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Let me tell you what I know for sure. After 14 years of building a business, becoming an entrepreneur is the most expensive personal development program you will ever pay for. And I'm not even talking about the money. I'm talking about the version of yourself that you have to let die. The people pleaser in you who waits for permission. The woman who apologizes before she even speaks. That little part of you who thinks if you just stay ahead of everything, you'll finally be safe. I have literally watched the Girlboss era rise and fall. I've witnessed in a part of Hustle culture and watched it get worshipped and then finally questioned. I've been in rooms that I thought I needed to be in, only to realize those weren't my rooms at all. And here's what I know to be true. Entrepreneurship is not just about building a business. It's about becoming someone who can. For women especially, this journey literally is going to ask us to unlearn almost every single thing we've ever been taught. To stop making ourselves small. To stop waiting for permission. To stop apologizing for wanting more. And so, as you embark on this journey, you start unraveling. And listen, this is good news. Because if you let it, I promise you this path is going to heal parts of you that you didn't even know you needed healing. It's going to take you back to the version of yourself who knew exactly what she wanted before the world taught her to doubt it. This episode is about the things that I know for sure. I'm talking about the hard won lessons. I'm talking about the truths that only come from doing the work and putting in the reps. I'm talking about the things I wish someone would have told me when I was just starting out. So if you have ever felt like building a business is pushing on literally every bruise you didn't even know you had, you're not crazy. You're just doing the real work. So let me tell you what I know. 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 feels as. As it looks you're in the right place. This is the Gold Digger podcast. So here is one thing I know for sure. Before anyone is ever going to clap for you, you have to decide that the thing that you want to do is actually worth doing. So when I launched my blog back in 2011. Yes, 2011 free WordPress blog. Your girl was learning HTML coding on the side to make that blog as pretty as she could. I remember I had this option. I could wait or I could do. I could wait for someone to tell me I was ready. I could wait for someone to say yes. I could do all of those things. I could wait for proof that I wasn't just dreaming this idea up. But I know one thing for sure. If I would have waited, that permission would have never come, right? I learned so early I had to give myself that permission. I had to name myself a photographer before anyone had paid me. I had to call myself a business owner before the revenue really proved it to be true. I had to believe that I was an entrepreneur before anyone else did. And here's what I know for sure. Especially for women. We have been trained our entire lives to wait. To just wait and be chosen. To wait and earn the right to speak. To wait and let others go first. I will never forget the first time that I told someone I was a photographer and I didn't add in all the caveats. There was this stage of my life when I was starting to build up my business. It was a side hustle. I was working my regular 9 to 5 corporate ladder climbing job and oftentimes if people would ask me what I did, I would use that professional title that sounded really impressive. And then I would add in at the very end. And you know, in my free time, I really want to be a photographer. And I'll never forget the first time I said I'm a photographer. Just I am a photographer, full stop. No asterisks, no caveats. And it happened at the dentist office. And I remember the dentist asked me, what do you do? And because her hands were in my mouth, I couldn't add in all the words I wanted to add into. You know when you usually respond with like a grunt or like a noise or like a haha. Yeah. So I said I'm a photographer. And I didn't say, you know, I work in corporate, but I also photograph weddings on the side, I just said I'm a photographer. And so this was the first time I said that. And it's wild because I just remember this memory so viscerally. It was Like, I was forced to be in this position to answer that question in a way that wouldn't have me backtracking. I couldn't soften it. I couldn't make myself smaller. And you know what happened? Nothing dramatic. She just said, oh, that's cool, and kept cleaning my teeth. But for me, that moment changed so much for me, because here's what I know to be true. Before anyone else on planet Earth is going to clap for you, you have to decide that it is worth doing. Before anyone ever claps for you, you have to decide that it's worth doing. Like, before anyone recognizes your name, you have to name yourself, your business. It is not gonna wait for you to feel ready. It is going to require you to be bold before you feel brave, to take up space before you feel entitled to it. And here is the incredibly beautiful part. When you give yourself permission, you're actually going back to the who you were before the world taught you to wait, before you learn to shrink, before someone told you that confidence was arrogance. There is a version of you that existed who knew exactly what she wanted. Maybe she was 7, maybe she was 9, maybe she was 12. But that version of you, she did not question whether she was allowed to want it. She just wanted it. And entrepreneurship is going to ask