
With Jen Hatmaker
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Today's episode is sponsored in part by Mercury, Morgan Stanley Skims and Bol and Branch. Mercury streamlines your banking and finances in one place so you can focus on growing your online business. Visit mercury.com to apply online in 10 minutes. Listen to Candid conversations about people's fears and hopes around money on what Should I Do with My Money? From Morgan Stanley? Search for what Should I Do with My Money? In your podcast player now. I've been a skims fan for years and the Fits Everybody collection is a favorite I keep reaching for. Shop the Skims Fits everybody collection@skims.com Golddigger start building your sanctuary of comfort this fall with bowl and branch. For a limited time, get 20% off your first set of sheets, plus free shipping@bolandbranch.com Golddigger as always, you can find all of our amazing deals in the show notes. Now let's dive in. This episode is supported by what Should I Do with My Money? From Morgan Stanley? This podcast makes getting advice about your money less intimidating. I checked out the episode about early retirement on what Should I Do with My Money and honestly, I couldn't stop nodding along. It really got me thinking about what financial freedom actually looks like. Whether that's being able to take time off without panicking, switching careers, or just having enough saved that you're not constantly stressed about money. The fear of never having enough while still wanting to actually enjoy life. I think we've all been there. Maybe you're wondering if you can ever get ahead, or if building any kind of financial cushion is even possible with everything else going on. What I loved was hearing about how you can build flexibility into your finances with smart investing and planning. No matter where you're starting from, it made financial freedom feel less like some impossible dream and more like something you can work towards step by step. Search for what Should I Do with My Money? In your podcast player and we'll also include a link in the show notes. My thanks to what Should I Do with My Money And Morgan Stanley for their support.
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When your instincts are saying, hey, I'm noticing this part of your work no longer brings you any joy at all. Or this part of your work used to feel really vibrant, but because your life has changed, it has run its course. It is now like a burden instead of a joy. You can trust yourself.
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I'm Jenna Kutcher and I help you trade hustle for purpose and build a business that gives you the life you actually want to live. From a $300 Craigslist camera to a seven figure business I run from home. I've learned that success isn't just about what you do. It's about how you live. Here you'll get strategies that work, systems that give you your time back, and steps that turn your effort into results and impact. If you're ready for clarity, confidence, and a business that feel as good as it looks, you're in the right place. This is the Gold Digger podcast. What happens when the life you built, personally or professionally, no longer fits who you're becoming? If you've ever looked at your business, your brand, even your personal relationships and thought this used to feel right, but now I'm not so sure. Well, you're not alone and you are definitely not broken. Today's guest, My friend Jen Hatmaker is no stranger to the hard and the holy work of reinvention. She's a bestselling author of 14 books, including four New York Times bestsellers, the host of an award winning for the Love podcast, and a beloved leader to a community of over 1.6 million. But let me tell you, her newest book, awake, isn't about business strategy. It's about what happens when your identity, your roles and your life fall apart and and how to rebuild from a more honest, more aligned place. I was a very lucky recipient of what she calls a bootlegged copy of the book. I got it months and months ago and let me tell you, I ate this book up. I would read parts of it to Drew. I would text Jen every single day about what was aligning me with this book. And while our stories are so different, this book holds so much relatability. It's unlike anything I've read in a very long time. So today, Jen is going to walk us through what she calls a midlife renaissance, not a crisis. And we are talking about being in a powerful season of reassessing basically everything you've been told about womanhood, about work, about hustle, about success, about your worth, and then reimagining a life in a business that actually feels like you. If you are an entrepreneur navigating change, if you are pivoting your purpose, if you are wondering what stays, what goes in this next chapter, this one's for you. Jen Hatmaker. Welcome back to the Gold Digger podcast. Okay, Jen, for the woman listening who has built something meaningful, maybe it's a business, maybe it's a platform, maybe it's a brand. But they feel like they've changed and whatever they built, it doesn't fit any longer. What is your message to her about staying versus Starting over.
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Oh, wow, I love that question. I'm someone who started my career in one zip code, and I have meandered and added and subtracted and expanded and in other places, trunk so much over the last 15 years. And I don't know that a lot of people talk about that, like, what happens. Because to be fair, my earliest business model was successful. I, I came up through a space where I had a lot of traction and a lot of momentum and a lot of favor, and I. I was having a lot of what would be considered commercial success there. And that was sort of in evangelical, like, women's subculture. That was where I began. And so I 100% have changed as a human and evolved as a person of faith around what I believe, what I care about, where I want to spend my time and energy. And that had massive impact on my career. And so I think what I would say to those women who were like, I'm not the same woman that started this space eight years ago or whatever it is for them, I have discovered I no longer want to do this portion of my business, but I really love this portion. I'd rather steer that direction. There's a million ways that we can evolve and change inside of our work. But I think the primary thing if I wanted to bring her all the way back to the absolute starting line of change or evolution, is that whatever your instincts are telling you, when your instincts are saying, hey, I'm noticing this part of your work no longer brings you any joy at all, or this part of your work used to feel really vibrant, but because your life has changed, it has run its course, it is now like a burden instead of a joy. If your instincts are saying, I didn't know about this new thing eight years ago, but I know about it now, and I would rather spend more energy here, you can trust yourself.
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Yes.
