Ladies & Gents:
Special edition of the newsletter today! I am reprinting a piece I originally wrote for the Freelance Success newsletter. I have been a member of what we call FLX for my entire freelancing career, and I never would have gotten to where I am today without it. If you are new to freelancing, or struggling, it can quite possibly be the best investment you can make in your career.
They didn't pay me to say that – though I do get paid to write for them, of course. I just love it. I really found and continue to find a home there.
Enjoy!
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Lessons Learned from 20 Years of Writing Essays
By Jen A. Miller
In 1998, as a brand-spanking-new freshman at the University of Tampa, I published my first personal essay.
It was, well, dreadful — a piece called “Coping With College,” in our weekly college newspaper, about how desperately homesick I was to be so far away from home, alone, for the first time in my life.
“Am I the only one who feels like this?” I wrote in the closing paragraph. A subsequent issue featured an anonymous letter to the editor suggesting that I be pushed out of a plane.
Twenty years later, anonymous trolls are still suggesting me bodily harm. But in essays published in The New York Times, Washington Post, Self, USA Today, Runner’s World, Guardian, and a dozen outlets in between, I’m still asking, “Am I the only one who feels like this?” (in a more subtle way). Here’s what I’ve learned:
Extraordinary details make your experience different enough to write about it, but still universal. In one of my first New York Times essays, I wrote about coming back to running after my first big injury. A cow was involved. I didn’t want to lead with that, but my editor said, “Of course you lead with that.” Starting to run again is a fairly common experience, but the cow made it my own story, and a way for me to write about it in a way that was engaging, amusing and still in a way people would connect to. When I wrote about losing weight, I tied it to training for a 1-mile road race. When I wrote about how much I hate running in the summer, I wrote that my shoes “squished like spent diapers” from sweat. When I wrote about hosting my first Thanksgiving, I wrote about my mom’s penguin salt and pepper shakers. And when I wrote about my dog dying, I included exactly what happened, like how I “gripped both a counter and a vet tech to keep from collapsing,” because it couldn’t just be about any dog dying — it had to be about my dog dying in order to make an impact on other people. (That essay went viral and was one of the most shared New York Times pieces on social media in 2017.)
Sometimes you need time to make sense of your experience. Yes, sometimes writing in the thick of your emotions can make for a powerful essay (I wrote about my dog dying less than two months after it happened), but more often, I need space from the thing to process it in order to write about it. I spent years trying to write about a relationship I had with an alcoholic, but it didn’t work until nearly a decade later (and then, it was in a book, but excerpted as an essay). I was too wrapped up in everything I felt about what happened to write about it with clear, open eyes. Time helped.
Essays should be researched as much as articles are. A personal essay recently whipped through the running world, and as much other people gushed about it, I couldn’t get into it because the writer hadn’t bothered to find out why the policy she hated had been enacted. Of course, writing about a cow or losing weight or my dog dying is intensely personal, but when I wrote about the gentrification of my childhood vacation spot, or Why Miss America wasn’t going to save Atlantic City, or having eczema, I gave those assignments the same treatment as anything else I’d write. Your essays will be more effective with that kind of legwork.
Get editors you trust. When a very large newsstand magazine asked me to write an essay about running that would be published the same month my running memoir came out, I jumped at the chance. But the process ended up being a near disaster (involving almost a year to get paid). The editor didn’t just chop up my words — she put them in a blender and then mixed in things that were just plain wrong, including that I started running while in graduate school. I knew one of the runners photographed for the piece on the next page, and she said, “It doesn’t even look like me.” My response: “Yeah, that doesn’t sound like me either.” While I do still cold-pitch finished essays, I try to work with editors whom I trust, or at least within an organization I already know. When I wanted to write about my dog dying, I knew I’d want to try The New York Times first because I’d trusted them with very personal pieces before, even if it wound up with an editor in a section I’d never written for before (Metro).
Don’t give up all rights. I’m not going to sell away my life story for $350 to an outlet that’s going to buy all rights to my story, including all future book, movie, and TV deals. There are rotten contracts going around. Don’t sign them.
Keep learning. I read other memoirs, and other personal essays, not only to see what the market is buying but also because I’m still learning. I have also referred to Theo Pauline Nestor’s Writing Is My Drink more than a few times since it was published in 2013, because it keeps giving me new ideas, even if it’s just some of the writing prompts.
The trolls will find you, and they don’t just need to rely on a cozy relationship with a college newspaper’s editor who lets them write anonymous letters to the editor. They email me and ask me who I gave sexual favors to in exchange for a spot in the paper. They scream at me on Twitter that I really just need a good man, and, well, I don’t read comments anywhere I write for, but I imagine they’re yelling in there, too.
If you open up your life to other people, you have to expect that they’ll want to comment on it. They will definitely overstep boundaries. You have to be prepared for nasty responses, even if you don’t do anything but glance at and ignore them like I usually do.

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