever Written (Journalism Edition), Part 8: Some of My Favorite Things I’ve Ever Written (Fiction Edition), Part 9: How to Promote Your Book Without Going Crazy, Part 10: The Pornification of My Life, Part 11: How to Be More Creative, Part 12: The Fine Art of Applying to Writing Residencies, Part 13: How to Be a Consultant, Part 14: Cranking the Flywheel, Part 15: Why You Should Have a Newsletter, Part 16: An Excerpt From My Memoir.
I’ve been writing on the internet for a very long time. Since the ‘90s. First, I co-created and co-edited an online literary magazine. Then I had a popular blog. Along the way, I wrote for various publications, digital and print. Today I have my own website with its own blog, and I have various social media channels. Throughout it all, there have been many trends for sharing content online. At one point, you had to have a blog. Then there was that whole pivot to video thing. Somewhere on the route, it was decided that if you weren’t an influencer with clout, you didn’t count. These days, newsletters are the current supposed must-have, and there’s a competitive frenzy over who has the most subscribers, and whether they’re paying subscribers or not, and what said newsletter’s open rate for its emails, and wait how are you monetizing your newsletter in other ways, by the way? In my opinion, newsletters are just one more fad that will boom and bust, but that doesn’t mean you shouldn’t have one. In this edition of Fuck You, Pay Me, I share 10 reasons why you should have a newsletter.
It’s an experiment. Should you have a newsletter? Should you not have a newsletter? If you have one, will anyone read it? If you do it, should you monetize it? If you start it, what should you write about? Who cares? Who knows? Everything is an experiment in the beginning, and things only become successful (or not) in hindsight. My first newsletter was called Valleywood, but when that didn’t feel like a fit for me, I started a new one called The Reverse Cowgirl. The latter feels like a better fit. It took some experimenting to figure that out. But the experimenting, the not-knowing, was required to reach the solution.
It’s creative. Before I landed on my current newsletter format, which is kind of written like a personal and professional diary, I tried writing my newsletter in various formats. A listicle. A bunch of photos. An essay. More personal and less professional. More professional and less personal. I even used AI to write one (a fact that I disclosed). More recently, I landed on a format I seem to like the best, which is both personal and professional, which incorporates, among other things, a mini-listicle and what I’m doing writing-wise, and which combines a set of different things that appeal to me. This means I have a basic structure that makes the newsletter easier to do and more consistent, but it also means that I can do a bunch of different things within that format, which basically sums up my entire career.
It’s multimedia. If you’re posting on social media, you’re probably posting content in one or two mediums. On X, that may be text. On Instagram, that may be an image. On TikTok, that may be video. On Substack, which is the newsletter platform I use, you can do all of those things: write, post images, share video. You can embed social media posts. You can use Substack’s stock photos or its AI image generator. You can share live video. This multimedia approach appeals to me, someone who writes and takes photos and spends too much time on social media. I want to do all the things, not just the one thing. This multimedia approach may also be more appealing to your subscribers, some of whom may be more text-oriented and some of whom may be more visually-oriented.
It’s free. On Substack, as long as your newsletter is free to subscribers, there are no costs. You don’t need any special equipment, it’s easy to set up and get started, and there’s no charge for you to send your newsletter to your subscribers. If you enable paid subscriptions—start charging your subscribers to read some or all of your newsletter content—there are fees, which are outlined here. But otherwise, Substack is a free tool, one that you can use to experiment with, create multimedia content with, and share with, and that makes it an attractive option. Of course, Substack isn’t the only newsletter platform, and there are others, which have their own pricing.
It has no editor. As someone who has been writing forever, I’ve had a lot of editors over the years. Some are great and have improved my writing. Some are so-so and don’t have much of an impact. Some are terrible and shouldn’t be allowed to edit their own shopping lists. With my newsletter, I have no editor. No gatekeeper who gets to green flag or red flag what I want to write about. No person meddling with my prose. No point-of-view I have to take into consideration when trying to decide if I should or shouldn’t write about something of interest to me. If you’re a weak or inexperienced writer, not having an editor may be a downside, but for me, it’s all good when the editor is not only not in my head but doesn’t exist.
It’s uncensored-ish. This isn’t exactly true and not without complications, but I would argue that Substack takes a mostly hands-off approach to content moderation, within reason. (You can find Substack’s Terms of Use here and Content Guidelines here.) This aspect of Substack is not without complications, but for someone like me, whose newsletter’s subject matter is sex, it makes a difference that I not be creating on a platform that has a hair-trigger approach to content moderation, like, say, Instagram. Substack allows “depictions of nudity for artistic, journalistic, or related purposes, as well as erotic literature, however, we have a strict no nudity policy for profile images.” And that’s good enough for me.
It’s personal. There’s something intimate about email, isn’t there? Set aside the spam, the generic newsletters from Big Companies, the annoying notes from your boss wanting to know when that thing you’re supposed to do will be done. When the email is from the right person or strikes the right tone, an email can generate a kind of intimacy that random shit posted across the internet can’t. It seems personal. It seems like it’s for you. It allows the subscriber to feel like they have an intimate relationship with the newsletter writer. And that’s valuable. Because that sense of intimacy, even if it’s an illusion, even if, as in the case of pornography, it’s a known illusion, is what will keep subscribers subscribed.
It’s not content calendar driven. Those who have toiled in the content mines of social media copywriting, as I have, know that content calendars are ravenous beasts. Your words and images become content. Your posts become empty spaces on a digital calendar that must be filled. You start googling the holidays for the month you’re working on in hopes that will inspire you to create something really high performing in honor of National Hot Dog Day. Unless you want it to, newsletters don’t have any of that. And for free newsletters, you can feel free to write whatever you want to write whenever you want to write it. Deadlines? Fuhgeddaboudit. Maybe you like deadlines—in which case, go for it. Maybe you want to have a content calendar. By all means, don’t let me stop you. But the strategic plan for your newsletter is for you to devise and execute as you see fit.
It’s a revenue generator. Your newsletter may make you money, or it may not. It may generate revenue for you directly, through, say, paid subscriptions. Or it may generate revenue for you indirectly, by, for example, getting your name and work in front of someone who likes it, who reaches out to you, and who pays you to do something for them because they saw you do something similar in your newsletter. Or by selling some other product you’re selling, like, say, a book. But one thing is for sure: You will never make money from a newsletter that you never create, that you never publish, that you never write. The only way to find out if your newsletter is a revenue generator is by starting to write it with no guarantee that it will deliver a return on your time and effort investment.
It’s fun. For those who are tired of hustle culture and monetizable stoicism and the self as brand, a newsletter can be a place to return to one’s original state: a state of play. When you can do whatever you want, you start to do interesting things. When you realize there is no fence around the field, you start running beyond the old perimeter. When you allow yourself to not be right, to not care, to forget what you’re doing and just start doing, you begin to change what you’re doing, how you’re doing, and who you are. And that’s worth it, not matter who you are or what you do, how much you have or how much you don’t, whether anyone reads a word of it or if it’s just a thing for the only person that matters: you.
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