How to Become a Risk Taker

I’m going to read a few quotes for you. And if they resonate with you, if you feel like this is what you need more of in your life, then you’re going to love today’s episode.

So, the first one is from Sheryl Sandberg. She says, “If you’re offered a seat on a rocket ship, don’t ask what seat; just get on.” Neil Gaiman wrote, “If you dare nothing, then when the day is over, nothing is all you will have gained.” Finally, Sarah Parish said, “Living with fear stops us taking risk. And if you don’t go out on the branch, you’re never going to get the best fruit.”

So, are you ready to become a risk taker? If so, let’s dive into today’s episode.

Welcome to the School of Self-Image, where personal development meets style. Here’s your hostess, master life coach Tonya Leigh.

Hello, gorgeous friends. Are you having a good day? I hope so. In fact, I hope you say, “I’m having a great day.” But we have all kinds of days, don’t we? They’re not all amazing and great. And that’s okay. But I did have the most incredible weekend.

I had some girlfriends that flew in. We went to great dinners. We went to see Bocelli. We had so much fun. And then, when they left, I have been head-down working. I am in a work season of my life. I believe that we have seasons. I believe that sometimes, we’re ready to rest and rejuvenate. And then, we have seasons where we just feel that inspiration and we’re like, head down, “Let’s work.”

So, over the last few days, I’ve been getting so much done. I have been writing a lot. I have been jotting down so many ideas, and really just thinking over the last couple of years. They have been crazy, y’all. I know everyone will agree with that statement.

But for me, it’s been crazy in an incredible way. And if you’ve been listening to this podcast for a while, you know that I’ve said that 2020 was one of the best years of my life. And it’s because it was the year that I made the biggest decisions in my life. But what came with those decisions were a lot of risk. And that’s what I want to talk about in today’s episode.

I want to share with you specifically how to become a risk taker. Anything you want and don’t yet have is hanging out I the mystery of life. It’s hanging out in uncertainty, which is why most people just continue to choose the same things over and over, day after day.

They complain about their jobs, but they stay in the same job. They complain about their marriage, but they stay in the marriage. And what really is happening is that we’re just afraid. We’re afraid to take the risk of changing our lives.

And I get it. In fact, I’m just going to be very transparent with you all. When I decided to leave a long-term relationship back in 2020, I was afraid. And for a while, I had known that this was something I was being called to do. Not because the relationship was bad. It wasn’t bad. I just felt myself being pulled towards something different. And yet, it was almost like I was paralyzed in fear.

And so, for a bit, I just kept choosing the same thing over and over again until I just made the decision. I’m like, “I’m leaving.” And then all of the fear came up, the risk of, “What if this doesn’t work out? What if I regret this decision? What if I don’t do well living in a big city?” all of the questions that we have when we make a big decision that involves some level of risk.

But I did it anyway and I grew into that decision. And it changed my life in the most beautiful way. And I see my clients do this. And I’m the kind of coach that loves to push my clients out of the plane. I have never personally been skydiving, but I have many friends who have, and they’ve told me what the process is like.

There you are, standing on the edge of the door to the plane, which usually there is no door, it’s just open. And you are attached to your skydiving instructor. And as they count to three, before they say three, they push you out of the plane. And they do this for a couple of reasons.

Number one, they know that if they wait for you to decide that you’re ready, you’ll probably never do it because fear will set in and you will talk yourself out of it, even though they know that it is completely safe. I say completely – everything in life comes with a risk. We get in our cars every day. There’s a risk involved with that.

But statistically speaking, the amount of skydiving accidents are very, very tiny. And because they know that, they have to be the ones to push you out and trust that the parachute will open and that you will have the time of your life.

And so, that’s what I end up having to do with my clients because I am so grateful for my mentors and my friends who pushed me out of the plane when I was so afraid to take the next step. But I’ve done it so much now that I’m not as afraid anymore. I have so much evidence to prove what comes with your risk-taking ability.

And so, I’ve looked up the definition of risk as I was preparing for this podcast and it says, “A risk is a possibility of loss or injury. It involves uncertainty." So, again, anything you want and don’t yet have is in that area of uncertainty, which means you’re going to have to be willing to take risk in order to create what you want.

When it comes to risk-taking, there are many different types of risk. For example, there are physical risk. And this is something that could potentially cause harm to your body. For example, the skydiving. Or, let’s say, learning to snow-ski or learning to do any kind of physical sport, or walking around in a quote unquote bad neighborhood. Those all involve a physical potential risk.

There’s also social risk, and this is where you put yourself in the position where you could be socially judged or humiliated. For example, speaking onstage, putting your work out into the world – which I do a lot. Every time, even this podcast, there’s a risk involved that I could be taking a social risk.

