Challenged to Fail

Like everyone else, I’m listening (again) to the cast album of Hamilton. And my writer’s brain latched on to “The Room Where It Happened.” There, Burr expresses his envy and bewilderment that Hamilton, the loud-mouthed impetuous immigrant, is achieving his objectives while Burr (“talk less, smile more”) is left on the sidelines.

In that song, Hamilton explains to Burr,

“When you got skin in the game, you stay in the game,
But you don’t get a win unless you play in the game.
Oh, you get love for it. You get hate for it.
You get nothing if you …. [Wait for it, wait for it, wait!]”

And that reminded me how, three years ago, my son Jeremiah challenged me to fail. I’d been promising to get serious about writing. About finding a journal, a pen, a quiet room, a discipline, a forum and — maybe — a byline.

Jeremiah listened patiently as I bemoaned the long odds of getting a piece published. I muttered something about getting twenty rejections in a year. Jeremiah locked eyes with me: “I challenge you to get twenty rejections.”

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Kateri Tekakwitha (1656-1680), American saint, Santa Fe, New Mexico. Photo by Anne Ryan

Wait. What? Embrace — even court — defeat? Well, of course that’s the life of a writer who wants their words picked up by a wider reading audience. But do I really want the latter enough to risk the former?

Writing is personal, writing is hard, writing (for me at least) is entangled in identity — and rejection risks shattering all that, as though each piece sent into the world is a delicate glass bauble, too fragile for someone to hand back to me without damaging it and its creator. If I’m going to make a glass bauble, I’d better wrap it in tissue and tuck it under the bed.

So I had to decide. For some things, I’m very fragile, very risk-averse, very willing for others to define the terms because the costs of a mis-step are too high. Was writing one of those things?

Certainly not. The possibility of publishing what I write is akin to a baseball pitcher challenging the batter with each pitch. Any number of things can happen once the ball is in play. Some of it is good for the pitcher, some of it is bad. But every time the pitcher propels their body off the mound, they say, “Here’s my best stuff. See what you can do with it.”

The hands and wisdom of a Nats ballpark usher.

The beauty of Jeremiah’s challenge was not only that it forced me to stare down my fragility, but it also forced me to find places to submit and, darn it, to actually write. Twenty rejections means twenty submissions, which means I need to propel myself off the mound twenty times and take a chance.

The goal of twenty rejections actually freed me to submit risky (= not very good) stuff. Twenty, for me, is a big number. So each piece couldn’t be a precious bauble, but instead a well-stitched baseball delivered with just the right torque to make it do interesting things. “Oh, you get love for it. You get hate for it.” And you get rejections popping up in Submittable for it. Naturally, that’s Jeremiah’s point: You get nothing if you wait for it.

I started hitting the submit key. I had a goal to achieve: Once I hit twenty rejections, I could go back to “baubling.” Some of the pieces I submitted were, shall we say, unfinished. (You won’t see them in this blog.) Other pieces were actually pretty good. And I discovered I couldn’t guess the outcome. One of my favorites, Promise, earned a coveted rejection; another earned a surprising “yes.” Two perfectly ordinary pieces got published.

That’s the way it is in baseball, too: your perfect pitch — yes, I’d do it again! — gets manhandled by the batter, while other times you get away with lesser stuff.

Washington Nationals pitcher Max Scherzer taking the mound, along with the black eye he got earlier that day. AP Photo by Patrick Semansky.

Jeremiah helped me enjoy the rejection game, like a pitcher enjoys baseball. What should I write? Where should I send it? How fast can I move on from failure?

Now, I have skin in the game and the game has made my skin thicker.

Fourteen rejections to go. I can’t wait.


I wrote this piece for Five Minute Friday, a faith-based community site. Follow this link to see other short essays about “Progress.”  

Woo hoo! Readers, now that I have reached nearly 100 posts (!) I invite you to browse my past essays. The easiest way is to explore the “word cloud” featured at the very bottom of this post. Find a theme or two that interests you and sift through the sands…

Also, do you want to receive notifications by email each time I make a post? Just scroll all the way down this page (next to the “word cloud”), look to the left and click on the black button that says “Join Me!” 



4 thoughts on “Challenged to Fail

  1. Ryan, Anne M - (anneryan) August 9, 2020 — 12:03 pm

    I love this post Carol Ann! Especially your description of what writing is to you. I greatly admire your willingness to accept and carry through with your son’s challenge. He’s very wise and clearly knows you well! Xoxox Anne

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  2. Jeremiah’s wisdom is profound. Thank goodness you took what he said to heart–we would all be poorer without your gratitude-infused words. Now I feel inspired create something and fail, too!


  3. Words of wisdom there, thanks for sharing! Visiting from FMF #32 spot this week!


  4. I enjoyed reading “Challenged to Fail”. An insightful piece, and it demonstrates the wisdom that children have. For me, having something that I wrote get published is exhilarating, but I have learned not to interpret a rejection as a failure on my part.


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