Confidence Classic: Turn Your Passion Into Purpose with Jess Ekstrom

Failure is research. It's like we now have more information than we did before, even if it's not the outcome that we originally wanted. We have all this data, you know, and so if we can think about like the hiccups and the speed bumps as like just collecting research for what we're going to do next, it makes it feel less like a death sentence and more like a educated decision making. Because each time we fail, we have learned something new about ourselves or about our business. And, and the other realization that was huge for me was this comfort knowing that failure will always feel better than regret. How many times have we like closed our eyes about something? You're like, man, you know, I wish what would have happened if I had done that? And we might never know the answers, but at least when we fail, we know the answers and maybe we have something else that we hadn't even thought of. So knowing that failure will always feel better than regret and then classifying the failure as research is really helpful just for our mindset when we are going after what we want.

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Hi and welcome back and if you can tell, I have a major frog in my throat. Well, not literally. It just feels like it sounds like it. So I have definitely let myself get run down and have had some high level stress going on the past two weeks, but things have worked out fine in the end. I was not sleeping enough. I was definitely pushing myself way too far. And as you know, stress is that killer that you don't even realize it, but it's eating away at you all day. I mean, I could sense that I was having anxiety and I knew I was stressed out, but one situation that occurred was I found out I had mold in my bathroom and we were going to have to completely gut the bathroom. I have a 12 year old. I was really questioning if I should move out of here temporarily. I didn't know what to do. I didn't know what the ramifications were. You know, just all that fear around. Oh my gosh, what could happen is my son Going to be sick? Am I going to be sick? Am I being a good parent? How did this happen? Just questioning everything, which is not a good idea, by the way. So it ends up in the end I got multiple estimates and had multiple people come in and it turns out I don't think I have mold. Instead it looks like there's mildew, which is a vastly different issue. And it doesn't look like I need to gut my bathroom and it looks like I need some very minimal work done. And again, I had multiple estimates. So the best thing that I did was I took action immediately and called people who've had mold, talked to them, called mold companies, called different contractors and called trusted friends that I know had the same issue and really gathered as much information as I could and then just took action on it and then compared everything and went with my gut and just feel really good about where I'm at with it now. So that was, I guess, a four day process, which was a nightmare and a number of other things. As you know, I believe in the octopus strategy and revenue around my business. And so I've been working on some major brand partnerships and it's been taking a lot of time and you'll see some of these will be forthcoming soon. But there's a lot that happens behind the scenes that you don't always know is occurring with others. I've also just finished the 12th iteration of my book proposal. The amount of time I have put into this thing far exceeds anything that I thought I would ever have to do to get a book proposal done. But again, I didn't have prior experience, didn't really know what I was doing. And I'm working with really high level professionals that are helping me to create a great product to go to publishing houses and, and get it bought. So live and learn. This has been a really lengthy process as well as I've been working with another vendor on a clothing line and this has been months in the making and, and we actually just got it sent back to us telling us we need to be more inventive and fill a white space that somebody else doesn't own yet. And they asked us to take another swing at it. So it's, I mean, months of work that now it can be very frustrating. So all these things sort of were happening at the same time and I was pushing my limits. And you know what's funny is that I remember last Monday I could feel a tingle in my throat. And since I've been speaking for a living the past two years, last Year, wintertime, I lost my voice once and I actually went and got a Z pack right away so I could get it back. This year, I could feel a tingle and I thought, oh, it's fine. I never get sick because I really typically don't. I really. I work out all the time. I take care of myself. But I felt that tingle and I had an important private event to go to that evening and I went. And I should have never gone, or if I was going to go, I should have gone just for, you know, a quick show up and do an Irish exit and leave. But I didn't. And I stayed there for hours and then I got home late and then I fell asleep later because I picked up the house when I got home and I woke up in the morning and my voice was gone. So none of this is surprising. You know, it just reminds me, listen to your body. Put yourself first. Sleep is everything. And when you're not sleeping, you can anticipate if things are not going to go well. So great reminder for me, however, I'm not taking a Z pack this time. I don't give my son a Z pack, so why am I? Because my son has a really bad cough, cold sinus right now, and he's getting better and I thought, I need my body to heal itself instead of taking the quick out. So we're going a different route this time. Trying not to take too much medicine. And it seems to be working because I am feeling a heck of a lot better four days later. So today on the show, there's two themes that come up as a result of the guests that I have. One is finding your purpose, your passion, which a lot of people ask me about, which was a long road for me for sure. I didn't even know that was a thing, by the way, when I was younger. I don't know if you knew about this, but that you're supposed to follow your passion and purpose in your work. Who knew? I just knew you were supposed to make money. Okay, well, I was mind blown when I figured this out. In my late 30s, someone told me that, why aren't you following your heart and your passion, your purpose in life? And I said, I don't know, why would you? I was told you couldn't do that as a young kid. So here's the thing. I've watched some close friends over the past two years follow their passion and purpose and really change for the better because they're happier. But I've also seen the challenges that go along with it. I mean, look at the ones I went through, right? I was in that grind in corporate America, making a lot of money in the C suite, doing what I thought I was supposed to do. I mean, you can't be that successful in corporate America and not think this is what you're supposed to do. I did, but what I found is you can be really good at a lot of things. Doesn't mean it's just one thing in one lane for you. And I talk about this so much is that blow up the lanes, take your talents wherever you want to go. Am I grateful I made the switch? Yes. It's much more rewarding what I do now, but it's been incredibly challenging along the way. Having a one man company and being a rookie at everything. I'm a rookie podcaster, a rookie author, a rookie at writing book proposals, you know, a rookie speaker, a rookie brand partner. All these things I had never done before because I was a chief revenue officer. So, you know, the journey is really challenging. And people say, oh, love the journey, enjoy the journey. I see people who are independently wealthy, healthy, loving the journey. But there's moments when you're going through the struggle where you're questioning, holy cow, should I have left this job? Holy cow, should I be doing this to myself? I see my other friends on vacation all the time and I, you know, can't take my eye off the ball right now. I've got to continue to push forward. So there's pros and cons to both. But I will say this. I garner passion, purpose every day. I feel so grateful. I get messages every single day about how I impact people's lives. I never got that before in corporate America. And there is this sense of meaning that I'm supposed to be doing this that I didn't have before. So just ask yourself, do you get that meaning? Do you find it if you don't start taking small steps to remember what it was you love to do? What were you drawn to do if money didn't matter, what would you do? And start moving towards that, even on the weekend. Spend time doing it at night whenever you can, but start dipping a toe into it so you can start the process of evolving yourself out of where you are and into where you're meant to be. I have a really good friend who's an attorney. She loves fashion. She's been drawn to it her whole life. She started doing pro bono work for the law firm with startup fashion companies, and that was putting a toe into something that didn't exist. And over the last Couple years she's been in the grind trying to build a business around fashion law and it's been really challenging. However, it brought her to a place where another law firm recognized all that she was building, all that she was doing. And she inevitably left the law firm she was with, joined this new law firm which values her and values her initiative. The last one didn't. And now she's slowly making this move into this completely different world where she's feeling more valued, she's aligned with the people she works with. But none of this would have happened if she didn't start off saying, I'm going to try to do some pro bono work for fashion brands because I love fashion. And something tells me that I'd be happier if I was working in. It did not happen overnight, by the way. That was a two year run. Just like with me getting fired. That was two and a half years ago now. So these things take time. And it's about staying committed to the grind that is the hardest thing. When everyone else is questioning why you're doing it. Stay focused on your why. Stay focused on your thoughts, your vision and belief, and that's how you can bring things to fruition. So that's one of the things we're going to talk about today. The other theme that came up to me that I thought was really interesting was shame and how shame affects you. And how shame affected my guest today in a very public way, which is interesting. I've dealt with shame, which I'm sure you have too, in my life, but I've dealt with it in private ways. You know, shame of being divorced, shame of being arrested, shame of, you know, growing up poor. So much shame in my life. And the more I would try to bury it, the more it would pop up in my life today without realizing it until I'll never forget this. In my late 20s, hearing a siren and feeling, oh my gosh, you know, I'm busted. I wasn't doing anything wrong. And I really believe that when you push shame down for a long time, it's like you're hiding from something. You feel to blame and that starts creeping into your life in so many ways that you feel to blame for your shame, responsible for your shame, that you could be found out. And that was that direct connection that I finally realized when I heard a police car. I thought, oh my, I'm found out. And I had to say to myself, for what? What did I do? I'm not speeding, I'm not doing anything wrong. But for so long I was Blaming myself for my shame and trying to hide from it. It was popping up in my day to day life, which is no bueno. Not recommended for anybody. So what I learned by all of that is that shining a light on shame frees you from it. Shining a light on shame ends the shame. And here's the thing. Everyone has had shame. It's been cool for me to watch my son, who doesn't seem to have very much shame. He wanted to have friends over the other day, and I said, oh, my gosh, the house is a mess. And I. I immediately went into my old way of thinking, and he said, who cares, Mom? I said, because I don't want your friends to see the house messy, and I want to get home and clean it. And this night, he said, mom, that doesn't bother me and that doesn't bother my friends. No one will care. You're the only one that cares. If you want to clean up when we're there, you can, but it's not a big deal. And I just thought, yet again, I'm going back to this. Like, oh, I have to hide that things aren't perfect all the time when the reality is I know they're not perfect. I talk about that so much that my life is far, far from perfect. There is no such thing as perfect. And if you see someone trying to act perfect, run. Yet I still have my moments where it's recovering from hiding from shame for a long time that you almost feel that's your job, is to cover those things up. And he's been teaching me in the greatest way as well. We roll. Boy, can that. These things don't matter. No one cares. No one's judging you. People are more concerned with their own lives and having fun and enjoying life. So why don't we jump in the game with them? So I'm really excited for you to meet my guest today because she's got so such an amazing story. Her name's Jess Ekstrom. She's the founder and CEO of Headbands of Hope, a company she started as a junior in College in 2012. Holy cow. For every headband sold, a headband is given to a child with cancer. If that is not purpose and meaning, I don't know what is. And I'm so proud of her. She's such a light. Her first brush with success was selling all her toys on ebay when she was 12. Since then, Jess and our company have been featured on the Today Show, Good Morning America, everywhere. I mean, this girl's been everywhere for Reaching out and helping children's and children's hospitals in the US and in 15 other countries. She's a professional speaker and the founder of Mic Drop Workshop, an online course and community dedicated to empowering more people to share their stories on stage. Jess and her husband are currently traveling around the country. Get this. In their Airstream with their dog. Okay. That's wild. She's definitely different, she's definitely curious, and she's definitely giving back so much. So I'm really excited for you to meet her. So hang tight. You're about to meet Jess.

