I was re-reading an old essay of mine that I’d sent out nine times but could never sell. As I finished it, I thought, “Damn, I like this essay. Why did no one want it?” I decided to send it out one last time. I sent it to a publication a friend had just told me about, and within 10 minutes, the editor wrote back: “I like this a lot. We haven’t run a story on this topic yet.”

I was elated. Maybe my luck was turning. I had a great run two years ago where I felt like Midas. Editors were buying everything I sent out, including a piece for The New York Times’ Modern Love column, the holy grail of essay markets. This year has been the opposite. As they say in basketball, “I can’t buy a bucket.” I’d lost my touch. So when this editor liked my essay, I felt resurrected.

The editor went on, “How long is this piece? We rarely run anything over 800 words. And we pay $500 for an accepted piece.”

If I could just cut it down a bit, she’d buy it. So me, exuberant but a bit of a motor-mouth — usually I’m just trying to be funny but sometimes my foot, wedged between my teeth, gets in the way — sent this in response: “You rarely run pieces over 800 words? Well this one is, um, 799. Actually, it’s not. It’s about 1,500. What should we do? If I can shave off, say, 300-400, can this be one of those rare occasions where you run something that’s more than 800? (I don’t know why I care; it’s not like you pay by the word. Vanity, perhaps?)”

Yes, I wrote all that.

Her reply: “Vanity? I’m not sure what you mean. I thought it was an interesting piece but please feel free to pitch it elsewhere and hopefully you can earn more for it. Thanks.”

I was flabbergasted. Why couldn’t I just keep my mouth shut and my fingers still?

In an attempt to remedy the situation, I quickly wrote back: “Oh my goodness. By vanity, I was referring to ME, not you. I was making a joke about how I was trying to hold on to the length of my essay when it wasn’t as if I was being paid by the word. I was trying to be clever. Oops. That certainly backfired. No, I’m really pleased you liked it. And I’d love to work with you. Sometimes, I talk too much, when I should just keep it simple.”

Yes, I wrote all that, too. And then, still fearing I’d chased her way, I fired off another missive, telling her I was actually quite pleased with her rate, that I was sorry if I had offended her, and added, “I can’t believe how badly my attempt at cleverness went awry.”

When I didn’t hear from her for more than an hour, I sent off yet another email that said, “Did I just lose the sale?”

Tone deaf emails

Not hearing from an editor for an hour is not unusual. She could be eating lunch, getting out an issue on deadline, visiting her uncle in hospice, burning an effigy of my face. But an hour to someone who has fired off a self-sabotaging email feels like a week.

I tried to make myself feel better by thinking, “Okay, Caren, you messed up, but don’t crucify yourself. It’s not the end of the world. Just take a lesson and move on.” But how could I? I’d brought this upon myself. I suffer from diarrhea of the mouth. I talk until I do damage. If my husband overhears me leaving a voicemail, he’ll wave his hand across his throat, the international symbol for “cut it off.” I feel like the character the actor John Cleese plays in the British comedy series, “Fawlty Towers,” when this old war veteran with PTSD comes to stay at Cleese’s hotel, and Cleese is warned, whatever you do, don’t mention the war, and all Cleese can do is keep bringing up the war. (By the way, that episode has since been removed by a BBC-owned streaming service, apparently due to offensive content.)

It wasn’t the first time I nearly lost a gig by talking too much. I once pitched a story to a stand-up storytelling show in Boston, and when the editor said my story had been chosen for their live event, I said, “Oh my God!!! And now I feel sick. With nerves! My performance-anxiety self was sort of hoping you’d say ‘no!’” To which she replied: “To be honest, now I’m wondering if I should say no.” I was  expressing my insecurity through self-deprecating wit, but she was not amused. She feared if I bombed, it would reflect poorly on her. I promised her I wouldn’t raise the issue again.

Misery loves company

In need of a kindred spirit, perhaps someone else who shoots themselves in the foot as routinely as I do, I asked members of a writing group if they’d ever done something like this.

One member told the story of a misstep with an online magazine editor she had worked with many times. She sent an email to a friend, complaining that the editor doesn’t respond as quickly or reliably as she wanted. She accidentally included the editor on the email thread.

“He told me he wasn’t offended, but he never answered an email from me again,” she said.

Another said, “I had to learn when I moved to Texas that my East Coast sarcastic sense of humor was offending people right and left.” She went on to say she’d once sent an email to a writer colleague checking out a particular editor before pitching her — and of course inadvertently sent the email to that very editor.

“Somehow the writer was implicated. I can’t recall the details, but he was super nice, as was the editor,” she said. “But by then I was too mortified to pitch her.”

While their experiences took different routes, they met similar ends. And they all advised me that with new sources, one should tread carefully and formally, at least until a relationship is established.

Learning (or not) from your mistakes

After reading the commiserating emails from my colleagues, another email came in, from the editor I feared I had offended. She had noted my address and now enthused that she, too, was a New Jersey resident.  She went on, “If you could just cut it so that it’s less than 1,000 words, that would be great.”

And just like that, my world was right-side-up again.

I’d like to say I learned a valuable lesson, but I probably haven’t. There’s a self-sabotaging aspect to my behavior that doesn’t listen to reason. I take risks with people who don’t know me, knowing it may backfire, and then when it does, I chastise myself until it hurts.

But then perhaps that’s why I do it, snatching defeat from the jaws of victory. After all, if I didn’t, I might succeed. Perish the thought.

Caren Chesler is an award-winning journalist whose work has appeared in The New York Times, Scientific American, Slate, Salon, and Popular Mechanics. She has a blog called The Dancing Egg, about having a baby through IVF at age 47.