147: Chasing the Bright Side with Jess Ekstrom | Tanya Dalton
Jess Ekstrom podcast interview on The Intentional Advantage
November 5, 2019   |   Episode #:

147: Chasing the Bright Side with Jess Ekstrom

In This Episode:

Optimism permits you to dream big. Today I am joined by Jess Ekstrom, founder and CEO of Headbands of Hope, an expert in optimism and the author of Chasing the Bright Side. Jess came on to share her realization that bad things can happen to anyone, and why, despite knowing this, she chooses to look at the bright side of life. She shares how you can choose to live in the fear of the unknown or live in the excitement of the possibilities of what could happen. She also dives into why she’d rather try and fail than to regret never trying, and why you should give yourself permission to take small steps toward your dreams.

Show Transcript:

The Big Idea

Optimism allows you to dream big.

Questions I Answer

  • How can I be more optimistic?
  • How can I come back from failure?
  • How do I achieve my goals?

Actions to Take

  • Do an audit of your own thoughts. Are you living on the bright side? Think about how you can incorporate more optimism into your daily life.
  • Take part in our virtual book club for my book, The Joy of Missing Out. If you haven’t already picked up your copy, head to joyofmissingout.com or your favorite retailer.

Key Topics in the Show

  • Why Jess came to the realization that anything can happen

  • Deciding between the fear of the unknown or living in the excitement of possibility

  • Jess’s thoughts on why she’d rather fail than never try

  • Giving yourself permission to make the small steps toward your goals

  • Staying optimistic and Jess’s belief of what could happen if everything worked out

Resources and Links

Show Transcript

Welcome to productivity paradox with Tanya Dalton, a podcast focused on finding true happiness through productivity. Season 12 is different from any she’s done before with real conversations with real women, applying strategies and concepts explored in The Joy of Missing Out. 

This season, you’ll learn how to live more by doing less. And now here’s your host, 

Tanya Dalton. 

Tanya: 

Hello, hello everyone, welcome to Productivity Paradox. I’m your host, 

Tanya Dalton, and this is episode 147. This season is all about the joy of missing out and speaking of the book, just want to give you a quick reminder before we dive into today’s episode that we’re going to have our second live book club today. So, if you’re listening to this episode the day that it drops, join us today, I would love to have you there. Go to joyofmissingout.com/bookclub for information on how you can join in on the conversation. And if you’re listening to this afterwards, go ahead and go to the link so you don’t mis out on the other episodes. I’ll also be sure to have the replays available for you, so if you can’t join live, I still would love for you to be a part of that conversation. 

So, as I mentioned, this season is all about the joy of missing out. And a conversation about joy would never be complete without talking about its best friend, optimism. And that’s what I want us to talk about today. My guest on today’s episode is Jess Ekstrom and she is an expert on chasing the bright side. Looking at optimism through a new lens and really seeing how that gets us to success. So, today isn’t really a call in style, it’s more of a guest expert, which I’m really excited about because you will really on examination Jess. She’s an amazing woman. She’s the founder and CEO of Headbands of Hope, a company she started as a junior in college in 2012. And for every headband sold, a headband is given to a child with cancer. 

Her first brush with success was selling all of her toys on Ebay when she was 12. This is a woman who’s always had a mind for business and an 

outlook that is tied to optimism, Since then Jess and her company have been featured on Today and Good Morning America. She’s been in 17, Vanity Fair, Forbes and people. But even more importantly her company has donated hundreds of thousands of headbands, reaching every children’s hospital in the United States and 15 countries. I told you she’s amazing, didn’t l? Jess and her husband Jake travel the country in their airstream with their Dog, Ollie. She is incredible and I’m so excited for you to give a listen to what she has to share with you. So, let’s go ahead and dive into today’s interview. 

Jess, I am so excited to have you on the show today

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Jess: 

Tanya, thank you for having me, I am so excited to be here. 

Tanya: 

Well now Jess, your book Chasing the Bright Side, is all about optimism. And I don’t think any conversation about the joy of missing out, which is what our season is all about, would be complete without talking about optimism. So, let me ask you this, why are you so passionate about optimism? Why do you think people need more optimism in their life? 

