How to Overcome Fear and Take Action

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1:33There's no safe like SimpliSafe. From Entrepreneur Media, this is Problem Solvers, a show in which entrepreneurs do what entrepreneurs do best, solve unexpected problems in their business. We were completely wrong. And I'm just like, it's not selling. It was like, we have to start from scratch. I'm Jason Pfeiffer, the editor-in-chief of Entrepreneur Magazine.

2:00Tell me if this sounds familiar. You begin by feeling like this. I was so frustrated. I felt so constrained. I felt like I was screaming and nobody could hear me. And so you want to make a change. You want to take a leap. Maybe you want to leave the comfortable, familiar, frustrating, constraining place that makes you want to scream, but again, is comfortable and familiar and go do something on your own. But it's so hard and so scary. It was a really dark night of the soul period where I was wrestling with, do I stay in this career that I love and feel this way? Or do I chase these other things that I'm so passionate about?

2:45Today on Problem Solvers, we are talking about how to get from one side to the other, to go from that frustration and fear to having the courage to leap. What must transform inside of you before you're willing to make an external transformation to make that big change? And we'll be exploring that through the story of the woman who you just heard, whose voice might be familiar. That is Sherry Lynch. She is the co-host of a syndicated radio show called Bob and Sherry. They're in 70 stations nationwide, have about a million listeners a week, a proud member of the Armed Forces Radio Network. And Sherry led the charge to take their show independent, to leave the cushy, big radio network they were originally at and go it alone.

3:31That was the transformation we're talking about today, risking it all to own it all. And it wasn't easy. But Sherry's pushed a lot. Sherry's co-host, Bob, was actually the original sole host of a radio show, and Sherry was just tasked with going on air to promote some programming changes at the TV station down the hall. But Bob and Sherry had great on-air chemistry, and even though the bosses resisted, they turned the show into the Bob and Sherry show. That meant that she became the co-host of, and this is crazy, the first syndicated morning show with a female in a lead role. She also started podcasting before podcasting was called podcasting, which we'll talk about more later.

4:10But what I really love about Sherry is her honesty and empathy. She has been there, risking everything. Single mom, making decisions that don't just impact her, impact her kids. And, you know, at the beginning, she told me she didn't really think that she was up to the task. I always thought of entrepreneurs as people that weren't me. They were people who somehow were different from me. They had some essential component that I didn't get installed at the factory. But as she discovered, and as so many people discover, she had it. Today on Problem Solvers, how to find it, how to push yourself, how to go from the fear to the action.

4:51Coming up after the break. Hi, I'm Emily Washkovic, Yelp's small business expert and host of the podcast Behind the Review. We're back for season two, and this time we're keeping everything you love and adding so much more. Get ready to find out what happens behind the scenes at those businesses that everyone raves about. You know the ones. Learn how owners swallow their pride when getting critical feedback and what they do to turn around that unhappy customer. And don't forget the reviewers. We'll find out what inspires them to leave those rants or raves in the first place. Get ready for buzzy new guests like restaurants from Yelp's famed Top 100 lists and new short BizBite episodes.

5:41Just a few minutes of advice on how to set your business up for success and create connections with customers, both online and off. Subscribe, like, and follow the show to hear new episodes every Thursday. All right, we're back. Today, I'm talking with Sherry Lynch, co-host of Bob and Sherry, the nationally syndicated radio show about what it took to go from being really afraid of leaving the comfortable but unsatisfying thing to going out into the unknown. And to start, I asked Sherry to describe what Sherry in handcuffs looked like. Who was Sherry and what was she dealing with back when she was working for a very large radio company that was paying her salary and paying the bills, but just not fulfilling everything that she needed.

6:29The best analogy that I have is for a long time, I was a very pampered fish in a tank and I would swim by the same treasure chest every day and the food came raining down and things were okay. But over time, I outgrew my tank. It's just what it comes down to. I outgrew my tank. I wanted to try things and experiment with things. I wanted to innovate. And in order to innovate, you have to have not just the freedom to try, but the flexibility to fail. And when you are part of a big corporate environment, the scale is such that they're not really in a position to be super nimble and super agile and super innovative.

7:16because every decision that gets made in a big corporate environment has to almost be a one-size, it has to be engineered to be a one-size-fits-all. So if we let Sherry do this in this market, then we're going to have to make changes in all of these other markets. And that became a huge problem for me really early on, long before we separated and became independent. Can you give me an example of what that felt like? What was something that you wanted to do that you weren't able to. Perfect example. We turned our show into a podcast back in the days when they were called RSS feeds and Apple podcasting didn't exist, right?