Meet a different guest each week. Hi, and welcome back. I'm so excited for you to finally meet this guest that I've been trying for so long to connect with. Jess Ekstrom. She's the founder and CEO of Headbands of Hope, a company she started as a junior in College. In 2012, for every headband sold, a headband is given to a child with cancer. So freaking amazing. Her first brush success was selling all of her toys on ebay when she was 12 years old. Then her sisters. But we can get into that after. Jess has been featured everywhere from the Today Show, Good morning America, Forbes, People, Vanity Fair. I mean, some major cred that you've got going on right now, but more importantly, you've donated hundreds of thousands of headbands to reach children in hospitals with cancer across 15 different countries. She's also a professional speaker and the founder of the Mic Drop Workshop, an online course and community dedicated to empowering women to share their stories on stage. Jess and her husband are currently traveling around the country in their Airstream alongside their dog, Ollie. So, Jess, thanks for being here.

Oh, my gosh, thanks for having me. I'm so glad we could finally do this.

It's been kind of crazy, but, yeah, I'm so excited that you're finally. So can you take us back through and really how you started out, some of the challenges, major public challenges you and your family faced when you were younger and how that took you down this path to where you are today.

Yeah, so I think, you know, when I was a kid, I mean, hence the ebay selling, I always kind of loved learning how things tick and what people need. And I remember one time we had this family camping trip, and my dad's an entrepreneur, and I was a teenager, and I was getting out my headphones, and it was like when we had, like, Walkmans, and I was, like, gonna listen to the Backstreet Boys or something, and my headphone cords kept getting tangled in this knot. And I was getting so frustrated that these headphone cords were getting tangled. And I said to my dad, I was like, you know, headphone cords should just roll up like a slinky so they don't have to get tangled anymore. And then I told him, I was like, I'm just gonna invent this. And I remember he sat me down, and he looked me in the eyes, and he was like, that's already been invented. But I want you to keep thinking that way. Just keep looking at the world through a lens that you can fix it. And really, I mean, that was such a defining moment of my life, where I didn't think about being an entrepreneur. I thought about being, like, a problem solver. And that was kind of how I started walking through the world. Until my senior year of high school, we had some very shocking news where my family was involved in this very public scandal that I talked about for the first time. And in the book, which has been another thing of its own, finally coming forward with it. But it was something that, like, you think would never happen to you. You know, things that you read in the headlines or, you know, on your Facebook feed, and you just kind of categorize it in this box like, oh, that'll never happen to me. And then when it does, you realize, like, you're not immune to anything. And that gives us a choice of how we want to live our life, whether that's, like, the fear of the unknown or the excitement of all the possibilities. And it took a while, but I think now, 10 years later, it's definitely living more in the excitement of possibilities.