Jess: 

I think that I am living proof that optimism is that initial seed that has to be planted for anything else to happen. But a lot of times we think it’s like success is derived from these fancy skillsets, or we need these shiny accolades or qualifications in order to begin. But really it just starts with that believe in better. Thad this idea when I was a college student to give headbands to kids with cancer. I had no idea what I was doing. I couldn’t even spell entrepreneur. I still can’t spell it, not going to lie to you. 

Tanya: 

I still cannot, 

Jess: 

Thad this belief that something could be better, and I had the courage that maybe I could be the one to do it. And so that’s how I started Headbands of Hope. For every headband we sell we donate one to a child with cancer, but it was really just that optimistic belief. It wasn’t anything else that we kind of sometimes think that success comes from. It was just that belief in better, so that’s why I’m so passionate about it. 

Tanya: 

So, it’s the idea that understanding anything can happen, that’s the key to optimism, right? That’s what you talk about in the book. 

Jess: 

Yeah. And I think that sometimes we think we’ll walk through life and say, “Oh, that can’t happen to me.” We’ll look at our newsfeed or something like that. But when we realize that really anything can happen, and I talk about this in the book, I have this chapter where I’m kind of freaking out about it, not going to lie, where I talk about this international scandal that my family was involved in. And for so long, I kind of hid it in my closet as like I don’t want anyone to ever know that I’m associated with this. I don’t want anyone to know that … this is just compartmentalizing this away. But the fact that it taught me that we’re not immune to anything. Anything could happen, and that gives us two choices. That first choice is fear of the unknown, if anything can happen then why go out there when a meteor could crash? Or, if anything could happen that means that we can live in the excitement of possibility. 

Tanya: 

Mm-hmm (affirmative). 

Jess: 

Like you could pick up a guitar today and be on tour with Coldplay a year from now. Anything can happen. 

Tanya: 

It’s true. 

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Jess: 

And so how can we look at that in a way that is positive, that is optimistic, instead of living in fear? 

Tanya: 

So, you talk in the book of the idea of embracing our yes’s, right? 

Jess: 

Mm-hmm (affirmative). 

Tanya: 

This idea of yes and moments that we have. Do you want to talk about that, because I found that so fascinating, this idea of yes and. Because so many people talk about no. And you’ve heard me, you’ve read my book 

and you know that we talk about the finding your yes. But I love this whole idea of embracing your yes’s, and then saying and then what. 

Jess: 

Yeah. So this kind of came from when I had started my public speaking career and I was really trying to get into it and one of my friends suggested, he’s also a public speaker, that I try improv comedy classes to get me more comfortable and loose on stage. And so, I would drive 45 minutes every Wednesday to this random improv comedy theater and I would take these classes. And the golden rule of improv is that whenever you’re up there doing a scene with someone, if someone says lie, “Hey Jess, we should go to the moon.” I have to say, “Yes, we should go to the moon.” So, you affirm what they just said. “And, maybe we’ll discover life on other planets.” And so, it’s like you’re building on top of your yes. 

And sometimes we are so quick to realize think about why wouldn’t this work. What are the things … what are the fears that I have? What are the self doubts? And so, wed kind of be like, “Yes, but. …” or like, “Uh no, that’s not going to work.” But imagine if we just said yes and then we talked about all the possibilities. And so that’s something that I talk about in the book when I accepted this random internship in Disney World, I didn’t really have a lot of reasoning, I didn’t have a pros and cons list, I didn’t have this deep organized thought. I just said yes, I’ll go to Disney World and become a photographer and maybe it’ll lead to something great. 

And that one decision to go to Disney World as how I got connected with Make a Wish, which was how I eventually started this company that has now helped hundreds of thousands of kids around the world. 

Tanya: 

It’s amazing, it all sparks from this one yes and then what it leads to. 

Jess: 

Yeah. 