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Now, that is not to say that whatever the subsequent actions and follow up will be are not disruptive, because they probably will be. I'm not saying that's an easy path to say I need to make a change inside my work or inside my career or inside my trajectory. But you know what you know, you know what you want, you know where you're at, you know which part of your business now feels out of alignment with your integrity. You know it. So trust yourself that you know what you know, that your wisdom is telling you something on purpose and that she can be trusted. I have never been led poorly by my own intuition, ever. Now were some hard choices in front of that, for sure. And some loss and some risk and all that. But you're not wrong about you. You're not wrong about your work, you're not wrong about your career. So put your chips on you and move in that direction. That's my best advice. Okay.
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I am obsessed with this. I am in a season of that right now again of like, re listening and like, what no longer fits even if it's successful. Right. I actually write team. The other day, I have this vision of myself putting a book on the shelf and I might revisit that book someday, or I might just look at the shelf and be like, that was a good one. And I know, I feel like it's interesting because as you were speaking, Jen, I think that so many entrepreneurs let their intuition guide them into the business, but once they create something or they see some semblance of success, it's like that piece of. You kind of get shut off and you start listening to even people like me or like everyone that knows everything else. Because all of a sudden, you know, you're like, I don't know anything about doing this. And it's like, how do we turn that back up? Let's talk about that. Because actually I was laughing, but I have a, like a. How do you consider this? Like, it looks.
B
It looks like you have a bootleg copy.
A
Yeah, I have a bootleg copy of your book. It's the best bootleg copy of the book ever with my kids own little bookmarks in it. And you talk about embodiment and you talk about like learning how to trust yourself again or how to almost like turn the volume back up into your inner knowing. And so how did you discover that? How did you even learn that you had maybe muted yourself in parts that you weren't paying attention to?
B
Boy, it's such a huge question. So for me, I'd have to go back earlier in my story and go to the root cause of who told me I was not trustworthy, who taught me that I could not listen to my own wisdom, who. So although I kind of came up through a niche culture which was kind of like a conservative church space, I don't think it is just exclusive to that community. I think a lot of young girls, but me, particularly in my space, I was told from the earliest that I can remember that my body was a bit of a problem. Now, I got that message in a thousand ways. All of us did. Every. If you're a living woman, you got that message that our bodies were a problem. So I learned that my body was a Problem sexually, for sure. Yeah. I came up through purity culture, which.
A
Meant I texted you after reading that your chapter about true love weights. And I said, jen, I had a ring that said, true love waits on my wedding finger.
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That's right.
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I remember. I was there. I was there with you. So, yes, I know exactly what you're talking about.
B
That, like culture, it almost just idolizes, like, virginity for girls. For girls, let's be clear. And this sort of idea of sexual purity, which has been so bastardized, frankly. And so I was taught my body is a problem. I am deviant for having any sort of sexual impulses, desires, just like a normal person would and does. That's how we're made. But then I was so I was in charge of my own pure sexuality, but I was also in charge of all the boys. Because depending on how I looked, depending on what I was wearing, depending on how I was carrying myself, I was a real problem for them. And that was my responsibility, not theirs, I guess. And so. So on one hand, I had this like, whoa, your body is a. It needs to be policed, and it is dangerous, and it is the source of a lot of sin. And something about your body is bad. Message received. I got that. So bad. And then, of course, we get this ancillary mainstream message. And I won't belabor the point. So much ink has been spilled, but about how our bodies look and how they're supposed to look and what is beautiful and what is pretty. And by the way, that's a shifting target. Just pick a different decade. And that has changed.
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Yes.
B
And so how we are supposed to look, to attract the male gaze, to have success. And frankly, the. The deeper message is more insidious, how we're supposed to look so we can finally be happy. I took that hook, line and sinker. If I can get to this weight, go. God, I will just finally be happy all the time like I've been wishing to be. And so I learned early on, there's nothing good in here. And then you add this faith layer that says whatever it is that I want my desires, something about those are highly suspect. I am not a trustworthy narrator in my own life.
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Life.
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If I want something, it's probably selfish. And so I learned early on to outsource all authority. I had no personal authority in my own life. I was not trustworthy enough. I was not reliable enough. And so I handed that to everybody else. You guys tell me what to do. You guys tell me what to believe. You tell me how to act and who I am. And so that is a very hard reversal. That is a very, very hard reversal. And I'm still working. I'm 51 years old. I do not have this reversed. I have a lot of it reversed. But that voice still creeps in all the time that we are whatever it is we want, think or need, it's got a question mark attached to it. And so I think it's the work of our generation to change that narrative. And I see that happening. You know, I've got a 25 year old daughter. I have a 19 year old daughter. They're different. They're different. They're coming up different. It's a wonder to watch, like, the way they are with their friends, the way they feel about their bodies, the way that they feel about how they look, who they are, who's in charge of them. Subplot. They're in charge of them. Spoiler alert. They're in charge of them. And they know it. It's amazing. I think this work is slow and laborious, but I do see it having its effect.