And when you say it took a while, what did that look like? Was it your family just went under a weighted blanket for a month, or did certain people evolve out of it? How did you evolve out of that, and how did you push forward?

I think there's a lot of pressure to see silver linings immediately. You know, whenever you go through something, it's like, well, what's the meaning in this? And you have to jump out of bed the next day and be like, seize the day. Because everyone else around you, you see just living life what appears at, like, their highest volume. You know, you see everyone's highlight reels on social media and Instagram. And so when you experience something that's really hard, you know, for me, it was a public scandal. My uncle is Bernie Madoff, and he's the biggest financial fraud in history. And so we went through something very public. And also just losing all of our money on top of that just kind of having to start at zero. But it wasn't something that we could just jump out of bed the next day and say, you know, like, we're stronger than this. It was really tough. And so I think giving yourself, like, a grace period to just be upset and feel what you feel and realize that this isn't permanent, that it'll pass. But I think that now I can look back and see that that one single experience, like, unknowingly started to write a different story for all of us. So, you know, my parents, they became park rangers eventually, and my grandparents, they lost their entire retirement, and they started a cab driving company. So they became entrepreneurs at, like, 80 years old. And so I think little by little, we found meaning through engaging with life again and getting back on her feet. But it wasn't this, like, snap your finger, snap out of it, drink some water and move on. It was a process.

Yeah, I definitely. I felt like that very different.

But when I got fired, it definitely wasn't. The next morning, you just wake up and you have an epiphany, and, you know, you ride off into the sunset. Those things stink. They take some time, but like you said, they can lead you to a completely different course in your life that you would have never found otherwise.

And I think that, you know, sometimes when we think about optimism, or we think of it as this, like, Pollyanna, just fluff, you know, just see the good in things. But really when we need optimism the most is during the dark times. And it's not as much of a mood as it is a strategy. And when you think about, like, any great movement that has happened or any great change or progression, it always began when times weren't good. And so when we can see sometimes, like, the problems, maybe not immediately, but as opportunities for something better, we can kind of connect the dots back to our life and realize, like, when those pivotal moments were. And it usually wasn't a time when there were hearts and flowers all around you.

Absolutely.

So you went through this time. You were in school, in college, and that's when you founded Headbands of Hope.

I think when I can really think about some of the changes that happened in high school, I started to kind of rethink what is the American dream for me, Is it something where I want to have stability? Because I saw my parents do everything right in my eyes, where they worked hard, they saved all these things, and then something like this happened. And so it just kind of made me think of, like, well, what do I want to look back on and see and it wasn't something where it was like, oh, I just want to sacrifice a paycheck and work for a cause. It was more along the lines of, like, I want to see what I can do that can be bigger than a job and be more meaningful than just clocking in and clocking out. And so it started kind of that seed was planted, but it wasn't very clear. And I was actually interning in Disney World my freshman year of college, and I was a photographer there. And that was when I got to photograph a lot of kids that were there on their wish through the Make A Wish Foundation. And I fell in love with the foundation. It was just amazing. And I got back to school my sophomore year, and I interned at Make a Wish. And that was when I started to discover a lot of kids that were losing their hair to chemotherapy would be offered a wig or a hat. And a lot of them weren't really concerned with covering up their heads. They just wanted something to feel good about themselves. And so I would see them wearing headbands. And I just remember thinking, like, what a cool gesture of confidence to not care about covering up your head and just wanting to feel like a kid and, like, express yourself through fashion, through headbands. And I just did this, like, Google search. I mean, I remember exactly where I was. I'm like, I wonder if someone's doing this and looked up headbands for kids with cancer and saw that that wasn't a connection that had been made yet. And I think that, like, those are the moments, some of the most pivotal moments of our life, when we're searching for something that we want and we can't find it, and we have to decide, like, is this just something I'm going to brush off, or is this my mountain to climb? And it wasn't even this decision, like, should I do this? Should I not? It was like, I couldn't help myself but just start dabbling, like, oh, I wonder if, you know, this domain's available. Or, I wonder what it would look like if it was kind of like a piece of paper that got caught in the wind and I just started moving with it.

That's amazing. But you didn't know how to make headbands back then.

You didn't know how to.

Yeah, I still don't know how to make headbands. I started. I remember, like, I, like, tried to. I looked up some, like, sewing YouTube tutorials. I was like, well, these look like crap, and no one will buy these. But. So the idea was for every Headband I sell. I'm going to donate one to a child with cancer. It's called Headbands of Hope. And so I was a college student, and I just started, like, looking at what I had. I went over to, you know, the business school and asked professors that were smiling in their directory photos for 15 minutes of their time, and I'm like, okay, you know, what are taxes? And should I be concerned about them? And I just went to try to look at what I had and build from there. I think I would say. A lot of times, the direction that I see people take is they think about the super bowl, then they think about this long plan ahead instead of just thinking about the first down. And it is so much easier to keep going after your goals when you give yourself permission to just do what feels good and do what feels like to you right now. You don't have to quit your job and go all in on this idea. You don't have to try to get around to funding before you make your first sale. Like, what are the small things that you can do today? And I think that that is how Headbands of Hope wasn't built based off of, like, one big thing that happened to us. It was just the day after day, small things that eventually added up to something big.

But this business grew very rapidly. So rapidly that you ended up giving your commencement speech when you graduated from school. And I think that came as a direct result from this business, correct?

