The perfect conditions for a creative block
#Blocktober continues
Welcome to the 101st issue of Subtle Maneuvers and part two of #blocktober, my three-part series on creative blocks. Last time, I mentioned that much of my own writing life has been defined by blocks. This time, to try to understand what causes this “awful jackass feeling,” I thought I would briefly describe my most stuck periods. I think you’ll pick up on some themes.
2002–05
After graduating from college, I decided that I wanted to write fiction—a novel!—and my plan was to live somewhere cheap, get an undemanding day job, and write in the mornings before work. I achieved parts one and two, with a library job and a little apartment in Nashville, and over the next three years I wrote . . . nothing (and felt terrible about it).
This block was finally resolved when a family friend suggested I attend a summer program on the publishing industry, in New York; through that I managed to get a job at a small architecture magazine, where I was forced to generate a substantial amount of writing on deadline. Saved by deadlines!
2013–16
Fast forward a decade and I’ve managed to publish my first book. After several years writing magazine stories that I wasn’t always so enthusiastic about—and working on the book in my spare time—I thought this was my big moment. The book opened up doors, gave me a higher profile. And I had switched to a part-time job, so I had much more bandwidth available. Now I’d show everyone what I was really capable of!
Instead, I spent a solid three years repeating the same cycle: I’d come up with a new book idea, get really excited about it, do a bunch of research, and start trying to write a proposal—only to lose confidence in the idea, feel that I could not possibly write an entire book on this subject, avoid working on it, and finally drift toward a different idea, the idea, for sure this time . . . and do it all over again.
This miserable cycle was finally broken when my publisher asked if I’d be interested in doing an e-book mini-sequel to Daily Rituals—dear god, yes!—which eventually grew into a full-fledged sequel published in 2019.
2020–22
After the second Daily Rituals book came out, in February 2019, I was determined not to repeat what had happened after the first book. I was going to settle on an idea—it didn’t have to be perfect—write and sell a proposal, get a deadline, and get back to work.
This worked—sort of. I returned to one of the earlier ideas I had abandoned, wrote an outline and a sample chapter, sold the book, got a deadline, and buckled down to work—only to become increasingly mired in a whole new species of block: I had a plan, and I was doing the work, but somehow everything I was writing was just bad. Lifeless, dull. Worse, it felt phony, like I was impersonating a different writer.
This block was finally solved by basically abandoning my whole original plan for the book, coming up with a looser, more improvisatory approach—and getting a nine-month deadline extension from my publisher in order to execute this new version. And that’s what I’m doing right now! It’s due February 1st.
So—What are the perfect conditions for a block?
A partial list:
Wildly overambitious goals
That’s a major theme in my case history above, as well as in many of the blocks I’ve read about. Last time, for instance, I quoted the writer-editor Norman Podhoretz on a block that felt like “the most complete condition of self-hating despair this side of insanity.” Here he is describing the project that got him to that point:
I conceived of the notion at first of writing a series of long connected essays on key American (“nonfiction”) writers of each decade since the twenties which, put together, would tell nothing less than the whole story of the changing role of the American intellectual in the past forty years and his changing relation to American society.
. . . As anyone with any sense would have known, the project was far too ambitious.
Middlemarch fans may be reminded here of Edward Casaubon and his Key to All Mythologies, the ultimate overambitious book project and the centerpiece of one of the all-time great portrayals of writer’s block, by an author intimately acquainted with it herself.
Perfectionism
Is this the same thing as excessive ambition? Not quite—I think even a fairly doable project can become insurmountable with a sufficiently perfectionist mindset. I wrote about this in the advice column last July, so I won’t spend too much time on the subject here, except to acknowledge that: a.) perfectionism can be deeply hard-wired and is not such an easy thing to just “turn off”; and b.) let’s be honest, a certain amount of perfectionism is a good thing for an artist, so I think the solution is more about selective suppression rather than complete reform.