I might say something in the wrong way and potentially offend someone, which I would never do intentionally. I might have people who think it’s a terrible episode. Every time I put my work out into the world, there is a social risk involved.

There’s also business and professional and career risk. And that’s any kind of risk that pertains to your work. So, for example, it might be you changing jobs. It might be you asking for a promotion. For me in 2020, even through this year, I’ve been taking a lot of risk in my business. And it’s scary. I get it.

Back in October in 2020, when I decided to completely rebrand my business, change my entire business model, I had no evidence yet that it would work personally. And that was scary. I’m like, I am getting ready to let go of everything I’ve known for 10 years, my programs, the way I had conducted business, even some of my team members, in order to grow my business, in order to feel more aligned with my mission.

And yet, I had no certainty that it was going to work. What I did have was a knowing that I would regret not trying. And again, throughout the year, I’ve been making decisions behind the scenes around my business and my team that all have involved a level of risk. And I’ll tell you about one in just a minute that I’m so excited to share with you, but I’m going to share that when we talk about, like, how to approach a risk.

So, you can have career and professional and business risk. The other risk that you can take – and this one sometimes is the hardest, my friends – and that is emotional risk. And that’s when you expose yourself to potentially feeling negative emotions.

And the best example I can think of around this is when you fall in love. I did that this year too. I’ve done all the things this year. And I realize, wow, when you fall in love with someone, you are opening yourself up for potential pain. That’s just part of the process. There are no guarantees.

And I see this so often with many of my clients who want to experience a relationship. They want to dive deeper into a loving connection. But because of their past and the pain that potentially they’ve experienced, they are so afraid to do that again. But you have to be willing to feel that in order to put yourself out there and truly connect with someone.

The last risk that comes to mind is financial risk. And I hear this a lot from clients. They’ll want to potentially join a mastermind or they’re thinking about making an investment in their homes or anything that requires money. And they’re so afraid of taking a financial risk.

But what I have noticed, you all, is that the more I am willing to invest in myself, in my growth, in my learning, and in elevating my life, the better my life gets.

And I was thinking about why that is and, with each of those investments, it evolves my self-image. I have to see myself differently, number one, in order to make the investment. And then also, depending on what my intention is for the investment, I’m going to have to change how I see myself in order to get that ROI.

And sometimes, the ROI is not money. Sometimes, the ROI is experiencing more joy, more experiences, more comfort. That’s why, when you make an investment, you need to be clear on, “What is my intention? What do I want to get out of this?” Then, you can end up creating that experience for yourself.

But you have to be willing to take the financial risk first. And it’s so crazy to me. Everyone wants the rewards without taking the risk. But you have to be willing to take the risk in order to get the rewards. So, I’m going to talk you through how I think about risk and why my mindset is when I am taking a risk.

So, the first question is, how do you know what risk to take? Because not every risk is a good risk, y’all. Trust me, I’ve taken some risks and they were dumb. I was like, why did I do that? But I look back now, and I realized that was all a part of the journey. Because I know what will happen is, if you’ve taken risks and they haven’t worked out and they made a mess of your life for a period of time, you will use that as evidence not to take risk any longer.

I don’t do that. I just realize, part of learning to be a really smart risk taker is learning from the bad risks that you took. Not that they didn’t work out well, they just weren’t risks you should take in the first place.

So, when it comes to taking risk, there are a couple of things that I need to point out. A lot of you all don’t want to take a risk unless you are convinced that it’s going to be a success. And that is what holds so many of you back.

I think most of the risks that I took over the last two years, I didn’t know 100% that they were going to be a success. What I did know was that I had a burning desire to do it. And that’s the thing; you have to be willing to take the risk and whatever comes along with it. You have to be willing to fail or succeed.

A lot of you only want to succeed, which is why you don’t succeed, because part of succeeding is being willing to fail and probably failing many, many times. So, for me, a risk is worth it whether I fail or succeed.

Let me give you all an example. I told you I had an example for you. So, for the last three years, 2019, I started to dream about doing a larger event. And at the time, my company was different. And historically, I had taken a small group of women to Paris with me. And I loved that. I did that for six, seven years. One of my favorite things ever.

But after our last trip in 2019, I just had this inkling that that was complete. I didn’t have the desire to do it in 2020. And at the time I was thinking, maybe I’ll do it in 2021 or 2022. But all the while, I kept thinking about bringing a bigger group of women together.