I don't know if it grew rapidly in terms of, like, the buzz. I mean, I think the fact that I was a student and I was doing something, it meant something to people. But, like, my first order was, like, from my mom. And it took months before I saw someone's name come through on the website that I didn't know. And I remember exactly how it happened. It was like months of radio silence. And you think, like, oh, I'm gonna start this idea and I have everything in place and they will just come. And they didn't. And I'm just like, what the heck am I doing? Like, should I start applying for jobs after graduation? And I remember I saw this article in fitness magazine, and it was like, five fitness bloggers to watch. And I reached out to each fitness blogger and told them what I was doing, and I said, oh, I have this company, Headbands of Hope. I would love to send you some product, and if you like it, then if you could post about it, I would really appreciate it. And so, out of those five fitness bloggers, two of them responded to me. And then one of them actually ended up posting on her blog. And that was the day that I made like $500 in sales when this girl posted about me on her blog. And to me that meant that was like retirement money. I was like, I'm good to go. But that was the moment where I was like, someone out there who doesn't know me is buying this because they believe in what I'm doing, not just because they want to support Jess. And so I think like, that really solidified that I was doing something that meant something to other people and that I needed to keep going. But it was slow growth. I mean, it was not fire right out of the gate. So I like to be transparent about that because that's the narrative I hear all the time, is like, oh, I had this idea and the next day I'm on Oprah's favorite things list and we're, you know, the number one product. And it's like, really? Is that how it went? I'm calling a little BS there.

Well, that's good to hear. Meet a different guest each week.

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I asked you to try to find your passion. Did you always know that you were gonna stay the course even if the sales didn't accelerate? I mean, did you ever have moments where you thought, all right, really, I've gotta hang this up?

Yeah, I did. And I think that that is a healthy mindset to have. I'll be honest, I think like this, no quit mentality is not doing us any favors. I think like, the narrative that we hear is like, quitting means weakness. But quitting for me means I have a reminder of a choice. Like, no one's forcing me to do this. You know, no one's telling me that I have to do headbands of hope. And so to remind myself that, like, if I'm not enjoying this or if I'm not believing in this or if it's taking a toll, then like, I can walk away. And that is my choice. So when we can present ourselves with that option, and we choose to recommit to doing it. It's like we're kind of digging our heels in it again and getting deeper and deeper. But I don't think that I would have the fire and passion eight years in in this business had I not given myself the option to quit many times.

Well, I'm so glad that you didn't, because you've helped so many people.

It's amazing. So how did you transition from this business into the speaking business?

So I started to get asked to speak after I gave the commencement address of my graduation. I thought, what a great opportunity for me to share about Headbands of Hope and maybe hopefully inspire some other people to go after something that they believe in. And I mean that. I had no idea speaking was even an industry alone. The first time someone was like, what's your rate to speak? I was like, you mean that people get paid to do this? That is crazy to me. And so I told that school it was Marshall University. I was like, don't even pay me. Just cover my travel and buy me some dinner and let's call it a day. And so my first gig was for a slice of pizza, which I was very excited about. But then I just realized that, like, speaking, storytelling, I mean, what you do with your podcast, it's such a great way to influence change based on just, like, authenticity. You're not lecturing, you're not teaching people about business. You're sharing real stuff that has happened and the lessons that you found and hopefully can help people with whatever they're going through right now. And so it really speaking turned into this whole other mission and then whole other business for me. And so I started speaking. What went from like, twice a year is now around 50 times a year. So hence living in an airstream and traveling around. Most of it is for speaking engagements. One of the things I also noticed, too, was that there's just not a lot of women on stages, especially when it comes to tech business. And the numbers are just so imbalanced when it comes to equal representation on stage. And so I started Mic Drop Workshop, which is an online course and community to get more women not just speaking, but getting paid to speak. Because that was the other thing I found was a lot of women thought they had the exact same mindset that I did. It's like, oh, if I enjoy doing this, if it's meaningful for me, then that means I shouldn't. I don't need to get a paycheck. And that couldn't be further from the truth, we don't have to choose between making a living and making a difference. Let's do both at once.

And how long was this trajectory? Did this happen over a year, two years, or is this a couple of years?

So I gave my first speaking engagement in 2013, and I started doing a lot of colleges at first because I was a college student, so it was perfect. And then now that I've gotten a little bit older and my message has evolved, I now do mostly corporate and conferences and events. I love speaking at women's events. And so it was really evolved into something that I just never would have predicted for myself. And I think that's the other thing I like to kind of sit back and think about. Like, when we think about our goals and our plans, you know, we can kind of hold them with this clenched fist, like, I'm starting this idea or this is what I want to be and this is what I want to do. But we can't let our plans kill all of our possibilities because there's so much out there for us. And when we're so set on that, like, one destination, that one pinpoint that we're aiming for, we might miss something that you don't even know exists yet.

It's so true. Which is.

I mean, I'm so impressed by it. I read some of the reviews of your course. I mean, you've gotten phenomenal reviews on setting these people up to become speakers themselves. And like you said, for so many, myself included, I didn't know that people got paid to speak speak. And, you know, I had 20 years in corporate America. We just never hired speakers in the industry I happen to be in. So we only know that limited amount of information.

Exactly.

Have in that bubble we live in until someone taps you and says, hey, let me, you know, access this information or share this information, which with you, which is so powerful. And I want to make sure that people do check out your mic drop course, because if you don't know about the speaking business and you're curious, this is a great way to find out really, really quickly, which, why not learn more about what is available to you out there. And like you said, sharing your stories, it's so powerful.

Yeah. And you're so right. Like, we know what's in our reach. And so to be able to be transparent, like, especially, you know, even about, like, money too, and getting paid like people, especially with women, it's so taboo. And I'm like, let's put it all out there. Like, let's support each other because we won't know what to ask for. Or sometimes we don't even know what we should believe that our value is. Have we not talk to other people? So, yeah, if you're interested, you can go to mikedropworkshop.com and check it out.

Thank you for that.

And I just recently have learned I've spoken with a lot of different people this year. And some of the stages, I mean, there are people getting paid $150,000 for 60 minute keynotes, and it's shocking to me that I felt just like you. Wow. I'm just lucky to even be on this stage at first. And then just gaining the insight, understanding how other people are valuing their time, their expertise. And. And I like to tell people, or frame it up differently to say, I'm not getting paid for the 60 minutes I'm out there. I'm getting paid for the expertise I've created across my lifetime in boiling it down into something very tangible, specific, and helpful to an audience in 60 minutes, which helps me to feel better about charging higher.

