That Sounds Risky · Episode 1
How to Take a Risk When You Don’t Feel Ready | That Sounds Risky Ep. 1
0:00 / 21:43
Readiness isn’t a feeling. It’s a decision. In the very first full episode of That Sounds Risky, life and executive coach Sara Emmerson shares why she almost didn’t start this podcast, every excuse, every “what if I fail publicly”, and what it really takes to begin something before you feel ready. Through honest and often funny stories (a childhood turtle named E.T., a painfully awkward high-school audition, an American Idol tryout at Soldier Field in front of 20,000 people, and a six-week leap that moved her across the country at 23), Sara unpacks why confidence comes after action, not before, and why the greatest risk is usually spending your life wondering “what if?” If you’ve been waiting to feel confident, prepared, or certain before you start the business, make the career change, or pursue the dream, consider this your permission to begin. Work with Sara at saraemmersoncoaching.com.
Most people don't struggle because they don't know what they want. They struggle because they're afraid of what it might cost to pursue it.
Key takeaways
- Confidence usually follows action rather than preceding it — it's built through competence, so waiting to feel ready keeps capable people stalled indefinitely.
- Readiness is framed as a decision rather than a feeling, which is the line Sara returns to throughout the episode.
- Saying yes to a risk and being prepared for it are two different things: Sara made it to the American Idol producer rounds but froze in front of the final judges because she hadn't prepared.
- Failed attempts still pay out in evidence — that you can survive uncertainty, show up imperfectly, and handle disappointment, which makes the next risk easier.
- Successful clients often plateau because comfort makes them forget the risk-taking skills that got them there in the first place.
In this episode
- 00:00:00Why this podcast almost didn't happen
- 00:02:00What capable clients say when stuck
- 00:03:00The turtle named ET invitations
- 00:05:00Auditioning for the High School of the Arts
- 00:07:00Rejection letter and redefining courage
- 00:09:00American Idol at Soldier Field
- 00:12:00Facing the final judges in Chicago
- 00:15:00A six-week job audition in Chicago
- 00:18:00The cost of never starting
Read the full transcript
Speaker: [00:00:00] That Sounds Risky, episode one: Why I almost didn't start this podcast. Welcome to That Sounds Risky with Sara Emmerson. I'm your host, Sarah. I'm a life, business, and risk coach, and I'm someone who's built a life and career by saying yes to opportunities long before I ever felt completely ready. And honestly, it's fitting that this very first episode is called Why I Almost Didn't Start This Podcast, because if I'm, I'm completely honest, I've thought about doing this for a really long time. I've had ideas. I had outlines. I had equipment sitting in the car ready to go. I've had notes in my phone. I even called people and asked them to be on the podcast that didn't even exist yet. And I had every excuse in the book. Maybe I needed more time. Maybe I needed to research longer. What if nobody listens? What if I'm not good at it? What if somebody else is already saying the same topic [00:01:00] better? And what if I run out of things to talk about? And this one, this one's actually the most personal. What if I fail publicly? Maybe you've asked yourself some of those same questions or versions of them, not necessarily about starting a podcast, but about starting something. The business, the ministry, the side hustle, the relationship, the healing journey, the next chapter. Because the truth is, most people don't struggle because they don't know what they want. They struggle because they're afraid of what it might cost to pursue it. And that's exactly what this podcast is all about and why it exists. Because I believe the life you were meant to live will require courage. It will require uncertainty, and it will require you to become someone who can take risks. Not reckless risks, not [00:02:00] just for the sake of risking or for impressing people, but meaningful ones. The kind that stretch you and the kind that shape you and the kind that change everything. And I know that because when I look back over my own life, I can trace almost every meaningful chapter back to a moment that sound ris- that sounded risky. As a coach, I work with leaders, entrepreneurs, executives, creatives, and people who are incredibly capable. People who have big dreams and even bigger hearts. And do you know what I hear over and over again? I hear things like this: "I know there's more for me. I think I need to make a change. I've wanted to do this for years, but I just don't know if I can..." Dot, dot, dot. These aren't lazy people. These are totally motivated people that are waiting. [00:03:00] They're waiting to feel more confident, they're waiting to be more prepared, they're waiting for more certainty. And if that's you today, I want you to hear this: confidence rarely comes first. Confidence rarely comes first. Most of the time, confidence is built through competence and action. And sometimes the greatest act of courage is simply beginning. In fact, most of the people that I work with are waiting to feel ready, but readiness isn't a feeling. Readiness is a decision You see, I've been making decisions like that since I can remember. When I was little, I had