How I Wrote 1,000 Articles During My Four Years at Wesleyan, by Lily Herman ’16

A journey of 1,000 articles and a career in writing began with pieces that Herman recalls as “atrociously bad.” But perspective was her key to success. (Photo by Meagan Hooper) 

During my four years as a Wesleyan student, I published over 1,000 pieces of writing on the internet.
Doing anything 1,000 times takes an impressive amount of effort, I get that. But beyond the number, it’s miraculous that I ended up writing for a living in the first place.

For one thing, no one in my family comes from a writing or media background, so I had no roadmap. For another thing, I was never considered a person of eloquent prose growing up; my writing career surprises anyone from my past. And lastly, my sophomore English teacher told me in high school that I was a terrible writer—and yes, she did, in fact, use the word “terrible.”

To fast forward a decade, I’ve come a long way from that “terrible writer” comment. I’m now a contributing editor at Refinery29 providing weekly political commentary, and I just wrote the cover feature for Teen Vogue’s digital May issue on young people running for office.

Given this unexpected trajectory, I often get the same line of questioning: How did I go from believing I was an awful writer to publishing so much in school and eventually “making it” in the industry? And how did I make it when so many talented folks who got so much early praise for their writing didn’t?

While there are plenty of writing hacks and productivity tricks to help with learning the craft, I can boil down my success to six words: Stop treating your work as precious. Or, as I jokingly say, drop the ego and come to terms with the fact that your work will be really bad for a long time. If you keep working towards making your work less bad, it’ll eventually turn decent, and hopefully good.

So, what do I mean by “precious”? Here are three definitions courtesy of Merriam-Webster:
Of great value or high price
• Highly esteemed or cherished
• Excessively refined

When I arrived at Wesleyan at age 18 with zero writing experience, my work definitely wasn’t “precious.” I didn’t see it as valuable, cherished, or refined in any way.

This turned out to be a good thing, because I can say without a doubt that my writing was objectively awful when I first started out at Wesleyan.

I went through my inbox and found the honest-to-God feedback I got from an editor on the first article I ever wrote for a real website when I was 18: “This needs a ton of work. I felt like you completely made most of this up, and as a result it mostly missed the mark. I stopped editing after the first section because it was so off base.”

Are you cringing? Because well over half a decade later, I still am.

I remember sitting in the Second Stage tech booth during a rehearsal and sobbing to my mom on the phone for two hours after getting this editor’s comments. After all, this woman had just confirmed what I’d heard all along: My writing wasn’t great. In fact, it was pretty damn bad.

Looking back on the experience, I understand why so many people who are labeled as “innately gifted” writers give up: Having your ego smashed is difficult. It sucks, and there’s no way around that. But I now realize I had an advantage over those people: I didn’t think that much of my writing to begin with, and I was able to adjust my expectations quickly. For my next piece, I just wanted to make it better than the first.

And guess what? The second article was still really bad; that editor ripped it to shreds. But at least this time around, she was able to get through the entire piece instead of stopping after three paragraphs. Success!

These small gains added up over the course of four years. My first 200 pieces were atrociously bad, while the next 500 articles I wrote were mediocre at best. It wasn’t until I got to the final 300 pieces of my college career that things started to look good. The final 50 articles I wrote in school were actually something to be proud of.

If I could give one piece of advice to anyone, it’s that you can overcome a lot in this industry—the creative blocks, bad feedback, rejection, and more—when you let go of the feeling that your self-worth is tied to any one “thing” you create. It gets a lot easier to take an honest look at what you’re making and improve when you stop pretending a product isn’t meant to be broken.

When it comes to the work you hold most dear, take a hammer to it, especially when it’s painful. Eventually, you’ll get to a point where you can, in fact, consider it worthy of being called refined, valuable, and precious.