A
Yeah, I love that. And I mean, I even see it with my kids who are so young, right? Like six and three. And today they were talking about my little one was like, got to get that protein in. Like, as in we're looking at food as like, how are we fueling our bodies? And like, do you know what I mean? And it's like growing up in the I can't believe it's not butter era of things. It's like, girl, you slather that butter on that bread and you eat that, like, that is fuel. And so it is. It's beautiful. And it's hard work, but I think it's interesting. And honestly, I think your book is so fun because as I was reading it, I would, like, read bits of it out loud to Drew, because you're so funny. And there were so many, like, instances where I'm like, oh, my gosh. But the thing that I think was so pure in it is, like, whether anyone has been through an experience that you have, which really, the book starts at the crux of, like, infidelity and that you go back to, to you as a child. And it's like any woman reading this, no matter if you are a woman of faith, if you've been through infidelity, anything, there are pieces of your existence that you see. And I think it's interesting to think about how we have lost our connection with ourselves. And again, how our eyes are, like, not going inward. We're looking out like, yes. Is this good? Is this right? Is this good? I just the other day in therapy, I was talking to my therapist, and I'm like, I am a glutton for punishment in the sense of if I am good at something and I've been told I'm good at something, I'll keep doing it even if I don't like it. Like, I. I was a collegiate diver, and I hate being wet every single day. I got into a pool, a freezing cold pool. I was telling my kids about it the other day, and I'm like, it was so cold. It was the middle of Wisconsin winters. It was freezing. I hate being wet. Nowadays. My kids are like, mom, why aren't you in the pool? And I'm like, I was in a pool for an entire decade of my life. I hate being wet, but I was really good at it. Right? And so it's just interesting to see, like, well, where do we stop listening to ourselves? And, like, where do we stop trusting ourselves? And I think it's a little bit. So one of the things that I think is really interesting and knowing you personally, I want to go deep on this is. I mean, your life literally crumbled. I met you in the aftermath. That's right there, eating a cookie, looking out at Lake Superior, and I want to know, after everything kind of crumbled for you, how did you know what part of, like, Jen Hatmaker, the brand, not just the person, was actually who you truly are versus who you performed as a diver? I was a performer. There's an aspect of that when you are your own personal brand. And so how were you able to separate real life from the role you had been playing.
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For a while? There was. I didn't have to be, like, cognitively aware of that distinction because everything was so busted. Yeah, everything was so shattered. There was no sorting out of the rubble at that point. It was all rubble. And I. I couldn't have even had the wherewithal to go, this rock, this crumbled rock is a keeper. This one is a go. It was just. It was all chaos, all trauma. Everything was frozen. And so emerging from that was really an interesting process and some of the requirements of becoming a single, absolutely independent adult at age 46, having been married at 19. So when I say that, that was a new experience. I'd never even. I was a literal teenage bride. So I. I had never had a moment of independence in my functional adulthood. And so, to some degree, coming out of that, going, wow, I am now in charge of my whole life. By myself, I do not have a safety net. I do not have a partner. The buck stops here. And so that caused me to take a really hard look at everything. What am I building? What, what matters to me? What, what needs to go, what needs to stay. And some of that, to your question, and I hate this word. I'm using it because it's such a shorthand to get there. Yeah. But then there's this question of what about, you know, like, that's. Yeah. Or what's, what's the. What is it? Yeah. What. Who am I? Yeah, like, who am I now? Because I had spent, I mean, I've been in the public space like leading women for over 15 years. It's a long time, almost 20. And I had spent, among other things, plenty of time talking about marriage and family.
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Yep.
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As something I always counted on, I. There is no amount of money I would not have put on the square that said, we're going the distance. We're going to be one of those 65 year couples. We are, we're going. We got the long game in hand. I had so much faith in our story and in our marriage. And so having lost that, it was interesting for me to kind of look around with clear eyes at my community and go, well, have I lost my credibility with every. Have I lost my credibility with. You have. Is this a deal breaker for my leadership in my own world? What. Who am I now? And it was really interesting to have my community be a very, very generous and clear mirror to who I am. It seemed foggy for me for a while because everything was. I mean, also, when have I not been a wife? How am I not a wife anymore? Like, I'm not a daughter in law anymore. I'm not a sister in law. Like, I'm not married. I, I mean, it was really hazy for me. And so it was interesting for my community to reflect back to me, hey, okay, you're not a wife anymore. Here's what we see in you still. Here's what we love you about you still. Here's who we see you to be still. This is the character of you that seems evident that was so incredibly anchoring and useful when I was still like clawing my way up to the surface. And so I am actually so grateful for that now. It's been five years and I can now see how much of the outer part of me, that outer optical part of me is just gone. Just absolutely gone as evidence. Because, Jenna, you have read it. The shit I say in this book is bananas. Like, I would have never before admitted some of the stuff I admit. Copped some of the things I copped to, Examined my interior life with such a fine tooth comb.
A
I mean, it's a woman who's been through things. Because when you've been through things and you survive them, you're like, ain't nothing gonna take me down. Right. Like, what else can I lose? Yes.
B
What else can I lose? I've already lost what I thought was the most precious thing to me.
A
Yes.
B
And so I see that that outward polished version of me, which, to your point, is what? Anybody who has a public job has a version of that.
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Yes.
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To whatever varying degree. But that part for me has. The shine is off the penny for sure. And it feels like a relief to me. Feels like a real relief. I wrote a piece just this week for, like, my community where I was like, look, I'm kind of trash in a lot of ways. I'm like, I'm not as good as I want to be. I'm not as good as I've pretended to be. I'm okay. I'm like, I'm all right. I'm medium at best. And it feels just so good to live in what is a undeniable truth of being a normal person in normal ways. And so, anyway, we'll see how that goes. I. I love it. Apparently, I'm not afraid to say almost anything anymore.