a turtle named ET. We called him ET because if he stuck his head out like this, on the side you could see his little neck, and it reminded us of ET. And I became [00:04:00] absolutely convinced that everyone in my neighborhood all wanted to meet ET. Everyone wanted to meet ET. Why not? So I created these handwritten invitations, and I passed them out to everyone. The only problem is I forgot to tell my mom about it. And so there was one afternoon when all of these people showed up at our door dressed and ready to go see the movie ET. The only problem with that was we weren't going to the movie. I just wanted to invite these people into my backyard and invite them to the, s- to come see my turtle. And so when they showed up, instead of taking them to the movies, I proudly escorted them into my backyard with my mom's face, I'm sure, in horror trying to figure out what to do with all these kids. And I just introduced them to my turtle very confidently. And it wasn't exactly what they had in mind, but looking back, I think that little [00:05:00] girl already understood some really important things. She wasn't afraid to invite people into new experiences, ones that she hadn't been even in herself yet. She wasn't afraid to connect with others. She wasn't afraid to try new things. And even when the outcome wasn't guaranteed, she wasn't afraid to risk disappointment I didn't know it then, but that was going to be huge in continuing my career, and in continuing my risk muscle over the years. Now fast-forward a few years. When I was in high school, I decided to audition for Orange County High School of the Arts, and I had practiced, and I had prepared, and I was terrified. Because rejection, obviously, rejection feels personal, guys. And because putting yourself out there means someone else gets an opinion, and I didn't want them to have a bad opinion of me. [00:06:00] And maybe you've experienced that, too. Maybe you're not afraid of hard work, but maybe you're afraid of what happens if you try your hardest and you still hear no. But for me, I decided I was gonna audition anyway, and I decided to hire a vocal coach. And I hired this vocal coach, and we worked really hard on the song, and it was the song From a Distance by Bette Midler from the movie Beaches. I'm totally dating myself, but if you knew that movie or that song, you will resonate with this. When it gets to the chorus, it goes, "And God is watching us, God is watching us," right? It's a really nice song, right? And I was singing it with my whole heart, um, and 30 years ago, I could sing it a lot stronger than I could today. But, um, the vocal coach told me that she wanted me to do something really bold and risky. Guys, as I explain this to you, I even now get nervous and so uncomfortable, because it was so bad. Um, I got to that audition, and [00:07:00] I boldly did what she told me to do. She said when I got to that last chorus, I was gonna step side to side and clap on two and four. And so I did that. And, um, it was to my surprise and to the judges' surprise as to how awkward this was. Not only did I feel awkward, but those judges looked like they felt bad for me, too. And I boldly kept going through it, and I boldly ended that song, and then boldly and quickly got off the stage. And a couple weeks later, I got a letter in the mail letting me know that I did not make it into Orange County High School of the Arts. And that wasn't a total shock, um, but it's something that I look back on now, and I look back at that version of myself with such grace. Because what I learned was courage isn't the absence of fear. C- courage isn't the absence of putting yourself out there and risking feeling awkward [00:08:00] or actually even fe- uh, risking failure. Courage is deciding that something matters more than your fear. And to me, the opportunity mattered more than my fear. And I continued to learn over my life that taking those opportunities that felt fearful in the moment actually led me to be able to take the next opportunity a little bit easier In fact, years y- uh, later, I still apparently hadn't gotten over the risk of singing opportunity because a friend of mine had asked me, called me, um, and asked me to audition for American Idol here in Chicago. Um, shout out to Karen. Tha- Karen, thank you for calling and asking me f- to do that. But, um, she called the day before and she was like, "Hey, let's go audition tomorrow. It's at Soldier Fear- Field." And I was like, "No. No, no, no, no. I don't..." It wasn't in, m- um, my cards or in my idea at all to [00:09:00] do that that weekend, and I was like, "I don't think so." And she's like, "Come on, come on." It didn't take much, um, probing, but I did decide, "Okay, I'll go with you." And I was practicing for another event, um, an- a different song by Faith Hill, There Will Come a Day, and I decided, "I'll just sing that one. We'll go for it." So we showed up at Sol- at Soldier Field, and we showed up with 20,000 other people. Guys, I'm not kidding. We showed up and there were thousands upon thousands upon thousands of people. And when you get there, you realize, if you've never been to one of those auditions before, you realize there's two types of people there. There are people that are serious about singing, and then there's people that are dressed up like the Eiffel Tower or the Empire States Building, and most of them have roller skates on, too. So you've got two different types of people, and