Okay… maybe failure isn’t the best thing, but it’s definitely not the worst! Amy and Cheri discuss the upsides of failure (their second-most-dreaded word) as well as a counter-intuitive perspective on expectations. Want to have a paradigm shift on two of the pitfalls of perfectionism and people-pleasing? Tune in today!



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Recommended Resources



  • Episode #155 Digging Deeper Download — coming soon!


Your Turn

  • What has God been teaching you about failure or through failure?
  • What has God been teaching you about evaluating expectations (others’ or your own)?



Kate Hollimon loves teaching God’s Word.  She delights in helping women grasp and understand the truths of scripture through her clear and practical teaching.

Her goal in ministry is to help women see the Wonder of God’s Word through her bible studies, writing and teaching.

Kate is married to Matthew and together they have two young kiddos – a boy and a girl – and a Golden Retriever named Norman. Connect with Kate thru her website, via Facebook, and on Instagram!


Jennifer Bryant is a Christian blogger and podcaster who lives in the middle of the Pacific Ocean with her husband of 13 years and 2 feisty kids.

She founded Practical Family after coming home from full-time ministry work, as an outlet for creativity and resource for mothers.

Jenn loves to study human behavior and help women to discover their own personality, passion, and purpose.  You can also connect with Jenn on Facebook and Instagram!


Transcript — scroll to read here (or download above)


Grit ‘n’ Grace: Good Girls Breaking Bad Rules

Episode #155: When Failure Becomes the Best Thing Not the Worst


Cheri: So Amy, I want you to explain the title of this episode. Because I love you dearly, you know I try to support you in everything possible, but you have gone too far, my friend. You have gone too far. [Chuckles]


Amy: [Laughs] I know. Listen, I re-read it this morning: When Failure Becomes the Best Thing, Not the Worst. And I was like, “Wait, I wrote this when?”


Cheri: [Splutters] [Laughs]


Amy: I was, like, I wrote this when?And at what time in the evening?” So, listen, I’m with ya. [Chuckles]


Cheri: Okay. All right. So you’re even questioning yourself at this point.


Amy: Yes. Best might have been a little overstatement. [Laughs] Not the worst.


Cheri: Okay.


Amy: Can we land on that?


Cheri: [Music Intro] Well, this is Cheri Gregory—


Amy: And I’m Amy Carroll.


Cheri: —and you’re listening to Grit ‘N’ Grace: Good Girls Breaking Bad Rules. The podcast that equips you to lose who you’re not, love who you are, and live your one life well. Okay, Amy, you posted this beautiful photo on Facebook and Instagram last week. It was you with a long-time friend, right? Somebody you’ve known for quite some time?


Amy: Yes.


Cheri: Okay, so a long-time friend holding a copy of Exhale. I want to know the backstory of that picture because you both were smiling so big.


Amy: Well, it was such an unexpected treat. My mom tells the story and jogs my memory about how I first met Jackie and Rebecca. Jackie is in the picture, but she has an identical twin, Rebecca. We had just moved to Greenville, and they had a sledding hill beside their house.


Cheri: [Gasps]


Amy: So we met when we were four years old—


Cheri: Aww.


Amy: —and I haven’t kept in close touch with Jackie and Rebecca, but you know because of the beauty of Facebook we have kept in loose touch over the years. Through Facebook, I have gotten to follow Jackie’s life and her story and her struggle with cancer.


Cheri: Mmm.


Amy: It has been revolutionary for me, Cheri, and I don’t say that lightly at all. Jackie has been overwhelmingly grateful at every stage.


Cheri: [Murmurs]


Amy: [Pause] She’s lost a lot over the years, and I know she would say the same thing. Her cancer diagnosis came on the heels of losing a job, of a marriage breaking up; it seemed like the worst. But Jackie, because of her gratitude, has just gained a whole new beautiful life. I shared that story in Chapter 9. Cheri, you know that I had a hard time—


Cheri: Oh yeah.


Amy: —because, Chapter 9, I wrote like three or four different endings for that chapter and they were all stinky.


