Fail Hard and Take It Easy

Fail harder foxprint editorial tiffany Yates martin

Fail Hard and Take It Easy

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I know I promised, when I first took up pickleball about a year ago, that I wasn’t going to be one of those people who get obsessed with it and talk about nothing else.

But let’s talk about pickleball. 😊 (Just for a moment…I promise.)

I’ve been playing purely recreationally, once a week if I’m lucky and usually even less than that. It’s fun for me, and I don’t much care if I win. I just like being active, playing with friends and meeting new people on the court, and going after that ball with all the fervor and focus of my dog Gavin.

But lately I’ve been trying to improve my game so I can play closer to the level of my husband and best friend, who have indeed been inducted into the cult of pickleball and play four to six times a week. I recently took a pickleball clinic, have been trying to practice more often, and last week I joined in with a group from my husband’s gym who play together regularly, thinking that my skills were improving enough that I would be able to hold my own among more experienced players.

Folks, I stank up the court. I literally dropped the ball—so many times I can’t even count—whiffing easy shots, losing every game but one, and by the end of two hours wanting nothing more than to abjectly apologize for wasting everyone’s time and slink home to hang up my paddle forever.

Like most of us, I hate not to be good at things. I especially hate not to be good at things when I thought I was better at them, or at least getting there. 

But here’s what I’ve been trying to remember since that day I came home and morosely apologized to my husband for dragging his friends down and embarrassing him: that this is how you learn any skill, and failing is not just a normal part of the process, but a necessary one. If I’m not pushing myself past the level of what I’m currently capable of, how will I ever improve? And when you first start to do that, chances are good that you’re really going to shit the bed.

There are two ways to respond to that. One is to do what I did: feel discouraged and embarrassed and want nothing more than not to put yourself in a position to feel those uncomfortable things again.

The other is to pick up your paddle and get back on the court.

Be Gentle with Your Failures

Have you figured out yet that I’m not really talking about pickleball? I can’t tell you how often I see this happen to writers—and because you’re here I assume that you are one and you already know that for yourself as well as anyone.

Writing, like pickleball, starts out as pure enjoyment. But also like pickleball, it’s a skill that is far more involved and complex than it may initially seem. (Ask any pickleballer about dinking—i.e., gently tapping the ball just over the net—and prepare to hear a litany of intricate skills involved in this most basic of shots.)

This past week I spoke with a writer who has literally decades of experience and is a major bestselling author. She’s on her third pass of the manuscript we’ve been working on together, a complex story that deals with extremely deep and sensitive issues, and she was feeling daunted.

I’m working with another author, a very skilled and experienced writer whose expertise is in technical and academic writing, who decided a year ago to tackle her first full-length fiction: a dual timeline story with a broad scope and significant emotional depth. I just returned an extremely in-depth and extensive editorial letter to her after my first pass—what one author I work with refers to as “a literary root canal” that I know is going to hit this author like a plank in the face.

But these writers aren’t failing at their craft. They are pushing the boundaries of it, stretching themselves to master new skills and tackle deeper and more complex stories.

I am very deliberate in my editorial feedback, taking a positive and constructive approach that amply points out a story’s strengths and offers plenty of encouragement and support amid frank feedback about where it may need development. Because after many decades of doing this, I know how easy it is to get discouraged when pushing yourself beyond what you’ve been capable of before, especially for those who are deeply invested in what they are tackling, and most especially in something as personal and sensitive as our deepest creative efforts.

As Fezzik tells the Man in Black while he’s going a bit easy on him in their grappling match, it’s important that we feel we’re doing well, even when we’re struggling. That’s what gives us the confidence to continue to work at the thing we’re trying to master, to continue to fail and not lose heart so that we can stay in the game and get better. So that eventually we can triumph, just as Westley finally does with the Giant.

Before I hung up the phone with the bestselling author who was struggling in her third revision, she thanked me for bolstering her confidence. She needed that shot in the arm, she said, to remind herself that she was capable of getting the story where it needed to go.

But Fail with All Your Heart

This morning my husband was telling me about his latest pickleball game and how he’d whiffed a few easy shots, the other player on his team giving him devil eyes every time. “I don’t worry too much about missing shots, though,” he said. “Everyone does it.”

I think he was Mr. Miyagi-ing me, trying to subtly send me the message not to be so hard on myself about my pickleball game, and certainly not to let it make me give up—just as I do with authors in our editorial work together. Everyone indeed has off days. And everyone started as a beginner and honed their skills with practice and study and experience. And everyone has to fail, over and over again, to move along the path to success.

