Welcome to the latest edition of Subtle Maneuvers, my fortnightly newsletter on wriggling through a creative life. It’s been one year since I turned on paid subscriptions for this newsletter, and I thought I’d use the occasion to ask a question that’s been nagging at me, namely: Why is it so hard to ask for money for my work??
Specifically, why is it so hard to ask readers—all of you—to pay for my writing? Because I do find it difficult in a sort of complicated way. I feel bad for asking you to chip in, and then I feel bad for feeling bad. What a mess! Here are two theories for why this may be.
But, first, for all of you who have opted to support the newsletter: Thank you so much! It means a ton, and I’ve been thinking about a potential new subscriber perk for you—more on that below.
Explanation #1: Too many brains
Writing, for me, is already a high-stakes negotiation between two parts of my brain/personality: the critical “editor” brain, which is continually telling me that what I’m writing is not smart enough, that I don’t understand my subject well enough, that I haven’t found the right insights, that I need to dig deeper; and the optimistic “creator” brain, which is saying, in reply: Actually, um, maybe this is good, maybe I’m onto something, maybe this is worth sharing.
Asking for money introduces a third brain into the mix: the promoter! This is the excitable hustler-schemer within me, and though it can be fun to indulge this side of my personality, he has a tendency to: a.) scare away the creator side; and b.) bring on the full judgmental wrath of the editor side, which loathes his self-promotional schtick.
I know through long experience that part of producing new work is selectively suppressing the critical editor voice, especially in the earliest stages. But I also know that the editor voice is often right, and that I shouldn’t shut him down completely. When it comes to the promoter voice, hmm, I’m not sure—should he be in the room at all?
I remember once reading about the old days of the New Yorker, when the editorial and advertising departments occupied separate floors of the same building, and the magazine’s longtime, normally mild-mannered editor, William Shawn, would become furious if anyone from advertising even set foot on the editorial floor (or vice versa).
Now we’re all being asked to occupy all the floors at once. I think that’s part of what makes this complicated.

Explanation #2: Gifts vs. commodities
Another possible explanation comes from Lewis Hyde’s classic book The Gift, first published in 1983. The central premise of the book is that in order for something to rise to the quality of art it must be made in the spirit of a gift—that is, made to be given away, without thought of remuneration or reward. Hyde writes in the preface:
[I]f I am right to say that where there is no gift there is no art, then it may be possible to destroy a work of art by converting it into a pure commodity. . . . I do not maintain that art cannot be bought and sold; I do maintain that the gift portion of the work places a constraint upon our merchandising.
For me, this helps to explain why writers and artists generally have no trouble asking intermediaries for money. Plenty of us are canny and hard-nosed negotiators (or shameless beggars) when it comes to extracting funds from our agents, publishers, gallerists, dealers, or other middlemen between our work and the marketplace. But embedding the appeal for money inside the work itself is a much trickier proposition. If the work is supposed to exist outside the marketplace and even in opposition to the marketplace, then can it also be explicitly framed as a commodity?
Or maybe I’m—as usual—overthinking things. As always, I’m curious to read your thoughts in the comments section.
TORTURED ARTIST BOOK CLUB™?
As long as we’re on the subject of paid subscriptions, I was wondering: Would people be interested in a virtual book club as a new perk for supporting the newsletter? I was thinking we could read a new book every other month, with a Zoom discussion at the end, and some online chat threads along the way, either via email, on Substack Chat, or on the subscriber-only Discord. The overarching theme could be the creative process and its discontents—a Tortured Artist Book Club™?
I like the sound of that. I don’t think I could launch this until after I finish the second draft of my book (I’m going as fast as I can, which is to say: extremely slowly!) but I can start to lay the groundwork if people are interested. Let me know! I will consider all new paid subscriptions generated by the following button as votes of enthusiasm.
ONE LAST THING
As I was putting the final touches on this issue, I remembered an interview with the rapper Talib Kweli that I heard on the radio last spring. Kweli was talking about the latest Black Star album, which he and collaborator Yasiin Bey (formerly known as Mos Def) released on the subscription podcast platform Luminary. In the interview, the host suggests that this was a risky move, “putting your music behind a paywall like that.” (The only legal way to listen to the album is to purchase a Luminary subscription for $4.99/month or $34.99/year.) Kweli’s reply is pretty great:
A risk for who? . . . That means the artists get paid. If you are truly a fan of Black Star, then you will respect the fact that what made sense for us, business-wise, was for us to put it on Luminary and get paid regardless of what happens in the music business. . . . You know, people come and say, “Hey, what about what I want? I want the vinyl. I want it on Spotify. I want...” What you want does not matter. Know what I'm sayin’? What Black Star wants matters.
Ha! I wouldn’t quite so far as to say that what you, my readers, want does not matter—but I admire Black Star for privileging their financial needs over the audience’s preferences. Going forward, maybe we’re going to need more of that kind of obstreperousness on the part of creators?
Thanks for reading! This newsletter comes out every other Monday—and you can help keep it coming by becoming a paid subscriber, buying one of my Daily Rituals books, forwarding the newsletter to a friend, or even just clicking the “like” button below
I have been thinking about this a lot! As I come out of period of book promotion where I have 'gifted' so much time to share the book, which also means I haven't been earning much. I'm trying to convince myself that this is all part of a long game - but it's hard at 2am when I can't sleep and the bank balance is front of mind.
I agree with your two points but also want to add a third that as a society we have devalued creativity so it is often free - to ask for money isn't part of the modern creative economy. I have just finished reading Chokepoint Capitalism by Cory Doctorow & Rebecca Giblin and it blew my mind how payment for creative works has been eroded over time, accelerated by technology. While most things have become cheaper & easier to produce over time, painting, writing, composing still takes time and effort - which is no longer rewarded in the free to stream age.
In short, it's not you, it's the system!
Great read, thanks Mason.
I honestly have no idea. I haven't been in that position--I'm still new to Substack and writing is a hobby that I'm passionate about (would love for it to become serious, but I'm not holding my breath and I'm still grateful for my day job, as much as it doesn't tick the creativity juices that writing does). But I can begin to understand how it might feel, even just the notion of turning on paid subs for a small fee.
However, from the reader perspective, this platform really does feel like it fully supports and rewards the notion of "I love what this author is doing. I'm going to gladly support them."
The only downside is once you have subbed to several, if then you discover a new Substack/writer you find you enjoy, the issue of paying another sub becomes more and more expensive. I'm not sure what the solution is there. I'd gladly sub to you (I'm sorry I don't yet), but I set myself an initial budget when I joined the platform earlier this year.