you to find that version of you again. To find her once again. That first act of self belief when nobody's watching and nobody's clapping, that's you going back to the little girl who dreamed big and telling her, guess what, little you. You were right. You were always right. Here is the second thing I know to be true. Your humanity is your competitive advantage. Now, I have been in positions so many times in my life where I have been a performer, right? I was the little girl in the leotard doing back handsprings. I was the collegiate diver who absolutely hated being wet. I was in theater. I was on stage. I was a part of a performing church group. I was the perfect photographer on the wedding day, right? And as I became an entrepreneur, I recognized that I could be an imperfect leader, that I didn't have to show up having everything figured out, that I didn't have to be perfectly put together. I mean, half of my shtick is that I am just a mess. That is who I am. And the world has taught us that it takes being perfect, right? I mean, I even see this in my young daughters, how women are wired for perfection in ways that I would argue I don't believe men are. Women want to color within the line, so to speak. Both metaphorically and in reality. And we're taught that being professional is being perfect. That's what success looks like. That's what we see. And I believed that for a long time. Like, I used to picture myself in a corner office suite with windows and high heels and a power suit. Like, that was what success was painted to me as. But for me, so much has shifted. I mean, when I think about how I have shown up over the years as a human, I remember over a decade ago posting on social media. Me, no makeup, sweatshirt, hoodie, pulled up, working at the table, saying, this is what it takes. This is what entrepreneurship looks like. I have let people in. I've talked about the messy part. I have talked about the doubt. I have talked about the exhaustion. And I've talked about the fact that I'm literally figuring it all out as I go. And what I have learned is that when I have shown the most human parts of my existence and my journey, people have leaned in. I will never forget years and years and years ago, I did a Twitter poll back when Twitter was Twitter. And I remember asking my audience on that platform at the time, I said, what do you want to see more of? And I had these little categories, and it was like wedding photography, engagement sessions, you know, family photography. And one of the options was my real life. And the overwhelming majority of people chose my real life. And I remember I literally thought it was a mistake. Like, I just threw that in there as a category. I thought, there's no way that people actually care about me. They care about the work I create. Like, I wanted to hide behind the beautiful photos. And I remember when I saw that, as a curious human that I am, I was like, I'm going to test this out. And so as I moved forward, I challenged myself to start showing myself more, to start showing me and telling the story about me. And it's interesting because when I started my career, I think all I wanted to do was blend in. I had the worst imposter syndrome of all time. I felt like I just needed to look like every other photographer out there. I didn't want to be called out. I didn't want someone to say, you know, where is your photography degree from? And so I wanted to just blend in until I realized that the only thing that made me different than every other person with a camera was me. And I started leaning in to showing that. And so I started testing it. And there was this one month where I challenged myself. Instead of showing my face one out of every five posts, I'm Going to try to flip the script and I'm going to try to show my face. Four out of five posts. Okay. I basically was like, I'm gonna try to post photos of myself 70% of the time for one month. It's gonna be an experiment. It's gonna be 30 days. I will never forget that month. I had to face so much insecurity. I had to step in front of the camera as a person who is predominantly behind it, and I had to start showing up. I had to think about, what do I wanna say? What is worth saying? What can I share here? That month, I doubled my follower growth from the month previously. My engagement had gone through the roof. And the people who started following me weren't just following me for the work I did for my wedding photography, they were following me for me. Which meant that years later, when I completely pivoted away from photography. I haven't shot a wedding in seven years. They were still there. They had come to me because they cared about who I was, not just the work I created, not just what I was producing. And so here is what I know to be true. People will hire you for what you know. Yes. But they will stay because of who you are. Your realness, your humanness. It is your competitive advantage. And I would argue for women in business, this is such a minefield. Because we are taught that being emotional means being unprofessional, that vulnerability equals weakness, that showing up with feelings and struggles and humanity makes us less credible, less of an extrovert. But I know for sure that the opposite is true. The version of you trying to have it all together. Guess what? She is freaking exhausted. And honestly, I would argue she has been in the way of your success. What entrepreneurship teaches you, if you let it, is that the parts of yourself that you have been trained to hide are the parts of you that actually make you magnetic. It's your humanity. It's your honesty. It's ingrained in who you are at your core. And