A
You know, I only share stuff I'm genuinely obsessed with. And so when I kept seeing bowling brand sheets all over Instagram, I was like, okay, are these actually worth the hype? Drew and I have been using their sheets and duvets for over a year now, and honestly, our bedroom feels like a completely different space. Space. The moment you touch these sheets, you'll get it. They're incredibly soft to start, but they literally get softer every time you wash them. They're made from 100% organic cotton, so they're super durable. And they're breathable, which is perfect for piling on cozy layers without turning into a furnace at 2am this is hands down the best bedding I've slept on, and I am so genuinely excited for you to try it. Start building your sanctuary of comfort this fall with bowl and Branch. For a limited time, get 20% off your first set of sheets, plus free shipping@bollandbranch.com gold digger. That's bowl and Branch. B O L L a n d branch.com Gold Digger to save 20% and unlock free shipping, exclusions apply. When we were young, we dreamed of castles in Fairy tales. And as we grow up, those dreams might shift into building something real. Like starting a business. You need a website, payment systems, a logo and a way to reach customers. It can all be overwhelming and confusing. But thankfully that's where today's sponsor Shopify comes in. Shopify powers millions of businesses around the world and 10% of all US E commerce. From big brands to folks just getting started. They offer beautiful ready to go website templates so you don't need design skills to look professional. Their AI tools help with product images, descriptions, detail, discount codes and more. Shopify also makes it simple to run email and social campaigns so people can find you. And if you ever feel stuck, their award winning 247 support is always available. Turn those dreams into and give them the best shot at success with Shopify. Sign up for your $1 per month trial and start selling today@shopify.com Golddigger. Go to shopify.com Golddigger shopify.com Golddigger well, you know, I think it's interesting as you're talking, it makes me reflect on how as entrepreneurs and stuff, a lot of times the brands start as being incredibly relatable. And as you put yourself out there, people try to box you back up and remind you to like stay in your lane, stay in your space. And all of a sudden the version of you that's being presented to the world, world is the polished version, right? It is the shiniest bits of it because people are like, no, don't talk about that. You, you, you're a business person, don't talk about body image, you're this, don't talk about that. And so all of a sudden it's like the package on the stage is a manufactured based off of criticism of strangers where again, it's the world telling you get back in your lane, get back in your lane. You're not meant to be over there. And I feel like sometimes when you lose it all or you've been through something, you kind of are like, screw this, this is, this is not it. This is not me. This is not it. And like I'm willing to risk it. Because you've risked it all many times before, right? And so it just makes me ponder for somebody listening to this who is building something that is tied to you as a person. Like how do you invite the whole person in, right? Not just the parts of you, like not the palatable pieces, but like the whole existence. Because either you have to create insane boundaries around where the brand starts and stops and where the human life begins. Or you've got to figure out a way to be the whole messy, beautiful person and not care about what is thrown your way and not let that alter you. And I don't. I mean, I don't know if that's possible.
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What could go wrong, Right? That seems easy, right? What an easy needle of thread, right?
A
I mean, hey, it's. It's crazy on this topic. One of the things that I think is really interesting, and I actually was having a conversation right before I hopped down with you, that made me think, I have to ask Jen this. One of my dear friends was telling me, you know, I feel like I'm aging out. I feel like I am irrelevant. There are young people popping up every free day, and they've got the language, the cool thing. And one thing that I think you have done really beautifully is, like, you've looked in the mirror of what is aging gracefully, specifically in the public eye, but also with, like, what you've built. And you kind of basically said, screw it. And you've reinvented yourself, your life, your career, the way you write at 50. So tell us why the pressure to maintain consistency or to stay palatable is kind of a weapon used to keep us small?
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Well, first of all, there is a secret that I have discovered because I'm older than you. And so there's no way to discover the secret except to get there, which is that the fallacy of getting older equals irrelevance in any way. The way that we look, where we are located, inside our particular business or, like, career space. What pick a thing is, oh, my God, that's a big lie. Because guess what? Me and all my friends, we're 50. We're in our 50s. We're up here at this. My. A lot of my mentors are north of me, and I was like, oh, guess what? We get better. We are better. We get better the older we get. We are smarter, we are wiser, we are better leaders, we are better partners, we are better builders. We are way more in tune with our own integrity. We are less afraid of change or risk or loss. We are less afraid to disappoint other people. So that is a story that has been told to. To young women in order to keep them in line, in order to keep them small. But the truth is our best days are ahead of us. And so that does not mean that what we cannot do is look at the next generation coming up, doing that, building their little dreams just like we did, and imagine that that is a threat to us. That is such Small thinking that is patriarchal thinking, that there's only so many seats at the female table, and when the young girls start pulling up their chairs, we're effed. It is not true. It's just not true. It's not functionally true. And so we need that because they're coming up with innovation and energy. They've got the energy of youth.
A
Vitality.
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Bless. Bring your fresh energy into the room, please. But what we have, because our seats are still at the table.
A
Yes.
B
Is we've got the leadership acumen. We have the experience. We have the generosity of spirit, hopefully that wisdom has given us, having led and lived this long. And so I just don't find it true at all. And even in my life, in best practices, I am going to women ahead of me going, is there any way that you could speak to me for 10 minutes about what you know about this thing? Like, I need somebody to tell me something. And then, boom. The most brilliant thing you've ever heard. And so I kind of reject. I reject the message. I reject the message that we are irrelevant simply because there's a next generation coming up. Yeah. They will add to what we have built, but we are not done building. And so I just turned 51. It's so awesome here. And so now when women ahead of me tell me, hey, Jen, wait till your 60s.
A
You're like, all right.
B
I'm like, I believe you. I absolutely believe you. Now, like, I think you're telling me the truth. I think that women in midlife and north of midlife are the shit. And so we'll only be irrelevant if we take ourselves away from the table. So that's up to us.