I’m at the stage in my game now where I’m trying to move from beginner level to intermediate, and there are going to be some speed bumps, just as there are when you’re attempting a story that may be more complicated or challenging than you’ve written before, or when you’re trying to bump your writing to a publishable level, or when you first share it with outside readers, or when you think you’ve been doing pretty well in your writing or career and then read someone else’s story that reminds you you’re still early on the path.

Yes, those moments may smart, but they’re necessary to give you a clear picture of where you are and what you still need to master and to learn. That’s the process of mastering your writing craft—of mastering any skill—and it never ends. No matter how long you’ve been at something or how good you get at it, I promise you someone is going to be better than you, and you’re going to feel like a neophyte when you hold your skills against theirs.

I appreciated—and needed—my husband’s reminder of that, and his encouragement. But we can’t always count on getting those from our support system, and one of the most important skills we have to master as writers is that of being our own cheering squad, our own champion, our own voice of reason.

It often helps me to think of what I might tell a loved one or a friend or a child trying to master some new skill. I’d never berate them or exhort them to stop trying. I’d build them up, remind them how far they’ve come, and that learning anything—in fact any kind of growth—means you’re going to fail repeatedly before you succeed. In fact if you’re not sucking, at least periodically, you’re not challenging yourself, and you’re not growing.

I remind myself to bring that same grace and kindness and realistic acceptance to my own endeavors as well. It’s a process: I have a long history of beating myself up over failure, and learning not to do that is yet another skill it takes practice to master.

So fail harder. Push yourself beyond what you’ve done before, beyond what you may be capable of at the moment. It’s killing me, but I’m going back to that pickleball group next week, and I’m going to keep pushing myself even though I know it’s probably going to take a while before I start to see improvement.

I’ll see you out on the court.

Authors, how do you handle those times of struggle and feeling less than sanguine about your work? What do you do when you fail?

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18 Comments. Leave new

  • Lisa Bodenheim

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    February 13, 2025 12:30 pm

    Hi Tiffany, for a previous itieration of my story, I had two crit partners. One was highly critical of my story and the skillset I demonstrated, but not of me as a person. The other crit partner found some enjoyment in my story despite its flaws.

    I took time to process the critiques, for which I am grateful, and signed up for writing classes that addressed my pacing issues, and read blogs, like yours, to help me improve my craft and stir my enthusiasm.

    I’m now ready to hand out the revised story in whole to a couple beta readers, hoping I’ve honed the story.

    Reply
    • Not every beta reader is skilled at offering constructive, actionable feedback that centers on the work–not the person. And on what they did and didn’t find effective, rather than value judgments or prescriptive advice. (I have a whole chapter on this in The Intuitive Author–the difference between criticism, commentary, and critique). Sounds like you handled it in as productive and useful a way as possible. Other eyes are so often essential for getting a clear picture of what’s working well and what isn’t in our stories–it’s helpful to know how to process and use their feedback (and know when it isn’t relevant for you!). Thanks for sharing, Lisa.

      Reply
  • Nan Cappo

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    February 13, 2025 12:56 pm

    Tiffany, this came at a good time for me. I’ve been writing for 30-some years and know I have good skills and some publishing success (just not enough). But I found pickleball 3 years ago and have become obsessed. I’m scheduled to test for a higher level on Saturday–so I can keep playing with my friends who are definitely getting better–and can’t tell you how many YouTubes I’ve watched, or practice balls I’ve hit against the living room wall. (My husband says I’m on borrowed time there….) My game is getting better, which made me realize I should do drills for my writing too. So now I’m underlining sentences from writers I love, and using them as models for my current project. I think it’s helping. Obsession is not always a bad thing. PS–best of luck with your game!!

    Reply
    • Oh, Nan, you’ve inspired me–I realize that part of getting better means I need to be more diligent at what you describe: practice, drills, and watching the game. I apparently want to just osmose myself into the skill. 🙂 As rarely as I play, that kind of intentionality would really help me improve. (BTW, speaking of the living room wall play–have you seen the foam balls specially designed to have the same weight/flight as a regular pickleball? That’s what we use indoors.)

      Analyzing other writers’ work is the BEST way to master craft in your own writing, because you have the objectivity we often lack with our own stories. I’d urge you to go deeper than line level, even–analyze structure, character arc, stakes, suspense and tension, momentum–everything. I’ve learned more as an editor than I ever learned writing my own work. (And yes, I’m obsessive about this kind of analysis–in my work but also in everything I watch and read. I’m told by the hubs that it’s not the most fun thing about watching a movie with me…. 😉 )

      Reply
  • Elisa

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    February 13, 2025 4:22 pm

    LOVE this. It had the double-effect of making me want to get back to the manuscript as well as the pickleball court. It’s been years. Thank you for holding up a mirror for us.

