Jess Ekstrom on the One Small Thing That Can Help You Be More Optimistic
Optimism may seem like an increasingly rare concept in today's world, but that doesn't mean we shouldn't strive for it. In her debut book, Chasing the Bright Side, author, speaker, and entrepreneur Jess Ekstrom hopes to help people rediscover the power of positivity and apply it to all aspects of life.
Ekstrom credits optimism as a key factor in her own career path. As a young girl, she sent 100 writing submissions for a book (and finally got one accepted) and in college, she started her own company, Headbands of Hope, which donates one headband to a child with cancer for every item sold. Below, Ekstrom shares advice on how to believe in something better, how she once paid someone in Chipotle burritos, and why it's okay to fear failure.
Brit+ Co: In a world where the news seems to grow increasingly bleak, how do you keep up your sense of optimism?
Jess Ekstrom: When we walk through the world with a lens that we can make it better, then we’re practicing optimism.
Today, the news is tough. We’re constantly feeling like we’re being warped into this dark hole of negativity. But optimism is not about staying positive all the time or jumping to your happy place; it’s about seeing and absorbing the bad but still believing that the future is good. More importantly, believing that you will be one of the people that create the good.
I started my company, Headbands of Hope, out of my dorm room in college. I was interning at Make-A-Wish and I saw kids losing their hair to chemotherapy and being offered wigs and hats when a lot of them wanted to wear headbands. So I created Headbands of Hope: For every headband sold, one is donated to a child with cancer.
B+C: What is the best way to get back to childlike optimism as an adult?
JE: Something happens when we’re kids or early teens that rattles our childlike optimism. Something happens when we become aware of the watching world and stop raising our hand. For me, it was an experience I had my senior year of college when my family was involved in a very high profile scandal, which I describe in the book.
Snapping our fingers to bring back that childlike optimism is borderline impossible because we have more experiences to pull from and reasons to believe that maybe it’s not our turn. But one of the strategies I talk about in Chasing the Bright Side that we can practice is just throwing darts.
When we throw darts, we’re just aiming for the board, and if you’re like me, sometimes you miss the board entirely and have to cover up holes in the wall. But throwing darts is just about putting yourself out there time and time again without gripping the result of the bullseye.
In Chasing the Bright Side, I share a story of how, as a young girl, I submitted over 100 writing submissions to Chicken Soup for the Soul because I was obsessed with that book series. One day, I got a letter letting me know that my story was accepted into their teenage edition. Fast forward to now, Jack Canfield (the co-author of the series) endorsed my debut book!
I got published in Chicken Soup for the Soul not because I spent years writing one single poem that was perfect. I threw 100 darts and hoped one would stick. When we miss, we learn something and get better the next time we throw.
B+C: . Can you explain how you landed on the title of your book? Is the “bright side” a destination, or is it more about the journey?
JE: When we think of the bright side, we think of optimism or our “happy place.” But my book Chasing the Bright Side is not about reaching a destination of happy; it’s about using optimism as a strategy for better. It’s the journey.
Sometimes optimism can be hard, because you have to progressively think about things that haven’t even happened yet. You have to let yourself dream of a better “next.” But the threat of not being optimistic is stagnancy. We can’t move forward to a better tomorrow if we don’t believe and visualize what could be, and remain confident enough to actively march toward that vision.
The "Chasing" in front of the "Bright Side" insinuates that there will never be an arrival, which was a tough pill for me to swallow in the beginning. I wanted to cross the finish line of success and feel like I made it. But one of the best things we can do is find comfort and fulfillment in making things better not best.
B+C: What is one small thing everyone can do to have and maintain a more positive outlook?
JE: I firmly believe that comparison can be the thief of positivity and confidence. Especially today, it’s so easy to look on social media and feel like you’re not enough or feel unqualified. But someone’s perfectly curated photos are just heartbeats of a life and are not encompassing of the full picture.
But because of the social sharing age we live in, we focus on how things look. How will it look if I fail? What will others think? How will I seem if I post this?