you're trying to just figure out, how is this gonna happen? And they bring everyone into the stadium, and then four by four, they bring you to all of these different judges all over the field and have you sing for the judges, [00:10:00] and they weave you out into more auditions throughout the day. And if, if you ever get to audition for the final judges, you've been through four or five auditions already to get there. So very quickly, I realized that my strategy side needed to come in fast if I wanted to make it through this first round. So I knew that the other people I was coming with were, um, good singers, so I thought to myself, "I've gotta break out and go into a different group that I'm pretty sure I can out-sing in order to make it through this first round." So we separated, and yes, I did strategically go and stand next to the person who was dressed as the Eiffel Tower in roller skates, and got in that group, and I sang my heart out for my song. And I made it through that first round, and I was ecstatic. It was so fun. And I got the golden ticket to the next round. They actually gave me a gold piece of paper, and if I have the picture, I'll post it somewhere for you guys to, to look at. But [00:11:00] I got to go to the next round, and I got to the next round and took another risk, and they said, "Hey, do you have a, a different song to sing?" Well, the only other song I could think of in that moment was the song by Brian McKnight, One Last Cry. I don't know if any of you remember that song. But I decided I would sing that song. And so I belted that song out, took another risk, and made it through that round. Then they asked me to learn a song on the spot from Moulin Rouge- Um, that movie, and I did that, and I made it through that round. I'm now three rounds in, and I'm g- got, um, shoulder to shoulder with some incredible singers, many of them gospel singers that could out-sing me in a heartbeat. And so we get to the final audition of the day, and I'm seeing all these incredible people come out of the room with nos. And so in my mind I'm thinking, "That's it. This is the end of my journey. The risking is over. It's time to go home And I get into the room, and [00:12:00] the judges for that last audition... I don't know if any of you watch Dancing With the Stars, but Simon Lithgow, um, was the judge for that last audition. And so he was in there. I sang my heart out, and I got done, and him and the other judges were there conferring. And he said to me, he said, "Hey, we really like your vibe and your voice, but I don't know that your voice is big enough to win the whole thing." And in that moment, my humor and personality took over, and I said, "Well, hey, Clay Aiken's on tour, and he came in second. I'm fine if I don't get first. I'll take second. That's fine with me." And they all started laughing, and he said, "Okay, fine. You can come, and you can make it through." So I made it through that round, and they asked me to come back a few days later to audition for Randy, Paula, and Simon. And so my husband and I came back a few days later, and, uh, we were at the W Hotel in downtown Chicago. And I got the chance to meet Ryan Seacrest and to see all the behind-the-scenes stuff and how they did [00:13:00] everything. It was so incredibly well done. And then I walk into the room, and it makes it feel like there's just three or four people in the room when you see this on TV, but there's really, like, 50 people in the room. And I was so nervous. And I walked in, and I sang my song. And I didn't do poorly singing my song, but I got so nervous, and I just closed my eyes, and I stood there s- um, almost paralyzed. I was so scared. And I got done singing my song, and I opened my eyes, being ready for the criticism because this was back in the day where Simon would really give it to people. And I opened my eyes, and they were all very gracious and kind. Uh, but I just remember Simon looking at me, and he said this. He said, "If I was a stray dog, I would want you to pick me up and be my owner." And to this day, I have no idea what that means at all. But I'm really grateful that I took the risk again, one, because I get to tell this funny story, but two, because again, I [00:14:00] recognized that saying yes and putting myself intentionally in uncomfortable situations grew me to the place where I can do that way easier now than I used to be able to. H- Helping myself come face to face with disappointment, even though it stings in the moment, helps me become a be- better version of myself later. And looking back on that moment, we'll talk about this more in the podcast in the future, I was willing to say yes to the risk, but I wasn't ready for the risk. I hadn't fully prepared for the risk, and so that's something that we're gonna learn in the future is how to fully prepare for those risks. Um, I gained something important that day. I gained evidence, evidence that I could survive uncertainty, evidence that I could show up imperfectly, and evidence that maybe I was more capable of taking those risks than I believed [00:15:00] And a few, um, years before that, even before I moved to Chicago, I actually had learned that in my career in a new way too. In fact, what brought me to Chicago originally is a risk story as well, and it goes a little bit like this. I was living in Seattle at the time after graduating college, and I had met some people out here in Chicago, and I was here for a conference. And