The Jasmine Star Show

Break Free from the Fear of Failing with James Wedmore

• Jasmine Star

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There was a time I believed failure wasn’t just something I did—it was who I was.

But that belief got flipped on its head the day I had a transformational conversation with entrepreneur and coach James Wedmore.

In this episode, I’m sharing a powerful clip where James breaks down the real reason so many of us get stuck: we're building businesses with belief systems we picked up as students and employees—ones that no longer serve us.

We unpack:

  • Why failure is just feedback (not a flaw)
  • How to release identities that keep you small
  • What being “coachable” really means (this moment changed me)
  • How to rewire beliefs that are holding you back

If you’ve ever feared failure or felt defined by your mistakes, lean in. You’re about to see your story—and your future—differently.

Failure isn’t something to fear. It’s something to celebrate. 💥

Click >>PLAY<< to hear all of this and:

[00:51] Why I defined myself by failure—and how James shifted that narrative

[01:21] James explains how our “model of the world” keeps us stuck

[03:12] The surprising trait James says changed my life (and no one had ever told me before)

[04:25] How our experiences as employees and consumers shape limiting beliefs in business

[05:32] James’ analogy: Why applying football rules to basketball explains why most people struggle in business

[07:49] Why failure must be deconstructed—and fast—for entrepreneurs to succeed

🎧 Listen to the full episode: From Broke Bartender to Million Dollar CEO: A Conversation with James Wedmore

Listen to Related Episodes:

Connect With James Wedmore:

James Wedmore is a renowned entrepreneur and business coach who helps digital CEOs grow scalable, sustainable businesses. Known for his contrarian perspectives and deep coaching work, James is the founder of Business By Design and host of the Mind Your Business podcast. His work focuses on mindset, identity, and dismantling the mental blocks that keep entrepreneurs from success.

📧 Join my Newsletter for a weekly cocktail of insider business strategy, personal reflections, and the journey of being a thought leader. 📧

For full show notes, visit jasminestar.com/podcast/episode546

Katie Haahr 00:00:00  I'm Katie, president of social curator, and you're about to hear a powerful segment from one of our most transformational conversations on The Jazmin Starr Show, a conversation with entrepreneur and business coach James Wedmore. Now, this episode gets right to the heart of something we all wrestle with, and that's failure. Jasmine opens up about how she wants to find herself by her failures, and James unpacks why that narrative is not only false, but one of the biggest reasons so many entrepreneurs stay stuck. If you've ever felt like you were the failure, not just that, something failed. This conversation is going to challenge you, empower you, and shift the way you see your role as a business owner. Let's jump right on into it. My whole life, I had defined myself by my failures, and I never defined myself by what I thought was success. So I met James.

Jasmine Star 00:00:51  And during the first year he told me there is no such thing as failure. You're simply learning a lesson. And I want to say, I really wish, like what I want to do is be like, I heard it, my life changed and I was never the same.

Jasmine Star 00:01:05  But it took a couple years for you to really reprogram like what that was. Can you help us? Like for people who say, I don't want to do this because I don't want to fail or I have failed in the past, or worse, I'm a failure. How then do we change that narrative?

James Wedmore 00:01:21  Yeah, well, I want to take a step back because I think it'll create another context for the context you've created for this episode. So you can almost hear what Jasmine are saying from like two different vantage points. There's a lot I'm doing behind the scenes that Jasmine still doesn't know that I was doing with her and the other members. I'm a contrarian by nature, and how that serves me and working with clients is that what we have to understand is that there's a reason why success is not common for entrepreneurs. It's becoming more common, but it's not traditionally, it's most. You hear most people fail, most people don't make it. And we have to start looking at why. And there's a lot of reasons, but what we can pinpoint or the angle I take on it, is this based on what we would like to call your model of the world? In other words, if you imagine that we all have a model of the world that we've already kind of established is the way the world is.

James Wedmore 00:02:26  It is not the world. It's just our model of it. And you can even hear it in the way that Jasmine's talking about this first big breakthrough for her. What did she say? She goes, I developed the belief of. And so what I do when I'm working with someone is I challenge the F out of their model of the world, and I start to break it down and crumble it in the ways that serve them. And I challenge a lot and it can get it can be a little bumpy. Now, Jasmine is someone who is uniquely coachable. And so what would take someone else? Maybe a few years? More years? She was able to do very fast because she was one of the most coachable, open minded and open hearted entrepreneurs I've ever had the privilege to work with. And so she.

Jasmine Star 00:03:12  Can I can I stop you there, James? Because do you know that in my entire life nobody has ever said that I was coachable? And when you told me, but Jasmine and you just made it like it was flippant, it was so passing as if it was something I had heard ever before in my life.

Jasmine Star 00:03:26  And you're like, oh, Jasmine, you're just coachable. Yeah. And I just nodded my head and I'm telling you, it felt like if I was wearing like a Girl Scout like sash, I would have put a pin on it and say, yeah, I am coachable because it was the first time in my entire life that I heard truth about myself with a capital T that I had never, ever acknowledged before. And that was a big shift in my enlightening along my journey to well.