Now, I had no idea that we were about to enter into a pandemic. And I’m like, what was happening? Was the divine looking out for me? Because I usually would have sold Paris out at the end of the year and had that happened, I would have had to cancel it because of COVID. So, I didn’t do the event.

But especially over the last year, I’ve just had this deep, deep uncontrollable desire to host an epic event. And so, months back, I hired one of the best event managers, producers in the industry. I mean, she’s worked with some of the biggest names.

And we were on a call, and she was going through the numbers with me, of what it takes to run an event at the scale I’m going to be doing this. And it’s not even that big. But it’s bigger than what I’ve done in the past.

And as she was going through the number and we were looking at all the different scenarios of, if we sell this many tickets then this is what it’s going to cost. And then she started talking about worst-case scenarios. And the worst-case scenario is I could lose a lot of money. I’m talking about well over six figures.

And I was scared. But I asked myself this question. And this is the question that I always ask when it comes to taking a risk. Will I regret, at the end of my life, trying this and failing, or never trying at all? And the answer was clear to me. I’m like, I am willing to fail, and I am willing to lose six figures just to see.

And that takes some courage, let me tell you. And whenever I’m looking at risk too, I always look at the worst-case scenario. And the worst-case scenario in this particular example was that we sold no tickets. And I knew that wasn’t going to happen because I know my community. I know how women have been emailing us and asking us to do something in person.

But I wasn’t convinced that we were going to sell out. I didn’t know. You don’t know what you don’t know. I’d never done this before in this way. But that’s no excuse not to do it.

And so, I had to really make a calculated risk. I’m like, “Okay, worst-case scenario, I’m out over 100 grand. Like, more than that. Am I willing to take that risk?” And the answer was 100% yes. And so, we actually opened this up. It never got to the public.

We opened it up to School of Self-Image members who have been with me the longest for 24 hours. Less than 10 minutes, VIP tickets were sold out. It was crazy. I’m like, what was happening. I was texting my team like, “This is amazing. I’m so overjoyed right now.”

And then, when we opened it up to the entire membership, we sold out I think in less than an hour. All the tickets were gone.

Now, I didn’t know that that was going to be the result. But I was willing to take the risk. And that’s the other thing, you all. When I am taking a risk, I decide, and I have my own back. I have written about this. I’ve talked about this. I have done a podcast about this. But it’s so important. When we make decisions, especially risky ones, that we have our own backs.

I knew that no matter what happened, I was going to be proud of myself for trying. I was going to learn from it. And if I lost that money, I was not going to beat myself up over it. I was just going to move on, like let’s go, what are we going to do different next time? Maybe not an event. I don’t know. But I have my own back.

I think, when you become a risk taker, you have to be willing to hold your hand, no matter what the consequences. And not beat yourself up over it, but learn from it. That’s what I want you all to understand. Life is one big experiment, and we’re going to have failures. Trust me, I talk about the success, but you all don’t know all the failures that I’ve had.

And those failures grew me to the point that now I’m at a different level, but I had to be willing to fail over and over again. And that’s the other thing. If you’re going to be a risk taker, which I recommend all of you do because it’s going to grow your life in such a beautiful way, you have to be willing to fail.

A lot of you only want to take risk if you think you’re going to succeed. And if course, I want you to go into it with confidence, with thinking about the best-case scenario. But a lot of times, especially if we’re taking big risks, we don’t have 100% certainty. And a lot of times, you let that stop you versus believing in yourself, versus having your own back, versus just taking the action and learning along the way. And you have to be willing to fail over and over again.

The other thing I do when it comes to taking risk is that I make backing out as hard as moving forward. So, what does this mean? I told the women in my membership, “Hey, I’m going to be hosting a live event. I’m going to be announcing it in the fall.” And my word is everything.

And if I ever back out on something that I said I was going to do, you better believe I am super clear on why it’s not because I’m afraid. And so, by doing that, I put that out there so that I had to show up for it. Because by the time I met with my event manager and my brain got involved, my crazy brain, it was convincing me that this was a terrible idea. And had I been left alone with it, without that accountability, without the people around me to be like, “Listen, we said we’re doing this, we’re doing it,” I don’t know.

I don’t think I would have backed out at this point, because I’ve done this so much. But there was a time where I’d have been like, “Listen, you all, this is just too much.” And I would have tried to justify it. You all know what I’m talking about. You do this too. It seems reasonable, and yet, that burning desire is there. And that’s how you know it’s a good risk.

I love what my mentor Martha Beck said. She’s like, “A good risk feels like you’re jumping into a clear, cool pool on a hot day. A dirty risk, a risk that doesn’t really serve you feels like you’re jumping into a swamp.”