Oh, absolutely. There was this story about Picasso. Whether or not it's a real story isn't really the point. It still sounds good. So he was like, at this cafe, and it was after, you know, his work got really famous, and someone came up to him and was like, oh, my gosh, you know, you're Picasso. Will you paint me a picture? And so he just takes a napkin and he kind of draws this, like, stick figure on it and hands it over and says, okay, that'll be $5,000. And he goes, wait, how is this $5,000? You just drew this in two minutes. And he goes, no, it's taken me 20 years to draw this. And that is like, what is the framework for not just speaking, but so many of these jobs that, like, we have to bring ourself that we've learned over so many years, the mistakes that we've made, the dollars that we've invested, you know, bettering ourselves. And it doesn't come out to the time that you're on stage. It's exactly as you said. It's the time that you've spent being able to be on stage and the.

Risk that you've taken because while you're much younger than I am, you've taken and made some extremely bold moves, taken some big risks, really gone all in on your ideas and on you at a time and an age where a lot of people don't. So there's a tremendous amount of value there. And that message, because it's so unique and different, I feel like that deserves to be heard. How is it that you transition from being a CEO, a founder, then a speaker, then someone who's created a course, teaching, speaking, to deciding that you wanted to write Chasing the Bright side and become a best selling author?

It started with speaking and realizing that my stories can change people and everyone's stories can change people. And you don't have to be an expert to do that. That's one of the things we talk about in Mic Drop Workshop is like, you don't have to have a library named after you or be like this doctor or something. People actually crave authenticity and realness now more than ever. But I think with Chasing the Bright side, it came from this exhaustion that we've talked about already of like, the success narrative that we hear from so many people being this overnight and that they had this perfect plan and it just worked out. And none of us were born knowing how to do anything. And none of us were born knowing how to, like, start a business or, you know, do our taxes or anything. And so we all had to start somewhere. And we all had to start with this belief that something is better than here of like, what's next? And this optimism. And so Chasing the Bright side is really about how we can use optimism to not just believe in better, but go create it and channel it as, like, this grit and resilience along the way. When times get tough. Part of the book, I, you know, interviewed a ton of different entrepreneurs, Olympic athletes, you know, musicians, anyone who's ever done something they're proud of. And they all had these stories of times where they just royally messed up or a time when it would have been so easy to throw in the towel. And the difference between the people who kind of made it and the ones that didn't really didn't have anything to do with how good their plans were or how much money they had to start with, or even where they went to school. It was this rooted belief in what could be. It was like this unsinkable optimism that what they were doing and what they were creating was something bigger than them. And so Chasing the bright side is like, how can we channel that and the things that we want to do and let the hiccups and speed bumps just be a normal part of the process and not a reflection of our worth.

So what are the important keys that you found that people need to employ in order to do that? Because we all know hitting those road bumps can be really hard Depending on how many road bumps you're hitting at once, which sometimes when it rains, it pours and it is hard to find optimism then.

One of the things that I talk about in the book that I think is really shaped the way that I think about failure and messing up is realizing that failure is research and when we can reframe the way that we talk about it. So at headbands of hope, we don't call it failure, we call it research. It's like we now have more information than we did before. Even if it's not the outcome that we originally wanted. We have all this data. And so if we can think about like the hiccups and the speed bumps as like just collecting research for what we're going to do next, it makes it feel less like, you know, like a death sentence and more like educated decision making. Because each time we fail, we have learned something new about ourselves or about our business. And the other like, realization that was huge for me was this comfort knowing that failure will always feel better than regret. How many times have we like, closed our eyes about something? You're like, man, you know, I wish what would have happened if I had done that? And we might never know the answers, but at least when we fail, we know the answers and maybe we have something else that we hadn't even thought of. So knowing that failure will always feel better than regret and then classifying the failure as research is really helpful just for our mindset when we are going after what we want.

Meet a different guest each week.

Confidence.

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Yeah.

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I asked you to try to find your passion. Depending on who you are, you know, and how you were raised. I think that all these things impact how we perceive failure. But I love Sarah Blakely, who I had the opportunity to interview, was raised where she was challenged every night at dinner. Tell me how you failed today because it was something they celebrated in her home. And what a powerful mind shift that was because how I grew up, I was a competitive kid and you weren't supposed to fail, you were supposed to achieve. And, and I look down on that idea of failure. So becoming an entrepreneur for me and as you know, being one, that's the failure game. You're failing all of the time, which is the antithesis of corporate America where you're not supposed to fail. And it's just these really seismically different worlds and trying to acclimate and of course failure accepting failure and learning from it. It should be a part of everyone's life everywhere. However, just learning this at such a later stage in life, it's challenging to, you know, to take on and really immerse yourself in it. I still get completely stressed out when I see something failing and like you said, it's taking a step back and looking at it as data and instead information to process and learn from. But I can just say from personal experience, it's a challenge to do.

Yeah. And don't get me wrong, it's not like when I fail, I'm like wonderful. Like what we learned here, I mean, it sucks. And it's not something that it's like, like let's celebrate it and let's aim for it. But I think that if we let it define us, that's where we get in trouble, where we connect our wounds to our worth. And I did that in the beginning of my business where I got a loan from my dad for my first round of production because I didn't have the money to put up to get our first round of headbands in. And he Wanted to be my first investor. And I wired that money to the manufacturer, and I never heard from them again.

That was a $10,000 investment that you lost.

$10,000.

Oh, my gosh.

The fact that he believed in this business and that he was willing to put up the money that we frankly didn't have at the time. And it was one of those moments where I was like, maybe this is a sign, you know, maybe this is a sign from the universe that, like, I need to just get out while I can and get a job and start paying my dad back. But then I started to think about, you know, I went to bed that night and was just like, this isn't about the embarrassment of failure. This is about this need, you know, that isn't being met. And what I'm doing is meeting that need. And so I really. I can't let this be it. And so I remember I got this, like, 2 or $300 grant from my school that was giving away to students who were starting businesses. And I bought two types of headbands from this supplier on Etsy who let me buy, like, really low minimums, and I put them up on my website. And I never took outside money after that. But it was this moment where I now know. I'm like, if I could get past that, if I could not let that define me, then I can surpass anything. And so sometimes those failures set the tone for our resilience, and it makes us believe in our capabilities that we didn't even know that we had, which is kind of a cool thing.

Well, I also like the fact that you didn't harp on that $10,000 going missing and harp on focusing on that negative. Because sometimes I see people do that, obsess almost about that negative incident, and it becomes all consuming.

