92. Remove the Fear of Failure From Starting a Business
Starting a business sounds exciting until your brain whispers, “But what if you fail?” For so many moms, the fear of failure shows up fast and loud, turning a spark of possibility into a spiral of worst-case scenarios. If you have ever felt excited about an idea one minute and completely shut down by doubt the next, you are not alone, and you are not broken.
In this episode, I talk about what fear of failure actually is and why it feels so personal when you’re thinking about starting something new. I walk you through a powerful shift that helps you stop letting your brain define failure in the heat of the moment. Instead of reacting to every no or every slow week, you will learn how to decide ahead of time what success and failure really mean for you.
You will hear why mini setbacks are part of the process and how to move forward even when fear shows up. Whether you are just exploring an idea or already building quietly on the side, this conversation will help you loosen the grip that fear of failure has on your next step so you can actually take it.
If you're ready to see exactly how to protect your finances AND grow your confidence around starting, join my *FREE* webinar, Start a Business Without Fear of Failure or Financial Risk. It's happening on Friday, February 20th, 2026, at 1 pm ET. Click here to register.
What You’ll Learn from this Episode:
Why fear of failure feels so intense when you think about starting a business.
What your brain is actually afraid of when it spirals into worst-case scenarios.
How to create timelines and metrics that build confidence instead of sabotage it.
Why hearing “no” is data, not proof you should quit.
How to take action and move forward even when fear is still present.
Listen to the Full Episode:
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Episodes Related to Fear of Failure:
89. Why Other People’s Opinions Hold You Back (& How to Take Your Power Back)
91. Building a Business Without Quitting Your Job (For Moms Who Want Financial Security)
Full Episode Transcript:
Have you ever noticed that when you think about starting a business, your brain immediately jumps to the worst-case scenario? What if this doesn't work? What if I embarrass myself? What if I try and fall flat on my face? That spiral happens fast, and unfortunately, it's completely normal.
Life would be much more fun without it. So today, I'm going to show you how to stop that spiral before it even begins.
Welcome to How to Quit Your Job, the podcast for moms ready to ditch the nine-to-five and build a life and business they love. I’m your host, Jenna Rykiel. Let’s go.
Hi, mom friends. Welcome to episode 92 of the How to Quit Your Job podcast. I'm so excited to talk to you today. That's right. This is one of the biggest fears and obstacles that I hear when I ask moms, what is your biggest fear when they're thinking about starting a business? And we're just going to remove it before it becomes a problem.
This topic, as well as last week's, were inspired by real obstacles I hear every day from moms when they are considering starting a business. And although these might feel insurmountable, they just require targeted strategies and mindset work. So they inspired a couple of episodes, and they inspired me to take this work a step further for you, to go deeper into those strategies.
So I created a free webinar called Start a Business Without Fear of Failure or Financial Risk, which I will tell you about at the end of this podcast. And I know it sounds too good to be true, but trust me, once you hear about some of the things that I talk about in that webinar and even in this episode, it will start to open up your understanding of how you can do this without those obstacles rearing their ugly head.
So stick around, and if what I talk about today resonates with you at all, or if you find yourself being super resistant to some of the concepts and ideas I share, I want you to be honest with yourself because that means this is your work. So going deeper might be exactly what you need in order to start taking action.
And that webinar is happening Friday, February 20th, so you'll want to stay tuned for that information.
So last week, I talked about the obstacle of finances, the real fear of letting go of a steady paycheck, and how we can truly mitigate that fear when starting a business and why doing that is actually the smartest thing that we can do, even though it feels hard in the moment. But what I'm talking about today is fear of failure.
And this is probably the number one stated fear that comes up when I ask moms what's holding them back from starting a business. It's a fear of uncertainty, a fear of not knowing how something is going to pan out, especially if moms come to me and they know they want flexibility and freedom, but they aren't sure what the business would be. That alone can feel really uncomfortable.
And fear of failure is also about saving face. It's about the messy emotions that come up when we do fail. It's about not wanting to feel embarrassed, not wanting to feel disappointed, not wanting to have to explain ourselves if something doesn't work out. When we think about fear of failure, we're usually thinking about moments in our life when we felt like not enough, when we went for something and fell short, maybe when we told a lot of people about something possible in our life and then had to backtrack when it didn't happen.
Maybe we even think about failed relationships. There are certainly moments in our life where things didn't work out ideally or as we thought they would. And absolutely, that feels bad in the moment.