When I thought about this event, it felt like jumping into a clear, cool pool from a high dive. And if you’re afraid of heights, you’re scared. But still, when you think about doing it, there’s such clarity and such commitment to that decision.

That brings me to my next point. Do not fear the fear. Whenever you take a risk, your brain freaks out. And the reason it freaks out is because it’s hanging out in mystery land. And the brain is afraid of mystery land because the brain doesn’t know what happens out there.

The brain knows what happens in your life right now, what’s familiar, your familiar states of being, your familiar actions, your familiar beliefs. Your brain is like, “We got this. This is safe. This is comfy. This is home.” But your home may be a mess. And you want to rebuild your home.

So, you go heading out there into mystery land and your brain freaks out and convinces you that this is a terrible idea and that you’re going to lose all your money and all your friends and all your social standing. And the worst thing that can happen, your brain will try to convince you that that’s going to be the case.

And it rarely, rarely, if ever, is. But your brain doesn’t know that. And your brain’s not this mean part of you. It’s just this afraid, scared part of you. So, you have to understand that, when you’re taking risk, you’re going to be afraid. And the worst thing that you can do is to be afraid of the fear because then that just adds more resistance to it.

So, what happens is you’re afraid, and then you freak out because you’re afraid. And now, you’re anxious and afraid and the layers of resistance just keep piling up. Because then you’re anxious about the anxiety over the fear of the fear. Does this make sense?

And so, the secret is to just expect to be afraid, part of your life when you’re taking risk, because the brain is doing what the brain does. And your job is just to calm that part of yourself down.

And I feel like this is where coaching is so effective. Because clients will come to me and they’re wanting to take a risk. Many times, it’s around their business. Sometimes, it’s around leaving a marriage. Sometimes, it’s about getting married. Sometimes, it’s about having kids. Sometimes, it’s about making an investment. It doesn’t matter. The feeling is all the same.

And the moment I’m like, “Yeah, of course you’re afraid. That’s okay. That’s part of it.” I can just see them relax a little bit. Then, the work is to just feel the sensation of fear. Because that’s all it is. It’s just a sensation in your body that’s being produced by thoughts in your head.

So, once you feel the fear, then you can look into your own mind and look at, what’s the crazy stories happening in my head right now that’s causing this fear? And that’s when you can do some beautiful work. You can begin to reach for better-feeling thoughts. You can begin to question all of these assumptions that your brain is giving to you, like you’re going to die or be homeless. Usually, that’s where our brains like to take us, or we’re going to be lonely forever.

And you can just begin to question them. But if you don’t allow yourself to feel the sensation of fear, you will never get to the cause of the fear. Which is never anything outside of you. It’s not the risk. It’s what your brain is telling you may potentially happen if you take the risk.

So, one of the things that I do is I love to make peace with the worst-case scenario. As I said earlier, when it came to this event, I was like, “Okay, what’s the worst thing that can happen?” And I made peace with it, which then freed me up to then go out and create an epic event that’s going to be happening in Miami in February. I cannot be more excited.

But this was the process that I went through in order to take a burning desire and bring it to reality. When it comes to taking risk, I also love to ask myself, is this risk going to grow me and evolve my self-image? Because to me, that’s the best part. And I know, whether I succeed or whether I fail, it doesn’t matter. Just the act of taking the risk, if it’s a good one, is going to grow me in a positive way.

And then finally, when it comes to taking risk, I recommend that you practice taking even tiny risk every single day. It may be setting a boundary with someone. Maybe it’s saying no because you are overcoming people pleasing. Maybe it’s publishing a blog or a podcast. Maybe it’s wearing something that you would never usually wear because of fear of what people will say about you.

Every day, we have the opportunity to take risk that will grow us and lead us to an extraordinary life. You don’t live an extraordinary life unless you are willing to take extraordinary risk. So, with that said, I want you to tune into yourself and ask yourself, “What risk am I being called to take in my life today, this month, this year?”

And I would love to hear from you all. So, you can head over to Instagram. I am @schoolofselfimage. If you’re not following me on Instagram, please do. I’m always posting inspirational, supportive content for those of you who want to evolve your self-image. And I love getting your DMs.

Let me know over there. You can consider this an accountability tool for you. Because what I know is I’m over here taking risk. And I’m also over here cheering you on for taking those risks that will lead to your extraordinary life. Have a beautiful, risky week, my friends. And I can’t wait to see you in next week’s episode.

Hey, have you grabbed your free copy of the School of Self-Image Manifesto? If not, what in the world? Head over to schoolofselfimage.com/manifesto and get a copy that teaches you how to think and show up in the areas of mindset, style, and surroundings so that you can transform your self-image.