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The Fear Successful People Don’t Talk About [Poolside Confessions]

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Welcome to Poolside Confessions, my summer series where we gather around the pool and I confess the things I’ve been thinking, feeling, and experiencing – in hopes of normalizing these conversations and helping you know you’re not alone.

Today’s confession is one that almost every successful woman I’ve ever talked to has felt at some point. The fear of losing it all.

When I first started my business, my fears looked different. Am I good enough? Will I make it? What will people think? And in the back of my mind was this big fantasy of arrival – that when I finally hit a certain number, built a certain life, I’d feel safe. Secure. Like I’d finally made it.

You get there. And a new fear is waiting. The bigger the building you’ve built, the harder the ego whispers about the fall.

So many women end up creating a life their younger selves would have been so proud of – and they can’t even enjoy it because they’re too busy white-knuckling it. Too afraid it’s all going to be taken away.

In this episode, I’m walking you through the practices that have set me free from this fear – and that I’ve watched set other women free, too.

Here’s what we cover:

  • Why the fear of losing it all shows up the moment you finally build something you love
  • The thought pattern that keeps successful women exhausted and unable to enjoy what they’ve created
  • How to entertain the worst-case scenario… so you can finally make peace with it
  • The compassion practice I use with the scared little girl inside of me
  • Why getting clear on what is enough brings relief
  • How to stop building a prison out of your own success
  • The truth about freedom… and why it was never about the money

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Hello, friends. Welcome to my summer podcast series that I am calling Poolside Confessions, where we gather around my pool and I confess things. I confess things that I’ve been thinking, feeling, experiencing, in hopes that we can normalize these conversations so that you’ll know you’re not alone because it’s when you know you’re not alone and you realize, “Oh, my God, this happens to everyone,” that you start giving yourself more grace and you are able to move through these situations with more awareness and more clarity.

Now, with that said, I have to admit something. When I decided to do this summer series, I did not really take the weather into account. I just knew I wanted to be outside more this summer. In North Carolina, in the summer, it gets hot and humid. It has rained for the past three days and right now it is so humid I feel like my face is going to melt off, and who knows what’s happening with my hair. But as they say in France, “C’est la vie”. This is life and the show must go on and so it shall. Now, let’s dive into the fear that successful people have that we need to talk about.

Welcome to the School of Self-Image where our motto is simple, elevate your self- image, elevate your life. I’m Tonya Leigh, your hostess, and I’ll guide you to become the woman who doesn’t just dream bigger. She lives bigger. Let’s dive in.

When I first started my business, I did not have the fear that I’m going to talk about today. I had different fears. It was the fear of, am I going to succeed? Am I going to make it? Am I good enough? What will people think? It was all those types of fears. And in the back of my mind, and this happens to almost every single person without this awareness, but in the back of my mind, I had this big fantasy of arrival. When I finally make a certain amount of money, when I finally create the life that I want, then I will feel safe, I will feel secure, I will feel as if I have arrived.

The Fear That Appears After Success

Now, here’s the fear that we don’t talk about enough, because if you’re not careful, you will get to that place and you will meet a new fear, and I’ve never met a successful person who hasn’t had this fear at some point, and that is the fear of losing it all. I like to think of it as the bigger the building that you’ve built, the illusion of “the harder the fall”. That’s what our ego says. That’s what we experience. That’s what we feel. And we need to talk about this because what often happens is we end up building something that our younger versions would’ve been so proud of and we’re not even enjoying it because we have this fear of losing it all.

I know I’ve experienced it and in talking to probably a thousand entrepreneurs at this point of my career, almost every single one of them have experienced it too. So how do we get out of this? Well, the first thing is to realize that any emotion that you are experiencing, it’s not because of the outside world. It’s because of what’s happening in here. Even the thought, “I may lose it all,” is just a thought and it can feel so real in our bodies. Our ego is trying to protect everything that we’ve built. It’s trying to keep us in control. And so it feeds us these fears thinking, “Oh, my God, if we make her afraid enough, she’s going to get to work, she’s going to stay in the grind.” And it causes us not only to be exhausted, it causes us to not be able to enjoy what we’ve worked so hard to build. So if we have to question our thought patterns, I may lose it all as a thought, what would be a better feeling thought?

Making Peace With the Worst-Case Scenario

Now, this second one that I’m going to talk about may seem a little paradoxical, especially for those of you who follow my work, who are into manifestation or law of attraction, because our thoughts do impact how we feel and how we show up in the world. But what I’m about to share with you is to help you feel more free. What has really helped me in my life, especially around this topic, is allowing myself to entertain the worst case scenario only so that I can make peace with it. It’s not about just living in the worst case scenario and letting that nightmare wake you up every night. It’s entertaining it so you can ask yourself, “Huh, if that were to happen, how could I make peace with it ahead of time?”

