Two truths and a hat tip
Lessons after editing 70 essays in 5 weeks
I had three hours to publish my essay on Substack. But the draft felt so dry. There wasn’t a drop of personality in sight. It had twelve references and three subsections meshed into one long Google doc with no sense of story.
The more I meddled with it, the messier it became. I shuffled the paragraphs around, mashing the keyboard with mangled frustrations. The word count ballooned. I took a water break and reread my essay again for the umpteenth time that night.
I hated all of it.
It’s time to leave my draft alone for now, I thought, and switched browser tabs. Besides, I had some work to do. On my queue for a writing course I’m helping out with, there are four student essays to give feedback to tonight. My own essay can wait.
I skimmed through a student essay, marking bits that stood out to me or could use improvement. I referred to a pinned Notion page filled with feedback I gave most often. As I started to formulate some comments, I realized that I could apply these tips to my own piece.
These are two tips that can add extra oomph into most essays:
1. Insert yourself into the story
Writing about a journalist I looked up to was such a daunting task. I unconsciously distanced myself from her by not putting both of us in the same essay. I wrote all about her and nothing about me. But that’s the opposite of what my pieces are. They can’t be personal essays if I’m not in them.
Before: The economics of journalism - of expecting ad revenue to cover salaries of reporters, fact-checkers, editors, and the broader newsroom - doesn’t work. Kara Swisher, an American business and tech journalist whom I deeply admire, said this numerous times on her podcasts Pivot and On with Kara Swisher.
After: At the intersection of journalism and the news industry, business and tech reporter Kara Swisher said: “I really hate that journalists don’t understand business. If you don’t understand the economics of what’s happening, you’re fucked.” So I tried, at two different outlets, to understand the business model for news. [I then elaborated on my experiences there].
In my rewrite, I inserted myself back in as a mirror to Kara Swisher’s words. Since she said journalists should understand economics, I followed up that sentence with how I attempted to understand the revenue streams for each place that I worked at.
According to Substack’s statistics, the most popular pieces I’ve written have a strong personal angle. In the current order, the essays that resonated most with readers are:
Maybe men aren’t trash: on rebuilding a relationship with my distant brother
The makings of a queer corporate sellout: how my queer identity pushed me to work in a corporate environment
The break before the breakthrough: how uncovering trauma in therapy is deeply uncomfortable and why I’m pushing through it
2. Show vs tell
Writing about my thoughts is easy. I keep a journal and I write about my feelings every day. The harder feat is to show what actually happened and let readers come to their own conclusions.
Before: I admire strongly that Kara did not wait for the industry rules to change before she could push for it herself.
After: Kara co-created a tech blog and conference unit called AllThingsD during her time at the Wall Street Journal. It was spun off to Recode and eventually purchased by Vox in an all-stock deal.
A straightforward way to show and not tell is to provide proof after a statement. I tend to oscillate between one example (above) or three (below).
Before: Kara hosts podcasts in a way where she doesn’t hide her biases but still is able to ask questions that could elicit new answers from frequently interviewed guests.
After: I saw Kara crank the dial up on her opinions in a way that still leaves her journalism integrity intact. Some of Kara’s recent and iconic podcast interviews: a conversation with Parler’s then-CEO a day after January 6 (his responses to her questions subsequently got him fired); an on-stage conversation with Uber CEO Dara Khosrowshahi (she grilled him about treatment of drivers and couriers, safety policies, and increasing prices); and a reverse-interview where she spent an episode talking about her relationship and thoughts on Elon Musk.
A hat tip: Encouragement
The most important component of providing feedback is that I bookend my comments with encouragement and compliments.
As I go through essays, I leave emojis on sentences or phrases I find funny, surprising, and insightful. I then drop a comment on which parts I felt the writer is strongest at, such as knowledge about a topic or the ability to create a clear structure.
Feedback on prose is useful for that particular essay, but encouragement stays with the writer. I still remember when
told me, “I can see you’re a talented writer” just six months ago in this exact same course. A positive nudge makes the difference on whether or not the writer will hit publish.Encouragement fuels the momentum of writing. If someone is satisfied enough with the essay they just published, they will feel confident enough to write the next draft. The draft Nic commented on was my very first and it wasn’t very good. But knowing I came off as “talented” kept me going to write the second, third, fourth.
After going through the four student essays, I took these two tips and looked back at my own. I copy-pasted a new version of my draft to the top of the page, and started weaving my own stories in them. I also expounded on Kara’s achievements. I wanted readers to revel in her as much as I did.
It also helped that Write of Passage friends left comments throughout the draft. I read each of their feedback, made a decision on whether I wanted to take it in that direction, and rewrote the concerned parts.
I read my newly revised draft, encouraged myself it was good enough, then hit ‘publish’.
Thank you to friends who help shaped this essay: , , , , , , and .
Update log:
🏃♀️ I ran 5k... twice! Once for the Gay Games and once because I just felt like it. Fall is here and I’m really feeling like spending time outside, so running outdoors is perfect.
📺 Finished The Morning Show season 3. I’m really loving how they interweave current affairs into the show. I can’t believe we have to wait until, like, 2025 for the next season??
📖 Reading Same as Ever by Morgan Housel (33% completed). Morgan is such a great storyteller. He shared some of his thought process on David Perell’s How I Write podcast, and I jotted down every author he referenced.
💃🏻 Met Pangina Heals again but this time in Hong Kong. I haven’t been able to stop thinking about her since.
📕 Read Dear Sylvia, Love Jane by Erin Hall. It’s a queer noir mystery adventure, and I’ve been a sucker for detective stories since The Adventures of Mary-Kate & Ashley.
🍂 I’m hosting a fall picnic this Sunday because my childhood best friend is flying into town! I’m determined to be as good of a host as my friends have throughout this past year 😤
Thanks for sharing your before and after samples. I remember reading your piece last week and appreciating it, but the behind the scenes regarding where it started is generous. I’m always so appreciative when artists reveal the struggles they face on the way to shipping their work. It’s such a service to all creators to be reminded of the humanness of fellow artists. I tried to do a bit of the same this week by sharing a story of how nervous I can get with an audience as a professional speaker. What could be more worthwhile than helping each other to be more human on this planet!
This piece felt too close to home at times haha. But I think your truths and hat tips are spot on!