The Hidden Payoff of a Failed Risk

In December 2006, I sat in a Borders bookstore, typed an article that would pay a penny per word, and despaired of ever getting a national magazine-writing gig. I had pitched editors with all my best ideas (I thought), and no one seemed to be open to new submissions from inexperienced writers (go figure).

I had landed a remote position as the associate editor for a regional magazine, a couple of copywriting jobs, and a steady gig writing these low-paying bulk articles. But the higher-paying and higher-profile work I coveted was in national newsstand magazines.

That cold day, the windows of Borders were fogged near the base. I stared at the droplets as they trailed down the glass and longed to stop working on the article about wedding gifts and just wander the bookstore for a few hours. I had taken a huge risk a couple years earlier by leaving my full-time job and going freelance. Days like this, I wondered if I had made a mistake.

The Approach

Two women sat nearby. As they laughed and talked, the woman in her late thirties with black rimmed glasses spoke the name of a national newsstand magazine.

Much like the Grinch, my ears grew three sizes that day.

I listened with everything I had. Did I hear that right? Was this woman affiliated with this highly respected lifestyle magazine?

As I eavesdropped on their conversation—hard not to because they were ten feet away from me—I gathered enough to understand that, yes, this woman was indeed the managing editor of said national magazine.

Holy crap.

At this point, everything around me blurred and all I could hear was: Amy, if you don’t go up to that woman and introduce yourself, you will regret it for the rest of your career.

The editor’s friend reached for something in her purse, and I knew I had only a few minutes left to make my move. So before I could talk myself out it with arguments about how sweaty and shaky I had become, I stood and walked up to their table.

“Er-herm,” I said, ever-so-gracefully.

The editor with the black-rimmed glasses looked at me with raised eyebrows.

Then it all tumbled out: my name, what I did for a living, how I was sitting over there at that table with the laptop and I couldn’t help overhearing their conversation and could they forgive me for interrupting but I knew that if I didn’t come over and introduce myself I’d never forgive myself and I was wondering although I knew it was odd I was wondering if I might send her a pitch.

I think by this point I was panting.

She, however, was smiling. She reached into her handbag, pulled out a business card, and said, “Sure. I’d love to hear from you.”

I thanked her fifty-seven times then returned to my table. For the next fifteen minutes, I pretended to type the wedding gift article on my laptop. What I really typed was something like, “holy crap holy crap holy crap I can’t believe that just happened holy crap…”

The Article

Long story short, I came up with an article idea, wrote a pitch letter, and addressed it directly to the managing editor with a reminder of our meeting. She replied and offered me the assignment.

I was over the moon! It was my very first assignment for a national magazine. I did an incredible imitation of a pogo stick then sat down to start writing.

I put my all into it. Which was to say, at that point in my career, I put an English degree, some copywriting experience, and a love of poetry into it. Not exactly what you’d call cover story material.

After I turned in my article, I didn’t hear anything for a while. When I did, the editor who contacted me was not the one who had assigned the piece to me. Standard for some publications, this delegation meant that I starting dealing with an editor who was not at all charmed by my naïve approach in Borders a couple months prior.

She was also less than enthusiastic about my article. In fact, she had ripped it to shreds.

Now, if you’ve ever submitted a piece of writing to an editor and gotten back what looks like a red mess, you know what it’s like to endure “heavy edits.” This was not heavy edits. This was a total rewrite. This editor had completely rewritten 75 percent of my article. She hated it and didn’t mind letting me know.

The Silence

Well, I submitted the information the second editor asked me for, and then I mustered my courage to pitch the woman with the black-rimmed glasses with another idea.

After sending the second pitch, I heard nothing. Crickets.

Okay, it’s clearly no surprise looking back. I wasn’t skilled enough yet as a writer to work for a publication of that size and reputation. I didn’t really understand what made a strong magazine article. I didn’t know how to pace or introduce or bolster an article with substantial evidence. But at the time, I didn’t have much objectivity about my experience level. I just knew I wanted to write for them, had taken the risk of embarrassing myself in public, and now they were freezing me out! I thought I was on the verge of breaking through in my career, only to be rejected in the end. I couldn’t believe this was happening.

The silence of weeks stretched into months, even after polite follow-up emails.

So I turned silent too. When people asked me about my business and how things were going, I said something about lots of good clients and left it at that. I was angry, embarrassed, and confused.

The Surprise Turnaround

Here’s the thing about risk: It always pays off—just maybe not in the way we anticipate.

After a few years, I was flipping through a stack of magazines in my new home office. By then, I was the managing editor of SUCCESS magazine—yes, a national newsstand publication—and I was searching for some ideas on a feature I wanted to write.

I found the issue that held my first national magazine article. As I sat down to read it, I remembered that the person who actually wrote the article had no byline, that while my name was under the title of that article, I was not the one who had crafted the majority of it. The second editor at the magazine had written most of the piece herself.

In that moment, the risk finally paid off in a lesson that I have never forgotten: Entitlement is the enemy of growth.

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Back in 2006 when that editor rewrote my article—the one I felt I had put so much heart and soul into getting and writing—I felt only outrage. What I should have felt was gratitude.

I’m not saying that rewriting a contributor’s article is a good practice—it’s not actually. But what I am saying is that she saved me. Forever, there is a byline attributed to me over an article that is infinitely better than anything I could have written at the time. But I felt so entitled to advancement, opportunity, and praise for my risk-taking that I couldn’t humble myself enough to see the truth about what I actually had earned at that point in my career.

I didn’t deserve to be bailed out by that woman. But she did it anyway. And in return, I was curt and ungrateful.

Having big dreams is a good thing. Feeling entitled to reaching those dreams without doing the work necessary to earn them will keep you from learning, growing, and becoming the person who can sustain them.

I’m grateful today for that editor’s last-minute rewrite. And I’m experienced enough these days to know that I still have a lot to learn.