Sophomore Syndrome and that Successful Feeling, with Jess Ekstrom

Jess Ekstrom started Headbands of Hope back in college, and the demand was more than she could have ever imagined. With the success of her first business comes expectations for her follow-up chapters.  So how has she responded?  Plus, Jess talks about why everyone should create 100-year goals and why you should celebrate the parts of the business you dread.


Dana: Welcome everyone to Hustle and Gather, a podcast by inspiring the everyday entrepreneur to take the leap. I’m Dana 

Courtney: and I’m Courtney. 

Dana: And we are two sisters who love business. On this show, we talk about the ups and downs to the hustle and the reward at the end of the journey. 

Courtney: And we know all the challenges that come with starting a business. Between operating our wedding venue, doing speaking and consulting, and starting our luxury wedding planning company, we wake up and hustle every day 

Dana: But we love what we do. And today we’re talking with Jess Ekstrom, CEO of Headbands of Hope, author and speaker. Jess, welcome to Hustle and Gather. 

Jess: Thanks for having me. Okay. I’m an idiot. I did not know you guys were sisters, sisters. Wait, who’s older?

Courtney: It’s me. I know. I look younger. 

Jess: Are you taller? I’m the younger one, but the taller one, I love rubbing it in my older sister’s face. 

Courtney: Well, I was all fine. And like, when we were like 12, I knew one day I was going to get my comeuppance because my whole life growing up, they’re like, it’s this your older sister?

And I was like, no, height does not equate to age. That was like one day when we’re 40, they’re going to upping your older. And someone, one day, asked if she was my mother. And it was like the best day of my life. But then recently on my 40th birthday trip, someone asked me if she was my daughter and I was like, what the hell?

Dana: How old do you think I am? He goes 20. And I was like, oh, you’re my new best friend. Yeah, add 17 years. 

Jess: That’s awesome. 

Dana: And I feel like it’s negated. 

Yeah. I can’t say it anymore. 

Jess: Well, my sister and I are complete opposites, in the best way possible, but I don’t know if we could ever run a business together. She, her business is like it called Burning Daylight Expeditions that she takes people on like wilderness trips, like deep in the woods. And I’m like, let’s do headbands and fashion. 

Dana: That’s awesome. Well, thanks so much for being here. I was telling you earlier. I’m like watching you on Facebook and Instagram and 

Jess: Awesome. I’m so glad. Well, I admire what you guys do because I have tried doing events and stuff in the past, whether it’s for my business and they are like, that’s not my zone of genius. You know, there’s some people that are like, love the chaos and the coordination of it. . And I’m like, I could never, yeah.

Courtney: I definitely think it’s, it’s more of a lifestyle than a job. I think. So I definitely think it takes a certain, a certain personality for sure. I’m not even saying I have it and not get it for a long time it’s not my personality, really. 

Jess: I’m definitely like maybe I have trust issues or something because it’s hard, like sometimes working with people that are like, okay, you’re bringing the balloons, you know, and it’s like, you have to trust that they will bring the balloons and it’s, you know, been hard sometimes as an entrepreneur too and I find that the more that I rely on my team and believe in them, the better that they’ll do, but it’s definitely a muscle that you have to train.

Dana: Oh yeah, a hundred percent. I do think that that’s a really good point. I think that makes it easier while we could build our team much quicker because we were used to even when it was just us, we had to have a team to execute events, and you had to trust that person was going to follow through. 

Jess: You had to yeah, or else you couldn’t do your job well, yeah. 

Dana: That’s a very good point. Well, let’s dive into why you’re an entrepreneur. So let’s hear a little bit about your story because it is a pretty amazing one, like how and why did you start Headbands of Hope? 

Jess: So I started headbands of hope when I was in college. I was at NC state. and it was so funny. I literally walked in here and I was like, oh my gosh, I forgot my headband in the car. So usually I’m wearing one. If you’re watching live just imagine, you know, a beautiful headband on my head. And I was interning at Make-A-Wish, and when I was there, I was seeing a lot of kids that were losing their hair to chemotherapy and they’d be offered a wig or they’d be given a hat, something to cover up their heads.

And a lot of them weren’t really concerned with, you know, covering up their heads, they just wanted something to feel good about themselves after losing their hair. And so I would see them, you know, coming to the office or on their trips, like wearing these headbands. And I thought it was so awesome that they just didn’t care about covering it up, they just wanted to feel like a kid again. 

And so I remember, few weeks prior to that, Blake, the founder of Tom Shoes, who’s not named Tom, spoke at my school and he was talking about how you started this one for one company, you know, giving shoes for every pair sold and how he wanted more businesses to create, you know, business for good and for purpose where you don’t have to choose between being a nonprofit and a for-profit like find a way to work giving back into your business model.

And so that was kind of fresh on my mind. And I had looked up like on Google, like headbands for kids with cancer and couldn’t find anything. And so I call it like the dumbest smartest moment of my life. Oh, I could do that, I’ll just do what Blake did, and so I started Headbands of Hope and for every headband sold, we donate one to a child with an illness and it was not fire right out of the gate, lots of trial and error in the beginning. 

Now almost, I mean, we’re coming up on our ten-year anniversary in April, which is crazy. But, through that, I kind of realized about three or four years ago that this story of headbands of hope, the origin story, how I got started and the mistakes, was really like an impactful product in itself. And so I started writing and speaking and then through that realize that there’s not a lot of women doing that. and so that kind of started my next business, which is Mic Drop Workshop that helps women tell and sell their story through keynote speaking and writing books. So, wild journey, but learned a lot and happy to talk about it. 

Dana: I love that, that is awesome.

Courtney: Yeah. So I could imagine, like, it was like probably hard and scary, like starting in college. So how’d you manage to get it all going? Like, I’m just thinking supply chain, like how do you scale this to be something that is something and not just you like hot gluing things on something you might find it Michaels?

Jess: Well, I definitely tried that. It didn’t work so well. But I would say that it’s like scarier now doing ideas than it was then, because when you’re young, like you don’t have any data, you know, you don’t have any information, you don’t have any like history or stories of like, why things work or why things don’t.

