Might success be as simple as being willing to start where you are and have the required optimism to believe that things can be better than they are currently?
According to author, speaker, and social entrepreneur Jess Ekstrom, it’s that simple.
In her recently released book Chasing The Bright Side, she shares practical steps and stories of vulnerability to help embrace optimism, activate your purpose, and write your own story.
However, this isn’t one of those sunshine-and-rainbows type of stories. For the first time, she shares what happened when her family got caught up in her Great Uncle Bernie Madoff’s Ponzi scheme. Then she encourages the reader to “chase the one life you’ve been given”.
In our conversation, we cover why optimism is so critical to your success, the difference between uncertainty and possibility, starting before you’re ready, a new paradigm for failure, becoming more resourceful without any more resources, and choosing your purpose.
Take a read:
Darrah Brustein: Why is optimism your core message?
Jess Ekstrom: I was really tired of the same success narrative: one day I had this idea, then I did it and the next day I was a millionaire. But really, success is not born out of skill, school, where we’re from, whom we know, or what we scored on the SAT. None of us was born ready or knowing what to do.
But we are born with something more important than skills. 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.
I want Chasing the Bright Side 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.
Brustein: You share a story you’d never before shared about your familial connection to Bernie Madoff and the impact that had on you and your family financially and emotionally. What has surprised you since you shared that story?
Ekstrom: I really battled whether or not I wanted to share it. But at the end of the day, one of the main takeaways of Chasing the Bright Side is that our experiences and stories are two completely different things.
Our experiences are tangible life events that we can’t control: the weather, our flight delay, the post office’s being closed right when we need it. But our stories are how we internalize and respond to our life experiences. So although we can’t always control our experiences, we can always write our story.
Being related to Bernie Madoff was such a pivotal experience in my life that wrote such a different story that I can now see over ten years later. I hope by sharing about something so vulnerable, it helps readers come to terms with some of their life experiences that have blindsided them.
Brustein: Please talk about the difference between uncertainty and possibility.
Ekstrom: Sometimes we scroll through our newsfeeds or read the paper and we see these crazy things happening all over the world. We file these things away in this part of our brain that says, “That won’t ever happen to me.”
Never would I have imagined the scenario which my family went through with Bernie in 2008, but it taught me that anything can happen. And this idea that anything can happen gives us a choice: we can live in fear of the unknown or excitement about possibility.
Anything can happen could mean the apocalypse could happen tomorrow, or it could also mean that you pick up a guitar for the first time and you go on tour with Coldplay in a year. Optimism is about taking this idea that anything can happen and leaning into the excitement of all the possibilities.
Brustein: We both have studied improv and have taken away a core competency of the ‘yes, and…’ framework for life. Please share about this and how it applies to what you teach.
Ekstrom: One of the golden rules of improv is a response called, “yes, and . . .”. When you’re improvising with someone in a scene, they could say something like: “Hey, Jess. Do you see that big mountain of spaghetti off in the distance?” Then you have to acknowledge their improvisation as the truth by saying “yes” and justify it with your own truth built on top of that, which is the “and . . .”: “Yes, Billy, I do see that mountain of spaghetti off in the distance, and we should go run through these pastures of risotto and cross the alfredo lake to get to it.” Then, your partner would “yes, and . . .” to what you just said to continue to build the story. But imagine if the scene went like this:
Partner: “Hey, Jess, do you see the mountain of spaghetti off in the distance?”
Me: “No.”
End scene.
Not exactly a story we’d tell at parties. When we say ‘yes’ to something, it moves us from one place to the next. It takes us to the mountain of spaghetti and lets us ride down it on a meatball. But when we say ‘no’, we stay in the exact same room we’re in right now. Saying ‘no’ keeps the door shut, but saying ‘yes’ leads to possibility—even when we don’t know what that possibility is.
Headbands of Hope began when I said‘yes’ to an internship at Disney World. I really didn’t have any thought or reason behind it, but I knew that more opportunities could happen to me if I said ‘yes’ rather than ‘no’.
Sometimes we have these internal checklists for things to which we say ‘yes’. Who will be there? What’s the risk? Do they serve free food? But sometimes we just have to focus on the possibilities if we go for it, instead of trying to check all these boxes.
When we say ‘yes’ to an idea, an opportunity, a new relationship, or even a new item on a menu that you can’t pronounce, we’re expanding our palette of experiences. And when we expand our palette of experiences, we have more opportunities for stories and growth. We can’t taste food we’ve never tried. We can’t shake the hand of someone we’ve never met.
Brustein: So many of the readers struggle with not feeling ____ enough (ready, smart, pretty, thin, rich, prepared, etc). Please share your thoughts on this, particularly as someone who started her first business from her dorm room.
Ekstrom: A really freeing revelation for me was that every expert was once a beginner. Teachers first had to be students. Anyone who runs first had to learn to walk. Everyone who’s ever solved a problem was once just pondering an idea. But everyone who’s done something great had to have a moment where they turned that idea into action.
So if everyone had to start somewhere, why not here? And if success isn’t about our skills or all of our expertise, then why not you? Everyone who’s ever done something great has always had to believe that he or she could be the one to do it.
Brustein: I love your point about how you see companies fail not because they lack resources, but because they are not resourceful. Please share more about this.
Ekstrom: I got my first logo by persuading a graphic design teacher to make my logo creation an assignment for her class. I made my first website by paying a computer design student in Chipotle burritos.
When I got the idea for Headbands of Hope, I didn’t have a lot of money or experience, but I looked at what I did have and started there. It’s so easy to look over the fence and think about what you don’t have that’s holding you back. Instead, focus that time and energy into being resourceful with the things that are right in front of you.