Tanya: 

So, let’s talk about this idea because here you are in college, not much life experience under your belt, but it’s what do I have to lose? Here’s these kids with cancer, I really want to do something to help them out, So many people would say, “Gosh, I wish I could do something, but I 

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don’t know what to do.” But you did something different, you said yes and. So, why do you think you were able to just go for it? Why do you think you were able to say okay, these kids have cancer, I want to give them headbands, or I want to give them something to give them hope. So what do you think it was in you that made you oversee … like overcome all these obstacles and just not be scared of them? 

Jess: 

If there is one simple answer to that question, and I’m a pretty straight shooter and you’ll read that in my book, is that the reason why I went for it is because I know deep within my soul that failure will always feel better than regret. 

Tanya: 

Ah, yeah. 

Jess: 

And so, I would rather go for it and fail, which I definitely did at certain points, than wonder what if. 

Tanya: 

We all do. 

Jess: 

And wonder what would have happened. It’s so funny, when I was a kid, I would watch this show, All That, on the Nickelodeon Channel, and it was my favorite show. And so, my mom surprised me and she took me to the All Back concert. And when I got there, there was these tents where you could actually go and audition for the show. There were these camera tripods in there and they handed you a script. And I waited in line, I was like, “Mom, I have to do this.” | waited in line to audition for this show, missed the entire concert because the line was like three hours long. But I went in there and I read that script for 20 seconds, and I’m still waiting on my callback, but I could then go watch that show without any what if’s. And even though I didn’t get the show or really have any sort of acting or singing career, if you’ve heard me sing you’ll know why, but 

Tanya 

It was not meant to be, right? 

Jess: 

I know, and it’s not a clear connection I could make at a time, but failure will always feel better than regret. And so, I had this idea for Headbands of Hope to give headbands to kids with cancer, and I thought that I’d rather fail at trying something I really believe in, than be safe but have that dot dot dot, that what if. 

Tanya: 

Mm-hmm (affirmative). 

Jess: 

And sometimes we just need to give ourselves permission to do that. And when we sometimes just go for it, that doesn’t mean that we have to shoot for the moon, swing for the fences. Just give yourself permission to do the small things. If you have an idea, if you have something that you want to do, what is the small thing that you can do 

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right now that gets you one step closer? Because for one thing, the small things add up. And then another thing is sometimes when we just engage, it breaks that seal, like that fear that we have if we put one foot in the water. But when we just do one small thing, that is like training ourselves that you know, maybe this isn’t so scary, and maybe this’ll work out. 

Tanya: 

So true. And in the book, I know you say excuses are born out of fear. 

Jess: 

Mm-hmm (affirmative). 

Tanya: 

I think fear holds us back in so many situations, because we think well this is not what everybody else is doing, or this is not how it’s supposed to be done. We’ll say supposed to be in quotes there. 

Jess: 

Yeah. 

Tanya: 

But you’ve got to use some squirrel strategy. And I love how you give the idea of making a list of all your resources, because I think it’s so easy to think that we have to know someone big, or we have to take giant leaps. But really, like you said, it’s these small steps. It can be as simple as getting the word out, or calling and asking questions. And you use the term just for today, can you talk about that? What does that mean, “Just for today.” 

Jess: 

Yeah, and I love how you were saying we feel like sometimes we have to arrive at a certain place in order to … like we have to have all these contacts lined up. Well, I will tell you Tanya, Oprah still hasn’t called me back. And that’s been … I can’t believe it. 

Tanya: 

Still waiting. 

Jess: 

Yeah, still waiting. If you’re listening to this, give me a call. 

Tanya: 

Waiting for that, and the All That call back. [crosstalk 00:12:16] are sure going to come your way soon. 

Jess: 

They sure are, only a matter of time. And so, I think that … well, it’s like debunk the myth that we have to arrive in order to begin. We can just begin where we are with what we have, with what we know, because we learn on the way to our goals, not in the planning. I think sometimes our plans can paralyze us, and our plans can also kill the possibilities. Now, 1 know I’m speaking to like the Beyoncé of Productivity here, and I’m not debunking our plans and processes, but when we hold so tight to that, we miss all these other opportunities. And so, whenever I’m feeling fear or doubt, which are welcomed things by the way, I’m not saying that we have to quickly just into our happy place and pretend that they don’t exist. Whenever I’m feeling that I say what if just for today I went and 

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looked for a domain? Or what if just for today I called someone up whol know has been through this before? Or what if just for today I wrote up a list of all the resources that I had that could help me? 