Cheri: [Chuckles]


Amy: Horrible. And then I remembered, “Oh, I know who I need to talk to.” So Jackie’s story is in Chapter 9.


Cheri: Oh, very cool. That was so fun to see her knowing that—because one of the ‘a-ha’s’ you had because you kept trying to find a story of your own that was going to fit the chapter—


Amy: Right.


Cheri: —and when you realized, oh, maybe God was leading you not to have a story of your own, but to share somebody else’s story. Then suddenly you knew exactly what you needed to do. That’s so cool.


Amy: It was amazing. And to get to sit down with her after—we hadn’t seen each other for years in person.


Cheri: Wow.


Amy: We’ve been communicating back and forth. I did the interview on the phone, but it was just such a treat, such a treat. Well, Cheri, I talk about treats. One of the things that we’ve just been kind of blown away by and reveling in, basking in, are the Amazon reviews for Exhale. Tell us about what you’re thinking!


Cheri: Well, you know that I have stayed far, far away because one of the ways I stay kind of—as a recovered, reforming perfectionist—the way I stay in a healthy place is by avoiding too many numbers or too many evaluations. But, I realized that if I don’t look at all, then I’m missing out on the opportunity to be grateful—like you just said—and I realized that if I didn’t look at all, then I wouldn’t get to say thank you to our amazing readers who are reading our book and then taking the time to leave a review. So I wanted to share one that I saw today, and it just made me so excited!


So, she starts out by saying: “I had really been looking forward to reading this book and it did not disappoint.” Now, I don’t know what it says about me that I exhaled a sigh of relief that we didn’t disappoint her [chuckles]—


Amy: Absolutely. [Chuckles]


Cheri: —but then here’s just a few more things that she said. She said, “Doing the right things, but for the wrong reasons is not what we’re made to do. God made us to have a specific purpose and we’re supposed to do that. Even if it means not blending in with what everyone else is doing.” And I thought, “If that’s what she got out of the book—YAY!—because that’s what we were trying to say!


Amy: Yes!


Cheri: And then she said, and I thought this was so good, “I read this over a couple days because it was very good and hard to put down” –and I was like, “Yes! Okay, that was our goal!”—But she said, “I’m going to go back through it again more slowly now to more fully answer the questions at the end of each chapter and to look at the extra content I got from the website.” So I love that she’s kind of doing it in two steps. Kind of the way you and I do life.


Amy: Mmm.


Cheri: Like we’ll listen to an interview, and then we’ll process it together and keep living the examined life. So, I love seeing that in this review.


Amy: So beautiful. Well reading reviews to me is so astounding because, Cheri, both of the times I’ve written a book when you put it out there you think, “Yeah, maybe nobody’s as crazy as I am?”


Cheri: [Laughs]


Amy: [Laughs] “Or maybe nobody needs to change as much as I do?” So if you read the reviews you go, “Whew, I’m not alone.” That’s a good feeling.


Cheri: Absolutely. So you know, we just want to say to you—our listeners and our readers—we are so grateful to you. I can tell you without naming numbers that Exhale has come out of the gate strong, and we cannot wait to tell you more about the small group resources we’ve developed. We’ve got them in our hands, and we’ll be telling you about them in upcoming weeks.


In this episode we’re going to be talking about our least favorite topic—oh wait, we’re not talking about the ‘c-word,’ so maybe this is our second least favorite topic—Failure!


Amy: [Laughs]


Cheri: We’re going to talk about failure and expectations—woo! We’re just going to be more fun than a barrel of monkeys, Amy! [Laughs]


Amy: [Laughs] Oh yes! You guys buckle up. So Chapter 2 is one of your chapters, Cheri, that I just love; the title of it is so great. Even just the title grabbed me from the beginning, it said: You’re Not Exempt From Failure, So Join the Club We’re All Members.