Yeah. It becomes part of their identity. And I think that it took me a while to share it. I mean, that was eight years ago now. And I think I started sharing it, like, two years ago in my talks, and now it's in the book and where it gets into detail about what happen, how I felt. And it was something that I thought, like, if I share this story, then I'm a fraud. Like, if I'm out here teaching people about how to start a business or whatever it is, and I'm sharing this, then I'm doing them a disservice. And that couldn't be further from the truth. If anything, no one cares about the time when I was on the Today show or Good Morning America. No one can learn from that. But what they can learn from is a time when I was negative $10,000 and trying to scrape together, you know, pennies under my mattress and turned it into a multimillion dollar company. And so I think that it's a part of our duty now as entrepreneurs is to also share those things when we're ready to tell them and be transparent, because it's the people like me who are going through that, that those were the stories I needed to hear. I didn't need to hear about someone's success. I needed to hear about the time when they almost quit.

So the fact that in some ways, there's a lot of similarities in regards to you writing this book and showcasing, highlighting the failures and, and really stepping into your fears and shining a light on, quote, unquote, shame. Was this one of the biggest scary moments for you or moments where you questioned your confidence when you were gonna launch this book?

When I was writing the manuscript for a year, I was like, just by myself in a coffee shop or in the Airstream and just alone with my thoughts typing away. And then you just don't even really think about when this is gonna be in the hands of people. And I'm, oh, my God. I'm like, I talked about my first period and now it' like, gonna be like, like, like, who's gonna read this? And then, so leading up to it, I, like, had. I mean, I said to people, I was like, you know, and like, Britney, like, Spears lost and shaved her head. Like, that was the level I was at. I was so anxious. I was like, what are people gonna think? And especially I was also coming out with this, you know, people, some of my closest friends had no idea who my uncle was. And now I'm sharing in this book. And so that was really, really scary. But then the amount of readers and support and messages that I get every day that they had something that was in their closet that they weren't sharing or their first business plummeted, and now they're like, thinking about maybe their next idea or whatever it might be, I'm like, that makes it all worth it. And I think, like, what took me so long to understand about speaking and being an author and being a podcaster like you? I'm not a podcaster, but just having a platform, it's not about how to paint yourself in the best light. It's about how can you be of service to others. And a lot of times that means not painting yourself in the best light. And so I think that that's, like, how My nerves and, like, have been settled because I know that it's serving others.

So these are such great life lessons that you're learning at such a young age. I'm so proud of you. I'm so excited for you because it's really about celebrating when you are stepping into the fear. Because as you saw firsthand, having that Britney Spears scared to death moment, that I can totally relate to the book coming out and questioning if you're an author and why you're doing this and who it's gonna hurt and offend and upset and all of these emotions. But then like you said, once it's out and live, getting this amazing, meaningful feedback that you're helping one person time and time again, that feeling is sort of what it's all about, in my opinion. You know, when you start connecting with that and finding that, which I never had when I was in corporate America, it's really life changing. And that's what I want people to know and want them to see with your book, is that, you know, this was scary for you. This is real and it's petrifying when you're going through it. But when you're feeling that fear and still moving forward, that's where the magic really starts happening.

Yeah. And I always like to tell people, like, what can you do to just break the seal of fear? You don't have to, like, dive into the deep end. You don't have to do belly flop or whatever it is. Like, how can you just wade in the shallow end? Like, how can you dip your toes? Because a lot of times it's just that first step that's holding us back. And because we feel like that first step is kind of like going down this, like roller coaster, like once we take one step, then we're all in. And it doesn't have to be like that. And so how can you do something small that breaks the seal of fear? Is it looking to see if this domain is available? Is it, you know, exploring on Shopify? Like to see what it would be like to start your E Commerce company? Is it having coffee with someone who's been there? Is it listening to this podcast? You know, what can you do to just do something small that just breaks the seal?

And even when you do that small thing, if you get blocked, because when you said this, check the domain. I remember when I was first launching my personal brand and I wanted everything to be Heather Monahan so it'd be easy. And then it turns out Heather Monahan wasn't available on I forget if it was Facebook or Twitter or whatever.

And then I was like, okay, shut it down.

You know, we can't do this. Because it gave me that opportunity for excuse instead of. And it took me and some of my good friends saying, all right, hang on a second, then let's do the Heather Monahan or whatever. That stuff doesn't matter in the end. And here I am a couple years later. I have the hindsight to say this. It doesn't matter if you name it. My new website doesn't matter what you name it, but just the act of, like you said, researching it and then figuring out whatever is available and whatever suits for that moment. Because there can be so many different iterations and so much growth. And I mean, look how you've evolved from being a founder of a business to becoming a speaker, to teaching others to speak, to becoming an author. All these things don't happen overnight. It's an evolution, and it's just about getting started.

Yeah, I don't feel like we get clarity in our plans. Like, sometimes we want to tell ourselves, okay, if I just sit down and figure out what my next five years is gonna look like, then I'll be good. But, like, our plans are just guesses. We have no idea what the future is going to look like. And so I feel like we get clarity when we engage, when we take steps, when we have conversations, when we're not head down in a spreadsheet. Nothing against, like, planning. I think planning can be great in a certain level of capacity, but, like, if we're looking for the answers in our plans, we're not going to find them.

It's so true.

Action is always going to be the answer. I couldn't agree more. So just tell me, where can everyone find you? Where can you? They find Chasing the Bright side.

So you can find Chasing the Bright side anywhere books are sold. We're in Barnes and Noble and Walmart. You can go to chasingthebrightside.com and pick it up. We're also doing a book club this year, so you can go to chasingthebrightside.com and find that as well. And you can find me on Instagram Essextrom. And I would love to hear from.

You and your website. I love your website. It's fantastic.

Oh, thank you. Yeah. Jessextrom.com you can go check it out. And if you want to buy some headbands, you can go to headbandsofhope.com yeah.

And also at Jess's website, you can see the Mic Drop Workshop. Learn a little bit more and check out her reviews. They're really impressive. So thank you so much for making time, taking time out of your busy schedule. I appreciate it immensely.

Thanks, Heather. Thanks for having me.

All right, we'll be right back. I asked you to try to find your passion.