those parts that you want to hide away from the world are probably the parts that will be the ultimate connector for you, that will help you find your people. When I think back to when I bought my first little Craigslist camera, I had no clue that it would change my entire life. Like, I didn't have this big plan. I just took the first tiny step. And that's what the new year is for. A clean slate. A chance to finally start that business idea that won't leave you alone. If 2026 is your year to launch Shopify makes it feel doable. You can sell online or in person and they give you everything you need to get moving. Millions of people have taken this leap from total beginners to well known brands. You can pick from beautiful templates, customize them to fit your style, and use Shopify's built in AI tools to write product descriptions, headlines, and even clean up product photos. When you're ready to grow, Shopify grows with you. All from one simple dashboard. In 2026, stop waiting and start selling with Shopify. Sign up for your $1 per month trial and start selling today at shopify.com goaldigger go to shopify.com goaldigger that's shopify.com goaldigger Hear your first this new year with Shopify by your side. My cousin's getting married soon and I haven't been to a wedding since I stopped photographing them seven years ago. We're so because we're getting our entire family together and booking a home on Airbnb for the festivities. Coco even asked if she can be the flower girl, so now I need to teach her how weddings actually work. After sending a few options, we found the perfect spot. There's this pool table for my father in law to be a pool shark. Enough room so that we can all actually get decent sleep and plenty of space to make memories together. Where you choose to stay truly has the ability to elevate everything, and it got me thinking about the hosts behind the stay. They make sure the space feels warm and cared for, which makes these special moments even more memorable. And here's something I learned. You don't need to own a vacation property to consider hosting your own home on Airbnb. You can start with the space you already have and that extra income. It can be put towards future travel or a fun splurge item you've been eyeing. Your home might be worth more than you think. Find out how much@airbnb.com host this is good news. Like you do not have to have it all figured out. You do not have to be someone you're not. You get to be ruthlessly yourself. Not the edited version, not the Instagram version. You get to be you. Unapologetically you. And listen, in a world where AI is trying to automate everything, where you can generate content and copy an entire marketing campaign with a click, your humanity is the thing that no one else can replicate. Yes, use AI as a tool. I love it. Let it help you work smarter. But never let this world that we're stepping into strip away the Thing that makes you you. Your voice, your story, your perspective, your messy, your beautiful humanness. That, my friend, is where the magic happens. I know this to be true. When you get it wrong in public, you also get to grow up in public. Let me tell you, I have gotten so many things wrong over the years. I have contradicted myself. I have messed up. I have done things in the wrong way. I've showed up in the wrong way. I've done a million things wrong. Okay, I've gotten called out. I've gotten canceled. I've gotten so many things wrong. And one of my core wounds is wanting to be understood. There is this deep desire in me, like my inner child just deeply wants to be understood. I don't need you to agree with me, but I just need you to understand me. That is like the littlest version of me crying out. And when I've gotten called out publicly, I have wanted to run. I have literally wanted to delete everything. I wanted to apologize and disappear. And I have learned so much through the experiences that literally felt like a spotlight on everything I've gotten wrong. Those experiences have challenged everything I have believed to be true about myself and my leadership. And I have had to learn what it means to mess up, and not just mess up in life, because we're all going to do that. But I have literally had to know what it feels like to mess up in front of thousands and even millions of people. What it means to literally have to sit in discomfort and learn how to do so without centering myself in it. What it means to let actions rebuild what words can't fix. And here's what I know to be true. In the past, when I have messed up, I have tried to rush to move forward, to just fix things, to prove that I was one of the good ones. And in that, I have missed the part where I could have gotten still, where I could have really separated impact and intent, where I could have just stepped away and let others stepped in to lead. And so listen, entrepreneurship is probably going to put you in situations where you will get it wrong, where you misjudge, where you hurt people you don't mean to hurt, where your blind spots become literally visible to everyone, maybe even not you. The question isn't necessarily if you're going to mess up, it's what you do after I've had to learn this hard way. And this is why I want to share this with you, because you have options. Do you center yourself in the pain that you've caused? Do you perform an apology and move on. Do you actually pause and listen and learn and let it change you? This is about becoming someone who can handle being wrong. Someone who doesn't need to be right all of the time in order to feel safe. Someone who can stay in the room even when it's uncomfortable. And here is what I know