Which on one hand, you’re just kind of shooting from the hip and hoping something sticks, but on the other hand, it’s like, you’re not paralyzed by, you know, all of like, what if this and what if that, so I wish I could tell you that it was like, at the time, I like really thought long and hard about it and like went back and forth in my head, but I didn’t, I was just kind of like, great, let’s do it.

And I’m now like, you know, starting Mic Drop Workshop or starting, you know, I have an online journal app that I created called Bright Pages, and like those felt scarier to me. One, I had more information of how hard things were and two, once you’ve hit some level of success with something, you feel like your next thing has to be like, you know, I think people call it like sophomore syndrome.

It’s like the next one has to be even better, which can be really paralyzing sometimes. But in college, I was fortunate enough to have a lot of resources at my disposal when you’re a student, you know, I got my first logo from working with the, bribing the graphic design class, you know, to make me a logo for a grade. I made my website by paying, computer design students with like Chipotle burritos and, little by little, you know, things started to come together with Headbands of Hope, 

Courtney: So a masterclass in like efficiency, I get things done for nothing. 

Jess: For some reason, I like, college students, you know, and to this day it’s like the way to their heart is through food. So I would like find ways like use food to get what I wanted. I remember I got Jimmy John’s to donate like a hundred Turkey Tom sandwiches for like a photo shoot for people to come out and like take photos of wearing headbands. I’m like, this is the way to, this is my currency of choice, you know, Jimmy John’s sandwiches.

Courtney: I know we had a podcast I don’t know, a couple of months ago and she was talking about she’s a marketer and she was talking about how, when you don’t have money, you’re super creative, you get so creative to be able to like, get that product out and get to where you need to be. And sometimes like, once you have resources, you get a little less creative, like your fallback is just I’m going to pay for that.

Jess: Yeah. You, I think that that’s really, really profound, because I would say at the beginning phases of Headbands of Hope we’re so creative. I mean, it was like, I would recruit my college friends to be like campus representatives and put like a fancy name tag on it and just say, hey, go sell headbands and it helped me, you know, donate them. And then as you get older again, it’s like, you just have more information, which can be a good and a bad thing as to how you run things. 

Dana: Yeah, I totally agree. Yeah. I feel like it’s that fear of failure is stronger after you’ve been successful. Like I think when we started our company, it was just very much like, oh just do this, I’m like okay. It was never on my mind that we could fail or we would fail or if we did fail, it was like, what’s the harm to… but now, like when we’re thinking about our next step, the it’s not, how can this be a hundred percent successful, it’s like what are all the pain points that we see that could possibly make this fail, and what’s going to talk us out of actually doing it right.

Jess: Once it, you know, what it feels like to win, it’s really hard to know what it feels like to lose, and so true. I totally, I totally get that. But you know, one of the things that I feel like I discovered over the past couple of years as to like, you know, Headbands of Hope is still a big part of my life, but I’m not the CEO, I’m not running it anymore. I have an amazing team behind it. I’ve moved on to more Mic Drop Workshop and Bright Pages, but, one of the things that I realized was I always thought that I was going to reach like a point where, you know, I felt like I’ve made it or, you know, once I can do this, then, then I’m going to, you know, just drink Margarita’s and call it a day and like, you know, not challenge myself again, like once I hit these points and then you hit them and then you realize like that you just start all over again in a new way. 

And so it’s like, it’s not really the outcome that I’m chasing. It’s like the build that I love, and so you kind of have to come to a look yourself in the mirror and just say, look like you love the game. Keep playing it, stop trying to think about when the game is going to be up and just enjoy playing in it. 

Courtney: That is so true. It’s like, hard and wonderful to have that like entrepreneurial spirit, you know, like it is really, really hard, but there’s literally never an end. There’s not a destination. I think you have to come to the point where you accept that I’m not actually about the destination. I’m literally just about the journey and wherever it is at the moment, like hit those wins and you think that’s going to be enough and it’s not enough, never enough. 

Yeah, you know, it’s always something that comes in your mind, something that you can make better, some other product you can put out or like some other great idea that you want to foster. And then for us, I don’t know for you, it’s always been about like, how can I scale my OG business or my sophomore business or whatever it is that allows me the bandwidth and the mental capacity to do my next passion project.

Jess: Yeah, totally. And I think that people don’t, even when you’re a kid and you’re told to select what you want to do for the rest of your life, which I think is crazy. It’s like, but no one really, I mean maybe you talk about pay, maybe you talk about passion, but no one ever talks about lifestyle. Like what lifestyle do you want to have?

And I think that like when it comes to scale in your business or your, whatever it is that you want to do, like I don’t want to have a skyscraper in Raleigh with thousands of employees that I have to do. Like I want to live in an airstream and go in the woods and like, it’s very different, so when you think about building your business, it’s not just about the financial part is, or essentially what you’re doing, but it’s like, how do you want it to create a lifestyle that you want to live? Is it, do you want to surround yourself with people all day, every day? Do you like being by yourself? Like, what is it? And so thinking about lifestyle too, I think isn’t really talked about.

Dana: I totally agree. I think I do feel like this next generation is getting that more correct than our generation, like I definitely see those Gen Z-ers, it’s all about lifestyle and it’s all about how can this job, that into the life that they want, although sometimes it’s very unrealistic what they’re expecting.

Courtney: Totally. Like that work-life integration, you’re like you’re a little heavy on the life and heavy on the work. 

Jess: I think it’s obviously a process, but I’m sure like with you guys, in being an event, The hours. 

Dana: It is. So it’s, it’s a, they’re odd schedules. They’re all over the place. We have some people that work, you know, Tuesday through Saturday, some that work Wednesday through Sunday and some that we all have Mondays off, you know, and it’s, they start at nine, but maybe they end at three, but then their work, their wedding day, it’s, you know, 14 straight hours.

So it’s just, it’s very variable. It’s really important for us, like in our office culture, it’s all about like communicating and talking about how you’re feeling and burnout and making sure everyone has this space to recharge and regroup and to feel like they’re not coming into an office, but they’re coming into a really fun community. 

Courtney: Yeah, community. Cause that’s, you know, it’s full of messy people.

Dana: But I’m really curious. So you talk a lot about, or one of your speaking topics is on attention and success and how they’re not codependent. And so you kind of touched on this a little bit, how would you define success? 