Brustein: I’m such a believer in the power of relationships, and you share about the power of in-person relationships, not just virtual (to the point that you’ll hop on a plane to connect). How have those benefited you, and what do you say to someone who is only connecting online and by phone with his or her network?
Ekstrom: I share stories about how I hopped on planes to meet with people who agreed to meet with me since I was “in the area.” If there’s one thing I take a gamble on, it’s meeting in person. Relationships move so much more quickly face-to-face, and it’s also so much more productive than a long email chain or even navigating phone or video conversations.
It might sound like more legwork to meet in person, but those in-person meetings were pivotal to the future of my company.
Brustein: Let’s talk about quitting and failure. There’s a lot of conversation that leads one to believe that ‘winners never quit’ or that failure is the thing to fear (or the opposite these days: fail fast to fail forward). What’s your take on quitting and failure?
Ekstrom: I had a massive failure in the beginning of Headbands of Hope. Let’s just say it had something to do with a loan from a family member and a fraudulent manufacturer. In the wake of this event, I seriously thought about quitting.
Most of what you read says something along the lines of “quitting is for losers”, which is usually printed on a poster of a lion chasing its prey or a snow-capped mountain with a guy hanging on with his pinkie. But that’s not my take on it. I don’t want to feel trapped in what I’m doing, because we always have choices. I want to work toward something I want to do rather than work toward something I feel as if I have to do. And if that feeling changes, I’ll pass the baton and do something else.
Telling yourself you can quit at any moment isn’t a reminder of weakness; it’s a reminder of choice. And when we choose to keep going, we’re choosing to recommit to our purpose.
Brustein: The courage to begin where one is can be the thing that makes all the difference. How do you encourage people just to start?
Ekstrom: One question: what feels light to you right now?
Don’t think about all the things you have to do and the long journey ahead, just break the seal and do something small today. Sometimes we can get so distracted and discouraged with trying to win the Super Bowl that we don’t focus on just getting the first down.
Start with what feels easiest and what you’re most excited to do. Maybe that’s sketching out your idea for how it would look. Maybe it’s doing a bit of research. Maybe it’s asking to meet with someone who’s walked a similar path.
Baby steps are still steps. When we don’t burden ourselves with the heaviness of a massive to-do list, it makes everything seem more manageable. And the baby steps add up. One day you’ll look back and all the small things you did will accumulate to something really big.
Brustein: Focusing on our success, our journey, and the timing of it can make a massive difference in our progress and trajectory. You talk about the downsides of things like comparing our chapter one to someone’s chapter seven or thinking that someone’s failure makes room for our success. Please expand on this.
Ekstrom: I’ve realized that most judgments about ourselves are in relation to someone else. Isn’t that crazy? Anytime I’m hard on myself, I can usually point it to feeling less than someone else, not because of my own personal standards. It’s a flaw I’m working on.
We can’t compare our chapter one to someone else’s chapter seven. What we see across from us on the subway, on Instagram, or parked in people’s driveways is not a good metric for how we’re doing . . . because we only see what people are willing to expose. We don’t see all the things they’re not willing to admit.
Someone else’s success does not make yours any less. Someone else’s failure does not make you any better. The only metric that matters is our own individuality.
Brustein: Please share about Give Gala as well as your suggestion to readers to do silent acts of giving.
Ekstrom: At Headbands of Hope we give a headband to a child with cancer for every headband we sell. It’s a small accessory that makes a huge difference in a child’s confidence.
Small acts of kindness are still super powerful, so we created an event that celebrates just that. Give Gala: The Worst Fundraiser Ever is a no-money fundraiser that raises acts of kindness for patients and families at local children’s hospitals.
However, when we hear about giving, it’s usually the Ellen DeGeneres–style giving that involves a massive check to charity or sending a kid to college who couldn’t afford it. Or funding a new jungle for endangered species to live in. And when we can’t give in a massive way, we sometimes feel that we can’t give at all.
When we focus on a mountain of trash, we don’t see the single piece sitting right in front of us that we could easily pick up and throw away. We’re too fixated on the impossible task of picking up all the trash instead of the small but very possible tasks that are right in front of us.
Optimism doesn’t mean you have to revolutionize the world. Optimism is about a perception of the world that influences positive behaviors: big or small.
Brustein: Please share about alignment versus attention, and the danger of chasing the notion that happiness is achieved ‘when’ something else transpires.
Ekstrom: I fell into this trap with my business where I was constantly chasing tangible achievements: awards, press, measurable goals. All of those are great and deserve to be celebrated, but we can’t treat them as our final destination.
Success is something that can’t be measured, it can only be felt. In other words, if you can quantify it, it’s not success. If what you’re chasing is only validated by the likes of others, then stop chasing it. But if what you’re chasing is something that is meaningful to you without the attention, then go for it at full speed.
Think about the last time you felt really good about something. For me, it’s my time spent in the hospitals interacting with patients.
When the likes go away and the applause falls silent, is what you’re doing right now still meaningful to you? If your next point of impact did not get a like, a retweet, a share, some followers, or a pat on the back, would you still go through with it simply because it mattered? Do you really think that one more award will make you feel fulfilled?
Brustein: Purpose is both a buzzword and hard for many to identify, however, you have a unique approach to it. Please share.
Ekstrom: I’ll give you an example of my definition of purpose. When I interned at Disney World, I met two other interns who were both custodians in the parks. One of them absolutely loathed her job and said she just picked up trash and it was dirty and she wanted to go home.
The other custodian who had the exact same job thought that he had the best job ever. He would greet guests as they walked into the park, he’d help them plan their day, he’d stop by the office and pick up Fast Passes and hand them out to kids, and he was helping keep the park clean so the guests could have a better experience.
These two people had the exact same assigned work: their contracts were the same, the list of tasks they are expected to do was both the same. The difference was one saw trash and the other created purpose.
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This article was originally published on Forbes.