A
Yes. Oh, I couldn't agree more. And I. I was recently on a trip, and there's one woman who's about a decade ahead of me and one woman who's two decades ahead of me.
B
Yeah. Yeah.
A
And like, I am just eating it up. Like. Like, let me just sit at your table and hear all the things you've learned and let. Like, it's just like, wow, it is so nourishing. And it's funny. My husband is on a bocce ball league with my dad and my grandpa. Blessed.
B
Very cute.
A
So Minnesota.
B
Very cute.
A
And my brother and brother in law. And so every week they would play bocce ball, and then they would go to this bar called T Bones, which is exactly what you would imagine. And Drew was like. He just said. He's like, I just, like, sit there. I don't say anything because, like, my Grandpa and his brother and my dad are just like, reliving so much and have so many stories. And I'm like, we don't do this enough. We don't put ourselves with other generations enough and just sit like, shut up. We don't know it all. They, you know, like. And so it's just. Oh, I just. I think it's like, I love that.
B
I wish I could be at that table with those men and just hear whatever it is they're yammering about. I want to know.
A
I don't want to save. I'm like, oh, it's so good.
B
So good.
A
So one thing that this. I mean, I've read your books. This book is so different.
B
Yeah.
A
Awake is like a whole new, spicy take. And one of the things I love about this book is I feel like for so many of us, we have been wired in this, like, show and tell way. Right? So it's like, let me show you this thing and then let me tell you what I learned from it. Or, like, what totally get out of it. Right. Which is a beautiful way to lead. This book is not that.
B
That's right.
A
This book is like, I'm going to tell you my thing and, like, the world will show you what you need to see in it or the world, like, it will be revealed.
B
And so a great way to put it.
A
I want to talk about authenticity because I feel like you have been authentic to your ability and to what you've known to be true at every step. Right. But this is a whole different gen, writing this book. And I want to talk about the cost of it because I think that it is risky. Right. This book probably feels a little scarier to put out into the world than your other ones because they were a little more palatable, they were a little more expected. Not that they weren't great.
B
They were just what we're 100, right?
A
What business opportunities or even, like, relationships did you stand to lose by being dishonest? Like, what were you thinking about when this copy got sent out? Because this is when it really becomes real, when it comes out of the Google Doc and it goes out into the world. What were you thinking about?
B
I feel like I lost sleep for one year over this. And I'm not being hyperbolic. I. To your first point, I just have never written like this. It's. I've always written in a very prescriptive way. Like, this is an idea. I have, like, worked it down to its bones. I will tell you all my conclusions. I will hand that to you. As a reader. And now, you know, I've done all the work for us. This is what we think of this. This is our conclusion about this idea. Just, it's done. And everything's in hindsight. Everything is commentary. Everything is distilled down to what I think is the. So this is zero prescription. It's. It's not in chapters, you know, it's written in memories. It's vignettes. So I started looking at all these little tiny moments and memories of my life spanning 40 plus years, going. I think a lot of these are connected. I think this experience that I had in fourth grade is somehow connected to the way I feel about my body in my 40s. Yes. And so I just put those on the page. And to your point, then it's the readers. You are going to have to take from this, what you need, what you conclude, how you evaluate this, how this applies to your life. That is so different from. I've never trusted my readers like that. I've always wanted to lead the Witness stronger than that because I'm so over con. I'm so over attached to people's perception of me and their. Their opinion of me. And so I never wanted to leave too much up to the reader, because what if you get it wrong? Right? What if you misinterpret what I meant or what I wanted you to think or what I concluded? So I just. I kept that so tight that there was really nowhere to go. So this is so different than that in every possible way. And, I mean, I don't think it's, like, surprising to say that in a memoir that includes the story of my divorce, the loss of a marriage that was 26 years long. I mean, our whole adult life. There are some relationships here in this suit pot that are challenging and have been challenging even before this book is coming out. Like, what does it look like when you're divorced? What about that family on the other side that you were a part of for all those years? What does that mean? What is. Where's the handbook for this? And I remember really early on, a really good friend of mine who had got divorced a handful of years ahead of me. Early, early, early in my divorce story, I remember just trying to hold all the threads of my family together. The one that I came from, my original family, the one I married into. Everybody, like, somehow we're gonna keep this ship afloat. Like, even if us. The marriage right in the middle of all this is over. And I remember her saying I was just like, we love each other. That's been like a second set of parents. That is. She said, I know you mean that, and I know that you're sincere and I know that you love them and I know that they love you, but I want you to be prepared that those relationships are not going to stay the same. And I was like, no, I think ours will. I think ours will. I. I think we'll be able to do it. We were not able to do it. And so I say in a wake, divorce breaks a million hearts. And that includes our families, our parents, everybody who used to be a brother or a sister in law and is no longer. It includes our friend group. You know, we were just smack in the middle of a whole friend group. What do you do there? The friend group got divorced. Right. Like, and so I was so mindful of this. This question that you're so mindful of it.
A
Yeah.