Hi, and welcome back. I hope you loved meeting Jess as much as I loved interviewing her. She really is the real deal and such. It's just such a bright light. That's the only way I can put it. And I'm so proud of the work that she's doing. Okay, so today in my question and answer period, I wanted to. I've got a lot of questions from LinkedIn actually, this week, and I wanted to dig into some of them. So one of the questions I got was about presenting. Here's the thing. You know, people struggle with the idea of giving a presentation if speaking isn't your jam, which is 99 of the world. It's not, and I get it. So here's the thing. Number one, people are not listening to you. The goal is to get their attention. People are always thinking, I want to get out of here. I want to do this or that. I want to think about the problem I'm having at home or at work. They don't really want to listen to you, so you're the only one that's focused on you, which I find entirely comical when you actually stop and think about it. The goal is to engage with these people. So I like to start off a meeting asking a question, how many other people are as excited to be here today as I am? And start laughing, you know, break the ice. They're in the boat with you. You've been sitting there before. No one is dying to be there, but it's part of your job. You have to be there. So I usually open with something like trying to get them to answer, because if you can get the audience speaking back to you, it makes it a little bit easier on you and on them. And then tell a story anytime you can open with a story, something relatable. I did this with my text. TED Talk, you know, you're really going to connect more. People will be more interested, and that's what they're going to remember from your meeting. So ask a question so that you connect with the audience and they see that you get. It's painful to be there to open with a story that's relatable to the material you're going to cover. Cover your material and then let them know that you're grateful they're there. You're grateful they're paying attention and open it back up to them to engage with them, to ask questions. It's so much better when you have more of a conversation and an interested audience versus you standing up, lecturing. Nobody wants that. The other thing I'd recommend for people to do is to go on site to the location where you're going to be speaking ahead of time so that you're familiar with it, you're familiar with what it's like, get clear on what the expectations are, clear on what's worked in the past before. You know you want to do your homework, work. The more you practice at home on your own, the better equipped you are going to be to deliver a confident, powerful talk or presentation. Put the time in. You know, these things don't happen by chance. I practice for my TEDx talk for I think, six weeks. That's more than I've ever practiced for anything in my life. So if it's important to you and you want to do a good job, put the time in. Then on your way that day, you know, make sure that you get ready, you got your package, power, color on that, you leave a note on the bottom of your shoes and when you are on your way, listen to that playlist of your life that fires you up, that reminds you that you can do anything and watch out world, you are going to crush it. And if you don't turn it into a joke. So many times when I've been giving presentations at work, I had to cover boring material and if I would make a mistake reading data from a chart, I would always say, did anyone even catch that? Is anyone even listening anymore? And they would laugh and, you know, any way that you can make it less painless on people to be there, that makes it more fun. So think to yourself, what are the presentations you've enjoyed at work? What's a presenter that you've liked that you've seen on some level? Think of those key points, like were they funny? Were, you know, did they make it less painful in different ways? Think about that. Because people are just dying to get out of the meeting. Sadly, that's, that's the truth. People in corporate America. Okay, next question. So I had a woman reach out to me saying that she's having a hard time. She wants to appear more professional. She works with a lot of men. She feels like they are not supporting her to get ahead. She wants to leverage LinkedIn more and maximize that opportunity. And she wants to take on more things to separate herself, like putting together events for people. But she's just so tired and worn down. Here's the thing that I would say is that, number one, put yourself first. Make yourself a priority in your life. You know, look at your sleep habits, look at your workout schedule, your meditation skill, whatever you do, right, for me, it's working out and sleep. Those are my two keys. And then, you know, spending time with my child is critical. But what for you, what is it that works? Figure out what that is first. Next, you know, look at, okay, if you're not being received professionally, how are you dressing? Are you showing up on time? Are you prepared? Are you organized? What are you bringing to the table? Are you showing up as yourself or are you showing up as a watered down version of yourself? You need to have this inner dialogue with you and assess where you are and why. What are the holdbacks? Why are you not leaning in? Why are you not taking a chance? You know, figure out what those reasons are that someone would not see you as professional. I was in a toxic work environment a few years ago and I was very professional at work. And while some people might not look like me, they always saw me as professional. So earlier in my career, there were some people that did not see me as professional because I would wear short skirts. So I changed that. I would not wear short skirts anymore. So I mean, listen, here's the thing. Look at your situation and say, why would someone not see me as professional? How can I fix it if that's important to you? Right? As I got older, I was further along in my career. Wearing a dress to work is something I do in a heartbeat. I. I wouldn't think twice. However, when I was trying to be seen as more professional, when I was younger, I would wear pantsuits. So again, it depends where you are in your career, how you feel with your confidence and about yourself and rocking. You know who you are. But really just think about it most of the time because you're showing up late, you're unorganized, you're not dressing the part, whatever. I mean. But if you don't feel like you have the answer, ask a trusted advisor at work. Ask your boss. Ask you know, someone that you respect their opinion and they're going to want to help you because most people are nice. Just don't ask the villain at work because they definitely won't want to help you. So invest in yourself, do an internal audit on how you can be better and put a game plan together to make that happen and make yourself a priority. When you start doing that, people will start changing around you because you're changing within you. And that's critical. The more you respect yourself, the more you value, value yourself and believe in yourself, the more everyone else will. And don't start taking on new projects and ideas until you're managing and feel really good about where you are with you. And that means if you're questioning that you're professional, if you're questioning you can't get to things on time. If you're questioning you can't handle your workload, it doesn't make sense to take on another project. Also, if these people are treating you poorly, you want to do an inventory of those people and that company that you're in. Sometimes we could be in the right job, but we might be in the wrong company. Sometimes we can be in the right job, but just on the wrong team. So you need to do an internal audit of all these things and start seeing how you feel when you're with these people. Start seeing how you feel when you're doing this job you're tasked with. But do this internal audit and really get real with yourself. Does it mean you should leave this industry? Does it mean you should leave this company? Does it mean you should lead this team? Or does this mean that you should make some changes, Changes about yourself and you want to give this team a shot? Do this audit, you know, take this opportunity to really assess where you are and who you're with and what's working and what's not and take action to change what you want to change. Start showing up as the best version of you and see what happens around you. Okay. I heard from another person who just left a C suite position.

What's up?

