Chasing the Bright Side with Jess Ekstrom
I first met Jess Ekstrom, our final guest for the National Women’s Small Business Month entrepreneurial series, in a bathroom at a women’s conference in Kentucky. That’s where all great friendships begin, in the bathroom, right? Jess is the founder and CEO of Headbands of Hope, best-selling author of Chasing the Bright Side, creator of online courses and her newly launched guided journaling platform Bright Pages for self-discovery and growth. She is a light in this world, using her incredible talents to make this world a brighter place for all. Tune in to hear all the goodness this kick-ass entrepreneur has to share, you’re in for a treat!
In this episode, we’ll chat about:
Creating a business with social responsibility
Turning failure into growth & success
The power of optimism
DORM ROOM START-UP
Jess’s entrepreneurial journey started when she was in college. She was interning at the Make a Wish Foundation working with kids battling cancer. When they lost their hair due to chemo, they were often offered a wig or hat but she realized that they didn’t really care about covering up their head. They just wanted something to make them feel good, like a headband.
Inspired, she started looking up headbands for kids with cancer and couldn’t find anything. At an event at her school she heard Blake, the founder of TOMS shoes, talking about the one-for-one model he created with shoes that helped bake social responsibility into their business model.
It sparked an idea. What if she used the one-for-one model to sell headbands and for every headband sold, one would be donated to a child with cancer?
She describes it as the “smartest, dumbest moment” of her life because she wasn’t thinking about what could go wrong, only what could go right with her idea, a perspective that was a blessing but had its downsides too.
Headbands of Hope was born as a college dorm room startup. For every headband sold, they donate one to a child with an illness. Fast forward to today, they have donated over 1,000,000 headbands!
FROM HEADBANDS TO BOOK DEALS AND MORE
Jess came to realize that the story of starting this company in her dorm room to growing it to its incredible success of today, and all the messy ups and downs in the middle, was a really incredible product in itself. She began speaking on stages all across the country and landed a book deal with Harper Collins for her book Chasing the Bright Side.
After getting involved in speaking, she realized there weren’t a lot of other women doing it. In an effort to get more women on stage, she started the Mic Drop Workshop, an online course and community to help women book keynote speeches and book deals.
When the pandemic hit, she didn’t know which way was up or down. She went back to her roots and started writing again, searching for an online or hard copy journal that might work well for her. She was seeking something to help her journal about her ideas and what she wanted to do and create but came up short. The prompts that were out there were just daily prompts that didn’t really have any correlation with one other.
As the go-getter she is, she decided to start Bright Pages, a guided online journal for doers and creators. It provides users with different prompt pathways to direct them in a certain area from topics like podcasting and entrepreneurship to building self-confidence and navigating imposter syndrome, and so much more.
BEYOND THE HIGHLIGHT REEL
At the beginning of Headbands of Hope she was a bootstrapper, hiring college students to create a logo and getting pieces into place. She found a manufacturing company that she was planning to work with for her first round of production. When they sent over the invoice, it was a large sum of money that she didn’t have. Luckily, her dad was willing to be her first investor. She took the money, ran to the bank, and wired the money to the factory…. And she never heard from them again.
It was one of those moments when she thought it was a sign that she shouldn’t be doing this, that she wasn’t qualified to be a business owner. It took her a long time to openly share the story because she thought that it proved that she was “playing dress-up,” as if this was the thing that was going to finally out her as a fraud.
It wasn’t until she was speaking to a college class that she straight up told them exactly how it happened, the messy and hard parts. THAT was the speech that she felt finally made her a speaker, a big turning point for her. We don’t learn from people when they’re at their best, we learn when they’re at their worst. The way that we make an impact as a speaker isn’t making ourselves look good but sharing with the audience in an authentic way, which sometimes means sharing our most honest, painful moments.
TURNING FAILURE INTO GROWTH
I love Jess’s perspective looking back at her manufacturing mishap now. She said the hard moments are the opportunities for you to prove to yourself how badly you really want it. If you really didn’t want it, those moments would be your time to say that it just might not be right for you, which is totally okay too.
Sometimes the moments when we mess up in our life are actually what prevents us from messing up in a bigger way in the future. The lessons that we learn in the beginning from those mistakes can help us so much in the long run. Our brain wants to be so black and white, wanting to know if this was a right move or not. But really, it can be both. Yes, it could be a crappy situation, but there can be an upside to it as well.
Jess believes that some of these tough moments are what created the culture in herself and her team of being the kind of people that figure it out. Just this year, they had their first airing on HSN. They ordered custom headbands that needed to be in a warehouse by a certain time. Unfortunately, the delivery driver dropped them off at an Amazon delivery center instead, essentially a black hole for packages. As a team, everyone did everything they could to contact anyone connected to Amazon, sending countless messages and making calls. Miraculously, they ended up finding them! If the manufacturing mistake never happened early on, she’s not sure they would have had the “hustle muscle” to figure out this challenge too.
She always thought that as she got better as an entrepreneur that she’d mess up less and have fewer problems which hasn’t proven to be true. What she’s discovered is that as she keeps learning, the problems don’t become less but she learns how to handle them better. The aftermath sting and bounce back period becomes shorter. It’s not that the issues become more infrequent, but you become better at handling them.
We’re never going to have zero problems. We don’t make changes to have no problems, but to have new problems. Essentially, we get to choose our hard.
HANDLING FEEDBACK
When you are a speaker, writer, or just a human in general, you get a lot of feedback. Jess used to find herself getting extremely defensive when people would share feedback or criticism. The first round of edits for her book made her want to bury herself in a pile of blankets for two whole days.