And so, by giving yourself permission to not go in the deep end, instead of going off the diving board, but just kind of swim in the shallow end. All of those things eventually add up. So, I think that one of the misconceptions around optimism is this quick switch that we have to 

flick on in order to jump back into our happy place or throw sprinkles on something and call that a day. But sometimes it’s really sitting in that fear, sitting in the bad and wondering how we can be the one to make it better, and just giving ourselves permission to do the small things to get there. 

Tanya: 

I love that, I love that. And I think you’re so right when you talk about those plans can hold us back because if we set these rigid, rigid plans, it makes it really hard when life shifts. And life needs to be flexible. We talk about that a lot on the show. And I think that’s really that flexibility that you’re talking about there, that it’s okay to not jump off the diving board, but just to go in the shallow end. Let’s get our feet wet a little bit. Let’s get used to the water temperature and then we’ll go over to the deep end. There is nothing wrong with that at all. 

Jess: 

Yeah, I think sometimes we think we’re waiting for that big break. But really big breaks are just this fancy term for the summation of the small things that we do every day. 

Tanya 

Mm-hmm (affirmative), I think that’s so true. And I want to get back to this idea of failure and stumbling blocks. 

Jess: 

I might know a thing or two about that. 

Tanya 

Oh trust me, I do as well. I think anyone who’s gotten anywhere knows a thing or two about that. So, let’s take a quick break for today’s sponsor, and then we’ll come back and chat about that. 

Today‘s episode has been sponsored by the University of California Irvine, or UCI. UCI’s division of continuing education can be a great resource for anyone who’s looking to gain credits towards a master’s degree or for those who want to reenter the workforce after taking some time off. Or, maybe if you just want to learn some new skills, it’ll help you with the new business you’ve been thinking about starting. 

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Registration’s now open and they have a great deal for Productivity Paradox listeners. Simply go to ce.uci.edu/productivityparadox and 

enter the promo code Paradox to get 15% off of one continuing education course. Again, that’s ce.uci.edu/productivityparadox. Don’t forget to use that promo code Paradox to get 15% off one course. That offer is valid until December 31st 2019. 

Okay, so before the break we kind of touched on this idea of stumbling blocks. And maybe we think we’re going to jump in the deep end but then we’re like you know, it’s okay to go to the shallow end. And I know you had some pretty big stumbling blocks. 

Jess: 

Yeah. 

Tanya: 

You had some pretty big, well we’ll call them failures, which they are, right? I’d love for you to share some of those, because I really think that it is so helpful when other people can see it … because it’s so easy to look at you where you are now, donating hundreds of thousands of headbands, impacting so many kids’ lives, really passing along that optimism to them. But we lose sight of all the work that it took to get there. So, can you share some of the stumbling blocks that you dealt with? 

Jess: 

Yeah, absolutely. I think for so long I thought that in order for me to be a speaker, or an author, or really have a message, that it needed to be born out of my success. But I think that we learn so much more from 

other people’s failures than we do success. And so in Chasing the Bright Side, I really wanted to be transparent about some of the times where just … it would have been so easy to throw in the towel. And I think that what I’ve learned is the difference between people who throw in the towel when times get hard and the ones that don’t is not really anything to do with their experience, skillsets, how much money they have. But it is this rooted belief in what could be. It is this anchored optimism of what would happen if it all worked out. 

And that really came into play in the most literal sense when I was first getting started with Headbands of Hope. I had this idea for every headband sold we’re going to donate one to a child with cancer. It’s going to be beautiful, Oprah’s going to call me back, all these things. And so I started working with this manufacturer in Kansas and it was the only manufacturer that would call me back. I was obviously this small fish at the time. And they sent me some samples of headbands that we could look at, give them feedback on. So, for about two months we went back and forth sampling the product. And finally, I was like okay, let’s do 

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  1. Let’s make this headband. And so, they sent me over an invoice for the first round of production, and it was for $10,000. 