James Wedmore 00:03:49  And so then what does that mean? What it means is, is that you're not attached. You're not committed to a model of the world that isn't serving you. That's what coachable means. In other words, we go up, we grow up, we have these experiences. And you look, you have to understand that. What are the two primary contexts in which most people experience life? They're a consumer and they're an employee. We work for others and we buy. And what people do is create that a context of life that is based on rules that that we create.

James Wedmore 00:04:25  We create rules for our life from that paradigm. Okay. Like selling is bad. It's a great example. I was dealing with a client with that today. Selling is bad, right? And where did that come from? That came from a time or a series of experiences where you had an experience of being sold to and you didn't like it, so you created a model of the world. You created a set of beliefs and a perspective from the vantage point of a consumer, a student and an employee. And then one day we said, I want to build a business. I want to start a business. I want to grow a business. Yet we held on to that same model of the world. We operate from that same set of rules that we created when we were an employee, when we were a student, and when we were a consumer. And that is synonymous, analogous to learning your whole life how to play football. Learning all the rules of football, American football, and then saying, great, let's play some basketball.

James Wedmore 00:05:32  And then wondering why you suck at it, right? And it's not you. It's just it's a different set of rules. And I go into all of these and all that stuff. But what would happen is someone like Jasmine come in with a set way in which she thinks business works, marketing works. This is the way it is, you know, common sense, but, you know, common sense isn't that common. And so I just start chiseling it away. You just start challenging it. You start breaking away that old mold, that old paradigm and create a new one. And so this first one that she's referring to is this idea that we developed from a very young age, which is that we shouldn't fail. Failure is bad. Failure is a failure. You know, failure means failing, right? Like it just seems like nothing good about that. And that's got to go. That's got to go so fast. Because that's a big one. That is such a big one. The first piece of that, and the thing is, is we know it conceptually.

James Wedmore 00:06:42  So what I will say to people here in this moment as you're listening to me, you will agree with me. But there's a whole difference. And this is why someone has to pay 20 and now the mastermind is 35,000, right? So it's gone up considerably.

Jasmine Star 00:06:56  You know what? It should be more than that for. I'm just we're going to get into that later.

James Wedmore 00:07:00  But please raise your prices. But there's a difference and you can do this to yourself. You don't need to pay somebody a ton of money, but there's a difference. There's a gap that exists with people. So first they're operating from the the model of the world or a perspective that does not align with the outcomes they want. Like I want to be successful, but I don't want to fail. That model does not work. It is impossible. That is like saying I want to go surfing, but I don't want to get wet. I want to be successful, but I don't want to fail. Will not happen. Can't do it because your life and the context you create for your life ends up becoming.

James Wedmore 00:07:39  How do I not lose? How do I not lose? I don't want to lose. I don't want to lose. And you get what you focus on. And what do you get when you focus on? I don't want to lose, lose, lose, lose. Right.

Jasmine Star 00:07:50  So that's what I did. That's what I did.

James Wedmore 00:07:53  My fear there was something there was something else you were doing, which was we'll see if we get to that.

Jasmine Star 00:07:57  Oh, shoot. He's about to spill the tea. Oh, shoot.

James Wedmore 00:08:00  But it's in the same vein of this. And so, you know, challenging that model of the world. But then once you understand the new model as a concept, nothing happens. Because knowledge isn't power. It's just it's the potential for power. Nothing will happen until you apply that knowledge, until you operate from that knowledge. So it's one thing to say, okay, James, I get it. Failure is a stepping stone to success. Yeah, you've heard it for 100 years.

James Wedmore 00:08:28  Napoleon Hill wrote it and Think and grow rich. The real question you have to ask is why are you not applying it? Why wouldn't you do that thing? And it didn't work? Why, when someone laughs at you, why wouldn't you get a criticism? Why when someone says I don't agree or this is stupid or it doesn't get the results you want, do we immediately curl up into a ball and recoil and shame ourselves, beat ourselves up and say, I knew it right? And so until these things become something that is applied action and put into practice, we're still operating from that old paradigm. And so it's as simple as this. We'll talk about the failure thing in three seconds now and then it just becomes a choice for anyone who's actually committed, who's a choice. You operate from this new paradigm, or you keep operating from the old model world. That's what we're going to keep going back for. Are you going to choose your old model and you choose the old model? You're going to keep getting the old results.

James Wedmore 00:09:15  You want new results. You're going to have to start operating from a new model. Because as Jasmine said, your business, well, she she alluded to it. The reason all the things that Jasmine is going to share today have nothing to do with your business is because your business is simply a reflection of you, because who's the one creating it? You. So your business is a reflection of you. If you went and built a house today and you know nothing about building houses, that house is definitely going to be a reflection of your craftsman skills. So your business is a reflection of you. You want to grow your business. We got to get to work growing. You okay. And it's it's not growing in the sense that you would really think like you need to be smarter. You need to hustle more. You need to work harder. It's we need to shift the model. And it's like a set of links or blocks of beliefs made up of beliefs about how you think, success, money, sales, business, etc. how it works.