Jess: So one of the things that I talk about in Chasing the Bright Side is if whatever it is that you’re chasing, like the thing that you’re going after, whether it’s in your business, in your work, in your life, like a goal that you have, if your name was removed from it, if no one knew it was you, would it still matter?

And I find that that’s a really gut check, you know, because so often we do things based on how they’ll look, not necessarily how they’ll feel, and we’re trained to do that now with social media. We are trained to put on like, what is the perception that people will think of me if I post this? Or what do I want people to think of me?

And it’s like, we have, you know, a front row seat to everyone’s like highlight reel, we are all seeing all their trophies. And so I think that it can really mess with our mind and what we see as success. So for me, if I’m doing something that I don’t care if my name is attached to it and I would still do it anyway, that’s success to me.

And another thing is, you know, realizing that. A lot of things that we maybe feel like are success can be quantified. Like, you know, maybe you get an award or maybe your podcast hits a great ranking, or maybe you get, you know, revenue milestone for your business. And all those things are great and they deserve to be celebrated.

But that’s what we classify as these achievements, you know, these tangible milestones that show that maybe you’re on the right track. But success is something that can’t be measured, you know, it can only be felt. And the last thing that I kind of like to think about when I am a I’m a visual person is, you know, I feel like achievements are your own race.

Like you are crossing a finish line, and success as a relay. And so I saw, I think it’s in Japan, they have like instead of new year’s resolutions, they have like 100-year goals, which means that they know that they will never be at the end of this goal. Like they will never see like, you know, Walt Disney never saw Disney World, right. 

But if they know that they’re using their life to put a foundation in place that betters the future, then that’s enough for them, which is like, 

Courtney: So un-American 

Jess: un-American, exactly. But it’s like knowing that like, yeah, I don’t need to see the outcome to know that it matters. Like I know that I’m building the bricks.

Like I know that I’m passing the Baton. so that’s honestly what kind of led me to, starting Mic Drop Workshop is like for so long, my version of success was like, how many books can I write? How many stages can I speak on? You know, how many Ted Talks can I give? And I’m like, not only is that formula like limiting, it’s also exhausting and it has no ripple effect. And so maybe now my success can be how many women can I help do that same thing and give them the tools to do that because that stretches way beyond than the hours I have in the day. So, there’s a lot to think about when it comes to it, but I would just say removing your name from what you’re doing and if it still matters is like the key part. 

Dana: I love that, so powerful. 

Courtney: Yeah. I know like one of the things, one of the terms, I don’t know if it’s a term, but like a thought that comes into my mind often, like when I meditating or when I’m in the shower or whatever, is that like constant like search for significance?

Like I think that there is a universal need for people to feel significant and like, whatever that is and someone else’s life may not look exactly how it is in yours, but like here this, you talking and I’m thinking like, wow, like this is like your journey to significance, like how you’re significant and how your legacy is going to move on beyond you. And I think that’s so amazing. 

Jess: Oh, thank you. Yeah. Legacy is a really interesting word too, because that is, you know, beyond your, like your lifetime, why that matters to you. So I like the word legacy. Yeah. Yeah, no, I love that. 

Dana: I did too, and I think it’s, I think it’s really hard and it you’re absolutely correct that social media and like where we are in our society makes it really, really, really hard, and it’s probably the reasons why I’ve pushed my kids. My 11-year-old, like not on it, not, and I don’t even know when and how, or we haven’t even been down that road, but I fear for that so much for her, because I feel like you do get stuck in this well, I’m not successful because I didn’t go on that great vacation or I don’t have this amazing car or I don’t have XYZ, you know? 

And it’s, it’s this comparison. And I think I love the idea of separating achievements. The comparison of achievements is very different than actual like success being a feeling, I think. And I think people rob you of that feeling. 

Jess: Yeah. And I think that for younger generations it made me think of your 11-year-old, and even for older generations, you know, you’re trained to think that like, go, like, find your passion, like, see like discover your passion or like what you were meant to do.

And I think that that can be really misleading because it feels like you’re going to find something that you love every day and every moment, or like, if you love what you do, you never have to work a day in your life, like that is bullshit, yeah. But I think that passion, you know, doesn’t have to be discovered.

It can be learned, you know, and what you’re doing right now in so many different jobs. Like a lot of people think that, you know, giving back and doing something meaningful means absolutely surrendering any sort of paycheck and, you know, going abroad somewhere and helping people less fortunate.

In events, you know, like I, you know, got married. I had event planners and it’s like those, the meaning behind making me feel like I was special that day, that I was valued that, you know, this, my dream was coming true was like a really meaningful role. And so I think that, you know, passion and like meaningful work is not something that can be like assigned to you or discovered. It can be taught and learned, which is in my experience, I think really optimistic because that means it’s not in someone else’s control it’s in ours, you know, like we can learn to be passionate about something. 

Courtney: And I definitely believe that. I mean, even like having been in events for 15, 16 years now, 2020 it was definitely a learning lesson of like how important it is actually for people to gather around whatever, whether it’s like a work project, social project, a wedding, a party, like people need community.

And as event planners, like we are fostering that, facilitating that for people like it’s really a big deal. I think if 2020 taught us anything it’s like celebrate everything, right? Like hug those people when you can hug them, be with them when you can be with them. And it’s kind of amazing to be a part of that.

Previously it’s like, I don’t, we throw parties. And it was fun, you know, we socialize a lot. We help other people socialize and it just kind of didn’t have the same meaning, but even like as life goes on and you experience more things, you can find more passion in what you do. So I think that’s totally true 

Jess: When we were in the Airstream. There was, I can’t even remember where we were somewhere in Maine, I think. And there was this island that we took a ferry to, and there was not a lot of things on this island, but one thing on this, oh, I had to like double check my Google maps. I was like, is this right? It was the museum of umbrella covers.

Courtney: museum of umbrella covers?

Jess: Covers. Not umbrellas, umbrella covers. And we were like, we have to go here. Like, I mean, this is, if there’s one thing, I have to do in my life now is go to this museum. And so we went and it’s this woman who one day in like 1990, like realized that she just had this passion for umbrella covers and that she just thought it was like so interesting that there was this attachment to a product that literally no one uses.

