Escaping the Rip Van Winkle Club

On Mistaking Preparation for Progress

Rip Van Winkle stirs from his 20-year sleep. Illustration by Frank T. Merrill for the 1887 edition of Washington Irving’s “Rip Van Winkle.”

This is the only piece of unsolicited writing advice I’ll ever offer: Don’t join the Rip Van Winkle Club.

Our current roster includes all the wannabe authors like me who you’ve never heard of—and most of us don’t even realize we’re card-carrying members. Once you join, it’s difficult to leave.

I stumbled across my membership only two weeks ago while auditing my 2025 writing progress. With each goal I didn’t achieve or idea I’d left rotting on the shelf, I unlocked a receipt for club membership dues.

The final bill arrived in the form of my annual word count: just over 16,000 across four short stories, one flash fiction, four poems, four humorous shorts, an unfinished short story, and a half-drafted personal essay.

It’s a dismal showing for someone who once wrote more than 104,000 annually as a journalist.

So… what the hell was I doing?

The answer: Daydreaming next to Rip Van Winkle, rocking in place, and confusing procrastination for progress.

The Spiral

Last January, an idea for a satirical short story burrowed into my mind, and I spent weeks carving out a 3,500-word first draft. It was the first piece of original fiction I had written in eight years.

Naturally, I decided I was ready to become an author.

Conventional wisdom persuaded me to start with short stories, essays, and flash fiction before braving a novel. Having never completed one—not even on FanFiction.net—I resolved to fuel up on quick wins. But what would I do with these stories once finished? A quick Google search turned up an answer: submit them to literary magazines.

If only I’d stopped my search there.

Sidelining my writing, I began wading through an ungodly number of videos, podcasts, and articles on submitting, short fiction markets, and writer success stories. When I’d chewed through the available content on submitting short stories, I graduated to novel publishing, author success stories, and book marketing.

I justified it as required reading for new or returning fiction writers; if I wanted to publish my stories, I needed to educate myself about the current literary landscape. (Despite obtaining an honorary PhD on Submitting, I have yet to report a single publishing credit.)

By June, I had dug myself into a trench: According to my Research, I needed a platform and a niche and beta readers and critique partners and so many more Important Things. Overwhelmed, I tackled everything at once.

To address my platform problem, I bought a domain name and WordPress package to design my author website. Two months later, I changed my mind, canceled my package, and built a beautiful site instead on Wix. Then I figured, whoops, I needed a pen name. Tear down, rinse, and repeat.

Rock bottom hit last month when I created a writer Instagram account to drive traffic to my nonexistent website, gather emails for my hypothetical newsletter, and attract readers to my unborn body of work.

I’d overlooked the most important thing: I had no book—or even a single published short story.

Imagine the stories I could have written in all the hours I’d spent spinning my wheels. The thought makes me want to drown my sorrows in several bottles of Port.

My dad would say my head was stuck in rectal defilade. I’ll use a more technical term: a bad case of analysis paralysis. One that took me a year to diagnose despite all the content I’d consumed about such writer hang-ups.

I tell myself that I’m a fantastic writer and don’t suffer from imposter syndrome. I wrote professionally for two years and earned eight awards. But in truth I was—and remain—terrified to embark on a career that might shatter my self-image and the authorial dreams I’d built up in my head for decades. What if my books don’t sell? What if I can’t sustain a yearly output? Hell, what if I can’t even finish a single novel?

Instead of writing, I window-shopped the publishing business, comparing self- and traditional publishing as if inspecting furniture for a house I’d yet to buy. Preparation, I thought, would grease my path to success. It felt like easy progress. Like gathering sources, quotes, and background for next week’s story.

In reality, I just gussied up procrastination and called it by another name until I believed it. As long as I researched, I wasn’t yet ready to write. If I didn’t write, I couldn’t publish and submit my self-image and dreams for judgment.

Thus, 104,000 words per year shrank to 16,000.

Sure, I wrote and submitted my work to literary magazines last year, yet I can’t help but look back and shake my fist at the black hole that sucked away my momentum—and the version of me who let it.

Before drowning in analysis paralysis, I had cranked out 5,000 words across two short stories. Once I began my research, however, I’d burp up a 50-word limerick on my lunch break and hail it as that month’s output before pulling up another video on some self-published author’s earnings.

My journalistic output proves that I can produce under the right circumstances. Accountability to my newspaper, readers, and bank account forced me to churn out weekly stories. Without it, I drifted into the Rip Van Winkle Club.

I need to escape. So, I’m going to reproduce the right circumstances: a deadline.

The Escape Plan

Consider this my resignation from the Rip Van Winkle Club, with The Jaded Fool as my signature. I pray I’m not signing in invisible ink.

I launched The Jaded Fool earlier this month without the analysis paralysis over niche, brand, and email marketing tools that crippled my previous three newsletter attempts. Its job: chain me to a deadline and bully me into coughing up at least two stories, poems, or essays a month.

To ease myself in, I’m going to cheat. Last year’s output will function as this year’s pipeline; I’ve got at least nine pieces, other than this essay, to publish through May while crafting new stories. Most of them are funny, though one may wreck you. I wish you a good wrecking, in fact. Two magazines are still considering it, but I’m not holding my breath.

I don’t know if I’ll be able to find an audience or update consistently beyond my pipeline—especially if no one’s watching. I might miss a month. I might fail. But I’m forging ahead anyway. The bigger failure would be never starting at all.

The Rip Van Winkle Club won’t ever refund my lost time—but neither will it claim any more. I’m through with daydreaming about becoming an author. It’s time to slap myself awake and get writing.