James Wedmore 00:10:18  You change that model, you change the results. So failure is a big piece of this. Failure does not exist. This is what really gets people. There's no such thing as failure. And the reason we can say that is in 3D reality, anything that you can touch or taste or smell or hold in your hand is something that we can see at least exists in the in in the 3D. So failure is not something you can put in your hand. You can't put it in your pocket, you can't put it in a wheelbarrow. So then what is failure? Failure is a label, judgment or opinion that we place on an event or circumstance or situation or ourselves. So we are choosing to call something a failure. That doesn't mean it is. And the problem is, is people collapse it. People say this thing happened. It's a failure and they collapse that. So they just say, this is failure. And then they do. The worst thing you can ever do is you say, I did this thing, therefore I'm the failure.

James Wedmore 00:11:19  And now the new model that you've created for yourself is that I am failure. And the fact is, is that you are such a powerful. And this is everyone's problem. And I love you so much because it was my problem. So I can see it is that we don't know how powerful that we are. We don't know how powerful our thoughts are. We don't know how powerful that we are at creating our world, that we will literally create ourselves in the moment. We say, I am a failure. We are literally creating that and bringing that into existence and then finding evidence of that everywhere. And then we become the creation of what we created, which is failure. And if someone feels like a failure right now, the very fact that you feel like a failure is all the evidence and proof that you need to. How powerful that you are because you created yourself as that. And when you get present to that fact you have the choice, the opportunity to create again and again. But remember to, to just remember that anything deemed a failure was your choice as a label.

James Wedmore 00:12:27  It's like putting a sticker over, over that launch, that promotion, that idea, that product and it and it just collapsing the two together. And what I like to do is say let's pull that label off. It's peel that label off and just look at the situation. Leaders are those that have the ability to deal with what is without without opinions and emotions and fears and doubts. They just look at what is. And until you're able to do that, entrepreneurship is going to be a little bumpy.

Jasmine Star 00:13:00  James can I jump in. And what you just said right now, you said, we want to put a sticker over it and label it a failure. Yeah. And I want to talk about the complete opposite perspective, because James is saying I am lifting the sticker. And from my vantage point, I did not know. I was subconsciously telling myself, I don't want to look at that. It's easier for me to label it a failure and then just say, it is what it is. Yeah, but James wanted to lift the sticker, and when you lift the sticker, you're bringing up your skin cells.

Jasmine Star 00:13:34  You're bringing up the tiny pieces of hair. You're bringing up the shrapnel from your, like, your perceived failure. And he's lifting it up and you're like, I can't bear to look. I can't bear to look. And he's like, inadvertently saying, look at the wound. You could heal it if you just look at it. Right. And I feel like for the course of, like, our years together, you were also you were always saying, look at it and learn from it. And the more I became accustomed to, he's going to rip the sticker off. Then I became empowered to rip the sticker off.

James Wedmore 00:14:04  So because when you're saying I don't want to look at it, I'm just going to call a failure and look away. It's a form of resistance. You're not accepting what is as the facts. And when you resist it, it will continue to persist. You guys have heard that before? Yes. Persist. This is what we're talking about. And the reason why it will persist is this.

James Wedmore 00:14:24  I operate from a context, and I believe this as as truth, as as gospel, as fact, that life is happening for you. And whatever desire is born within your heart, like it's what you want, not what your parents want, not what society wants, not what your spouse wants, but what you want. If it came from your heart, then you already have within you, whether it's the raw or mastered talents, but the raw talent, skills and ability to turn that desire into a reality. Which then would mean that if you're willing to commit to it, commit everything in your being to that outcome, that your success is inevitable. And when you begin to live your life from a place of absolute knowing and truth, that your success is inevitable. That's a new power that you find power. Because what most people are doing is that's where the fear and the failure comes in is they're operating from a place of, I don't know if this is going to work. What if it doesn't? What if I've wasted my time? What if I'm going in the wrong direction? So when you choose that and that's a choice, it's just another one of these choices.

James Wedmore 00:15:32  Life is choice. And that's a choice to live from. My success. Is inevitable. Inevitable means it's going to happen. Then one of two things is going to happen when you put yourself out there. This is what we call at bat moments. An at bat moment is when you put it on the line. You're either going to hit a home run or a strike, right? It's a it's a baseball analogy. And for the non-sports geek in the room, okay, I'm going to use a baseball analogy. When I didn't play baseball, it's an at bat moment. When you step up to the plate, everyone's looking at you and you're either going to strike out or you're going to hit that home run, right? So when you're doing that launch or that promotion, or you put it all on the line, one of two things will happen to you. Guaranteed. You will either get what you want or better, you'll get the result that you wanted. Or even better, right? That's that's option one.

James Wedmore 00:16:19  Or and this is so important for people to get this or you'll get the lesson you needed. I'd like you to consider that if your success is inevitable and the only reason you don't have what you wanted yet is because there's still something there for you to learn.

Katie Haahr 00:16:38  As James said, failure isn't real. It's not tangible. It's not who you are. It's just a label, a story. And story is, my friends. They can be rewritten. This conversation is a reminder that you are the creator of your reality, and that your business will only grow to the extent that you do. If this episode moved you, we'd love it if you shared or tagged Jasmine on Social. Until next time, keep growing and keep showing.