And so she had these walls and walls of different umbrella covers and she had this whole spiel and it was like interactive, like about like what you think of them and getting your feedback. There was different themes, but her tagline for her museum and this would have been on like NPR. I’m like, you are amazing, but her tagline for the museum was celebrate the mundane.

I don’t care if you to like umbrella covers, but like our world does not have to be explosive in order to be exciting, you know, like what, you know, celebrate like everything. And I just think about that all the time, ever since I’ve been there, it’s like, yeah, like sometimes we’re overly stimulated. You know, we have so much access to like Tik TOK videos or whatever that’s like constantly stimulating us that we feel like maybe our barrier to, you know, when we’re excited is now higher or our threshold, but she just reminded me that like little things can be exciting and it reminds me, have you guys seen Ted Lasso or you can give a chance? So I love it. No spoilers, 

But one of the things I saw like Jason Sudeikis saying in an interview one time was, you know, the success of Ted Lasso and I’m like paraphrasing, but the success of Ted Lasso proves that good guys can be interesting, ordinary good people. And yeah, that’s something that has just like, stuck with me since that I’m just like, man, how can I just find a little bit more fun and joy in the mundane?

Courtney: I have this picture and my house, and it says its hardest to love the ordinary things, but you get lots of opportunities to try.

I remember one time I was like doing dishes or something for like the bajillion time that week or whatever. And it was somewhere in the middle of 2020, and I felt a lot of like joy, just like contentment doing it at that moment. And I don’t always feel joy and contentment when doing dishes. In fact it’s quite the opposite most of the time.

Yeah. But I remember thinking at that moment, like, this is it. Like a lot of people work their whole life and they work really hard to build this life that they resent or they don’t enjoy like all the aspects of it. Do you know what I mean? And I felt like at that moment, and again, I’m not there all the time.

I was like, I’m, I’m here. Like I’ve worked to be here, I’m home with my kids. It was like sometime in the middle of the day in the middle of the pandemic and my life was structured in such a way that I could be home doing dishes at like one o’clock in the afternoon while, in between yelling at my child on a zoom meeting, you know what I mean?

So, but it was just like, I’ve worked to get here, and it was just like one of those like clarity moments where I just realized that there’s a lot of people who work their whole life to build a life that they resent, you know what I mean? 

Jess: Totally. I think that the idea that you have to love at all, it’s like so misleading. And so I try to aim for 70%. That’s good. I’m like, I just want to love 70% of my job, 70% of my relationship, you know, like 70% of like my marriage, like I just need 70% of the time, it needs to be good, 30% of it can suck like, and you know, that’s when, I have employees or something that are like, well, I really don’t like doing, you know, this one thing. It’s like, why can’t possibly remove everything from your plate that you don’t like because, but if it’s more than 30%, let me know. But if not, then it’s just part of the jobs, you know? Like let’s roll up our sleeves and do it.

Dana: Yeah, I agree. I feel that way. I actually feel that way every time I buy groceries, I know that sounds really weird, but like I, cause I, I loathe putting away the groceries. Oh, I know. Yes, once it’s all in the fridge and I opened the fridge and I realized like all the food that we have there is like this overwhelming wash of gratefulness that like, I have drawers full of fresh food, gallons of milk. Like we, and I think like I want for nothing at this point in my life, because I was able just to go to the grocery store and like buy the food that I wanted, recognizing that that’s not the case for a lot of people.

But it’s like the one thing that always, I feel like centers me and two, because I find sometimes like the meal planning and the prep and like getting ready for the week. Like, it feels, like just you’re on a hamster wheel and you’re just like, I have created this constant, like circle of life that I cannot break. Like I cannot get out of, and it’s always that moment that I’m like, okay, I’m grateful for this wheel right now that I’m on. 

Jess: Have you read a, either of you Marie Kondo’s Sparked Joy?

Courtney: I have not read it. I’ve seen the, like the show, the Netflix show. 

Jess: Well, one of the things that, you know, she says to do is like, obviously hold each item and ask yourself, does it spark joy?

And then she, I was like, okay, but what about like a hammer? You know, like I’m not going to get rid of a hammer, but it’s not like getting me super excited. So she’s just when you have some product that’s mundane that you need, that you can’t get rid of, but it’s not an exciting product like, just tell yourself, like, what is it that this product helps you do? You know, it’s like, wow, like I can hammer in nails. I can build, you know, a shelf with this hammer and remind yourself that you’re excited about it or that it has meaning in your life. 

And so in my work, you know, hate financial meetings. Like anytime that we have to go over spreadsheets or numbers, I just like totally glaze over. And so I find myself now saying, it’s like, well, we have financial meetings because there’s business that’s happening, you know, and stuff to be dealt with because there’s action happening in my business, right. And so sometimes it’s just these little like cues that you have to give yourself no matter whether it’s putting away groceries or running a company.

Dana: Thanks everyone for gathering with us today to talk about the hustle. Our conversation with Jess will be presented in two parts so we don’t leave anything out. To learn more about Jess and her story, visit or follow her on Instagram at jess_ekstrom. To learn more about her organization, visit headbands, a or follow along on Instagram at headbandsofhope.

And for those of you that are listening, just given you one free month of Bright Pages, her online journaling platform, you can go to and use the code gather. You can read more about Bright Pages and Jess’ other products in our show notes.

Courtney: And to learn more about our hustles visit,, and or follow us on Instagram at canddevents, at thebradfordnc, and at hustleandgather. If you liked the show, be sure to subscribe and leave us a rating and a review. This product is a production of Earfluence. I’m Courtney.

Dana: And I’m Dana.

Courtney: And we’ll talk with you next time on Hustle + Gather.

Dana: Welcome everyone to Hustle and Gather, a podcast by inspiring the everyday entrepreneur to take the leap. I’m Dana 

Courtney: and I’m Courtney. 

Dana: And we are two sisters who love business. On this show, we talk about the ups and downs to the hustle and the reward at the end of the journey. 

