From Near Defeat to Breakthrough: The Surprising Power of 99 Rejections in My Writing Journey
Facing failure made me a better writer than grad school ever did
Five years ago, months away from claiming a shiny new graduate degree in writing, I sent out 100 pitch proposals before landing my first freelance writing job.
Pitching didn’t feel like a showcase of craft — it felt like gambling with my self-worth. Each rejection chipped away at my confidence. I started to wonder if the only thing grad school had taught me was how to be bad at writing on the internet.
Then, someone said yes.
I don’t remember the specifics of that first project, but it probably involved a lot of keyword stuffing and a questionable understanding of SEO. Those early gigs included insipid copywriting for bland landing pages and “inspired” technical articles on the benefits of VPNs — a topic I still can’t quite explain to a reasonably intelligent adult.
Looking back, those early rejections taught me more than how to better showcase my writing; they helped me learn to navigate the messy, unpredictable world of professional creativity. They forced me to confront my insecurities, develop a thicker skin, and rediscover what mattered to me as a writer.
That first “yes” was a turning point for how I viewed rejection.
Rejection Reveals What You Care About
That first freelance gig led to more. Not necessarily better, just more. I wrote endless landing pages, SEO fluff, and blog posts for companies I’d never heard of. I was writing a lot, but I wasn’t writing well — not yet.
The real breakthroughs didn’t come from acceptance. They came from rejection.
It turns out, rejection is a mirror. When I pitched something half-hearted or rushed and it got turned down? I could shrug it off. But when I poured myself into a story, one that meant something, and I heard no? It hurt. That pain revealed what I actually cared about. The kind of writing I wanted to fight for. The stories I wanted to share, even if nobody cared to publish them (yet).