These are my kind of people. And it's really scared and doesn't know what to do but. But knew that that job was not for them anymore and really doesn't know how to move forward. You know, it's super scary. I've been there. But what I kept doing was taking action. And those action steps would take me to the next thing, right? So I posted when I got fired. This person didn't get fired. They left. But you could post. I just left my CC position. I'm super scared. That's what I did. I posted, just got fired. Super scared. If I've ever impacted you in any way, I'd love to to hear from you. That started a domino effect in my life that created so much opportunity for me. Landed me on the Elvis Duran show. When I was sitting there in front of Elvis Duran, he said to me, obviously you're writing a book, Heather. And I said, well, obviously I am. I wasn't. It's really important, you know, that I was not writing a book at that point in time. However, that man believing so much in me and having that conviction in me, I jumped on the plane, I googled, how do you write a book? And by the time I landed in Miami, I was prepared to be disciplined to sit and write every day. And within four months, I had my book done. So don't count anything out, but start taking action to get that domino effect occurring. And that domino effect took me from writing and self publishing my first book to getting into the speaking business, because I googled how do you promote a book? To getting into the podcasting business? Because I heard on my speaking trail that podcasting was another great way to promote my book, which led me to do my first TEDx talk, which led me to write my second book, because the speaker bureaus told me that, you know, it's great to have another book come out. All these things I didn't know ahead of time, I figured them out along the way. So start the domino effect. Take action today to start moving things forward and be open to where it takes you. Okay, finally, my last question, because I'm going on and on with the frog in my throat, it's probably killing you right now. So here's the thing. I heard from a woman that said she has men at work who are, quote, unquote, complimenting her or making comments, and it's really uncomfortable for her at work. Interesting. Yes, I am familiar with this. Especially when I was younger, you know, I was sexually harassed at work. And I'm not saying she's being sexually harassed, but I'm just giving you the backstory. I was sexually harassed at work when I was younger and a couple of different times. Here's what I know. Now that I'm 40, 45, no one would do that to me. Now, is it because those people changed or because I changed or the environment changed? My opinion is primarily it's because I changed. Now, I have seen some things in business the past couple years, which is there is more of this joking going on in the workplace. And I'm sure you guys see this too. You know, oh, I can't say that because me too. Movement or this or that or, oh, oh, they'll send up a red flag to corporate. You know, it's sort of a joke. I find that. And I don't know if you do. I'm interested, actually, to hear if you do, oh, I can't hug you because, you know, you might tell HR or whatever weird comments people make that, yeah, they're slightly uncomfortable. But listen, if business and life were all easy and swimmingly fun, everyone would be killing it, right? So there are difficult conversations. Sometimes we may be faced with how, however, there's a line. And when I explained that these things happened to me when I was younger, I was very naive. I would put up with so much, quote, unquote, put up with. But what I mean, I would allow things to happen and turn a blind eye to it because I thought if I do that, they'll think I'm cool. I'm positive I'm one of them, and then I'll get promoted, and then I'll be part of the team, and then I'll do better. I was wrong. And creating boundaries and being really clear about what's okay and what's what's not is critical to moving forward with respect in business. And I've learned that, you know, from my 30s and on. In business, people will treat you the way you teach them to look around you in your environment. Are they treating just you that way, or do they treat every single woman in the operation that way? I know they're not treating every woman that way because there's one woman there that's not letting it happen. And maybe some people call her a bitch. Maybe they do. But you have to decide what works for you. There's so many solutions. One is have a conversation with the person that you feel is complimenting you too much that makes you feel uncomfortable, or saying things in a way that you don't like. Tell them, hey, that's really uncomfortable for me. I don't really like thinking about, you know, how I look when I'm at work. I'd love it if you want to give me a compliment on my presentation. I'm totally down with that. But for me, it doesn't feel really comfortable when you talk about my dress. So can you and I just agree that that is over, and now you're gonna start complimenting me on my work? You know, you could literally say something that simplistic to someone. It doesn't have to be a fight that, you know, I'm gonna go to HR and charge you because you said that my dress was beautiful and I look really great today. People only know when we share and communicate clearly with them. If we aren't clear and we aren't honest in our communication, they are not reading our minds. That's important to know, important to recognize, and I believe people will respect you for that. You know, there's an older gentleman that I work with in LA that I love this guy and he will say things to me like, heather, you look amazing today. It doesn't bother me at all now if someone in a different capacity, a different person would say that and get so excited to see me. It might be weird if they were closer to my age or different people, different situations. You know, it doesn't have to be a blanket statement that you don't want, you know, this is. I want the company to know. No one should ever say anything about my hair. It can be unique and it can be, you know, there are different situations, different opportunities and interactions across business. But if you're having a problem with a certain person, my advice would be deal with them first and give them that chance to rectify the situation. They just might not know. It's that simple and truly, you know, or they might like you. We don't know.

Right?

We have no idea. And if that's the case, they're probably going to feel badly about it, but they'll probably change the behavior. So I would try to do it in an amicable way. Be honest, be direct and just understand that they can't read your mind. And then if that doesn't work, obviously, there's so many other things you can do. You can go to a trusted mentor at work, you can go to a manager. If you have to go to hr, you can go that route. I would always rather try to work things out on my own before you have to ask the company to take action. Once you get to that point, which that happened for me twice in my earlier years, things can really accelerate from there in a different way, you know, so if you're going to file some type of a grievance, that's when things can get a little weird at work. But in the end, you need to stand up for yourself, you need to create boundaries for yourself and you need to restart. Respect yourself. And you know, what might happen, which is what happened to me the first time I left the company. It got to a point where I had filed grievance. You know, things were really unraveling. I didn't like it and I said, me crying before going to work is not worth it anymore. I'm out of here. And I left there and started over a new, a different company, which led me to an amazing equity partnership opportunity where I made tremendous amount of money in my early 20s. So, yes, there was a micro challenge. I I hated the working environment, the culture, and how women were treated, especially how I was treated. I decided I tried to fix it. I couldn't. And I decided to leave that environment and went to an event, met a person that gave me an opportunity I would have never received otherwise. And so macro in the big picture, that opened up a whole new career and opportunity for me. So sometimes things come in front of you. It's about how you handle them, how you address them, how you take them on on, and how it may pivot you in a new direction that could be the best thing that ever happened to you yet. So hoping that you love this episode. Please subscribe. If you haven't left me a review yet, send me a screenshot of your review. I will sign you up for my $299 confidence creator video course. I get such great feedback on it and I would so appreciate the reviews. When you post about the show, please tag me. I will always repost, reshare and appreciate the love so, so much. Here's to you. Continue to create your confidence and I will catch you next week.

I decided to change that dynamic. I couldn't be more excited for what you're gonna hear. Start learning and growing. Inevitably something will happen. No one succeeds alone.

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