    Reply
  • Cate

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    February 13, 2025 10:05 pm

    I feel your pain! I took up playing basketball for the first time ever (coached it for years but never played) and found myself in a rec league with most of the women half my age wearing their college jerseys and running circles around me. I kept telling myself it was good for a workout. It’s hard to start something new, but it’s also hard to do something (for me, writing) for 20+ years and still not see the kind of success from it I’ve been striving for. What can we do, but keep doing what matters?

    Reply
    • WOW, how did you coach without having played? And yeah, those young whippersnappers are a bane in pickleball too–fast little suckers beat it to every ball. 🙂 I like it, though–keeps me hustling (also I feel less bad about the disparity in our abilities because at least I feel like there’s a good reason–it’s my contemporaries kicking my ass that stings).

      I get that we all want certain mile markers of success, and it can feel frustrating or discouraging if we don’t feel we’ve attained them even after years of work…but I also think it’s a privilege and blessing to get to pursue our creativity–on any level. I try to remind myself of that when I feel frustrated myself–my day-to-day is damn good, regardless of whether I top any bestseller lists or become a household name (you know, like editors do). 😉 If you’ve been writing for twenty years, hopefully yours is too. Thanks for the comment, Cate.

      Reply
  • Syl Waters

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    February 14, 2025 7:34 am

    It’s hard, but we must always be our own best coach cheering on from the sidelines – even when times get tough. Resilience and bouncebackability is everything! Thanks Tiff for an as-ever great post.

    Reply
  • Bob Cohn

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    February 14, 2025 9:01 pm

    You couldn’t have been more timely or helpful.
    The failure that is lowering my spirits and raising my blood pressure right now is querying(!). It’s like writing a resume for your book, and just as frustrating. The right resume leads to an interview; the right query leads to a request for the MS. It’s just marketing. But I don’t speak marketing.
    My feeling that I don’t know how to market my book to an agent leads me to wonder if that’s because the book isn’t appealing enough to be saleable. (I understand the buzzword right now is bankable.) A query is just a sales letter. And I’ve written those. Some of them produced results.
    When I read my book, I find it an engaging and satisfying reading experience. I realize that may have something to do with my lack of objectivity, but I’ve reason to believe I’m not alone in finding it engaging and satisfying.
    And, I know how the right query is supposed to work, what it’s supposed to contain, the font, the spacing, the length, the paper, etc., but when I produce that (for the umpteenth time) I still feel it’s a lousy representation of what the book and I have to offer.
    So, I’ve got the first part down—I fail hard, but I’ve run out of gentle; doubt and frustration have squeezed it out of me.
    What your blog has done is remind me that the surest, if not the only, road to failure is quitting. And, doubts notwithstanding, I still believe the book deserves a chance to satisfy readers, and in the process provide some benefit to me.
    So, I’m going to do an analysis of the book and (what I think) makes the book an engaging and satisfying reading experience and start my query there. I may need professional help translating the results of my analysis into marketing language, but I think I know where to find that.
    As always, Thank you. And how did you know that this was what I needed right now?

    Reply
    • Because I’m IN YOUR HEAD, Bob. 😉 Just kidding–I’m happy to hear this was a well-timed post for you… but sorry you’re in that vexing stage of querying, uncertainty, and self-doubt. If it helps…from what I see it’s a pretty normal stage. (No fun, though.) My next line of offense would have been what you’re already thinking of doing–talking to someone with extensive experience with query letters.

      Hang in there, friend. It’s so hard to be objective about our own writing. It’s so hard to try to convey everything it is inside of a brief summary and letter. So hard to find that right fit of a person to represent it. THis is when being our own pep squad is more important than ever. And I’m pulling for you over here.

      Reply
  • Emily WhiteHorse

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    February 14, 2025 10:30 pm

    Wow, perfect timing, as I have been kicking the can down the road and not writing on my novel. Why? Because after getting the first pass of constructive feedback from the editor I am working with, I realized how little I know about writing. Like one of your clients, I am moving from academic writing to a deeply personal novel and one in which I am fully invested in writing. I am grateful my editor is experienced in working with folks like me, so her approach is balanced. There is nothing she said that stopped me or discouraged me. I did that on my own when the enormity of what goes into writing fiction well ‘hit me like a plank.’ As an avid learner, I have dug deep into reading and learning as much as I can about character development, plot, theme, story and character arc, suspense, tension, and the central story question for the past several weeks. So much so, now I doubt everything, feeling utterly ill-equip to write this story that I feel I must tell. It suddenly feels overwhelming. I thought I had more skill than I do.
    My motto when I teach is that mistakes aren’t failures; they are how we learn, and they have the potential to help us grow if we choose. The goal of learning isn’t to arrive as in, I know everything, but rather to stay open and keep learning because that is how we continue to grow and evolve.
    Reading this post helped me remember that although I may not have all the skills I need, I simply don’t have them.
    So, I’m dusting myself off, putting Band-Aids on my scrapped knees, and getting back in the chair to work on my story as I continue to learn. It is definitely going to be an iterative practice!
    Good luck with pickleball – you got this!