So let me give you one piece of advice that I fall back on when I’m falling into the comparison trap: Success is not what it looks like to others, it’s what it feels like to you.
B+C: There is having optimism, but there’s also taking action based on that optimism. How do you encourage yourself and others to take that next step or leap of faith to move forward?
JE: When we take our minds down a journey of what could go right, we let optimism do its job. Because inspiration is the result of optimism. When we envision a better world, we’re inspired to create it.
Optimism starts with little sparks of an idea or vision, but it’s up to us to decide whether we’re going to follow through. And the follow through can be tough!
So a tip I give in the book is asking yourself this question: What feels light to you right now?
Don’t worry about creating the next Spotify or Airbnb, and don’t think that your next move has to be revolutionary. Just focus on doing the small things: Get your website domain, grab coffee with someone who’s walked the same path, doodle a business plan, create a logo on Canva.
When we assign immense pressure to the end result, we become paralyzed to take the first step. It’s like telling your kid their first day of gymnastics that they have to go to the Olympics. So instead, give yourself permission to do the small things (I built my website by paying someone in Chipotle burritos). The small things add up and completion of small tasks gives us the confidence to then go do bigger tasks.
B+C: How much do you think a sense of optimism is an innate characteristic vs. how much can it be taught/nurtured in someone?
JE: I believe optimism comes pretty natural to us as kids. Think about it, we had to have it when we learned to walk! But I believe it fades for everyone over the years and then it’s up to us to determine if we’re going to make an effort to get it back. That’s what I hope Chasing the Bright Side does for readers, whether you consider yourself an optimist and want to really tap into it, or if you feel you lost that balloon somewhere along the way, this book is here to help.
B+C: How has your company, Headbands of Hope, influenced the way your optimism and how you approach business (or life)?
JE: Headbands of Hope is the result of one flicker of optimism. I remember where I was when I got the idea... sitting in a Hibachi restaurant and I decided I was just going to do it.
I had zero business experience, but I did have a belief in something better. And when we believe our work is connected to something bigger than us, we will do whatever it takes to just figure it out.
So Headbands of Hope has taught me (and hopefully my story will teach you!) that success is not born out of skill, school, where we’re from, who we know, or what we scored on the SAT. None of us were born ready or knowing what to do. But we are born with something more important than skill. We’re born with optimism — the initial seed for success. Optimism fuels the belief that you can be the one to create the good the world needs.
My book was written to show a different success narrative: one where you don’t have to know what you’re doing to know that you can get there.
B+C: What was the biggest disruption/obstacle you’ve had to face and what have you learned from it?
JE: When I was first starting my company, I was working with this manufacturer and I needed money to start the first round of production ($10,000 to be exact). This was a problem because I had about $500 in my bank account at the time and still on the college Ramen Noodle diet at the time. I ended up taking a loan from my dad. Wired this factory the money... and I never heard from them again.
It took me a long time to finally start telling this story because I was ashamed. I thought my wounds were my worth. But overtime, I realized that failure is not the opposite of success, it’s just a part of it.
So in the book and in my speeches, I aim to be super transparent about all the mistakes I made and things that didn’t go right because those were the narratives I needed to hear but wasn’t hearing. I was seeing people “at the top” but not all the dips and dives it took to get there.
I used to think a clear path meant you were successful. Now I realize that a clear path isn’t success, it’s safety. Success is not about the absence of resistance, it’s just the navigation of it.
B+C: Should people fear failure?
JE: It’s actually okay to fear failure. In fact, it’s a necessity for survival. We should have a little fear if we go swimming with sharks or embark on a new adventure! So give yourself a little grace when you feel fear. But the real question is whether or not we let fear take the driver's seat, or if it’s just along for the ride.
One of my favorite analogies is that boiling water can soften a potato but harden an egg. So it’s not as much about the circumstance as it is about the subject. It’s okay to fail, it’s okay to feel fear, but no circumstance is more powerful than who we are as people.
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