And I was like … I’m in a bit of a pickle, because this is about $9,500 more than what I have in my bank account being a college student on a ramen noodle diet. 

Tanya: 

Just a touch out of reach. 

Jess: 

Just a little bit, still using my sister’s Netflix password [inaudible 00:19:10] budget. And so, one of the things I started doing I’m like okay, let me start to research ways that I can get this money. Should I get a loan from the bank and pay interest? Should I try to get an investor and give away some equity? This was all very new to me. And so, I was talking about it with my dad who’s also an entrepreneur, and seeing what his thoughts were on which direction I should head. And he was like, “Look, I’ve seen your business plan, I’ve looked at your website. I actually think that this is going to be something big. And one of the mistakes I made when I was first starting my business was, I gave away too much equity too early, and I don’t want you to have to do the same thing. So, I will fund you the $10,000,” which was huge. And I recognized the immense privilege financially and emotionally that that came from. 

And he’s like, “You can pay me back as the business starts to make money.” And it was like hearing my dog speak English. The fact that my dad just believed in this idea so much just meant the world to me. So, 1 ran to the bank, it was a Friday afternoon, I wanted them to get the money before the weekend started because I was a business woman 

and I was serious. And I wired them $10,000 from my dad. And I never heard from them again. 

Tanya: 

I mean that’s just devastating, right? 

Jess: 

Yeah. I had other words that I won’t say on this podcast. 

Tanya: 

I appreciate it. 

Jess: 

But yeah, it was awful. And it was something that it’s so easy to equate those moments and draw a straight line to our self-worth. It’s like that I’ve totally messed up. It’s like I failed, therefore I’m a failure. Or I’m not qualified. What am I thinking? But now, as I’m sure you know, I recognize that failures aren’t the opposite of success, they’re just a part of it. 

Tanya; 

True. 

Jess: 

Success isn’t about the absence of resistance, it’s just the navigation of it. And so, if we can all be a little more transparent about what’s going on behind the curtains, then maybe we’ll be more resilient because that 

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A to B is normalized. Like the hiccups, the speed bumps, it’s just all a part of the process. 

Tanya: 

Amen to that. 

Jess: 

But when we have front row seats to everyone’s highlights reel and you’re like, “Oh look, so and so is a New York Times bestseller.” “Oh, this person sips green juice every morning.” “Oh, this person is 30 days of Yoga.” And it’s like we feel that we’re less than. And so, I really wanted Chasing the Bright Side to be completely transparent about all of the hurdles, the speed bumps, the crazy things I did to get this idea off the 

ground, because I really goes to show that if every expert was once a beginner, then why not you? If everyone that you know is so good at something once had no idea what they were doing. So, then that qualifies everyone, like it’s within reach for all of us. So why not just get started? 

Tanya: 

Yes, so true. I think you’re so right. We’re so busy looking at everyone’s highlight reel, these little tiny squares on our phones. And we don’t really see what’s behind the scenes. And I think that so often we just don’t see … We see somebody floating on top of the water, we don’t see them paddling their feet feverishly under the water, do we? 

Jess: 

Exactly. 

Tanya: 

And so, we think it always came easy to them. They didn’t make any mistakes, there’s no errors. And it really is this whole idea of let’s drop 

these facades of perfection. Let’s stop all pretending like everything is fabulous and let’s be real and honest, because that’s when real conversations happen. That’s when real growth happens for everybody. When we truly get into the failures, when we get into the things that haven’t gone well. 

Jess: 

We’re going on QVC shortly. 

Tanya: 

Congratulations. 

Jess: 

Thank you. But it just makes me laugh because of course you look QVC and you’re on the show and you’re like oh, look at this successful company, they have it all figured out. It has been years that we have been trying to get on this show, and if you saw the hidden cameras of my team when there’s an inspection at our warehouse, everyone’s pouring over there, getting the shelves in order. In the training and I’m like getting shunned because I keep saying the word product, and it’s like it’s not a product, it’s a headband. 

