When Writing Stops Feeling Fun
Imposter syndrome, small rejections, and the quiet ways joy slips away
I have a sale going on now where you can get a permanent 75% discount for annual subscriptions. Sign up here: Annual Subscription Sale 75% off!
Lately it seems I am seeing a recurring theme among writers I know who aren’t writing like they used to.
They still think of themselves as writers. They still talk about projects, ideas, scenes that won’t leave them alone. But the act itself has stalled. The document stays closed. And it isn’t because they ran out of stories.
It’s because sitting down has started to feel like a waste of time.
There is a lot of talk about imposter syndrome, usually as if it’s a personal flaw. A lack of confidence. Something you’re supposed to power through. But what I’m seeing lately feels quieter than that. Less dramatic. It’s not fear of the spotlight. They have just lost confidence in themselves as writers.
A contest result. A form rejection. A comment meant to be helpful. A comparison you didn’t ask for. None of these are catastrophic on their own. Most of them are subjective, even arbitrary. But they land on a nervous system that’s already jittery.
Recently, I sent the opening of a rewrite to a “best beginnings” contest. I was actually really proud of that opening. I thought it was some of my best work. It didn’t make it past the first round.
That should have been the end of the story.
But that same day I was rewriting the first page again.
Dammit.
That’s how it happens.
No one told me the opening was bad. No one said it failed. It just didn’t advance. But my brain translated that into something harsher. Maybe I don’t actually know what a strong beginning is anymore. Maybe I suck at writing and wasting my time.
And once that thought gets in, everything is suddenly up for renegotiation.
This is where imposter syndrome and loss of joy start feeding each other. Imposter syndrome attacks the start. It questions whether you should to be here at all. Loss of joy attacks the reward. It drains the pleasure that used to make the risk worth it.
Put those together and you don’t get dramatic writer’s block. You get paralysis that looks responsible. You get endless refinement. You get page one rewritten twenty-five times while the rest of the book waits patiently, untouched.
Rewriting the beginning is the most respectable way to avoid finishing. Can I put an LOL here? It sure feels like it deserves one.
What makes this especially tricky is that the better you get, the more vulnerable you become. You know the rules now. You’ve heard the advice. You understand what openings are “supposed” to do. Every outside signal starts to feel diagnostic, even when it isn’t.
Contests don’t read like readers. They read fast. They read comparatively. They reward efficiency and clarity under pressure. That doesn’t make them wrong. But it does make them incomplete.
Somewhere along the way, writing stopped feeling loose. It started to feel like it needed to justify itself. Like every hour had to earn its keep. And joy doesn’t survive long under those conditions.
I don’t have a cure for this. I still rewrite too much. But I’m trying to remember that trust is part of the craft. Maybe stop taking input for now. Finish. Quit worrying about whether or not you will be able to sell this story.
I need to take my own advice.
I find way too many things to distract myself, like going down that YouTube rabbit hole, reading email, or playing a video game instead of closing all that stuff and focusing on the writing.
Joy doesn’t come back when you’re validated. It comes back when the door closes and the room gets quiet and you reach for that ever-elusive flow state. When you write as if no one is scoring you. When you ignore the “no” and write for the sake of it.
I’m not trying to silence doubt. I’m just not letting it drive.


Great thoughts here, HH. Caring too much about what others think can at times lead to a type of stifling.
I've been amused recently that my book, which was added to Kirkus Reviews' best 100 indie books of 2025 (they review 10k+ books/year) was also rejected in the first round of the sci-fi subcategory my state's annual writing contest (something like 280 entries). The majority of readers have loved it, but I still remember the reviewer who rated it 3 out of 5 and declared that the story makes no sense, or the fellow writer who read the first page and diagnosed that the critical acclaim was misplaced and what I really needed to do was hire an editor and work on my fundamentals.
In the winter, I was approached by a well-known foreign rights agent who loved the book and wanted to sell it in France. But as an indie author, all sales come down to my (lackluster) marketing, and once she saw my sales numbers, she rescinded her offer because she's got to show to foreign publishers that I have a proven track record. No hard feelings, plus an offer to reach out again if the numbers are up, but the drama is real.
I wrote some years ago on the question of why some people quit writing, and I think we have not merely the right but the responsibility to determine if we're going to stop doing this, when, for how long, and why (https://danielrodriguesmartin.substack.com/p/why-do-people-quit-writing-dear-writer).
I am not interested in guilt-tripping other authors, and two contrasting notions can be true at the same time: That if we want inspiration, we have to go after it with a club (J. London), and also that life is not a support system for art, but art for life (S. King).
Basically, I think Anais Nin was right: "If you do not breathe through writing, if you do not cry out in writing, or sing in writing, then don't write, because our culture has no use for it."
Anyway, I feel your pain. For me, work is slow-going right now, as my SS hiatus evidences :)
I am so glad I kept your words flowing into my inbox, HH. In just about every other way I had completely disavowed all meaningful reading, as an extension of a distaste for writing anything else. If I can't enjoy my own words, why should I care about anyone else's, right? It was the very things you are talking about, in my case manifested as a grudge against all of literature. This is in contrast to a few years ago I was re-invigorated to read more seriously. So much so that I wrote a novel on the subjectivity of our interdependencies with technology. It's an allegory of free will in the guise of a subtle techno-conspiracy. Herein lies the paradox. My main characters are all saddled with a Machiavellian need to acquiesce to algorithms in order to further their best intentions. It was a compelling storyline to pursue. Sadly, upon completing and publishing my work, I found that I too was expected to be a programmatic pied piper, consuming and contributing to the rotting hay of social media such that I might somehow lure the shortform attentions of readers back to something more meaningful. Agents and publishers demand social media presence, yet consumers can't escape social media to crack open a book. And as an author of something that decries this whole sordid cycle, it's an impossible situation. It's the ultimate loathe-hate relationship where my only strategy has been to crawl back into the shadows of impartial literary influence, my disdain for any promoted publication weighing heavily on my drooping posture, such that even holding a book causes me to fall flat on my face. I look at the bookshelf as the thing that manifests the end of reading, and the bookshop as the herald of the last word. Thank you and good day to you sir.