But what's even more significant is that we carry those experiences with us. So depending on the situation, they can stay with us for a long time. When I think about failures in my own life, I think about jobs I didn't get, the schools I applied to that I didn't get into, sports games I lost, grades that didn't live up to my own high standards, relationships that didn't work out.
And oftentimes when those things happen, it holds us back from the thing we want most. If we have an ugly relationship that doesn't work out, we might be closed off to any future relationships. That failure that we experienced makes the fear of future failures even more pungent.
One that really stands out to me, a failure that I think about all the time, or that I had to, we'll say, really redefine for myself, which I'll talk about in a second, is the first MBA program that I applied to. I remember getting the rejection letter and feeling really inadequate. It wasn't just, oh, I didn't get in, bummer. It was this deeper spiral of not-enoughness. If I'm not good enough to get in, if I'm not smart enough, if I'm not hard-working enough, then what does that mean about me in other areas of my life?
So it can be very easy for it to feel like a dark cloud is upon us. I know that's how I felt in that moment. And let's be honest, for maybe even days and weeks and months after that.
And that's what fear of failure really is. It's not just fear of something not working out. It's fear of what we will make it mean about who we are. Fear of failure is about taking failure personal. It's not just something that didn't work out. It's something that didn't go as planned necessarily. It's about what that means about us.
So the Olympics are going on right now, and I can't help but think about Lindsey Vonn and use her as a bit of an example here, right? She's an Olympic downhill skier, and a week before the Olympics, she tore her ACL. And she decided to race anyway. She ended up getting caught up in one of the flags and had a really bad wreck and fractured her leg. She's 41, so this is what I can only imagine is her last Olympics. And it would be really easy to look at that race and call it a failure.
I'm sure there are people out there who are thinking of it that way right now in this moment. But she released a statement on social media afterwards that I just thought was so beautiful.
She said, "While yesterday did not end the way I had hoped, and despite the intense physical pain it caused, I have no regrets. Standing in the starting gate yesterday was an incredible feeling that I will never forget. Knowing I stood there having a chance to win was a victory in and of itself. I also knew that racing was a risk. It always was and always will be an incredibly dangerous sport. And similar to ski racing, we take risks in life. We dream, we love, we jump, and sometimes we fall. But that is also the beauty of life. We can try. I tried, I dreamt, I jumped. The only failure in life is not trying."
I have to get myself together. I'm getting emotional. The only failure is not trying, okay? She could have told a very different story about that crash. She could have made it mean, I ruined my Olympics, or my career ended in embarrassment. I ruined my career, or I shouldn't have risked it. What was I thinking?
We all have human brains, and our brains are very good at slipping into regret and shame and self-loathing when something doesn't go how we planned. But she didn't. Her story wasn't about the wreck. Her story was about the courage to stand in the gate.
And that's what I want you to see. Sometimes we fall, but the story about the fall is what determines what happens next. Failure is never permanent. Even in the middle of something that feels like a massive setback, it can be the start of a comeback story, depending on how we decide to frame it.
And of course, Lindsey Vonn has an Olympian human brain, which is just operating on a whole other playing field of mind management. And you have to at that level. And I want all of us to invest the time and energy to get our brains on that level too. I want us to be able to immediately, days after or moments after something that feels really heavy or like it didn't go the way we had planned, I want us to be able to find the empowering story in it.
But here today, like I just needed to take that opportunity to set the stage about failure because it will always be something worthwhile to redefine our relationship with.
And in the webinar, I will definitely dive deeper into this, but for today's conversation, I actually want to take this a step further and offer a very simple strategy that will change everything. Because it's one thing for me to say failure is about the story, and that's true. It's another thing entirely to access a helpful story in the moment when everything feels like it's falling apart.
Let's be honest, when we receive the rejection letter, when we lose the race, when someone says no, we have these human brains, and it's really hard to suddenly become enlightened and empowered in that moment. Lindsey Vonn can do it. Like I said, she has an Olympic athlete brain, and most of us don't have that. We haven't spent our entire lives practicing that.
So the step further and the strategy I think is so important when we're setting business goals or really any big goal where failure feels possible is to decide in advance what failure means. What does success look like, and what does failure look like? And deciding how we answer those questions in advance. Most of us never answer that question ever. And that's a problem, because if you don't define failure ahead of time, your brain will define it for you in real time. And I promise you, it will not be generous.
It will not be generous like Lindsey Vonn's brain was for her. It will move the goal post, it will look for evidence that you're behind, it will find ways to make you feel like you're not doing enough. I see this all the time with my clients and myself. When I ask, what does success look like and what does failure mean? There's usually a long pause. We haven't even thought about it.