to be true. Somewhere along the way, you learned that being wrong meant you were bad. That making a mistake meant you were unworthy, that you had to be perfect in order to be loved. And entrepreneurship is going to straight up dismantle that belief over and over again. It is like eating the biggest piece of humble pie and allowing your ego to. To die a slow death so that you can show up in your humanity, so that you are willing to get it wrong in order to learn how to get it right. And so that you will not take yourself out of the fight, but you will commit to showing up again and again and again until you get it closer to being right. It's going to show you all the things you need to see. And let me tell you that it is a gift. It is a gift to understand that you can be imperfect and still be valuable. That you can mess up and still be worthy. That growth is not going to be linear. It lives in all of the messy middles that we all will encounter. And I look back at all of those times that I straight up messed up. And I am so grateful for the people who called me in. And I'm so grateful for the people who stuck around and believed in my ability to learn and to listen. I also know this to be true, that hustle culture is really just control issues with a vision board. I know that's a harsh take. It is hard to take that in, right? Hustle culture is just control issues with a vision board. We have lived through an era of wearing busyness like a badge of honor. Like, we have been walking around saying, look at how busy I am. Look at how exhausted I am. Look at how hard I work. And I want to just call this out right now. I may have unknowingly perpetuated that through my content. I sincerely hope I haven't. But I understand. I have an awareness around me enough to say that in my teachings in over 900 episodes, there's a chance that something I said made you think you needed to just work harder, just push more. Now, I have said that time is my currency for over a decade. So I believe, hopefully, that I've been one of the ones that has been preaching stillness and a beautiful life. But there have absolutely been ways that we have bought into this idea that we should be working weekends and answering emails at 10pm and saying yes to everything, because that's what successful people do. And that being always on means you're dedicated and that rest is something that we'll earn later. And spoiler alert, if we've believed these things, we start to realize that later never comes, right? We are never done. I built a business when I first started up that required all of me, all of the time. I will never forget, and this is a trigger warning. If miscarriage is a tricky topic for you, just scoot ahead about a minute. But I will never forget experiencing our second loss in two years and getting the news and having to literally go and shoot a wedding the next day before my body had even recognized that a loss was occurring. And I remember being there on somebody's happiest day of their lives and having to plaster a smile on my face while feeling like my body was literally a ticking time bomb. And all I wanted to do was be in the fetal position. And I will never forget that day. Committing to myself. I need to rebuild. I need to destroy this successful six figure business that I've built because it does not allow me to be a human. If I don't show up, I don't get paid. And there has to be a different and a better way. And I am so grateful that I was able to learn that heartbreaking lesson so early on. Because what it's unlocked is a decade of entrepreneurship that was not built that way. And so when I look at how I figured out how to build systems, how to create something that could work without me constantly feeding it, how I was able to build the infrastructure that allowed me to have a business that was predictable and reliable. Like, I am so grateful for that. But here's the thing, is that burnout is a part of the journey, right? It. It happens. I believe it is just a piece of it. And it often comes in different flavors. Like different seasons bring different breaking points. Because I have seen that there are different ways that we leverage our deep desire for control and we can convince ourselves it's for the greater good, right? It's just a part of the system, right? Like, even in the last few years of therapy, I have started to unpack things that were unconscious beliefs that just kept me on the hamster wheel. As much as I have tried to stay off of it, I uncovered this one core belief that I have held onto for so long. And that belief is if I can just stay ahead, nothing can ever catch me off guard. If I get ahead and I stay ahead, I will have peace in my life. But here's the problem then. I was just working ahead. I was working months in advance. I was planning launches a year out. I was staying ahead of deadlines, ahead of my calendar, ahead of anything that could surprise me. And when I got ahead, I would just keep working further ahead, because being ahead meant safety and control and security. And here's what I know now. The hustle culture that we've been sold, it's not really about success. It's really control just cloaked in different garments. It's this belief that if we just do more, push more, stay ahead, we'll finally be safe. We'll finally be enough. We'll finally prove that we deserve to be here. And however you are clothing that, however you are tricking yourself, that hustle culture isn't really a part of your life. It probably is. And if it exists in your life in any form, it's a lie. There were so many years when I look back now, where I was just operating out of pure force. I'm talking, like, straight