Courtney: And we know all the challenges that come with starting a business. Between operating our wedding venue, doing speaking and consulting, and starting our luxury wedding planning company, we wake up and hustle every day 

Dana: But we love what we do. And today we’re continuing our conversation with Jess Ekstrom, CEO of Headbands of Hope, author and speaker. On our last episode with Jess, we talked about building your career for your lifestyle, celebrating the ordinary things, and loving at least 70% of what you do. Here’s Jess with more great insight. 

Jess: I used to think I had this belief that I could one day reach zero problems. Like if I just worked, you know, like, oh, well on Friday, I’ll be done with this speaking gig and I’ll be, so that way I’ll feel totally euphoric, you know, and just blissful. And then of course, like it email pops into your inbox.

That’s like, whatever, you know, I’ve got to pay this invoice or something like that. And you’re like, oh, well, there goes my bliss. And it’s like, no, never going to have zero problems. If you’re actively engaging with the world, then your things will be circulating back. And so if that’s the case, then we can’t keep delaying joy until we have zero problems, you know?

And then sometimes we make changes in our life, like thinking that this change will solve our problems when really, we have to think of changes as like bringing about new problems. And I used to think like, well, oh, if I am not doing Headbands of Hope as much anymore, but I’m focusing on a Mic Drop Workshop or whatever then, then all the problems that I have over here will go away. It’s like, well, now I have, you know, new ones over here. And so thinking about like the pivots and the changes, they real life is not like eliminating your problems, but like bringing new ones. Would you be excited about those problems? 

Dana: Oh yeah, totally. That’s totally the same vein as, our September was absolutely nuts and it was a lot of things I didn’t overly enjoy having to do. But I had to deal with it. We had to get through it, some projects we had to get off our plate and I in October happened and I was like, and I’m looking at my calendar. And my October calendar looks much scarier than my September calendar.

And I told my husband, I was like, it looks scarier, but I, I don’t feel as stressed. Like not nearly as stress is what I did in September. He’s like, well, that should tell you what you enjoy doing. And I was like, that’s and I never thought about it. I just thought that this was taking up my time. It takes my time, stresses me out, but, and like, well, you’re right. That’s not the case. Like I’m really enjoying, working on this aspect of our business and growing in this way. Whereas the other stuff a month ago, I was like, I don’t want to do it. So maybe, more angsty. 

Jess: Yeah. I think it was in Marie Forleo’s book, Everything is Figureoutable where she talked about like two different kinds of fear that we feel. And there’s fear that makes us feel like we’ll be constricted, like, oh, I won’t be able to move. And then there’s the kind of fear that is like expansive, and lean into the expansive fear, not the restricted, right. And so I think about that a lot, whenever I’m feeling angsty or fearful, because like, you know, you hear people that are like fear is good, or then you hear like, you know, survival of the fittest of like no fear is telling you something.

And so it’s like, what am I supposed to listen to, listen to fear or not? And so now it’s like, if I am fearful or angsty about something that makes me feel like I’ll be limited or restricted, then I’m not going to do it. But if I’m fearful of something, because there are so many different ways that it could go, then I’ll give it a shot.

Dana: You know, that’s a really good barometer.

Courtney: Because there’s definitely times like, even like conversations with employees that I have, like some sort of like fear of going into, or like I concern or whatnot, and 

Jess: I think you don’t know how it’s going to play it out. 

Courtney: Cause I think it is, I am afraid, of being like sucked back in, like I’m afraid of like the restriction.

Do you know what I mean? Like you’ve moved beyond here and you’re like, I thought, I thought I would know beyond this, like I’m going on to here. And I thought I put this to bed and it’s that like restriction, like being stuck doing something that I don’t want it to do, even though I’ve hired someone to do it, but yet here I am still doing it. You know, different kinds of feels different. It’s definitely different. 

For us, I think one of our, as far as fear and like moving forward and like new things that is like, I think one of our fears often is, I’m moving forward to this and even though I have systems in place and people in place, there’s always that fear of, like the response it’s going to land on your shoulders. Either way, it’s going to land on your shoulder so that you have we’re a little timid. I think sometimes 

Dana: we’ll because we, we still run our businesses. We’re still like, we’re not in the mix in terms of like, we’re definitely taking on more of a managerial role, but at the end of the day, especially if you’re talking about events, so you have a, a client that comes to you and is like, hey, I’m not jiving with my planner, right. And, and they’re upset or something’s going on.

So you’re a natural inclination is like, okay, well, I’ll take on this event, step in because you’re the owner or the boss. They trust you. They’re not going to trust another planner. And there is still that aspect of our business that we have to handle. And I mean, even just the other day, like a client was upset about something about the Bradford and they emailed me and I’m like, well, I don’t know anything about what’s going on with this and why, you know?

And so you still kind of get into that, that role. And there is that pressure that if we start something new or you grow too big, right? The something’s going to bite you, the maternity leave, have a baby, and then I’m going to be sucked back into this. And I don’t have, I don’t have the passion to do that anymore.

Jess: So how do you guys know what is like? Yep. I’m going to involve myself in this and what to hold firm on? 

Courtney: I think we’re still learning that out. 

Jess: Yeah, right. It’s hard to be like when you have an entrepreneur mindset and when you’ve been a part of like the zero to, you know, whatever, it’s hard to be, like one foot in one foot out like, like involved at an arm’s length. It’s like, you don’t stop, it’s like when you’re, I’m sure when, if your kid goes to college or something, it’s not like. You know, done here. I raised you, off to Hawaii. It’s what do you mean? That’s not what happened? 

Dana: That’s what I’m banking on. 

Jess: I mean, it’s still like I feel, and it’s something that I’m working on. It’s just like one of my friends, Kate Rosenow, her business is Work Well with Kate, and she helps business owners like systemize and automate their business. And she says, the best use of your time is doing the thing that you do best. And so I find myself like with headbands of hope, I still want to contribute the thing that I do best, which is the storytelling, which is the externally facing, you know, part of it.

I am not going to be the person that’s like, oh, like, well, if our conversion rate is down on the site, then we should really look at the analytics of Google, whatever. And, but I still, when you wear that hat or I say, wear that headband for so many years, it’s hard to turn off where you want to solve every problem, even though it’s not the thing that you do best.