7:562006 is when we launched our show as an RSS feed because one of the things that I'm super hyper-focused on is the customer experience, the listener experience. And it's not your job to come to me, it's my job to come to you. And so because our show was carried around the country, is carried around the country and around the world on Armed Forces Radio Network, we have a really mobile audience. They're very nomadic in a lot of ways. And so they would leave a market where our show was and go to a place where it wasn't and be super frustrated. So this was at the time when people were experimenting with RSS feeds, and it seemed like a really easy, low-cost way to make the show widely available.

8:45So our first RSS feed back in those dinosaur days, we thought of it as a free-floating digital affiliate. You could find it wherever you went. And for a long time, my corporate overlords, and I worked for a lot of people in broadcasting, there's a lot of churn, a lot of buying and selling. So I worked for a number of companies, my corporate overlords mostly ignored that for a very long time. You mean you were just like, Sherry's doing a weird RSS feed thing, whatever. It doesn't really matter. Yeah. Some weird thing they want to do. Who cares? It's not costing us any money. But then as podcasting, there's always that inflection point where something begins chipping away at your core business.

9:29So at the exact same time that people increasingly began streaming radio and not listening to the over air signal. People also began time shifting and listening to podcasts. And now suddenly some of these weird little ideas that we had and that we were experimenting with felt more like existential challenges. And there was at that exact moment, social media exploded. Social media, like we were one of the first shows on Facebook because again, I'm about connecting with my listeners. I'm about that connection experience. And so Facebook to me seemed, oh my God, it's free and it's super engaging.

10:06And it's a way to really meet people. On radio, the audience is disembodied, but social media changed that. So now we've got the podcast and we've got the stream and here comes social media. Company gets sold again. New owners come in. They slide a piece of paper across the table. They want me to sign away all of my social media. They want ownership of my account. They want control over what I say. And I slid it right back and was like, Okay, wait, let's break down a couple things that just happened here. So number one, I want to double click on this distinction that you made when you were talking about Facebook.

10:47And about how you at your core are interested in connecting with your audience. Because that shift had happened in your head at some point. which was that you realized I'm not in the radio business. I'm in the audience connection business. And that kind of shift is so incredibly important for anybody to make, because once you have a real definition of the business that you're in, you recognize what is and is not your constraints and what you are and are not willing to tolerate. And I was gonna ask, as you were telling this story, how did you get to the point where you felt confident walking away from a corporate environment.

11:28There are a lot of comforts in corporate environment. There's a lot of stability. I'm sure you were paid very nicely. And so how do you get to the point where you're willing to do that? And I guess a big part of the answer is, but you're here to confirm or deny, a big part of the answer is that you had gone through a shift at some point. And I don't know if you have a answer as to exactly how or when that happened, but I'd love an insight into it. You went through a shift in what business you're really in. and you realize I'm not in the radio business, I'm in the connecting to audience business.

12:00And if I'm in the connecting to audience business, then it doesn't just have to happen on the radio. In some ways, I was always a little bit of an oddball because I fell into radio as an accident. I actually grew up in the wilderness without much mass media, television, radio. We didn't have a phone. So I didn't come into radio the way a lot of people did. And when I fell into radio, the part that appealed to me was this ability to engage with people. I wanted to be an anthropologist. I just love people. I love talking to people. I'm enthusiastically curious, or you could say nosy, depending on your position.

12:37And so it was always that way for me. But by 2011, 2011 was the critical year for me. By 2011, I realized that every day was going to be a fight to push my ideas across the line and to do my job the way I believed it needed to be done. Every day was going to be a fight. Now, I was a single mom. I have two children that I'm 100 % sole support of. And I've got a job that has dental and a 401k and a tremendous amount of safety and security. And plus, I always thought of entrepreneurs as people that weren't me. They were people who somehow were different from me. They had some essential component that I didn't get installed at the factory.

13:26And so I went back to school. I kept my full-time job. I went back to school and got a master's in social work because, again, I'm about people. And that process really grooved it into my head that I have a choice. I can be frustrated and unhappy and shaking the bars of my beautiful golden cage, or I can dig deep and go out on that limb and take a chance and bet on myself. And knowing that the same, I wanted that freedom to be able to fail and pick myself up and try again. And I was asking someone else to give me that freedom. And yet I wasn't willing to take the ultimate step myself. And that's when I knew that it was time.

14:13And it took about a year and a half to negotiate that departure from corporate because they owned me. They owned my name, my intellectual property, my service marks, my archives. Everything I had done belonged to somebody else. Yeah, which is, that's such a scary realization. and a lot of people have it where they build something within a large organization. And that large organization has things that they needed at some point. They have resources, they have reach, but at some point there's a tip, there's a tipping point and you have to be armed to recognize it, which is why I want to rewind yet again to that moment where you got into social work or you started studying social work?