Cheri: [Chuckles]


Amy: And you know there’s just so much grace in that. We’d all like to, especially we reforming perfectionists and people-pleasers, we’d like to deny our humanity. But the truth is that we’re all human and that we have failures and mistakes. One of the things that you talk about in the book that’s so helpful is ‘competent mistakes.’ That was so helpful for me because as a reforming perfectionist I have often put failures and mistakes on the same level as sin.


Cheri: Hmm.


Amy: They’re not actually the same thing at all, so there is something redeemable about failures and mistakes.


Cheri: Absolutely. We’ve talked on the show before about when I went to that leadership conference, and it was an improv jazz quartet and the whole topic was leadership as improv. He talked about ‘competent in mistakes’ in terms of the music that they were performing. He said to them anything that doesn’t go quite as planned isn’t actually an error or a failure, it’s a competent mistake and they just weave it into the music and they roll with it. Instead of what people like you and me do which is go ‘deer-in-the-headlights’ [screams].


Amy: Fall apart. Stop playing. [Chuckles]


Cheri: Fall apart. Years ago when I was touring with students for drama and choir, before we had the ability to easily videotape them, I would tell them, “Guys, if you make a mistake just ignore it. Don’t look at your neighbor. Don’t roll your eyes. Don’t heave a sigh,” and I would get up front and show them what it looks like. And they never believed they were like, “Oh no, you’re exaggerating we never do that.” Finally, once we got video capabilities on our phones and stuff, I would start videotaping them they’re like, “Oh, I look terrible,” and I’m like, “Yeah, the mistake was a tiny blip on the radar. You rolling your eyes, heaving a sigh, looking at your neighbor, and then looking glum for the next ten minutes that became the real mistake.”


Amy: Wow.


Cheri: It is, I think, one of the signs of maturity—and the fact that we are living that life of more gratitude and being led by God—is we’re able to much more quickly, sure, recognize the mistake, pray about it. Is this something that needs contrition and Godly sorrow and repentance? Absolutely. But if it’s not on that end of things, then the ability to quotes “roll with it” and just “weave it on in” and move forward—I’m still talking mostly in theory here, let’s be clear, [chuckles]—


Amy: [Chuckles]


Cheri: —but I can at least imagine it and I see it happening in others and I feel myself being more able to do it myself. So we asked some of our interns, and former interns, a couple of questions for this episode and one of them was: “What has God been teaching you about failure or through failure?” Here’s what speaker and author, Kate Halloman, had to say.

Kate: I have definitely been in the camp of I don’t want to fail, so I won’t even try. But God brought me face to face with this fear recently when I entered into something and it failed, like crash and burned, and failed. It was awful, and it left me wounded and reeling. But in the months since, the shame I felt as a result of that failure forced me to cry out, “Lord, save me.” Much like, Cheri, you described in Chapter 2 of Exhale, when Peter cried out to Jesus, “Lord, save me,” in the midst of his failure.

And here’s something I’ve come to understand about failure. There are some lessons that can only be learned through failure, and as I learned most recently some of the greatest growth comes through our flops and crash and burn moments. For me, I learned more about God’s ability to heal a broken heart than I had ever known in my entire life. It’s those moments where we get to grab hold of Jesus because He’s the one who sustains and heals us. He’s the one who brings beauty out of the ashes of our failure. If we didn’t fail, we’d miss the beauty.


Amy: You know, I love what Kate said about some lessons can only be learned through failure. We can learn through other ways. We can study scripture and live out those truths. We can watch other people’s lives just like what I just described with Jackie watching her life taught me so much.


Cheri: Mmm.


Amy: We can read. We can attend conferences. The list goes on and on, but the truth is we are only human. There are some things we are not going to be able to box out of the school of hard knocks; we can’t completely avoid that. But then I started thinking about that as I was processing and writing that, and I thought, “But maybe we’re not supposed to.” You know one of those scriptural themes woven from the beginning from Genesis to Revelation is suffering.


Cheri: Hmm.


Amy: And humans suffering in this broken world. But our amazing God always teaches us through suffering, and redemption is a big part—Redeemer is a big part of who He is. It’s actually my favorite name of God. There’s no redemption without some failure.


