On Rejection: Michael Estrin
Making humor out of lemons, or something. I'm not the funny one here.
Hello hello, I’m so excited to bring you all another installment of the On Rejection interview series, this time with writer Michael Estrin! He is the author of Situation Normal, a slice-of-life humor Substack that is truly excellent. I’m a big fan of “We got a new garage door. It came up with an epic story.” from July of last year.
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Tell us about a time you experienced rejection.
Before I became a writer I was an unhappy lawyer, and before that I was a naive law student. The first day of law school, I went to my civil procedure class. As soon as I sat down, a woman came up to me and introduced herself. We chatted for a few seconds, then she found someone more important to talk to. She was working the room, but I had no idea why.
At the end of the first class, a member of the Student Bar Association (SBA) knocked on the door. He announced that student government reps would be chosen from each civil procedure section.
“Who’s interested in running?” Mr. SBA asked.
The woman who had been working the room before class raised her hand. It looked like she would run unopposed, so out of principle, and some misguided ideas about truth, justice, and the American way, I raised my hand too. Mr. SBA wrote our names on the chalkboard.
“OK, time to vote,” he said.
What!? It was the first day of school. How could we be expected to vote for student reps when we had only known each other for a few hours? I objected, but Mr. SBA said I couldn’t object because this wasn’t a court of law. Whatever. I made my case anyway. A hasty election was a sham, I argued. The candidates needed time to campaign. The voters needed time to consider their choice. Hell, we hadn’t even been given the opportunity to make speeches about how, if elected, we’d use student government funds for free beer and pizza.
“Good argument,” Mr. SBA said. “Now, let’s vote.”
What?!
Mr. SBA asked how many people wanted to vote for my opponent. Every hand in the room went up, every hand except for mine, that is.
“OK,” Mr. SBA said, “not that it matters, but who wants to vote for this guy?”
Everyone looked at me. I raised my hand. Mr. SBA circled my opponent’s name on the chalkboard, and wrote a big ‘W’ next to the circle. That rejection stung, partly because my loss was so lopsided, partly because all this played out in public, and partly because that was my introduction to many of my classmates. Also, the whole thing felt Kafkaesque. Although in retrospect, law school was Kafkaesque, so maybe a sham election was a good introduction to the next three years.
How did you get over it?
I think I probably ate some carbs, or something fried, or maybe some fried carbs. About a month later, I found my tribe, the people who would make up my study group for the rest of the year. Everyone in my study group had voted against me, but by then we all knew each other, and we knew my opponent too. She turned out to be the kind of law student who hides library reference material to gain an edge over her classmates, which is both a terrible way to behave and silly because that material was also online. Come to think of it, maybe she was a better representative of the legal profession than me. Anyway, I was able to laugh about the ridiculous experience with my study group. So, I guess you can say rejection helped me bond with my peers. There’s probably a good lesson there for writers. One of the easiest ways to bond with a writing community is to share a rejection story. Everyone has one.
Of course, there’s a coda to this story. A few years after I graduated, I saw that my former opponent was a contestant on The Apprentice. She screwed up some critical assignment like opening a lemonade stand, or something. Donald Trump fired her! I know schadenfreude isn’t the healthiest feeling, but damn that was some sweet, sweet schadenfreude.
If you could go back and tell yourself anything right before that experience, what would you say?
Sometimes rejection makes sense and sometimes it doesn’t. Either way, you have to move forward. Sometimes, when the rejection makes sense, there’s a lesson about whatever it is you’re pursuing, and you should apply that lesson for next time. But not every rejection carries a lesson. Sometimes it’s just bad luck, and if that’s the case, the only real lesson is persistence.
Do you have a favorite story about rejection and moving on? Why that story?
I often say the only thing better than hearing yes is getting a quick no. It’s not that I want to hear no (who does?), but the faster rejection comes the better because you can just move forward. That’s actually a gift, but it doesn’t always feel that way.
OK, storytime. I used to have a good job as a trade journalist. But for some reason, right around the time the housing bubble burst and the Great Recession began, I thought it would be smart to join a new humor publication. We borrowed office space from a coconut water company, and within 18 months we folded. But don’t worry, all these years later, the coconut water company is still a going concern.
Anyway, the day we folded, I gathered my clips, updated my resume, and threw a couple cases of coconut water in the trunk of my car. I started freelancing right away, mostly writing for editors who I had worked with in the past. If you’re going to make a career freelancing, you need to pitch a lot of stories. I tried to spend at least one day a week pitching, which is another way of saying I spent one day per week working without pay so that I could spend the rest of the week working for low pay. Writing is a hell of a business.
ANYWAY! A few months into freelancing, I saw this cheesy cable docu-drama about the apocalypse. The show told the story of a fictional family and their harrowing escape from an apocalyptic Los Angeles. Now, the people in this story had serious apocalypse skills. He was a paramedic, and she had been a soldier. I have zero apocalypse skills. The show freaked me out because I remember thinking, there’s no way a dude like me survives five minutes in a situation like this. For a week, I actually worried about my lack of apocalypse skills so much that I didn’t work up any pitches. Thankfully, my girlfriend, who later became my wife, suggested I turn my fear into a pitch.
I worked up a pitch that was basically a humor piece with some reporting about how the average dude would be toast in the apocalypse. I sent it to a bunch of men’s magazines: Esquire, Details, Maxim, etc. For whatever reason, I got immediate responses, some were encouraging, and some were pro forma, but they were all rejections. By the time lunch rolled around on the first day of pitching, I think I had a half-dozen rejections. I thought the idea sucked, and that maybe I had wasted my time. But on a lark, I fired off one last pitch to Penthouse, then went to console myself with a slice of pizza. Oh, who am I kidding? I ate two slices of pizza.
ANYWAY, by the time I got back to my desk, I had a yes from Penthouse. As it turned out, that assignment led to six more assignments, until some MBA-type at Penthouse realized the magazine business was dying. My editor got laid off, and I got a kill fee for the story I had in progress.
I share this story because I think there are some good lessons about rejection and the business of writing.
Receiving rejections means you’re in business to do business.
Increasing the rate of rejection increases the likelihood that you’ll eventually hear a yes.
Editors or other so-called gatekeepers are in a tough spot too. Turning words into money was never an easy business, but it’s been especially difficult business in the 21st century. I mention that context because it makes rejection less personal for me. Selling words is a tough business, unless those words happen to be a ransom note. Whenever I’m feeling down about a rejection, I try to remind myself that this is a tough business, and that rejection is just the unpleasant, ongoing process of carving out your niche.
What are you working on now?
I’m working on a few things. Actually, I’m always working on multiple projects at the same time. Part of that is about my rhythm and how I like to work, but it’s also about not putting all your eggs in one basket. Because if one project is rejected, or stalls out, it’s good to have two or three other things that need your attention. Anyway, one of those projects is a new novel, but it’s early days on that project, so the only thing I can say for sure is that it’s hilarious. This week, I’m polishing a piece that I’m submitting to my favorite humor magazine. I’m also developing a new section for my Substack to compliment my slice-of-life humor.
You can follow Michael Estrin on Twitter.