And when we don't think about it ahead of time, we default to feeling like we're failing, no matter the outcome. And this is really interesting because I have so many cases and examples where my clients are actually succeeding, but they still feel like they're failing.
So instead of this, I want to offer that we decide. We decide what we would actually deem a failure, and we decide it before we even start. There's really only success or learning. I don't believe in absolute failures, but if failure is the thing keeping you stuck, then we want to make sure we bring it into the light. We want to face it head-on. We want to understand what exactly it means for us, and we want to make it the devil we know.
So, let's say you're starting a coaching business. I want to give a concrete example of what this might look like. Let's say you've been a runner your whole life, you love organizing runs, your friends already come to you for advice, it's your thing, but you're afraid it might fail. You're afraid you won't find clients, you're afraid you won't make money, you're afraid it won't be fun once you start charging people for it. You're afraid people in your network will say, "Who does she think she is?" and they'll talk about you.
So let's answer the question because, we offered some vague fears, like not finding clients, not making money, it not being fun anymore. But when we think about it and answer the question, what would failure actually look like? What does it actually mean? We can get a little bit more specific and granular.
Is it not signing any paying clients? And if so, over what timeline? Is it zero dollars in revenue, or is there a different revenue marker? Are we looking at 30 days, 90 days, or six months? When I dig into this with clients, the logical part of our brain actually almost always gives us more time than our emotional brain would, okay?
So what this looks like is they'll say something like, "I'm going to give myself six months to sign a paying client. And if I don't sign a paying client in six months, I'll consider that a failure." I'm usually thinking you're absolutely going to sign a paying client before six months. Six months is a very long amount of time. It's a lot of time to figure this thing out, especially when we have commitment and desire and we're having fun with it. Six months feels like not a lot of time if you've never done this before.
But I love it because when I ask that question, we tend to create a metric that is not only realistic, but it's a metric that gives us abundant time and space. We've created space for this goal.
And we've created not just space, but a container, a timeline for experimentation. And this is so important because now, any mini failures that we experience, one person saying no to us when we make them an offer for our coaching or our running program, that doesn't equal failure because now we know that we've given ourself a timeline around the failure.
So let's say you spend your first month of this coaching practice building confidence, having conversations, making offers, right? You have your first sales conversation, which, by the way, can feel so icky in the beginning, but as a reminder, it's really just you being of service. I have a whole podcast episode on this, episode 14, How to Make Selling Easier.
Let's say you finally go and you have this conversation, this sales conversation, and you hear no. If you haven't defined failure ahead of time, your brain will immediately say, "See, this isn't working."
Maybe it's not just one no. Maybe it's five nos. Maybe you talk to five people and everyone says, "No, absolutely not. I run for free. Why would I hire a coach?" And maybe it's not just somebody saying no, maybe it's that you've been at this for a month and you still don't feel confident. Maybe it's you've been at this for a month and you overhear someone saying, "Who is she to think she can coach on this? She's never gotten a certification," or, "She's not even that good of a runner." Right?
And suddenly these little things happen over the course of a month that can feel like a massive failure, and you're only 30 days in. Nothing catastrophic has actually happened. You just heard some nos. You didn't get instant traction. People have opinions and thoughts about your business. I also have a really great episode on other people's opinions, so check out episode 89 as well if you are chronically held back by worrying about other people's opinions.
But again, nothing catastrophic actually has happened in those 30 days. But if there's no pre-decided metric or no agreed upon timeline, your brain will decide in the moment that you've failed. And once your brain decides you've failed, your energy completely shifts. You might avoid the business altogether, or you might stop talking about it as confidently. Maybe you stop making offers altogether because you keep hearing nos. You hesitate before sending out messages to your network, and you start taking this mental space of just like wanting to be realistic.
When we experience those what feels like mini failures that we make into something more catastrophic, make it mean that this isn't going to work, that's where so many moms quit. And it's not because the business failed. It's because they decided it failed, and they decided that way too early. And it's often based on emotional response in the moment. It's based on your primitive brain that wants to avoid discomfort.
When emotions are high, intelligence is low. And when we hear no or someone ghosts us or something happens that doesn't feel good, emotions are going to be high. And that's definitely not when we want to define failure for ourselves. We don't want to be making a decision at that point on whether this whole idea and thing that we were once so excited and energized about is working or not. Because then we throw in the towel too early.