Right? Yeah, so I kind of just go back to that mantra from Kate. It’s like the best use of my time is doing the thing that I do best. If I’m finding myself inserting myself or, or involving like, or being, even someone asks me. I have to say this isn’t this, isn’t what I do. This isn’t my lane anymore. You know, and hopefully, you know, we have a person that is, and if not, then now we know that’s a gap that needs to be filled.


Dana: I love that, that’s great. 

Jess: Yeah, it’s easier said than done for sure. 

Yeah, changed my job description. 

Dana: It’s easier said than done, but I think it’s wise advice. Cause I, I do feel that I feel like there’s a lot of times you spin your wheels as an entrepreneur and you look at it. I when you, when you quantify it and, or qualify it, I guess like it.

It’s not worth it at the end of the day. Like it’s not worth my time. It’s not worth my energy. It’s just not worth it. But it’s hard to get to that because you want it to be worth it and I can do this. Like I should be able to do this. It shouldn’t bother me so much or,

Jess: It’s really hard because I’m sure you all have experienced this, there are so many seasons to entrepreneurship or growth and the things that you did in season one, you should not do in season four. And so it’s like season one, I’m like, whatever it is, I’m going to figure it out. I will learn how to, like, hard-code an email pop up if that’s like what I have to do. And like I did those things, you know?

And then all of a sudden, you know, when you’re in season four or five, do not spend six hours trying to, hard-code an email pop up when you can find someone to do that for you, right. And so you have to learn like when is it time to move on from the practices that served you to the ones that don’t serve you anymore?

Okay. I, you know, remember like a time in my life where it was always like, whatever it is, like, I’m going to say yes, and I’m going to be the yes, girl, and I’m going to show up. Like, 

that sounds horrible. 

Yeah, exactly. And I did that and then, you know, a lot of great opportunities came from it and then a lot of wasted time as well. And then now I’m in a phase of my life where like, usually my gut default answer is no, and that’s served me really well where now if my gut default is no, then an opportunity really has to prove itself to say actually, yeah, like, let me look at that a little bit more, but it was a season that the yes season served me in the past. It doesn’t serve me anymore. 

So I feel like you also, always as much as you fine tune your business, you have to fine tune yourself in like always auditing the things that you used to do, the pattern patterns that served you once might not serve you today. So you really have to be self-aware and I think it’s awesome that you guys have a partnership too, because you can probably look at a distance a little bit sometimes, you know.

Dana: It’s true. And I think, and I really love that freedom to say to that. It’s just not serving me anymore. Cause I think a lot of times too, when you look at past behaviors and, you know, decisions that we made, like there’s a lot of times you looking at it’s like, oh, that was a mistake.

Jess: Right, or that was wrong. 

Dana: But in the moment and in the time, and like we say that all the time about our windows at the Bradford. We went from aluminum clad to wood windows cause it saved us like $15,000 and we just didn’t have at the time that we didn’t have the money. So now I look, I’m like, oh my God, that was the worst mistake, worst mistake.

And I’m like, well, actually, 

Courtney: no, because I didn’t do it any other 

Dana: way. Like there was, there was, there literally was no money there. And so either we had these wooden windows or we had no windows. Yeah. I 

Jess: think that’s a great example. I think right and wrong is so touchy, you know, it’s just like, I use subjective.

Exactly. Even like I’ve been working with my like life coach on it, because I was telling you guys in the beginning, I have it, you know, if someone’s supposed to bring the balloons, they better be damn sure bringing the balloons. And I would get really, yeah, I would get really upset at people if they didn’t do things like the exact way that I would want them to do them.

And, it would, get in the way of my work because I’m like, oh, this person, you don’t bring the balloons. And, she helped me instead of being like, that’s wrong, it’s like, oh, that’s not the way I would do it, or that’s not my preference. And it helped me so much to be like, oh yeah, that’s just not my preference, but it’s not wrong. Cause then when you say something’s wrong, it like almost just like flips a switch in you that can be hard to flip back.

Dana: Well, that’s just true for relationships in general. I mean, partnerships,

Courtney: literally we’ve had hard conversations. Like I understand that you want things done this way, but like philosophically, we’re not meeting here and philosophically, this is how I would do things and this is how you would do things and it’s not right and it’s not wrong, but it is different and we’re going to have to operate,

Dana: it’s creating friction that we need to, that we need to get rid of. So the question is who, who needs to adapt in the way. And at times, sometimes it does feel like if you’re the one that has to do all the adapting, then you’re like, well, apparently my way was the wrong way, you know? And, but we, for the most, 

Jess: yeah. So like, how do y’all resolve the scenarios is it like just, 

Dana: Arm wrestle?

So there’s a lot of arguments. There’s there is some, there is some fights, but I think I’m a, I’m a processor. Like I feel things deeply. I always felt that way. It takes me a long time to get through the root of my emotions. I was telling Courtney the other day. I was like super emotional and we had a good friend that passed away last week and, 


So we’ve been dealing with that. My daughter like was running this all-county track me at the like in sixth grade that normally seventh, eighth graders do. So she was running and I, and she’s like running towards me and I’m like, like getting emotional. And I was like, am I about to start my period? Like, and I was like, and I, I didn’t know the root of my emotion and really, I, and I finally was like, you know what?

I’m just emotionally strung out. Like I’ve been dealing with this death, and we were talking about Memorial that day and, you know, and then I was also like insanely proud of my daughter. And so there’s this fear for me, a lot of times is saying, are my emotions valid and true? Or are they just me being irrational crazy? Cause you know, those are the voices inside your head that you’ve been told your whole life.

So for me, when I met at Courtney, I like to process it. Like, I need a moment, like I’m going to mad at you. I’m not going to be lovey-dovey and I’m not going to be like overly kind, but I’m not going to be like, I’m just going to be like, This. Like just very flat lined and Courtney feels it and she’s like, what’s wrong, what’s wrong, what’s wrong.

And I’m like, I’m not ready to tell you what’s wrong because I don’t, I don’t really actually know what’s wrong. I just know I’m annoyed and pissed off at you for some reason, and I don’t know if it’s valid, so you need to give me some time. So a lot of times what happens is she like bombards me and then it ends up in a big fight and then we get to the root of it and then it’s fine.

