Failing to Fail, a Disappointing Success

I don’t even know how to write this post. It’s like my brain has been turned upside down, making left right and right left.

The “rustic tarts” failed. They came out as cupcakes, like the recipe originally intended. So maybe they succeeded? I have no idea how to say this–I failed at trying to deliberately fail. I set out to ruin the cupcake recipe a second time to end up with the “rustic tarts” people loved, but it didn’t work. I made them the same way I did when they failed the first time, but when I pulled the first tray out of the oven, they looked right. Errrr, well, wrong for what I was aiming for.

So, rather than prying them gently from the pan to keep the jelly balanced in the middle of the cupcake, I dumped them roughly onto a cooling rack, thinking the top would flatten and pull away, leaving the gooey center for me to scrape out and squash on top. That’s how the rustic tarts came into being.

But no, the rough treatment left 12 perfectly plump and cohesive cupcakes. I rolled them over onto their bottoms and sighed. One tray left to go. Will it be like last time, and one half fail and one half work?

Nope. Second tray, same thing: cupcakes.

So now, I have a bunch of cupcakes that would have looked fancier with liners, but I did not use liners because that was one of the ways I made the recipe fail the first time, when I wasn’t aiming to fail.

When I took a drawing class from my friend and former colleague Dave Andersen, he told a story about hitting a low point in his painting career, and to launch himself out of it, he decided to try to fail by making the worst, dumbest, stupidest decisions he could while painting, going against all good practice. If symmetry seemed right, he’d make it lopsided. If smooth brush strokes seemed kosher, he’d smear the paint, toss it, glop it wherever it landed.

This approach resulted in some masterpieces and a theme that received a lot of attention, praise, sales, and built his reputation as a great painter. He still sounds dumbfounded when he tells the story.

Fruit Boy

“Fruit Boy” by David Andersen

So what’s the universe trying to teach us here? Wake up each day and try to do a BAD job? Aim to fail? But in aiming to fail, find success?

When I was teaching college, I discovered a distinct, but not uncommon, kind of student: The student so afraid of failure that they aimed to fail. They did whatever they had to do to fail, even when instructors like me gave second, third, fourth chances.


If you intentionally fail, you can say, “Oh, that F? No big deal. I didn’t even try. I barely even went to class.”

If you put in effort, even a little, but especially a lot, and you fail, what can you say? “Oh, that F? I tried, but I still failed. I must be as dumb as I think I am. (Or as everyone else has said I am.) I suck at this.”

It huuuurts to attempt something, to risk showing others that you care, that you’re putting some heart and muscle into it, and then fail. It seems, at first, a lot safer and easier not to try at all.

Well, cupcakes/rustic tarts are no big deal. I’m not hurt by this failure, the wedding guests should be none the wiser, and although I don’t yet feel this way, I think the maid-of-honor was right, “Whether you get it wrong or right, sounds like a winner.” It’s just that the failed cupcakes were more interesting than the successful cupcakes. I guess there’s one clear lesson I can take away: sometimes failures result in a more interesting product than what you’d been trying to create.

Which is also true of more painful failures. Sometimes, a student would earn an “F” in one of my classes, and then show up the the next term to try again. At first this mystified me. They hadn’t taken it personally, weren’t mad at me, and were both brave and humble enough to show up again with a fresh notebook and give it another go.

These students would speak up in class and say things like, “It’s true, you really do have to write more than one draft and revise. I learned that when I failed this class last term.”

This motivated (or terrified) others in the class who stepped up their game, and the student who once failed the first time now becomes a leader in the class, quick to ask questions, to humble his/herself and ask for help from me or another student, and quick to openly celebrate a solid grade and encouraging comments on a paper. It’s as if that “F” showed them the worst, and now, asking questions in class and letting us see their effort doesn’t scare them at all.

Rather than attempting to ruin another batch of cupcakes in order to get rustic tarts, I’ll accept the cupcakes for what they are. I mean, they are what they were originally supposed to be, right? The dollop of jam in the center should surprise guests as well as the hint of nutmeg in the cake, and they look wedding-ly with a sprinkling of white powdered sugar on top.

Meanwhile, I’ll be contemplating all the other ways I might aim to fail … in order to succeed. First up–the query letter I’ve been trying to write to literary agents because aiming to succeed has resulted in stiff, self-conscious, vague writing so far. Can’t hurt to try writing an awful one, can it?

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8 Responses to Failing to Fail, a Disappointing Success

  1. heatherseattle says:

    love love love love this. full of so many truths it took my breath away! LOVE IT!

  2. Rose L. says:


  3. SD Gates says:

    That’s so true about the query letters. The harder you try to make them perfect the more boring they sound. Great post!!!

  4. Alex Hurst says:

    Good luck with your querying! Maybe the takeaway for the tartcakes is that some strokes of luck happen only once–not everything can be recreated. But that’s okay, because that is what makes them special. I used to cook the most amazing orange cranberry bread. So great that people asked for it every Thanksgiving and Christmas… I made it so much it started coming out generic. Without heart. The flavor suffered. My love of the bread suffered. Now, I’m not sure I could recreate that first taste if I even tried!

    Thanks for this post. There were many great things said, and it reminded me I need to imbue my own writing space with a little more heart. I’d forgotten it along the way, trying to keep to a schedule and building a platform. 🙂

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