So when I think about my life, my worst case scenario is not being homeless. Now, that’s not to say that could not happen, but knowing who I am, knowing how I think, knowing my drive, as long as I have my health and my faculties, I will do everything in my power to make sure that doesn’t happen. So when I think about my very worst case scenario, it’s maybe I lose my business and I have to sell my home, which I would make a profit off of, so I would have that money. Or even worse than that, I would have to go live with my mother, my mother who loves me and who would cook for me and take care of me. And I’m like, “Huh, when I think about all of those scenarios, it’s not as bad as just living in an unexamined worst case scenario, which is what a lot of people do. They don’t even entertain the worst case scenario. They’re just walking around afraid and they don’t even know what they’re afraid of.

So I love to entertain the worst case scenario so that I can make peace with it. And then what ends up happening is that now all of that energy can be channeled towards the best case scenario. I’m not spending my days worrying and letting my energy flow in that direction. I’m like, oh, I’ve made peace with that. Let me flow it to the best case scenario. There’s such a freedom to that.

Compassion for the Scared Part of You

The other thing that I do is I have so much compassion, so much compassion for that scared part of me. And this has supported me, not only around this fear, but in all of my fears, all of my crazy thoughts. I think about that little girl in me who she only ever wanted to know that she was enough. She only ever wanted to experience life in such a big way. And so obviously she’s afraid. She’s afraid of losing it all. But me as the adult in the situation, the adult who has built a strong sense of self, the adult who knows how to navigate her emotions, I just let her know, “You know what, babe? It’s understandable that you feel this way, but I got you. No matter what happens, I’ve got your back.”

Now, that doesn’t mean that we may not lose some things along the way, but I’m going to have you. You don’t have to be so afraid anymore. We’re going to have an amazing life no matter what because that is an internal experience. Who you are is not determined by what you have. Who you are is an amazing human being, and I’m going to remind you of that always. And so that’s been very helpful.

Defining What Is Enough

The other thing that’s been really helpful for me as well is getting clear on what is enough. As entrepreneurs and even in the personal development world, we’re sold this go harder, go bigger, keep growing, go to the next level. And I love all of that only when it’s coming from a place of enoughness. And so many of us haven’t defined what is enough? What is enough for you? And when I think about my life, I have more than enough right now, more than enough. And when I think about my minimum baseline, I could even let go of some of this stuff and still be okay.

And this even gets down to the point of your finances, knowing what is the baseline minimum that I need to keep up with in order to meet my baseline requirements. And when I did this exercise, I realized I don’t need that much. I really don’t. The things that I love the most actually cost nothing or very little, like my love of books, my friends, having dinners, the occasional weekend away, which that can cost unless you go and stay with a friend. That is my minimum baseline. A week in Europe, that’s just extra. That’s just a little bonus. But when I think at the minimum baseline of what I need to be happy, I’m like, it’s not that much. And all of a sudden, this fear of losing it all, it’s like, oh, but I will always be able to maintain that level of satisfaction in my life. So that’s been very helpful for me as well.

Why Success Doesn’t Guarantee Freedom

The last thing I want to leave you with is that so many of us go into entrepreneurship because we want a sense of freedom. We want to have freedom of time. We want to have the freedom that money allows you the options, freedom of our creativity and how we express ourselves in the world. And what can often happen is that you end up building a prison for yourself, because I want you to think about this, if you need something to feel free, are you really free? Freedom is an inside job. It’s something that you create from within and then you express it in how you live your life. I have known people with very little money who were so incredibly free. I’ve known people with lots of money who were not free. What was the difference? And it was all about what was going on in here and in here. This is where freedom lies.

I want the successful women in my life to enjoy their success. I want them to be able to sleep well at night. I want them to be able to take time off with their family and not worry about what’s happening in the business. I want them to be able to acknowledge all that they’ve built and created.

Trusting Yourself to Create Again

That’s the other thing, you have to remember, you created all of this. So many women have told me things like, “Well, it just happened. I was lucky I was in the right place at the right time. I had lots of support,” and we sell ourselves short. So no wonder we’re so afraid of losing it all because we think that we didn’t create it, so it can be taken from us. But when you realize, “Okay, I created this, which means I’m smart, I’m a problem solver, I can figure things out,” and then you pair that with making peace with the worst case scenario and getting clear on your enoughness and you work on your thoughts around the fear and you give yourself so much compassion, you will notice that this fear begins to dissipate and you can finally relax and enjoy all that you’ve built.

All right, my friends, this was my Poolside Confession. I hope you have a lovely, lovely week and come back next week for the next one where we’re talking about aging. So if you haven’t subscribed yet, make sure you hit that subscribe button down below and meet me here next week. Hopefully, it won’t be as hot or as humid and if it is, hopefully it’s not raining, and maybe you’ll find me in the pool. Have a beautiful week and I’ll see you on the next one.

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