Lack of accountability
This was a big one for me after college. How does a 22-year-old go about completing a work of fiction? I’ll tell you how not to do it: Working on a project without any deadlines or outside readers, which can take any form you like, and which no one will miss if you fail to write it. I wish I could go back in time and tell this guy: Dude, take a class! Join a writer’s group! Maybe try a short story first! Instead, I never made it past page three.
Fear of scrutiny
This is sort of the opposite of a lack of accountability—too much awareness of your audience and their potential reactions, which shuts down the ability to create new work.
Last time, I mentioned that Lorraine Hansberry suffered terrible periods of writer’s block after the debut of her play A Raisin in the Sun. Is this any surprise? Raisin was an immediate sensation. It was the first play by a Black woman to be produced on Broadway, and Hansberry became the youngest playwright, and the first Black playwright, to win the New York Drama Critics’ Circle Award. (She was 29.) After the premiere she was besieged by interview requests and all sorts of invitations: “Invitations to teas, invitations to lunches, invitation to dinners, invitations to write books, to adapt mystery stories for the movies, to adapt novels for Broadway musicals,” she said in 1959. Everyone wanted to know what she was going to do next. The result? “The days pass and pass and I do nothing,” she wrote in her journal in 1961.

Running away from what you’re good at it
This is one I’m still thinking about. Basically, I suspect that I’m not alone in achieving something and then immediately discounting that achievement. If I write something and people like it, I don’t think: Oh, good, I’ll keep producing more work like this. Instead, I tend to think: Oh, that was nothing, I could do so much better, I’ll show you! Oof.
Trying to do a project that sounds good on paper but is not what you truly want to do
There’s a popular piece of advice from Toni Morrison (that I’ve quoted before) that goes: “If there’s a book you really want to read, but it hasn’t been written yet, then you must write it.”
I tried to follow that advice with my new book project. The proposal I wrote—I’m really happy with it; in fact, I personally would love to read the book that I proposed, and I think others would too. Unfortunately, I don’t think I’m actually able to write that book, not in the way that I pitched it. It’s been a tricky thing to wrestle with, to preserve the spirit of the project while swapping out its bones. But that’s a good segue to my final “condition” . . .
Believing you’re blocked when, actually, this is just what the creative process feels like!
Several of you anticipated this point in the comments section last time. The “blocks” so many have complained of—it could be that what they’re experiencing is not a block at all but just what it feels like to be a writer or an artist! Did you spend the entire day “fighting to occupy a small clear space” in your head, from which to eke out
only the smallest morsel of work? Congratulations, you just might be on the right track.Next time—Solutions
For my third and final #blocktober dispatch, on October 31, I’m going to spend some time on specific strategies for avoiding and dispelling blocks. In the meantime, please keep the comments coming! It was so valuable to read your responses last time, they gave me a lot to think about it.
And while you’re eking out your own work this week, give a listen to my #blocktober playlist on Spotify—90 minutes of (surprisingly upbeat) songs of frustration and powerlessness.
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.
This description is frighteningly similar to my pitch for my next book, a history of all the ways artists have funded their art-making from the Renaissance to the present day. 🫠
I’m thinking here of a favorite Virginia Woolf line, in which she praised the Irish novelist George Moore for “eking out a delicate gift laboriously.” ♡
Oof. Thank you. I think I've worked my way through all of these perfect conditions since breakfast. The only thing that saves me is knowing that it's better to write something and fix it later. Or the only thing that saves me is knowing I need to work through the block, write anything, sit in boredom. Or the only thing that saves me is going for a walk, or knowing I need to write more, or knowing I need to sell something. Annoying how just like the process for getting every story done is different, each block needs a different strategy.
So much of this resonated with me! Ironically, when I’ve felt blocked, I’ve turned to your books. I randomly pick a profile and feel motivated by the person’s struggles and productivity. Sadly, this probably isn’t a strategy you can use, Mason.