But if you've already decided in advance from a calm, the prefrontal cortex portion of your brain that is responsible for decision making and mature thinking, if you've used that part of your brain to decide in advance what failure means, and if you've decided that failure actually means no paying clients after six months, then in that moment when you hear five nos in the first 30 days, you can remind yourself this isn't failure. This is data. This is learning. This is just the beginning of a six month experiment.
That is a game changer, mentally and emotionally, because there absolutely will be failures along the way. We need failures. We need to hear nos to get to yeses. And when you've defined what failure actually is ahead of time, you don't let those mini failures become bigger than they actually are. You don't let them become ultimate deterrents. They're just data.
So here's what I really want you to take away from this episode. Fear of failure is actually so normal. So let me normalize it real quick. Everybody's experiencing fear of failure in so many things in life. It is normal. But failure itself is not the scary monster that your brain makes it out to be. Failure is never permanent. It's not identity defining. It's not ever proof that you're not capable.
But it will feel very real and really monstrous and messy if you let your brain define it in real time. So instead of making those real-time decisions on whether something's a failure or not, you decide ahead of time, alright? You decide what success looks like, you decide what failure would mean, you decide the timeline, you decide the metrics. And then you give yourself the full experiment.
And I promise that when you're deciding ahead of time, you're going to be more fair with yourself. You're going to choose metrics and parameters and results that make it more likely for you to succeed.
A quick caveat on that, if you find that's not happening because I have met plenty of ambitious moms who really set themselves up for failure. Make sure that it happens, okay? If we know that we don't want to fail, don't create metrics that make it hard to succeed. This is like a secret of life. I'm giving it away for free. If you don't want to fail, don't set yourself up for failure by creating a situation that you can't win. Be kind to yourself.
So create metrics that are fair. Like I said, your brain hopefully will, for the most part, most people I work with, your brain will, when you think about it in advance, it'll set up metrics and parameters for you that are actually more achievable than if you don't do it. But if you find that's not happening, just stop. Create new metrics, okay? So that it doesn't make it so hard to succeed.
There are going to be moments in your business that feel like failures, like hearing no, not getting the response you want, people ghosting, people not engaging with you on your post or your emails. But those aren't failures. They're just reps. They're just practice. It's you learning and growing through experience. Building something out of nothing that gives you a more fulfilled and flexible life comes with some discomfort. That is one thing that's for sure.
So we need to practice, we need to be experiencing those mini failures in order to grow and get stronger. And those mini failures do not have to be big business ending failures.
And if you're listening to this and you can feel your brain resisting, if there's a part of you saying, "Yeah, Jenna, but what if I really fail?" That's okay. That just means this is your work. You don't need to eliminate fear to move forward. In fact, I always say that fear is going to be in the car on this journey, it just can't be the driver.
So instead of waiting to hit the gas until fear is out of the car, you just need to define it and understand what it is for yourself so that you can start taking action and release some of its power. No longer let fear take the wheel. It's like you take the power back. And you can actually feel empowered and afraid at the same time. But I promise that we have power over the fear of failure when we know exactly what failure means for us. And trust me, it's different for everyone.
If fear of failure is getting in the way of you starting a business, you need to be at this training on Friday that I talked about. I am hosting a free webinar, Start a Business Without Fear of Failure or Financial Risk. You can reserve your spot by clicking the link in the show notes or going to mom.jenna.coach/risk.
So inside that webinar, I'm going to go deeper into this conversation. I'm going to walk you through additional shifts you can make starting today to redefine your relationship with failure. So it becomes part of the strategy instead of the thing that stops you.
Because here's what I see all the time. We think fear is a stop sign. We think if I feel scared, that must mean I shouldn't do this. But like I've said, fear is normal. It's just your brain being a human brain. And the fact that you feel fear when you think about starting a business, that actually tells me something really important. It tells me you care, it tells me you have hope, it tells me you desire something different for your life.
Because we don't feel fear about things we don't want or care about. Fear shows up when something really, truly matters. And when something matters, that's not a stop sign. That's a signal that this work is important to you.
In the webinar, we're going to talk about risk, how to mitigate it intelligently, and how to think about reward in a grounded, strategic way. The reward of you having flexibility and autonomy and doing something that lights you up, the reward of being present with your family and never having to ask to leave early to go to pick up and never having to request PTO when you think of a really great trip that you want to take your family on, the reward of being the mom that you envision without the stressors of constant Slack messages and needing to respond to clients at all times.