they had told me about a job that was gonna be available and that I should, um, put my resume in for it. So I moved back to Seattle, put my resume in, and I started interviewing, um, for this live event producer role. And it took a few months to interview, and at the, um, end of those few months, they actually called me and they said, "Hey, look, we wanna ask you to do something a little different. We wanna ask you to come and do this job here in Chicago for six weeks. Le- leave your life behind. Come and do this job for six weeks. Let us watch you do the job, [00:16:00] and then at the end of the six weeks, we'll let you know if you got it or not." Well, here's the problem. I had never done this job before, you guys. Never. I had never done this job. I didn't live in Chicago. I didn't know anyone in Chicago, and they wanted me to move there and let them just watch me for six weeks and then see at the end if I got it or not. To most people, that would've sounded crazy. To most people, they would've said, "No way. Too risky. I'm not gonna put everything on hold to do that." But in the moment, I said, "Sure. Why not?" Nope, I've never lived in Chicago before. Nope, I don't know anyone. At the time, I was 23, moving across the country, and essentially I was gonna have a six-week audition. Forget the one day. I was gonna put myself in a scenario to be, um, publicly humiliated for six [00:17:00] weeks, and most people would've said no. And honestly, I had every reason to say no. But I said yes. I packed my bags, and I figured things out. I got here. I met people. I did the job. I learned on the fly. I remember one day they asked me, "Hey, we're gonna need you to produce a video now. Go to the video room and figure it out." And I did exactly that. I went to the video room, and I figured it out. I had never done that before, but the willingness to say yes and to learn how to do it along the way is something that has become so important to me and is something that I work with my clients on each and every day. Many of them have already done this time and time again, and that's why they've had success. But then they get to a level of success, and they plateau. They don't know what to do next because they've gotten so comfortable, they've forgotten That they need to go back and use those [00:18:00] skills that got them to where they are in the first place. And some of my clients are just brand new in this and haven't learned those skills yet, haven't learned to identify their risk tolerance, and haven't learned to say yes even before they're ready. And that is the scenario that I love helping people through. So why this podcast? Well, because I've realized that risk isn't something reserved for entrepreneurs or extreme athletes. Risk is a part of being human. It's a part of loving people. It's a part of changing careers. It's a part of setting boundaries, of pursuing dreams. It's saying yes to things before you have all of the answers. And here's what I know for sure. The greatest risk isn't always failure. Sometimes the greatest risk is spending your life wondering, what if? What if I had started? [00:19:00] What if I had trusted myself? What if I hadn't listened to the negative voices? What if I had just tried? And as a coach, I never have had a client say, "I wish I had played smaller." I have never said, "I wish I had played smaller." But I have heard countless people say, "I wish I had started sooner." Countless people say, "I wish I had started this sooner." I look at the journey of what I've done over the last seven years. I took a leap seven years ago to start this business. Honestly, it felt like I was jumping off of the Empire State Building with a parachute, hoping it was gonna open. But I can tell you now, I wish I would've started sooner. And at the same time, I believe that I started right when I was supposed to, right when I was ready. So let me ask you this: What have you almost started? What dream keeps finding its way [00:20:00] back into your heart? What conversations have you been avoiding? What opportunity are you talking yourself out of even right now? And what if you didn't need more confidence? What if you simply needed to take the next step? Because courage isn't built in theory, it's built in practice, one decision at a time, one brave choice at a time, one risk at a time. Remember, readiness isn't a feeling. Readiness is a decision. Thank you so much for joining me for the very first episode of That Sounds Risky. If today's conversation resonated with you, I would love for you to leave a review and subscribe and share this episode with somebody who needs the reminder that they are capable of way more than they think. And if you're listening today and you've been waiting for permission to begin, consider this your permission. Start [00:21:00] the thing. Have the conversation. Take the next step, because the life you want may be waiting on the other side of the courageous decision. And if you need support navigating what's next, whether you're building a business or making a career transition, strengthening your confidence, or learning to make meaningful risks, I would love to help you. I want you to visit saraemmerson.com and sign up for a coaching consultation. I love helping people build meaningful lives and careers one risk at a time. So until next time, I want you to remember the decisions that stretch us are often the ones that shape us, and around here, That Sounds Risky