Cheri: As I’m slowly moving out of the black and white thinking of perfectionism I’m starting to really see how labeling something as a failure can actually obscure the truth.


I’m thinking about years and years ago when we took our students on one of these drama and choir tours and we got back, one student—and I’ll just say it: she was like us, she was bossy, she had opinions—but she reported that the entire trip was a complete disaster. Every adult that she could get to listen to her she told all sorts of stories to support this failure label that she was putting on the trip. What struck me as I listened to her was that she wasn’t actually wrong about any of the individual incidents she had strung together, she wasn’t even exaggerating or embellishing like some things had gone wrong on the trip. Like there were no moral failures or big sins that I can remember, but there were parts that were hard.


Here’s what I realized in listening to her: While each of those incidences weren’t—she wasn’t lying, she was also not telling the truth because she was leaving out so many good things that had happened. So her perspective, because it was so skewed, while it was technically accurate it wasn’t actually true.


Amy: Wow.


Cheri: I’m trying to apply that to myself these days, because I’m in the midst of several things that feel like failures right now. And I keep asking myself, “Okay, and what else is also true?” Like, I’m not trying to contradict my concerns or my feelings about what feels like a failure, but by asking what else is also true I’m trying to get that bigger picture. So I’m getting close to something that is a larger truth about the situation, and it’s really helping me not slap that quick ‘failure’ label.


Amy: That is such a helpful tool, Cheri. When we run up against something that feels like failure to ask ourselves one simple question: what else is true?


Cheri: Yes.


Amy: That is—oh!—amazing. So helpful.


Cheri: All right, now speaking of a helpful tool, we are going to talk about expectations and you talk about this in Exhale Chapter 3. You have this amazing metaphor—oh my goodness—and you wrote a fabulous Proverbs 31 devotion about it. We’ll put a link in the show notes because I think everybody should read it. So, talk to us about expectations and share just a little bit about the metaphor.


Amy: Well, years ago I was talking to a friend of mine, I think I used a pseudonym in the chapter [chuckles], but I was talking to a friend of mine about a relationship she had with a close relative that was very difficult, very fraught. This relative had lots and lots of unfair, inappropriate expectations of her. So, emotional stuff was always being shifted to my friend, even scheduling stuff was always being shifted to my friend. One day she shared with me that she had come up with this metaphor, this picture that was really helping her. She said, “You know, my relative, on a regular basis hands me a plate of trash.” [Chuckles] She said, “In the past, I’ve always been like, ‘Oh, thank you for this plate of trash. Of course, I’ll take care of this plate of trash.’”


Cheri: [Chuckles]


Amy: She said that now, “I don’t even receive the plate of trash. I don’t hold out my hands for it and I say, ‘Oh, I’m sorry I don’t think that is my plate of trash.’”


Cheri: [Laughs]


Amy: She said she just allows her relative to handle her own stuff: emotional, scheduling, financial. We all have a list of people who try to put inappropriate expectations on us. That picture has been revolutionary for me because I’ve lived with this overdeveloped sense of responsibility where I thought everything was my responsibility and anything that went wrong was my fault. That is really how I felt, so having that picture from my friend has just been a tremendous help for me.


Cheri: Oh my goodness. Those of us who are these reforming perfectionists, people-pleasers, and highly sensitive—not only are we hyper-aware of others people’s expectations, but then we generate our own expectations for ourselves. We asked this question and Jenn Bryant, of Practical Family, gave us a great response. What has God been teaching you about evaluating expectations whether they’re others or your own?

Jenn: It’s been said that the key to frustration is unmet expectation. God has been teaching me about the expectations that I put on myself as a mother. I expect that I have to teach them everything they need to know to become responsible adults who love Jesus and contribute to this world. When they make mistakes, as we all do, or they don’t seem to get it, I think, “Well, maybe I wasn’t explaining it well enough, or maybe I didn’t follow through well enough.”