When we build a business, we're also building it around what's important to us in terms of our time and how we spend our time. But starting a business absolutely is not about reckless leaps. All of my moms, I encourage, and we create plans around doing it with thoughtful action. It's about building confidence before the results sometimes, and it's about helping you move forward without waiting to feel fearless.
If you know this conversation has hit something for you, if you could feel your brain arguing at any point in this episode or thinking about all the fears and obstacles, that's exactly why I want you in that room on Friday. So go to, again, mom.jenna.coach/risk, or click the link in the show notes to register and be there.
This could be the thing that gets you feeling like you're ready, and I want that for you. I want you to feel confident and to feel like you're ready to start laying the groundwork and building the foundation for this life and career that you envision. If you think that you are meant for more, you're right. I hope to see you live in that room and I'll also see you next week on the podcast either way.
Thanks for listening to this week’s episode of How to Quit Your Job: A Mom’s Guide to Creating a Life and Business You Love. If you want to learn more about how I can help you stop making excuses and start making moves, head on over to www.jenna.coach. I’ll see you next week.
Life would be much more fun without it. So today, I'm going to show you how to stop that spiral before it even begins.
Welcome to How to Quit Your Job, the podcast for moms ready to ditch the nine-to-five and build a life and business they love. I’m your host, Jenna Rykiel. Let’s go.
Hi, mom friends. Welcome to episode 92 of the How to Quit Your Job podcast. I'm so excited to talk to you today. That's right. This is one of the biggest fears and obstacles that I hear when I ask moms, what is your biggest fear when they're thinking about starting a business? And we're just going to remove it before it becomes a problem.
This topic, as well as last week's, were inspired by real obstacles I hear every day from moms when they are considering starting a business. And although these might feel insurmountable, they just require targeted strategies and mindset work. So they inspired a couple of episodes, and they inspired me to take this work a step further for you, to go deeper into those strategies.
So I created a free webinar called Start a Business Without Fear of Failure or Financial Risk, which I will tell you about at the end of this podcast. And I know it sounds too good to be true, but trust me, once you hear about some of the things that I talk about in that webinar and even in this episode, it will start to open up your understanding of how you can do this without those obstacles rearing their ugly head.
So stick around, and if what I talk about today resonates with you at all, or if you find yourself being super resistant to some of the concepts and ideas I share, I want you to be honest with yourself because that means this is your work. So going deeper might be exactly what you need in order to start taking action.
And that webinar is happening Friday, February 20th, so you'll want to stay tuned for that information.
So last week, I talked about the obstacle of finances, the real fear of letting go of a steady paycheck, and how we can truly mitigate that fear when starting a business and why doing that is actually the smartest thing that we can do, even though it feels hard in the moment. But what I'm talking about today is fear of failure.
And this is probably the number one stated fear that comes up when I ask moms what's holding them back from starting a business. It's a fear of uncertainty, a fear of not knowing how something is going to pan out, especially if moms come to me and they know they want flexibility and freedom, but they aren't sure what the business would be. That alone can feel really uncomfortable.
And fear of failure is also about saving face. It's about the messy emotions that come up when we do fail. It's about not wanting to feel embarrassed, not wanting to feel disappointed, not wanting to have to explain ourselves if something doesn't work out. When we think about fear of failure, we're usually thinking about moments in our life when we felt like not enough, when we went for something and fell short, maybe when we told a lot of people about something possible in our life and then had to backtrack when it didn't happen.
Maybe we even think about failed relationships. There are certainly moments in our life where things didn't work out ideally or as we thought they would. And absolutely, that feels bad in the moment.
But what's even more significant is that we carry those experiences with us. So depending on the situation, they can stay with us for a long time. When I think about failures in my own life, I think about jobs I didn't get, the schools I applied to that I didn't get into, sports games I lost, grades that didn't live up to my own high standards, relationships that didn't work out.
And oftentimes when those things happen, it holds us back from the thing we want most. If we have an ugly relationship that doesn't work out, we might be closed off to any future relationships. That failure that we experienced makes the fear of future failures even more pungent.
One that really stands out to me, a failure that I think about all the time, or that I had to, we'll say, really redefine for myself, which I'll talk about in a second, is the first MBA program that I applied to. I remember getting the rejection letter and feeling really inadequate. It wasn't just, oh, I didn't get in, bummer. It was this deeper spiral of not-enoughness. If I'm not good enough to get in, if I'm not smart enough, if I'm not hard-working enough, then what does that mean about me in other areas of my life?
So it can be very easy for it to feel like a dark cloud is upon us. I know that's how I felt in that moment. And let's be honest, for maybe even days and weeks and months after that.