up masculine energy. The push, the grind, the control. The harder I work, the better I be. If I just double down, then I'll be successful. And listen, that approach works. It can create really powerful things, but it works until it doesn't. I have built a business that way, But I also have recognized times in my entrepreneurial journey where the business or the things or the offers that I've built are not necessarily freedom. They're almost like a prison. I have had to learn and unlearn new ways to work. I have had to learn about ease and flow, about surrender instead of control, about working from a place of rest, not a place of stress. Even just today, we had a team call, and we were talking about a personal matter with a team member. And I said there was an entire year where I wore a necklace, and on that necklace, it said the word surrender. I had to learn how to stop white knuckling my business and just open my hands and let it flow. And so here's what nobody tells you. Letting go of hustle absolutely, positively feels like failure at first. It feels lazy. It feels irresponsible. It feels like you're falling behind while everyone else is racing ahead. But let me tell you, if you can loosen your grip, if you can let things just be a little bit easier, if you can unpack the ways where hustle culture has infiltrated your life and hidden itself in your agenda, you will Start the journey of coming home to yourself. You will go back to the version of you who knew how to play, who knew how to find joy, who had hobbies outside of the roles you played, who knew how to rest without earning it, who understood that your worth had never nothing to do with your output. Absolutely nothing. And so when you start to surrender, you start to get joy in the most unexpected places and your life becomes this enriched experience. There's so much fullness of life that we can miss when we are in the rat race. And so what I know for sure is this a business built on your depletion isn't a business. It is literally just another cage. And there's probably a really good chance that you didn't leave your job or you didn't leave behind your old life to build yourself a prettier prison. And so how do you start the pursuit of freedom? This leads me to my next thing that I know to be true. Freedom is not really free if it doesn't feel like is so easy, so ridiculously easy in entrepreneurship to chase all the things to chase. The metrics, the revenue goals, the download numbers, the Instagram followers. There have been so many times where I have hit milestones that should have felt like the biggest wins of my entire career. And maybe they did for like five minutes. But then I was just onto the next goal, the next number, the next thing to prove. There are so many ways that society and the structures and the systems and even the content we consume where it paints out this idea that more is better, that more is the thing that we need to be in pursuit of. There are so many moments in my life now where I just realized that success for me does not look like anything that you see on the Internet. It's not Instagram worthy. Success for me is my full presence with my kids. Just this morning today we played the floor is lava game. And I looked around my house and my kids are up on the couch and Drew is up on a bar stool and I'm standing on our coffee table and the dogs have decided to jump up on the couch. And I just like took a mental snapshot of this funny moment where we had been stressed out minutes before we put the floor as lava on and we're just all just giggling and laughing and I'm like, this, this is it, this is it. I have all of these moments where it is just the most mundane, full present moments. I mean, it could be as simple as laying out in my yard and watching the leaves in a tree, just being in Awe of life and this world we're in and all these different things. And so I have just had to redefine what success is for me over and over and over again and shed society's expectations and their illustrations of what success is. It is not the number in my bank account. It is not the chart position of my podcast. It is the ability to be present. It is the ability to be still. It is the ability to not feel like I am constantly running towards something or running away from something else. And so here is what I know for sure. Freedom isn't really free. If it doesn't feel, feel like it, I don't care what it looks like. Okay? I have had to redefine success from the inside out. I have had to lean into peace and alignment and presence. And no, those things don't land on charts. And they don't write news articles about those things. But those are the things that I define success with. The ability to say no. The freedom to say yes. The spaciousness to be with my family without my mind being 10 steps ahead. That is when I feel most successful. Not when I hit a revenue goal, but when I can slow down. And the slowdown doesn't scare me. It doesn't make me feel like I've lost my mojo. It doesn't give me that feeling of falling behind. It's just this beautiful way of moving through life. And listen, we're taught that success as women means doing it all. That being the CEO and the mom and the wife and the friend and the volunteer and the woman with the clean house and the thriving business and the homemade meals. We are taught that that is what we have to achieve. And let me tell you right now, that is not success. That is a straight up setup. Here is where you have to get brutally honest. What do you actually want? Not what do you think you should want. Not what Instagram tells you success looks like. Not the rooms you think you're supposed