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And so, it’s like you’re going to see these three minutes of bliss, but if you saw the four years behind it, you would be laughing. And I hope you’d also be inspired. 

Tanya: 

I love that. I love that, I feel like that’s like your mantra. That you’ll be laughing but you’ll also be inspired. I love that. 

Jess: 

That’s what I hope anyone that reads the book is what it is. 

Tanya: 

Yes, well I love too how you say that optimism gives us the permission to dream big. But it doesn’t mean we have to do big every day. It doesn’t mean we have to be perfect, it doesn’t mean that we have to be 

at the destination right away. It’s going to be a journey, it’s going to take us some time. And it’s going to take the right attitude to get there, because you’re going to fall down. 

Jess: 

Absolutely. 

Tanya: 

You’ve got to pick yourself back up, right? You’re going to get mud on your face, you’ve got to wipe it off. You’re going to have people say things about you that maybe you don’t like. All kinds of things are going to have to happen. But that’s just part of the journey to get there, and truly optimism, and I think I said this in the endorsement when I endorsed your book that people think there’s all these secrets to success. I truly do believe that you’re right, optimism is the key to success, because it’s all about attitude and the choices we make and how we look at what we’re doing. 

Jess: 

And I would say that optimism is that initial seed, but you have to water it. Like you can have the biggest beliefs and all of these ideas, but optimism is that first step. It’s that initial spark. But optimism is wasted if we don’t believe it could be us. We have to be the one that says yes, we can give headbands to kids with cancer, and I can be the one to do it, And I think that something about Chasing the Bright Side is just because something is not our job doesn’t mean it can’t be our responsibility. So, the way that we walk through the world, whether that’s the trash on the ground, whether it’s that someone that you see that’s having a rough day. What if our job, our only was having an active role in better, whatever that means? 

And I think the interesting thing about optimism and this belief in better is that better doesn’t mean best. We don’t have to live life at our highest volume all the time. Better could be 1%, 5%, 20% better than it was five minutes ago. And that is manageable and attainable for all of us. 

Tanya: 

I love that. I couldn’t not agree more, and Jess’s book is Chasing the Bright Side. It’s a fabulous book. As I mentioned, i endorsed it, I read it. I loved it. 

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Jess: 

And I’m so grateful for you for endorsing it, thank you. 

Tanya: 

I was very happy to because I truly am very particular about the books that I endorse. I feel like if I’m going to say that I like something, or I’ve read something, or I want to encourage people to get something, I want them to believe it. I don’t just do it for everybody who comes my way, I really did think this book, Chasing the Bright Side is such a great book. Like you said, laughter and optimism and being inspired and all of that, all wrapped together. So, I really want to encourage my listeners go out, chase the bright side, get Jess’s book, Chasing the Bright Side. It’s an amazing read and I think you’ll love it. 

Jess, thank you so much for coming on the show today, it was such a joy to have you on. 

Jess: 

Tanya, thanks for having me, I appreciate it. 

Tanya: 

Doesn’t Jess have just the best outlook on life? She’s so optimistic and I truly believe that is one of the key cornerstones of anyone’s success. She does such a great job talking about it in her book, Chasing the Bright Side, which I personally endorsed because I did love it, and I encourage you to go out and grab a copy yourself. 

I would love for you to share some love with Jess, and share your favorite take away from our conversation. Just be sure to tag Jess and me and we’ll be sure to comment back to you, because I would love to hear what your take away was for today’s episode. 

And next week we’re going to go back to our call in style format that I’m So excited about this season, where I will be talking to a listener about what’s it’s like when we’re waiting for our dreams to start, because it can be a really frustrating time, but what do you do when you know you want to start something big but you know you have to wait a little while to get started? We’re going to dive into that next week. And before ! sign off, I do want to remind you that today’s book club is going to be live, it’s going to be a lot of fun. Be there. I would love to have you be a part of that conversation. Go to joyofmissingout.com/bookclub so you don’t miss out, all the details are there. All right, until next time, have a beautiful and productive week. 

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