15:02Because here's the thing, Sherry, you might remember this because we talked about it on your great podcast. I have this philosophy, which is called work your next job. The idea is in front of you at any time are two opportunities, opportunity set A, opportunity set B. Opportunity set A is everything that's asked of you. So you go to work and you have expectations and your boss expects things. You got to do a good job. That's what's asked of you. That's opportunity set A. And then opportunity set B is everything that's available to you that no one's asking you to do. And my argument has always been that opportunity set B, what's available to you, nobody's asking you to do is always the more important one because it's where growth happens.

15:42And that can mean anything. That can mean taking a class. That could mean joining a new team at work. But your example here is so interesting because while you were in this corporate job, you also started studying social work because it fit this personal mission and understanding of yourself, of connecting with people. and doing that work didn't lead you into social work. It led you, or at least not traditionally speaking, at least, but what it led you into was having the confidence and vision to leave the corporate job. People might not see that as a one-to-one. How did Sherry go to social work and then leave her corporate job and rebuild her radio career independently?

16:32And yet there is a connection there and it's an important one, I think, for people to understand because when you go and do the thing that's available to you that no one's asking you to do, you don't necessarily know what the return on investment is, but it could be a nonlinear one. It could be something that doesn't seem logical that you draw a line from one to the other, but it was exactly what you needed. So can you tell me how that experience actually made that shift for you? I was so frustrated. I felt so constrained. I felt like I was screaming and nobody could hear me. I felt like I had a vision for the future that I believed was correct.

17:07But I also thought that maybe I'm a crazy person yelling at clouds. And so I decided, and it was a really dark night of the soul period where I was wrestling with, do I stay in this career that I love and feel this way? Or do I chase these other things that I'm so passionate about? And I made the decision to chase the other things. And then something wild happened. My emphasis in social work was clinical inpatient mental health, because I really love connecting with people and working with people. And the process of that training, you go deep and you meet yourself there, whether you're ready for it or not, you meet yourself in that place.

17:53And it made me realize that I was forcing myself to stay in a safe place at the cost of my sanity and my soul and my passion. And that therapeutic training, all of that training in active listening, reframing, meeting people where they are, engaging the reality as it is, turned me into the mother of all negotiators. Because suddenly, I was no longer negotiating from a place of, I got to feed my kids. I've got to keep this job. I've got to keep it going. Got to keep it going. Suddenly, I was in a place where I'm in these negotiations. And it's not about me at all. It's about you. And I'm listening to what it is.

18:45What is it that you, why are you clinging to me so tightly? Why won't you let me breathe? Why won't you loosen the leash? And the more I understood what the fear was on the other side of the table, the more it empowered me to take ownership of my own future and destiny and my own career. And I just was suddenly a lot more understanding of the challenges that these middle managers that drove me to drink, what their challenge, what their unique challenges were and that they were coming from the same place of fear that I have been coming from. And at the end of the day, Jason, I just knew that one of two things was going to happen.

19:25I would stay in the corporate world and I would be a passenger on someone else's ride. And at the end of it, I would be like, oh my God, woulda, shoulda, coulda. Or I would grab the wheel and veer in and out of the ditch and blow my tires out a thousand times. And at the end of the ride say, wow, I really learned a lot. I'm so glad I did that. And going back to school, which by the way, is no joke, graduate school while you're a full-time employee and a single parent. And I was working also many hours a week in a hospital setting as part of my training. I don't know how I survived it, but all of that really prepared me for the reality of being an entrepreneur where I've got to go hunt if I expect to eat.

20:10And I've got to keep all the balls in the air all the time. And I've got to develop skills in areas that not only do I not have these skills, I didn't even have a glimmer of interest in these skills. Like I'm an IT person and I have to solve technical problems. And there's a million things that go into this particular entrepreneurial journey. But the day that I realized that what was holding me back was the same fear that was making my management choke up on the leash with me was the day I became free. Hmm. The line that is drawn from social work to becoming a great negotiator because you understand people, to having that revelation, to then having the final needed confidence to make that change is such an interesting one, but also that's how things happen.

21:13And I think it's worth pausing to appreciate that. How going out and developing one skill doesn't mean that is the skill you're going to use in exactly the way that you used it. But growth happens in these very nonlinear zigzaggy ways. I think the reason why I'm able to have this conversation with you right now is weirdly because I worked at a health and fitness magazine a long time ago. For example, the line that I draw is that I worked at Men's Health writing about how to get abs, which I never got and how to lose weight or whatever. And what that really taught me was what is in my business is called service journalism, which is to take storytelling and be aware of how often you need to turn to the audience and make sure that it's relevant to them and don't hit them over the head with it.