    Reply
    • Oh, Emily, those editorial notes can be a real mule kick in the teeth! I’ve written before about my own experience with getting them: I basically proceed through all the stages of grief: denial, bargaining, anger, depression, acceptance. And I’m an editor. 🙂

      Taking some time to regroup and regather your fortitude is helpful. And please remind yourself it’s not a reflection on the worth of your writing, your story, or you. It’s the damn truth that writing a story is incredibly complex–like conducting an orchestra of countless instruments, I always say, plus being the composer and every single musician. I don’t think any of us are ever through learning and mastering this craft.

      And your comment helped me too–to remember that failure means we’re learning. I’m headed back out to the pickleball court tomorrow…wish me luck!

      Reply
  • Amy Potts

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    February 15, 2025 1:40 pm

    Thank you for this article! I have recently started to write a picture book when all I have done in the last fifteen years is MG and YA. I am horrible at picture book writing, and it’s kind of exciting to be at the very beginning of the learning curve again. This also reminds me of the very first critique I received for my very first (at least very first that saw the outside of my desk drawer) manuscript. I was at a workshop where we had all received the first twenty pages weeks in advance and, therefore, has ample time to prepare extensive feedback. I was the first person to hear feedback, and the first person to provide it set off on a ten minute list of all the things I needed to fix. I sat and listened and wondered how I was supposed to react. Should I break in with questions? Nod and smile while I planned the complete erasure of all things writing from my computer and a writing journal bonfire? Cry and beg forgiveness for sucking so much? Eventually our moderator broke in and redirected my critique partner to point out some not-absolutely-horrible things about my story, of which she had one: My grammar wasn’t bad. Luckily the remainder of the group had a more strength-opportunities-strength approach to their feedback, which kept me from throwing myself out the window. Anyway, ten years later that first person to give me the laundry list of fixes is actually one of my closest writing partners. I even edited one of her books a few years ago. I know when I need a quick and honest truth, she is the person to go to. She was right all those years ago when I had just started out. Her criticisms were spot on, and as I got to know her that weekend (and in the ten years since) it is abundantly clear her style is to get to the point and don’t sugar coat, which when it comes from a place of true friendship and caring, is a wonderful thing. If I had decided after that first experience that there was no hope for me as a writer (or no reason to keep contact with this person after our workshop), I would have missed out on so much. The next time I stepped out onto the “court” I was more prepared and ready to hear the good with the bad.

    Reply
    • OUCH on that critique, Amy! Especially your first time out. I give you kudos for taking it well, and getting past it with the author who became a friend and trusted crit partner. Those are invaluable, and a good “fit” helps (as does your friendship!), but those critical ones can be tough to process and utilize. As you say, though, it’s helpful to get authentic input on what’s working and what could be strengthened.

      I love that feeling of a fresh challenge, too–stretching myself. Good luck on your picture book!

      Reply
  • Leslie Budewitz

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    February 15, 2025 9:23 pm

    “I have a long history of beating myself up over failure, and learning not to do that is yet another skill it takes practice to master.”
    I so relate to this — and sometimes it’s simply a perceived failure that no one else would see that way.
    I just started taking swimming lessons, at 65. I’d learned as a kid, had an incident with a beaver dam, got afraid. Now we’re going to Hawaii and I want to snorkle and see the pretty fishies, so back in the water I went with a kind, compassionate, firm instructor. Before the first lesson, I had to tell myself not to be hard on myself for not being good at this — that’s why I’m taking lessons.
    I’m not sure how any of it relates to my writing, except that your comment that learning not to be hard on yourself is a skill of its own relates to pretty much everything I do! So — thanks for the reminder!

    Reply
    • “Had an incident with a beaver dam” sounds like a story. 🙂 Good for you for getting back in the water! Anytime I “fail,” I do know enough to realize I need to not quit at that moment, or I’ll never try again. That day on the pickleball court, it was my last game–the one I probably wouldn’t have played if they had had one more player out there and my leaving didn’t mean three people would have to sit out and not play–that I played much better on, and finally helped win a game. If I’d left before that, I think I might have been too stung to try again. Today I played my first game since, and it was probably the best and most intentional game I’ve ever played, as far as placing my shots. Go figure. 🙂

      I think experiences like that do tie into our writing–and everything, really. It’s such a good reminder at what enjoyable experiences and triumphs may await us if we keep at something and don’t give up. Thanks for sharing this!

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