Yeah. But she’s been better. It’s been better about giving me my space and I’ll tell her. And then from my side, I’ll say, hey, I don’t want to talk about this right now, but let’s talk about tomorrow, whatever. 

Courtney: But also, I think saying, I think being clear about like, this is how I like to work. This is what I need. Or like, this is where I feel like my pain point is, or this is how I am seeing things right now. It may not be the truth, but this is how I’m interpreting it. Is that, is that the case? No, actually that’s not the case.

Dana: Like you taking some ownership that how you feel isn’t necessarily what’s actually happening.

Courtney: And I, I personally think that that’s super important because I think so many things are like up for interpretation. I think, especially when you’re in a partnership and probably even when you have like a CEO or a life or a relationship or whatnot. Think about what you know about that person. And even though you’re feeling this way, do you think that that’s their intention?

Like what do you know, do you ever think that my intentions are to hurt you or my intention to do XYZ or to make you feel this way? Is it my intention to burden you unnecessarily with all the company stuff? No, that’s not my intention. I’ve told Dana this before. I was like, so when you’re feeling like emotionally spun out about what’s going on with us, like get back to me, you and me, is that my intention at first, the answer is no. 

And then, but let’s talk about what it is that I’m doing. That’s making you feel that way. And then it can be, it can come from a much less personal space. Like, hey, I know you, and I know that this isn’t directed in a malicious way towards me, even though I feel that way.

But like, you can work from that point, but you can’t work from like, you know, you don’t care about our company or you don’t care about blah, blah, blah, or you’re right. Like all it’s kind of like irrational S talks is what I call it. 

Jess: Well, I was listening to this relationship. I think it was like a guy on Tik TOK or something last night. And he was saying try instead of saying to your partner, like, I feel like you burdened me with, you know, the business stuff and that’s my husband and I have the same, cause my husbands involved my business too. And he can like, literally it’ll be like 9:30 PM and we’re like in bed and he’ll be like, oh, we got to pay Q4 taxes tomorrow. Like goodnight. 

Why would you tell me that like, no, I’m going to be thinking about taxes and I’m just like, has such good compartmentalization to the point where he doesn’t realize when things will like spin me out. If you say, oh, I feel like you burdened me with tax stuff before we go to bed.

Instead of saying that, say what you would like to feel like, I would love to feel like at the end of the day, it’s like signed, sealed, delivered, and anything we need to talk about can like, wait till tomorrow. Or like, I would love to feel like you value me as like a, the business partner and it, because when you say like, I feel this, cause I, I would say that all the time, like I go, 

Dana: they tell you to say that. They always said use I feel statements. 

Jess: I know. And now it’s like, I would like to feel because it gives them. Oh, what are we aiming for? Not like, what do you feel? Because the way I feel on a moment can change on a dime without the circumstance changing. Just me changing. 

Dana: Yeah. That was like my husband, he hates I feel statements. I’ll say, and he’s like, I can’t help you then. Like, I can’t change how you feel. 

Jess: Well, it’s, it’s like saying, you know, oh, I feel cold in this room. It’s like, you know, that’s the way you feel, instead of saying like, oh, I would love to feel warmer in this room. It’s like, well then, okay. Now I know that we need to turn up the temperature. 

A little bit more actionable 

but I will say that hearing y’all talk, it’s like the things that make you guys different and probably the points of contention are also the things that make you operate so well. And so I used to think that like, oh, if I could just edit my husband to be exactly like me, then we’ll take over the world and I’m like, no, I need someone who is like totally, you know, quote unquote, emotionless around numbers. Like he can just be like, oh yeah, we lost money here. That’s fine. We can make money here.

Whereas. I would be, oh, my God, we lost money somewhere. Like, can you tell me, can we find it again? Yeah, exactly. And he can just be totally like, oh, like, no problem, whatever. I don’t want to change him to be like me in that need someone like that. Although it drives me crazy sometimes, you know? So it’s like the points of differences, again, it kind of goes back to that 70, 30. It’s like if there’s 30% of the time when we might hit friction. Yeah. That’s fine. If 70% of it is good, yeah. 

Dana: That’s probably, it’s pretty true. Yeah. I would say it’s about 70, 30, 70, 30. 


Courtney: mean, 30. We’re doing better than that. 

Dana: It could be, I don’t know. 

Courtney: My love that I felt like therapy, 

Jess: Jess.


Dana: Well, we like to ask this of everybody. it’s what we call their oh shit moments 

Courtney: and your whole journey, like thinking about all back, the whole thing, could be anything. Did you ever have that moment where you were like, oh shit, I’m in over my head. What am I doing? 

Jess: Oh my gosh, like five minutes ago. Okay, I would say that my, I actually have a chapter in my book, in Chasing the Bright Side called “she made it work” and it’s like 10 stories about just like random shit, but like she made it work. But the big oh, shit moment was when I was just getting started with headbands of hope and I needed a manufacturer for the headbands.

And found one in Kansas. And I had no idea like anything about manufacturing. Yeah, I ended up, you know, they sent me an invoice for like the first round of production. It was $10,000. This was money I did not have at the time. 

Cause you were in college 

In college. I was like, this is about $9,500 more than what I have in my bank account. And I was talking to my dad about like, I literally Googled, like, how do you get $10,000? And it was like, you can get a loan from a bank. You can get an investment, giveaway equity. My dad ended up being my first investor. He was like, this is a great idea. I’m going to be part of it, which was, you know, incredible.

And I recognize like the privilege that comes from to, wired them the $10,000 and never heard from them again. Oh my gosh. Yeah, yeah. probably a lot of tears after that. Oh my God. I still, what was that like 10 years ago, I still get like so wound up about it. When I say,

like, literally you never heard from them again?

Um, we went to court and we tried to get it back and it was like, at that point, the money was gone and we were spending more money in legal fees trying to get it back. And it was like one of those things where we just had to cut our losses and like move on. And it was really hot tar, like, it was just such a gut punch. but I would say, you know, it was one of those things. Like I hid in the closet for a long time where I was like, I don’t want anyone to know that I like messed up so bad. 