22:12Although the men's health, they really did hit you over the head with it, but to make sure that you're always thinking about your audience and you're serving them in a way that A lot of other writing doesn't. A lot of other writing might be a little more self-indulgent or it might just be like, I'm writing a nice thing and I hope you enjoy it. But this was really service-oriented. I didn't connect with that stuff. I didn't connect with the health and I didn't really care about people's abs. And it's great if you go build them, congratulations. But I never did. And yeah, it taught me about how to understand and serve audience.

22:41And then when I found something that I really did connect with, which was business and entrepreneurship, I was able to summon that knowledge of what it meant to be turning to an audience and then start to apply it in different ways. So as you and I are having this conversation, a thing that's going through both of our heads because we both are in the business of serving audience is you and I, Sherry, we're not just having a conversation, we're having a conversation that's meant to be listened to, which means it has to be a useful conversation, which means that it has to serve the audience. And that's a weird line that I draw.

23:10I think it's really powerful for people to give themselves that freedom and flexibility to explore directions that they don't necessarily know why they're doing it, because it's going to pay off in ways that they didn't expect. And just to put the finest point on it, let me ask you, what did you think was going to happen as a result of getting that degree in social work? I thought I was going to leave this career and start a whole new career. Yeah, how about that? I really did. And for the longest time, I still thought I was going to leave this career and start a new career. But then I had the chance to jump in August 1st, 2017.

23:53And I knew I felt safe because I knew by August 1st, 2017, I knew that I could leave this career and roll the dice on being an independent media person, independent media company, all of that across multiple platforms. And if I failed, I'd be okay. That I had these other things that I was super passionate about. And to your point about audience, serving the audience, one of the conflicts that I had my entire corporate career is they would come to me and they would go, we want you to try this product. And then we want you to tell your listeners how much you love it and how much it's changed your life.

24:35And I was always like, ew, gross. Who cares if I love something or if it's changed my life, you care if you're going to love it, if it's going to change your life. And so I was always like, can I flip the mirror and show the audience themselves? Who gives a damn what moisturizer I'm using? What's it doing for your skin? So that was one of my ongoing conflicts. And that was all really sharpened and amplified for me when I went back to school and submerged myself in this entirely different discipline. But I also knew if I could do that, I could do this. And if I wanted the freedom to try and the flexibility to fail, I needed to be ready to fail and know I could survive it.

25:21And I will tell you that as everyone listening knows who went out on their own, you will never work harder in your life than when you work for yourself, but you will never have greater clarity and peace of mind and satisfaction in what you do than when you work for yourself because your mistakes are your own and your victories belong to your team. And you're never asked to make a decision that makes no sense. I had to participate in a lot of decisions that I felt made zero sense as a corporate employee. And I had no choice but to, again, ride in somebody else's vehicle. And I cannot agree with you more about the nonlinear thing.

26:08We want stuff. We want to follow a recipe. We want it to be simple. Step one, step two, step three, success. And a lot of times it's step one, step 52, step four, period of really devastating, challenging issues, success. And we have to let go of that expectation because people that are married to that expectation of a linear formula, they hit a rough patch and they're like, I tried, I failed. And what you don't realize is those rough patches, that is where you grow. That is where you expand. Yeah. Yeah, this line that I repeat all the time, Ryan Reynolds once told me, I think I even said this to you already before when we were recording your show.

26:53Ryan Reynolds said, to be good at something, you have to be willing to be bad, which I think about every time. Sherry, I am thinking back to something you said at the earlier point of our conversation about how you never thought you'd be an entrepreneur. You thought those people have just something different. There's something built into them that I don't have. And now here we are hearing the end of this phase of your journey, right? This conversation was really about how to find that inner strength to take a leap into the unknown, to leave something comfortable, even though it might not be satisfying anymore.

27:34And I just heard you talk about how incredibly fulfilling it is to work for yourself, how liberating it is, how your victories are your own, even if your mistakes are also your own. And I'm curious what, as a final point here for our conversation, what you discovered about yourself when you one time thought, I don't have whatever entrepreneurs have, to discovering that you do. Wow. I'll be honest and tell you that I still look at other entrepreneurs and think, Like, boy, I wish I was an entrepreneur. People that are really like very businessy, very financial businessy. What I discovered was that what I thought of as a very defined and limited skill set, just a handful of colors.

28:23I'm a writer. I've written books and I write all the podcasts and stuff that we do. That's one skill. And I'm a storyteller and I'm a talker and all those other things. What I learned and what I hope other people who take this trip learn is that embedded within each of your handful of skills is an entire universe of other sub skills that you've never considered, ever considered. I tell stories for a living. When I'm selling my business and I'm selling my show, I'm telling stories. I connect and engage with people. That's my passion and my joy. I connect and engage with my clients. and my affiliate partners, and my advertisers.