to be in. I have spent a lot of years wanting to be in the hyper masculine, the strategy obsessed, the scale at all cost rooms. I thought that's where the real successful entrepreneurs were. But now I know. I know for sure. I don't actually want to be in those rooms. I want to be in the rooms that are community based. I want to be in the rooms that care about the collective good, not just individual wins. I want to be in the rooms that are not ignoring the issues that are happening in our own backyards. I want to be in rooms that value presence as much as they Value productivity. I want to tell you this right now. There is a version of you that already exists, that knows exactly what you want. Maybe you haven't been conditioned yet. Maybe you haven't even given yourself a minute to think about it or dream about it. But there is a version of you who is ruthlessly honest about what feels good for you and your life in this stage and season versus what looks good to everyone else. And I want this episode to be a call back, to go back to her, to check in with her, to let her tell you what success actually means. Here's a hard truth. If you know you need this, I want you to do this one thing. Your calendar. It doesn't lie. It is literally the perfect reflection of your actual priorities, of your values. Not the things you state, not the things you put on your website, not the things you tell people. But what is the reality of it? Take a look. Do an audit. Are the things and the people and the moments and the passions, are those prioritized? Are they penciled in? Are they there? Are they a part of your life? Not someday, but like literally the life you're living right now? Because I know this to be true. Real success is having the courage to define that word for yourself. It is building a business that actually fits your actual life. Not like the highlight reel version, but like the life you want to live. Real success is letting go of what you think everything should look like and building what actually feels good for you. Like that's the work. And let me tell you, it is richer and more rewarding than any marketing strategy I could ever teach you. So. So here's what I know for sure. I. I still don't know a lot of things, but I know a few things for sure. If I could sit down with a version of me who is just starting out. I'm talking about the girl who is hitting publish on that first blog post. The one who is nervous. The one who is doubting every word. The one crying in her car after being misunderstood. Here's what I would tell her. This path, the path that you are about to embark on. It is going to ask everything of you. It is going to shine a light on your money wounds. It is going to shine a light on your need for control. It is going to illuminate your fear of being seen. It is going to expose your blind spots. And it will push on every bruise you didn't even know you had. This journey is going to require you to name yourself before anyone recognizes your name. To show up as a human Being first, not an expert, and to let go of hustle and come home to yourself. It is going to invite you time and time again to redefine success on your own terms. And if you let it, this journey is absolutely going to transform you and it is going to heal you. It is going to take you back to the version of you who was ruthlessly honest about what you wanted. The version of you who took up space without ever apologizing. That little you who knew exactly who she was before the world taught her to doubt herself. Because here's what I know for sure. After 14 years, entrepreneurship is not just a career path. It is a literal becoming. It is a journey back to yourself. And if you let it, it will make you more honest, more grounded, more fully you than you ever thought possible. Not because you're going to figure out all the answers, not because you're going to get it perfect, but because you're going to learn what it means to trust yourself, to take up space, to believe that you are worth listening to before anyone else does. This is the most expensive personal development program you will ever pay for. And again, not in your money, but in your ego deaths, in the surrendering of control, in the versions of you that you have had to let go of to get to where you want to go. And I know this. It's worth every single moment. It is worth every hard lesson learned, every time you had to get still instead of pushing forward. This work will change you. And that's not a warning. That's the promise. So listen, if no one's told you this lately, let me be the one. The path that you're walking, it matters. The messy parts, the doubting parts, the moments where you feel like you're making it all up as you go. Those parts especially, you do not have to have it all figured out. You do not have to be perfect. You just have to stay in the room. You just have to keep showing up. You just have to be present and honest. Your growth doesn't live in your wins. It lives in your willingness to keep showing up, to be a human being, to get it wrong and try again. And here is what I know for sure. This work will change you. And I believe that is exactly why it is worth doing. Gold Diggers thank you so much for listening to this episode of the Gold Digger podcast. Until next time, keep on digging your biggest goals. But more importantly, keep on becoming the kind of human you're proud to be. I'll see you in the next one. Thanks for listening to the Gold Digger podcast. I hope today left you 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 because of listeners like you who show up and share. You are 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.