And then I started speaking one day. I just had a really tough day, told that story and I feel like that was a speech that made me a speaker because it was like telling the honest truth about how I got here and how those moments in our life, where we have those shit moment, it’s a reminder that we can quit too. Like you don’t have to do this, 

like you’re at a fork. 

Yeah, exactly. but I would say that sometimes I feel like we mess up in points in our life that at the time might feel big, but in the long run, it was actually a small mistake that prevented me from making it in a much bigger way in the future.

Now our purchase orders with suppliers are like six figures and I’ve learned about 30% deposits and like contracts and all these things of how we quality control. And I feel like if I had not made that mistake so many years ago, I would have definitely made it in a much bigger way down the road. And so it’s kind of like the windows it’s like it was the right choice at the time, even though at the time it felt like what the heck was I thinking right now?

But it definitely tests me as to how bad I wanted this and really kind of reassured, like dug my heels in the ground a bit of like, now I’m doing this, you know, so here we are. And eventually I paid my dad back. I was like, whew, I gave him $10,001. I was like, there was some interest.

Courtney: I remember that though. I remember like when, like a $2,000 mistake, would wreck us, literally I’m sure, I remember our very first wedding at the Bradford we weren’t ready, and we told this person we weren’t going to be ready, but they insisted on booking and we need the money. And so we booked them. We should’ve said no, and they stay. 

The brides people stayed in the house and we actually strung the lights, cause we didn’t have lights over our terrace, at that point, we’d have the landscaping in, like, we didn’t have walls in the bathroom stalls. Like we hung these like tarps and like rig this tarp thing to like, have it separate all the bathrooms.

And then everyone was fine. Like the night went fine. Caterers are fine. The dad was so happy, and then we get an email, like the next couple of days, 

Dana: they’re trying to pay the final balance, trying to pay the final balance. 

Courtney: And he wanted his room fees back. Like I think it might’ve been like $400, very nominal, because there was still dust covers on the smoke detectors, from the painting. And like had something happened, his people wouldn’t have been safe. Clearly you weren’t ready which we were not ready in many ways. And then there’s the most minor ways we were not ready. And I remember we were so upset.

We were so upset about not getting this $250. It was just seemed like the end of the world. We were so angry. And then I look back on that day and I’m like, that’s it?

Jess: Yeah. 

Courtney: We were clearly not ready. Can we have a redo of that wedding? Imagine what it looks like now?

Jess: I mean, I think that you train yourself to like take the stings and they become less and less as time goes on because it’s just like stuffs, shit’s going to happen.

It’s going to happen. 

Dana: But I think too, like really what developed from that is the ability to say we weren’t perfect because I think, I think there is a part of egotistical-ness about being an entrepreneur. Like you have to think highly of yourself. Like you have to think that you have the best product that you have the best, this whatnot.

And for us, like, we put so much of it into us and we were like, but we did all these things, like we did this for you, right? Like, but we couldn’t take a step back and recognize that there was a lot of truth in what was said, you know? And I think that was the first time we realized that, okay, like we’re not going to be perfect.

We’re going to make lots of mistakes and you have to get okay with saying, I’m sorry, saying, how can I fix this? What can I do to make this better? And sometimes that’s going to be a nominal cost. You know, and it’s okay to have that. Yeah. Yeah, totally. But I think it was a, it was a hard lesson, but it was one that I think helped us so much and dealing with.


Jess: you just file it away in your toolkit for how you test stuff moving forward. And that’s just like what it is. Yeah. 

Dana: Well, we wouldn’t love to end on two things. One, we want to know what the most rewarding part of your journey has been?

And then like, is there a moment that stands out to you? 

Jess: Oh, most rewarding part.

Dana: I mean, besides this obviously. 

Jess: You took the words out of my mouth, I would say, I mean, there’s countless like hospital visits that, you know, you walk away from it and you’re like, this is what I was meant to do, you know? But I would say like, you know, in right now what I’m feeling in Mic Drop Workshop, we have like a closed community that of students who are in the course and, you know, every day there’s someone that posts in there.

Like I just had my first speaking engagement at like United Way or, you know, and I just see that I’m like, wow, something that like, I built, helped someone do that. And so every time I see, I think I, in, for a while, I had a tough time, like in my twenties, like watching other women win, even though I was someone who believed that women should win.

Like I was, I was telling myself that it meant less about me, you know, like. And now I’m like, oh, it feels so cool to genuinely want women to win. And that’s just such a better way to walk through life. It’s just like, your success is not robbing me of my own, right. And there’s room for everyone at the top. 

Dana: Yeah, 

Courtney: Anything come down the pipeline, anything exciting for our listeners? 

Jess: Well, the, I guess I could say this I’m coming out with a children’s book. so that was just signed, but it’ll be in 2023, so excited and it’ll be something along the lines of helping kids create their ideas. so that’s, what’s in the pipeline. Yeah. 

Courtney: Yeah, that sounds 

Dana: amazing. Yeah. Well, I don’t think we had enough time today. I know. I 

Jess: know. Thank you so much for having me. This has been awesome. Really enjoyed it. Yeah. I think you guys keep up doing what you’re doing. It’s awesome to watch. Yeah. Thanks. 

Dana: To learn more about Jess and her story, visit or follow her on Instagram at jess_ekstrom. To learn more about her organization, visit headbands, a or follow along on Instagram at headbandsofhope.

And for those of you that are listening, just given you one free month of Bright Pages, her online journaling platform, you can go to and use the code gather. You can read more about Bright Pages and Jess’ other products in our show notes.

Courtney: And to learn more about our hustles visit,, and or follow us on Instagram at canddevents, at thebradfordnc, and at hustleandgather. If you liked the show, be sure to subscribe and leave us a rating and a review. This product is a production of Earfluence. I’m Courtney.

Dana: And I’m Dana.

Courtney: And we’ll talk with you next time on Hustle + Gather.

Full Episode Transcript

Chasing the Bright Side, by Jess Ekstrom
Bright Pages (use the code ‘gather’ for one month free)
Mic Drop Academy

Hustle and Gather is hosted by Courtney Hopper and Dana Kadwell, and is produced by Earfluence.  Courtney and Dana’s hustles include C&D Events, Hustle and Gather, and The Bradford Wedding Venue.

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