B
Of wanting to be careful and generous in this book so that I was not just going to torpedo whatever relationships I have around this story. The question that I asked myself, Jenna, I asked myself this over and over and over because I was thinking what you were asking the whole time, always, always was, will I be proud of this in five years? Will I be proud of this whole book? And then I got more granular. Will I be proud of this memory that I'm deciding to include? Will I be proud of this paragraph? I got down to the nitty gritty. Will I be proud of this sentence? And when I tell you that kept me deleting things, because these are people. This is our actual life. This isn't just a book on a shelf like this. This is our real family. It's our real life. And so I hope that I have been compassionate. I hope that I have been self aware and that I did not just default to a victim villain trope. And I hope that I had my eye on the long game here. That however, this book will come and go, all books do. But we still have a long road in front of us that's going to involve graduations, marriages, grandbabies. I care about that. And I have to care about that. Yeah.
A
This podcast is brought to you by Mercury Banking that helps entrepreneurs do more with their money. Okay. I remember in the early days of my entrepreneurship journey, clients would literally mail me checks and then I would have to drive all the way to the bank to deposit them. It took me literal years to make things go digital. And I am ashamed to admit I still have a filing cabinet with paper contracts because I'm way too afraid to throw them away. But that's the beauty of growth, right? Like you learn what systems serve you and which ones hold you back. Mercury is one of those systems that just works where traditional banking websites and apps are clunky and hard to use, Mercury is meticulously designed to make doing just about anything with your money feel effortless. And the best part is it flexes to fit all types of businesses. Ready to see what powerful banking can do for your business? Visit mercury.com to apply in minutes. Mercury is a financial technology company, not a bank. For important details, check the show Notes okay, can we talk about bras for a second? Because honestly, for the longest time I just accepted that being uncomfortable was just a part of being a woman. Like those underwire digs, the straps that leave marks on your shoulders. Spending half of your day readjusting everything. I thought that was just life. But then I kept hearing about the Skims Fits Everybody collection everywhere and I finally gave in and I tried it and I totally get the hype now. The fabric is ridiculously soft and stretchy, but not in that cheap way where it loses its shape. It literally feels like it was made for your body specifically. And I'm not even kidding when I say I forget I'm wearing anything half the time. It is one of those things where you don't realize how uncomfortable you've been until you finally experience what comfortable actually feels like. Now trust me on this one. You just need to try it. Shop Skims Fits Everybody collection@skims.com Once you place your order, make sure to let them know we sent you. Just select podcast in the survey and choose the Gold Digger podcast in the drop down menu that follows. One of our favorite ways of earning extra income as a couple has been by hosting our spaces on Airbnb. Drew and I have always loved finding creative ways to make our spaces work for us, but let's be real. Between being parents, running a business and juggling travel, we don't always have the time to manage all the little detail details. On top of that, we live in Minnesota and our properties are in a different state, so handling the day to day just isn't possible for us as hosts. That's why I think Airbnb's co host network is such a smart option. With the co host network you can hire a high quality local co host to take care of your home and your guests. They handle all the day to day management from guest communication to on the ground support so the stay runs smoothly even when you're away for work or traveling. Think of them as your local hosting superhero who knows the ins and the outs of creating amazing guest experiences. If you've ever thought about hosting, but it seemed a bit overwhelming, now it is easier than ever. Find a co host@airbnb.com host. I love that. I think so many entrepreneurs, there are pieces of their story that, I mean, entrepreneurs are often people that have had chaos in their life at some sort and that want control and they're crazy enough to believe that they can get it. There's rude crazy stat, right. Of, like, people that go into this, like, are people that generally come from chaos. And it's so interesting. I think it's really interesting when it comes to our stories. I know. Even myself, like, I remember Bob Goff saying this line once of, you know, no matter what you share about somebody else, it's. It's almost like a group photo. They're going to zoom in and just look at themselves. Do I look good?
B
Oh, that's a great metaphor.
A
Yes. And I would when I heard that. It's so true. Right. Like, you could have a group photo. You've seen it all the time. People post group photos. Other people's eyes are closed, but they look great. Right. And when it comes to whether you're writing a book or you're sharing a story of your past or you're talking about your childhood or whatever, the people in your life are zooming in on themselves. Do I look good? And it can be a predicament when you're a creator and you have something to say. Right. Because.
B
Right.
A
You're trying to share your story, but there are always going to be people on the fringe. There's always going to be people in the arena judging. There's always going to be people in the nosebleed section that have thoughts. And so it's like how it's. It's just this interesting predicament that you don't necessarily find yourself in. If you're in a 9 to 5, you can clock in, you can clock out. It's a good day. And so I just think that it's interesting to consider. I love the long game. Thought of, like, what does this really look like? Not right now. What will sell the most books? What will get the most curiosity? What's the clickbait that will get people to do it? But also, like, can I sit with this in five years and feel right about how I presented? I just. I think that's really good.
B
Yeah. Yeah, that's right. I think that is why I'm so glad I did not write this three years ago. That there's a critique out there. I mean, isn't there always? Yeah. Yeah. But like, why. Why write about this five years later? Why dredge up this story when now you're like, happy and recovered? And I'm like, that's. I don't like the question. Yeah. That we can only tell our own stories of loss or suffering when we're still hurting. That it has, like, a shelf life.
A
Yeah.
B
Frankly, that is not the time to tell it. No, that is. You are writing from a wound.
A
Yes.