And that's what fear of failure really is. It's not just fear of something not working out. It's fear of what we will make it mean about who we are. Fear of failure is about taking failure personal. It's not just something that didn't work out. It's something that didn't go as planned necessarily. It's about what that means about us.
So the Olympics are going on right now, and I can't help but think about Lindsey Vonn and use her as a bit of an example here, right? She's an Olympic downhill skier, and a week before the Olympics, she tore her ACL. And she decided to race anyway. She ended up getting caught up in one of the flags and had a really bad wreck and fractured her leg. She's 41, so this is what I can only imagine is her last Olympics. And it would be really easy to look at that race and call it a failure.
I'm sure there are people out there who are thinking of it that way right now in this moment. But she released a statement on social media afterwards that I just thought was so beautiful.
She said, "While yesterday did not end the way I had hoped, and despite the intense physical pain it caused, I have no regrets. Standing in the starting gate yesterday was an incredible feeling that I will never forget. Knowing I stood there having a chance to win was a victory in and of itself. I also knew that racing was a risk. It always was and always will be an incredibly dangerous sport. And similar to ski racing, we take risks in life. We dream, we love, we jump, and sometimes we fall. But that is also the beauty of life. We can try. I tried, I dreamt, I jumped. The only failure in life is not trying."
I have to get myself together. I'm getting emotional. The only failure is not trying, okay? She could have told a very different story about that crash. She could have made it mean, I ruined my Olympics, or my career ended in embarrassment. I ruined my career, or I shouldn't have risked it. What was I thinking?
We all have human brains, and our brains are very good at slipping into regret and shame and self-loathing when something doesn't go how we planned. But she didn't. Her story wasn't about the wreck. Her story was about the courage to stand in the gate.
And that's what I want you to see. Sometimes we fall, but the story about the fall is what determines what happens next. Failure is never permanent. Even in the middle of something that feels like a massive setback, it can be the start of a comeback story, depending on how we decide to frame it.
And of course, Lindsey Vonn has an Olympian human brain, which is just operating on a whole other playing field of mind management. And you have to at that level. And I want all of us to invest the time and energy to get our brains on that level too. I want us to be able to immediately, days after or moments after something that feels really heavy or like it didn't go the way we had planned, I want us to be able to find the empowering story in it.
But here today, like I just needed to take that opportunity to set the stage about failure because it will always be something worthwhile to redefine our relationship with.
And in the webinar, I will definitely dive deeper into this, but for today's conversation, I actually want to take this a step further and offer a very simple strategy that will change everything. Because it's one thing for me to say failure is about the story, and that's true. It's another thing entirely to access a helpful story in the moment when everything feels like it's falling apart.
Let's be honest, when we receive the rejection letter, when we lose the race, when someone says no, we have these human brains, and it's really hard to suddenly become enlightened and empowered in that moment. Lindsey Vonn can do it. Like I said, she has an Olympic athlete brain, and most of us don't have that. We haven't spent our entire lives practicing that.
So the step further and the strategy I think is so important when we're setting business goals or really any big goal where failure feels possible is to decide in advance what failure means. What does success look like, and what does failure look like? And deciding how we answer those questions in advance. Most of us never answer that question ever. And that's a problem, because if you don't define failure ahead of time, your brain will define it for you in real time. And I promise you, it will not be generous.
It will not be generous like Lindsey Vonn's brain was for her. It will move the goal post, it will look for evidence that you're behind, it will find ways to make you feel like you're not doing enough. I see this all the time with my clients and myself. When I ask, what does success look like and what does failure mean? There's usually a long pause. We haven't even thought about it.
And when we don't think about it ahead of time, we default to feeling like we're failing, no matter the outcome. And this is really interesting because I have so many cases and examples where my clients are actually succeeding, but they still feel like they're failing.
So instead of this, I want to offer that we decide. We decide what we would actually deem a failure, and we decide it before we even start. There's really only success or learning. I don't believe in absolute failures, but if failure is the thing keeping you stuck, then we want to make sure we bring it into the light. We want to face it head-on. We want to understand what exactly it means for us, and we want to make it the devil we know.
So, let's say you're starting a coaching business. I want to give a concrete example of what this might look like. Let's say you've been a runner your whole life, you love organizing runs, your friends already come to you for advice, it's your thing, but you're afraid it might fail. You're afraid you won't find clients, you're afraid you won't make money, you're afraid it won't be fun once you start charging people for it. You're afraid people in your network will say, "Who does she think she is?" and they'll talk about you.
