1. Worked for free.
What a chump, right? Let me explain. When I graduated college in 1999 and moved to L.A. to work in entertainment, I applied for dozens of entry-level jobs. All of them required experience, and the only way to get experience was to intern. It's an inherently unfair system that stacks the deck against people who can't afford to work for free, so I felt a bit guilty about going that route, but I was lucky to have parents who were willing and able to support me for three months while I worked at a talent management company at precisely $0/per day. The internship led to a job in TV production, and the TV production job led to the job I hold today.
Cut to 2009. I was researching lit agents online and sending off queries when lo and behold, I noticed one of my bosses from the internship
ten years before was affiliated with an agency I really hoped to impress. The boss and I had kept in touch, so I asked if I could use her as a referral, and I included her name in the email subject line of my query. The agency I hoped to impress was Nelson Lit, and I got a partial request the next day. If my writing sample had sucked, none of that would've mattered but I do think name-dropping a trusted source helped speed up the process.
2. Wrote in the wrong genre.
I spent four months turning a college-set screenplay into what I thought might be a YA novel. Halfway through adapting it, I heard about a panel at a local bookstore featuring a Q&A session with established YA authors. I decided to go, so I could ask them about my story and have experts confirm how brilliant it was. Ha! Every single writer there told me in no uncertain terms you can't write about college in YA books.
Shocked, I scrapped the "brilliant" project and began writing something entirely different (the book I would eventually sell, with my wonderful agent at the helm of course). At the panel, I met people in the audience who would go on to become friends and critique partners of mine. If I hadn't done the wrong thing (and naively sought to have it validated), I wouldn't have met people who ended up being integral to my journey, nor would I have started a new project.
3. Took a day-job as a writer.
I recently read an article in a writing magazine that named the best jobs for writers. Teaching was listed first. Also recommended were office jobs and temp work, something you can leave behind at the end of the day. The only job they specifically advised against was the one I have: reading and writing. I read screenplays and create character descriptions for a living, and then I go home and read and write novels.
The article stipulated it was a bad idea because I'd have nothing to draw from and no clear cut break from my two jobs. I'll admit I get a bit tired of typing, but I love reading regardless of the format and I love my day job, and if I had to spend 8 hours a day (plus the commute) doing something I didn't enjoy, it would be very difficult to muster up the ability to create.
So there you have it. Three bad things I did that ended up leading (eventually...) to publication. Following the "rules" is overrated.
Or maybe I'm just a slow learner.
In your writing journey, have you made mistakes that later turned out to be blessings?