B
And it shows. Some of it. Some of you guys are writing from a wound and it shows. Yes. Like, that you just sacrifice your own, like, discernment. Yeah. When you decide to write, still broken. And so to me, there is a sense of clarity, a sense of self honesty that I probably would not have been able to access too early in my story. I was too hurt and I was still wanting somebody else to tell me, none of this is your fault. You have been harmed. You are innocent. And so I think that there is a place to give yourself the benefit of time, the advantage of time to settle into your own story, to settle into your own complicity, to settle into your own integrity. And to me, that is wise writing. I have learned this the wrong way because the Internet has Provided for me 15 years of opportunities to come in with my hair on fire about something. A hair on fire. Because it just happened. And I have not given myself time to process, research, think, evaluate, analyze, nothing. And I take my little fingers to my little laptop and I fire off a hot take. The amount of times I have regretted that is infinite. Even two days later, I can go, ooh. Oh, okay. Woo. That was. No, that was not it. And so I have done this so poorly, so many times because the Internet gives us this option to just like, absolutely, like, go into the stratosphere.
A
Yes.
B
So quickly.
A
It's like the reaction versus the reflection.
B
Right, Exactly.
A
It's like the Internet is like just waiting for you to be set off and react.
B
That's right.
A
With zero reflection. And I 0 argue. It's. It's not helpful. It's not helpful for us. It's not helpful for other people. Right.
B
Because.
A
Because that's. Oh, it's just. It's so true. And I. I was telling you right before we got on, you know, when you have sat with something long enough to feel like you can hold space for it and also, like, see it from the bird's eye view, it's a very different experience than when you're in the dredges of it. And, you know, I was telling you when I went through my miscarriages, I, like, put them out. It was the reaction. It was literally like the day I found out, here it is Internet. Like, what is. And if somebody came up to me, which this happened in the grocery store, and started telling me their own story, I had zero space and capacity to hold anything other than my grief at the time. Right. And so it's. I think it's beautiful to be able to sit with it and have the space now to hear those other stories, to welcome them in, to, you know, like, to have that perspective. And I agree. I think that's wisdom. I think that's. That's where ages are favorable and life experience is favorable. One thing that I'm so curious about, especially because all of a sudden you're now, like, single, you are independent. I actually remember talking to you about this very thing while we were sharing a trail cookie, is that a lot of times for us, when we hit places like that, whether we have a partner or not, we can use work as a distraction from pain. Right. Like, it's like this mode of, like, oh, I know this. I can do this thing. Right. You couldn't hide behind your work when everything fell apart. Right. Like, everything fell apart, including your work, in a lot of ways. And so what would you tell a woman who's overworking to avoid dealing with what is really broken in their life, whatever that is.
B
Oh, God, I have so much compassion for that impulse. You know, you and I are probably similar in this way that some of our instincts trend toward overworking, over producing.
A
It's easy.
B
I mean, not only is it easy, it's rewarded.
A
Yes. Yes.
B
So we absolutely get rewarded for that impulse. Like, for those of us who are sort of naturally predisposed to ambition, to big ideas, you know, just to sort of big career, whatever. And that has a billion, you know, slivers to the pie chart. But that tends to be rewarded behavior, which is a terrible reinforcer when we are using it as an eject hatch out of real life, like recovery, processing, evaluation. And so, I mean, I know I did that for sure. I. And I write about that, that there was a season that I overworked. This is an immediate aftermath. Yes. I just felt like I needed to control something. I. I needed. I was so out of control. So much had been done to me, unto me, without my consent. I need something under my thumb.
A
Yep.
B
And I couldn't control my kids. I tried to control their experience. Of their parents divorce, and turns out they just have to live their own hard stories. So spoiler alert for everybody. With youngs, with littles, you don't get to shield your kids from their own pain. I'm so sorry. I really did think I would be the first one able to do it, that somehow my kids would be the one that go unscathed, that they'll get through childhood, adolescence, early adulthood, just shiny, okay. So I couldn't do that. So I couldn't control their pain or their process or their relationship with their dad or any of it. And so I had to push that one off aside and so I could control work. And I guess, let me just fast forward that story and say where that ended up for me was landing me in the emergency room. So if you want to know if that works out. Yeah, I ended up in the ER with catastrophic blood pressure, panic attacks, depression, which I'd never really experienced in my life. I was a disaster. So my body decided to shut it down since my mind would not do it, since my mind was like, oh, no, the hell we will. We will just charge forward. We will. We will build and recover almost out of spite. And my body was like, hey, guess what? Let's go to the er since you won't listen. I had plenty of warning signs. As you can imagine, you don't end up in the ER without any warning signs. I had ignored them for, I guess, a year. And so that was a real wake up call for me. I was just telling Tyler, my boyfriend this yesterday, that I am still, like, having to be really careful with my heart and all my. My labs and my blood work and my doctors. I now have to be careful with my heart. I just treated my body like it was a machine that could run on adrenaline forever. And it's not. It just sure isn't. And so I have since made some changes. I've made changes in my work life. I've made changes in my availability. I've made changes in the scope of my work and parts of it that I no longer will do because I don't want to. And it's just. I feel my life getting smaller but.
A
More expansive, more in alignment.
B
Like some of that hustle.
A
Yeah.
B
Is just falling off the edges. And it feels really good, really good to me. I love that.
A
And again, that's something we all have to look forward to. I think some. I think that might be, like, one of the hardest learned lessons, especially when you're an entrepreneur, is that piece. And it might look different for everyone, but I feel like there is a part of you that can die in a beautiful way when you see that, like, this is not sustainable. This is not the dream. This is so far from the dream that it kind of forces you into alignment. So, Jen, where can everybody grab a copy of Awake? Where can we connect with you? There's so much more to the story that you have to read. And I love this bootlegged edition. Like, when I see you next, you're going to sign it and it's going to be a prized possession. Tell us where we can connect.