Title: The Price of Entrepreneurship No One Talks About (And Why I'd Pay It Again)
Host: Jenna Kutcher
Date: December 24, 2025
In this heartfelt solo episode, Jenna Kutcher dives into the unspoken emotional and personal costs of entrepreneurship—costs that transcend money and metrics. Drawing on 14 years of business-building and personal growth, Jenna shares the truths she’s learned through trial, error, and vulnerability. She reveals why entrepreneurship is the “most expensive personal development program you will ever pay for” and why, despite the pain and challenge, she would do it all again.
This episode is equal parts encouragement and reality check, especially for women in business. Jenna explores self-permission, owning your humanity, moving beyond hustle culture, redefining freedom, and coming home to your truest self—threading through personal stories and actionable reflection.
“Becoming an entrepreneur is the most expensive personal development program you will ever pay for. And I’m not even talking about the money. I’m talking about the version of yourself that you have to let die.”
— Jenna Kutcher, [00:00]
“Before anyone else on planet Earth is going to clap for you, you have to decide that it is worth doing.”
— Jenna Kutcher, [04:45]
“People will hire you for what you know. Yes. But they will stay because of who you are. Your realness, your humanness. It is your competitive advantage.”
— Jenna Kutcher, [19:30]
“In the past, when I have messed up, I have tried to rush to move forward, to just fix things, to prove that I was one of the good ones. And in that, I have missed the part where I could have gotten still, where I could have really separated impact and intent.”
— Jenna Kutcher, [28:00]
“Hustle culture is really just control issues with a vision board.”
— Jenna Kutcher, [37:50]
“Freedom isn't really free if it doesn’t feel like it.”
— Jenna Kutcher, [53:00]
“Your calendar. It doesn’t lie. It is literally the perfect reflection of your actual priorities, of your values.”
— Jenna Kutcher, [59:45]
“Entrepreneurship is not just a career path. It is a literal becoming. It is a journey back to yourself… And I know this. It’s worth every single moment.”
— Jenna Kutcher, [01:04:15]
“You do not have to have it all figured out. You do not have to be someone you’re not. You get to be ruthlessly yourself. Not the edited version, not the Instagram version. You get to be you.”
— Jenna Kutcher, [25:56]
“The question isn’t necessarily if you’re going to mess up, it’s what you do after.”
— Jenna Kutcher, [35:10]
“A business built on your depletion isn’t a business. It is literally just another cage.”
— Jenna Kutcher, [52:00]
“Real success is having the courage to define that word for yourself. It is building a business that actually fits your actual life.”
— Jenna Kutcher, [01:02:15]
Jenna’s tone is warm, honest, and direct—rooted in tough love and real encouragement. She normalizes entrepreneurial messiness and pushes back on toxic myths about women in business.
The episode’s core message: You can build a business that feels as good as it looks—if you’re willing to do the inner work, redefine success, and keep coming back to yourself. The journey won’t be easy. But, as Jenna promises, “this work will change you—and that’s exactly why it is worth doing.”