My kids are wonderful little people and they are both gifted in their own way by God. The expectation I put on myself is too unrealistic at times. I carry the burden that their outcome depends solely on my input. Realistically though, I can do the best that I can, but I need to do it with the help and the guidance of the Holy Spirit. God promises to be there for me just as He is there with my kids, leading them and loving them and guiding them.

I can’t be everything my kids need, but I can point them to Him. I need to let go of unhealthy expectations of myself and of my kids, and remember the truth that God is here with me, He’s here with my kids, and it’s His life and His love and His promises that will ring in their hearts. That is hopeful expectation. When I share my own testimony of how much I need Jesus every day and the grace he gives me in return, my kids can hopefully and joyfully expect good things from God, even when life is frustrating.


Amy: Well, can I just say that Jenn’s concept of hopeful expectations, expectations based on God’s promises, that idea has rocked my world today. It really, really has. I have never, I have kind of come to think of expectations as something heavy and hard and not good. We talk about in the book that there are appropriate expectations and there are inappropriate expectations, but Jenn just added this whole new layer to my thought process of hopeful expectations and those are not only things that are only good, but they’re things we should have based on God’s promises; it’s an aspect of faith.


Cheri: Let’s go straight to our scripture for this episode because you found a scripture that so beautifully anchors that concept.


Amy: So it’s Psalm 25:3a: “No one who hopes in you will ever be put to shame.” I was so excited to find that because it combines this idea of expectations and also the shame of failure. That if we hope in God, we’ll never be put to shame.


Cheri: So what’s the bad rule that we’re breaking with this episode?


Amy: These are directly from Exhale today: My failures are the worst thing in the world—is the bad rule.


Cheri: And I believed that for forty-five years.


Amy: Mmm. It’s a hard one to get rid of, but the truth is: God uses my failures to help me grow.


Cheri: And I can say that at fifty-two I not only intellectually believe that, but I am learning to really bridge that gap between the head and the heart, and feel that it is true, and experience it as true.


So for me the grit in all of this is: remembering to ask that question. When I feel like something is a failure: “And what else is also true?” What is the grace piece for you?


Amy: Well, it goes back to the Jenn’s point about hope-filled expectations. I can relax about expectations if they’re created on the foundations of God’s promises. So I loved, all the sudden I realized, oh, expectations and the word expectantly are related to each other—and I can wait expectantly for God’s promises because He is faithful.


Cheri: Oh, that’s such a beautiful way to redeem the word expectation.


Amy: Yeah!


Cheri: We hope you’ve enjoyed episode number 155 of Grit ‘N’ Grace: Good Girls Breaking Bad Rules.


Amy: Make sure to join us at the website today, gritngracegirls.com/episode155. There you’ll find our transcript and this week’s digging deeper download.


Cheri: If you’ve enjoyed this episode of Grit ‘N’ Grace, we would love for you to leave us a review. If you go to gritngracegirls.com/review you’ll find all the instructions that you need, you’ll find a link, and you’ll even find a little video showing you how to do it.


Amy: And if you’ve read our new book Exhale, we would love it for you to leave a review on Amazon or Goodreads, too.


Cheri: For today: grow your grit, embrace God’s grace. And when you run across a bad rule? You know what to do. Go right on ahead and break it.


Amy ‘n’ Cheri: Break it!



Cheri: You’re looking awfully cute in that pink and that cold-shoulder by the way. That looks really good.


Amy: Thank you. I’m trying to… Barry has had an indescribable few weeks, and I was like, well, at least his wife could take a shower today.


Cheri: I just love that you have such high standards.




I was like I’m going to talk to Amy. I am going to at least comb my hair.




Amy: I did not take a shower yesterday though, literally. That’s not good two days in a row.


Cheri: Hey, no judgment here. Well, actually, you know what I can’t live without a shower. When authors are like, “I haven’t showered in for three weeks and my book is done.” I’m like, “Eww, I do not want to read that book, at least, I don’t want to touch that book.”




Take-Away for Today:

God uses my failures to help me grow..



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