B
Thank you. It's everywhere the books are sold and over at my website, which is jen hatmaker.com is just everything about it, everything about this book and whatever else that I do and work on and create for the world. And thank you for having me on and thank you for reading it. Thank you for being a good friend. Thank you for texting me. Like, the early texts that I got from my friends who are reading this way before the watching eye, months and months and months ago meant so much to me. It meant so much to me because there was. It's such a. It was such a tender story to tell in a way that I have never told. And I thought, I do not know how this is going to go. I do not know how this is going to land. So, like, Jenna, when you are texting me as an early reader going, this is what I'm reading. This is what I'm hearing. This is what I'm relating to. I cannot. There's no way for me to explain, like, what. How much that meant to me where I went. Okay, this is my story. But so much of this is our story. Like, this is a unrelatable set of systems that we have all been plugged into. And so, anyway, thank you for being a friend and thank you for having me here in your space with your community. It just means a lot to me.
A
Right back at you, girl. I'm waiting for you to come back to Minnesota.
B
Love it there. You know, I do in the summer.
A
Thanks for listening to the Gold Digger podcast. I hope today left you insane, inspired and equipped with something you can put into action as you build a business that truly supports your life. If this episode resonated with you, here's how you can help this show reach even more entrepreneurs. Hit follow. Share it with a friend who's building something meaningful. And if you're feeling generous, leave us a review. Those reviews help other listeners discover these conversations when they need them the most. This show has become so much more than I ever imagined. And it's been because of listeners like you who show up and share. You are helping build something that will inspire entrepreneurs for years to come. For show notes, links and resources, head to golddiggerpodcast.com keep digging. Your biggest goals the world needs what you're building.
The Goal Digger Podcast
Episode 919: The Permission to Burn It Down (And Start Over on Your Terms)
Host: Jenna Kutcher
Guest: Jen Hatmaker
Date: October 6, 2025
Theme:
This episode centers on the courage to reinvent yourself and your business when your past version no longer aligns with your present self. Jenna Kutcher is joined by bestselling author and podcaster Jen Hatmaker, who discusses her own journey of midlife reinvention, self-trust, the evolution of personal brands, overcoming societal expectations about aging, and the process of letting go—both personally and professionally. The conversation is grounded in real, vulnerable storytelling and practical reflection, offering permission for listeners to pursue radical change on their own terms.
Recognizing When It’s Time to Change:
Jen describes how the inner knowing that a part of your life or business no longer serves you is a trustworthy signal. Even if certain things are still successful outwardly, it’s valid to honor the pull to pivot or let go.
The Disruption and Difficulty:
Acknowledging that following your intuition isn’t easy and often comes with risk and loss, but it’s not wrong to steer your business or life in a new direction.
Learning to Listen to Yourself Again:
Jen explains her upbringing in conservative religious culture and how young women, especially, are taught to distrust their own intuition and desires.
Generational Shifts and Hope:
Jen observes her daughters and their friends growing up with more body positivity and autonomy, offering hope that things are slowly changing.
Separating Self from Brand During Upheaval:
After personal crisis and divorce, Jen couldn’t immediately separate which parts of her public self to keep or discard; everything felt broken. The reflection from her community was key to rebuilding an authentic sense of self.
Letting Go of the Polished Persona:
Jen shares how her latest book is the most unfiltered she’s ever been, embracing her flaws and honest experiences publicly.
Aging as Empowerment—not Irrelevance:
Addressing societal fears about aging out of relevance, Jen argues that age brings greater wisdom, self-integrity, and leadership skills.
Rejecting Scarcity and Competition:
Jen encourages women to view younger generations as collaborators, not threats, and emphasizes the importance of intergenerational sharing and mutual support.
Shifting Away from Prescriptive Storytelling:
Jen’s new book, Awake, is written as a series of connected memories, trusting readers to draw their own meaning, rather than tying every story up in “life lesson” bows.
Navigating the Cost of Honesty:
She deliberated deeply over what to include, worried about harming relationships, but chose long-term integrity over short-term payoff.
Distraction Through Work:
Using work as a shield from pain is common and socially rewarded, but can lead to serious health issues—Jen details ending up in the ER after ignoring all warning signs.
Letting Parts of the Hustle Die:
Jen shares the paradox of a “smaller” but more expansive life, created by letting go of unsustainable ambition and realigning with what matters most.
Trusting Your Instincts:
“You're not wrong about you. You're not wrong about your work, you're not wrong about your career. So put your chips on you and move in that direction.” – Jen Hatmaker (07:18)
Outsourcing Authority:
“I learned early on to outsource all authority. I had no personal authority in my own life. I was not trustworthy enough.” – Jen Hatmaker (13:19)
On Aging:
“We get better the older we get... That's a story that has been told to young women in order to keep them in line, in order to keep them small. But the truth is our best days are ahead of us.” – Jen Hatmaker (28:08)
The Cost of Authenticity:
“Will I be proud of this in five years? ... Because these are people. This is our actual life. This isn't just a book on a shelf...” – Jen Hatmaker (38:09)
Overworking as Escape:
“I have since made some changes. I've made changes in my work life. I've made changes in my availability. I've made changes in the scope of my work and parts of it that I no longer will do because I don't want to.” – Jen Hatmaker (52:57)
For resources and to connect, visit jenhatmaker.com and goaldiggerpodcast.com.
This episode is highly recommended for anyone experiencing change, burnout, or the nudge to step into a new chapter—whether in business or life.