So let's answer the question because, we offered some vague fears, like not finding clients, not making money, it not being fun anymore. But when we think about it and answer the question, what would failure actually look like? What does it actually mean? We can get a little bit more specific and granular.
Is it not signing any paying clients? And if so, over what timeline? Is it zero dollars in revenue, or is there a different revenue marker? Are we looking at 30 days, 90 days, or six months? When I dig into this with clients, the logical part of our brain actually almost always gives us more time than our emotional brain would, okay?
So what this looks like is they'll say something like, "I'm going to give myself six months to sign a paying client. And if I don't sign a paying client in six months, I'll consider that a failure." I'm usually thinking you're absolutely going to sign a paying client before six months. Six months is a very long amount of time. It's a lot of time to figure this thing out, especially when we have commitment and desire and we're having fun with it. Six months feels like not a lot of time if you've never done this before.
But I love it because when I ask that question, we tend to create a metric that is not only realistic, but it's a metric that gives us abundant time and space. We've created space for this goal.
And we've created not just space, but a container, a timeline for experimentation. And this is so important because now, any mini failures that we experience, one person saying no to us when we make them an offer for our coaching or our running program, that doesn't equal failure because now we know that we've given ourself a timeline around the failure.
So let's say you spend your first month of this coaching practice building confidence, having conversations, making offers, right? You have your first sales conversation, which, by the way, can feel so icky in the beginning, but as a reminder, it's really just you being of service. I have a whole podcast episode on this, episode 14, How to Make Selling Easier.
Let's say you finally go and you have this conversation, this sales conversation, and you hear no. If you haven't defined failure ahead of time, your brain will immediately say, "See, this isn't working."
Maybe it's not just one no. Maybe it's five nos. Maybe you talk to five people and everyone says, "No, absolutely not. I run for free. Why would I hire a coach?" And maybe it's not just somebody saying no, maybe it's that you've been at this for a month and you still don't feel confident. Maybe it's you've been at this for a month and you overhear someone saying, "Who is she to think she can coach on this? She's never gotten a certification," or, "She's not even that good of a runner." Right?
And suddenly these little things happen over the course of a month that can feel like a massive failure, and you're only 30 days in. Nothing catastrophic has actually happened. You just heard some nos. You didn't get instant traction. People have opinions and thoughts about your business. I also have a really great episode on other people's opinions, so check out episode 89 as well if you are chronically held back by worrying about other people's opinions.
But again, nothing catastrophic actually has happened in those 30 days. But if there's no pre-decided metric or no agreed upon timeline, your brain will decide in the moment that you've failed. And once your brain decides you've failed, your energy completely shifts. You might avoid the business altogether, or you might stop talking about it as confidently. Maybe you stop making offers altogether because you keep hearing nos. You hesitate before sending out messages to your network, and you start taking this mental space of just like wanting to be realistic.
When we experience those what feels like mini failures that we make into something more catastrophic, make it mean that this isn't going to work, that's where so many moms quit. And it's not because the business failed. It's because they decided it failed, and they decided that way too early. And it's often based on emotional response in the moment. It's based on your primitive brain that wants to avoid discomfort.
When emotions are high, intelligence is low. And when we hear no or someone ghosts us or something happens that doesn't feel good, emotions are going to be high. And that's definitely not when we want to define failure for ourselves. We don't want to be making a decision at that point on whether this whole idea and thing that we were once so excited and energized about is working or not. Because then we throw in the towel too early.
But if you've already decided in advance from a calm, the prefrontal cortex portion of your brain that is responsible for decision making and mature thinking, if you've used that part of your brain to decide in advance what failure means, and if you've decided that failure actually means no paying clients after six months, then in that moment when you hear five nos in the first 30 days, you can remind yourself this isn't failure. This is data. This is learning. This is just the beginning of a six month experiment.
That is a game changer, mentally and emotionally, because there absolutely will be failures along the way. We need failures. We need to hear nos to get to yeses. And when you've defined what failure actually is ahead of time, you don't let those mini failures become bigger than they actually are. You don't let them become ultimate deterrents. They're just data.
So here's what I really want you to take away from this episode. Fear of failure is actually so normal. So let me normalize it real quick. Everybody's experiencing fear of failure in so many things in life. It is normal. But failure itself is not the scary monster that your brain makes it out to be. Failure is never permanent. It's not identity defining. It's not ever proof that you're not capable.