Someone told her once to try to approach feedback as if you are two surgeons entering the room and there is a body on the table. This perspective completely removes ego from all of it, and all you’re focused on is saving the body (or business) on the table.
She’s applied that now to problems and challenges in her business. Instead of self-identifying with everything in her business, she’s learning to separate herself so that she can improve. If we’re too tightly wound in our identity with the things we create, we’ll never be far enough away from them to make them better. You are your own human outside of your business and what you create.
POWER OF OPTIMISM
Jess wrote an entire book about optimism but she admits that she is not a natural optimist, she’s a trained optimist.
As kids we are all optimists because we don’t have life experiences to pull from to make us think any differently. Then things happen in our life where we start to gather data that make us think that maybe things are harder than they’re supposed to be or maybe we aren’t actually destined for greatness.
For Jess, one of those moments was in high school when she found out that her uncle was the biggest financial fraud in history, dragging her family through a very public scandal where 11 years later they are still reaping the repercussions of. It burst her bubble about what she thought was good in the world and who she trusted.
When she was working at Make a Wish, she met a girl named Renee who wanted to meet Sleeping Beauty. Unfortunately she was too sick to go on her wish at Disney World. Jess remembers sitting in the office that day thinking to herself that this can’t be the story that they share about her.
She realized at that moment that while we have these experiences in our life that are out of our control, our stories or how we internalize and respond to our experiences are 100% in our control. Optimism isn’t about optimizing all your experiences, it’s trying to write a story by taking those experiences and asking what it could look like if it all worked out.
When we think of optimism, most of us imagine this blissful good, but often times when we need it the most is amidst the bad. Hard times give us a choice. They can be the excuse for why we do less or the reason for why we do more. Optimism is training that muscle that helps categorize those experiences into the reason we do more.
Because of Renee, Jess noticed that girls felt self-conscious when they lost their hair, which ultimately led her to start Headbands of Hope. She wrote Chasing the Bright Side because she realized that optimism wasn’t as much a mood as it was a strategy, and strategies can be learned.
THE MAGIC OF 70%
Not every moment of the day is going to be good, but that doesn't mean it’s going to be a bad day. Jess said she’s aiming for 70% good. She doesn’t need every day in her business to be perfect, she doesn’t need for her marriage to be perfect, or her house to be in perfect order. She just wants 70% of it to be good, and if 30% of it sucks she’s okay with that.
We can mess ourselves up in thinking that happiness and success means that we’re never going to do anything we don’t want to do again or that you agree with everything your partner says. If that’s your metric, you’ll always feel disappointed.
Passion doesn't have to be found but it can be learned. You can learn to be passionate about aspects of the job you have today. It doesn’t have to mean starting over.
The destination mindset is a myth. We might have big goals and dreams, but once we reach them we realize that we aren’t even stopping to smell the roses. Now for Jess her focus isn’t on being more successful, but feeling successful. She wants to FEEL the things that she’s done instead of constantly chasing more.
BECOMING A WRITER
Jess was obsessed with Chicken Soup for the Teenage Soul, submitting stories until she finally got published. She describes the feeling like a surfer catching their first wave. She loved the feeling of writing words and having people reading them and feeling differently.
She started with speaking first and the meeting planners would ask her if she had a book to sell. Her first book was self-published and called the Freshman Fabulous that she claims is awful. It wasn’t until a few years into her speaking career that she knew she wanted to get a traditional book deal. After a lot of rejections, she finally fine tuned the proposal and landed a deal with Harper Collins for Chasing the Bright Side.
She’s found that the book experience, the legacy, the ripple effect, and the intimacy is a little bit deeper than speaking. It’s such a gift to feel like your words will live on forever.
Once she landed her book deal and had a manuscript deadline, she was waking up and starting each morning with two hours of writing before checking her phone or looking at her inbox. For those 6 months, she was in the healthiest mindset that she ever had. She wasn’t getting overwhelmed, didn’t feel the internal drama, and was handling problems well but hadn’t connected the dots to writing yet.
After turning in the manuscript she didn’t have a reason to keep writing every morning and she noticed her anxiety coming back and felt cluttered in the morning. She then realized that the difference was she was no longer writing and so her hunt for journaling began.
When she would open a blank sheet of paper, she would find herself only writing about the things that were wrong. She wanted to be prompted to write about things she was interested in or wanted to focus on for the week, but didn’t find anything to help her do that.
So, for herself and others, she started Bright Pages, a platform for people to choose different journaling pathways to guide their writing with purpose. We are constantly consuming social media and hearing advice outside of us, but we have a lot more answers than we realize if we ask ourselves the right questions.
Her goal is to make journaling feel light, easy, and accessible, right at your fingertips with Bright Pages, soon to be rebranded as Prompted.
EXCITING NEWS: As a gift to our listeners, Jess is giving a one month free trial of Bright Pages when you use the code CLIMB!
FEELING VS. LOOKING SUCCESSFUL
A golden rule that Jess tries to live by no matter what she’s chasing or wanting to build, is asking herself - if no one knew it was me and I had to remove my name from it, would it still matter?
Distinguishing if she’s doing something based on how it looks versus how it feels has become extremely important to Jess to ground herself and be conscious about attention vs. true success and that you can have one without the other.
If you’re looking for a little encouragement to start off your week, join Jess’s Monday hype text! Text the word HYPE to 704-228-9495 to get some goodness in your inbox. You won’t be disappointed!
Try Bright Pages! Use code CLIMB for one month free.
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Buy Jess’s Book and shop Headbands of Hope.
Visit Jess’s Website.