But it will feel very real and really monstrous and messy if you let your brain define it in real time. So instead of making those real-time decisions on whether something's a failure or not, you decide ahead of time, alright? You decide what success looks like, you decide what failure would mean, you decide the timeline, you decide the metrics. And then you give yourself the full experiment.
And I promise that when you're deciding ahead of time, you're going to be more fair with yourself. You're going to choose metrics and parameters and results that make it more likely for you to succeed.
A quick caveat on that, if you find that's not happening because I have met plenty of ambitious moms who really set themselves up for failure. Make sure that it happens, okay? If we know that we don't want to fail, don't create metrics that make it hard to succeed. This is like a secret of life. I'm giving it away for free. If you don't want to fail, don't set yourself up for failure by creating a situation that you can't win. Be kind to yourself.
So create metrics that are fair. Like I said, your brain hopefully will, for the most part, most people I work with, your brain will, when you think about it in advance, it'll set up metrics and parameters for you that are actually more achievable than if you don't do it. But if you find that's not happening, just stop. Create new metrics, okay? So that it doesn't make it so hard to succeed.
There are going to be moments in your business that feel like failures, like hearing no, not getting the response you want, people ghosting, people not engaging with you on your post or your emails. But those aren't failures. They're just reps. They're just practice. It's you learning and growing through experience. Building something out of nothing that gives you a more fulfilled and flexible life comes with some discomfort. That is one thing that's for sure.
So we need to practice, we need to be experiencing those mini failures in order to grow and get stronger. And those mini failures do not have to be big business ending failures.
And if you're listening to this and you can feel your brain resisting, if there's a part of you saying, "Yeah, Jenna, but what if I really fail?" That's okay. That just means this is your work. You don't need to eliminate fear to move forward. In fact, I always say that fear is going to be in the car on this journey, it just can't be the driver.
So instead of waiting to hit the gas until fear is out of the car, you just need to define it and understand what it is for yourself so that you can start taking action and release some of its power. No longer let fear take the wheel. It's like you take the power back. And you can actually feel empowered and afraid at the same time. But I promise that we have power over the fear of failure when we know exactly what failure means for us. And trust me, it's different for everyone.
If fear of failure is getting in the way of you starting a business, you need to be at this training on Friday that I talked about. I am hosting a free webinar, Start a Business Without Fear of Failure or Financial Risk. You can reserve your spot by clicking the link in the show notes or going to mom.jenna.coach/risk.
So inside that webinar, I'm going to go deeper into this conversation. I'm going to walk you through additional shifts you can make starting today to redefine your relationship with failure. So it becomes part of the strategy instead of the thing that stops you.
Because here's what I see all the time. We think fear is a stop sign. We think if I feel scared, that must mean I shouldn't do this. But like I've said, fear is normal. It's just your brain being a human brain. And the fact that you feel fear when you think about starting a business, that actually tells me something really important. It tells me you care, it tells me you have hope, it tells me you desire something different for your life.
Because we don't feel fear about things we don't want or care about. Fear shows up when something really, truly matters. And when something matters, that's not a stop sign. That's a signal that this work is important to you.
In the webinar, we're going to talk about risk, how to mitigate it intelligently, and how to think about reward in a grounded, strategic way. The reward of you having flexibility and autonomy and doing something that lights you up, the reward of being present with your family and never having to ask to leave early to go to pick up and never having to request PTO when you think of a really great trip that you want to take your family on, the reward of being the mom that you envision without the stressors of constant Slack messages and needing to respond to clients at all times.
When we build a business, we're also building it around what's important to us in terms of our time and how we spend our time. But starting a business absolutely is not about reckless leaps. All of my moms, I encourage, and we create plans around doing it with thoughtful action. It's about building confidence before the results sometimes, and it's about helping you move forward without waiting to feel fearless.
If you know this conversation has hit something for you, if you could feel your brain arguing at any point in this episode or thinking about all the fears and obstacles, that's exactly why I want you in that room on Friday. So go to, again, mom.jenna.coach/risk, or click the link in the show notes to register and be there.
This could be the thing that gets you feeling like you're ready, and I want that for you. I want you to feel confident and to feel like you're ready to start laying the groundwork and building the foundation for this life and career that you envision. If you think that you are meant for more, you're right. I hope to see you live in that room and I'll also see you next week on the podcast either way.
Thanks for listening to this week’s episode of How to Quit Your Job: A Mom’s Guide to Creating a Life and Business You Love. If you want to learn more about how I can help you stop making excuses and start making moves, head on over to www.jenna.coach. I’ll see you next week.
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