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Hear the Leaders: Episode 2 – Jess Ekstrom – Spreading Hope and Optimism through Headbands

Hear the Leaders: Episode 2 – Jess Ekstrom – Spreading Hope and Optimism through Headbands

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By Shoshana Friedman

We are pleased to introduce Jess Ekstrom, our second guest in the Hear the Leaders series where we highlight business leaders who are driving positive change.

When she was only a junior in college, Jess started her own company Headbands of Hope. After volunteering with children undergoing chemotherapy, Jess was inspired to help these kids feel confident and beautiful during such a trying time. Similar to TOM’s business model, for each headband sold, one is donated to a child with an illness.

Headbands for Change has been a springboard for Ekstrom to develop another passion of hers – motivating women through public speaking. Tired of being the token female speaker at events, Jess developed the Mic Drop Workshop, a course to give women the tools and community to develop their own public speaking career.

Jess sat down with WalkMe’s Josh Klawansky to talk about entrepreneurship, female empowerment, and her new book Chasing the Bright Side, about optimism as a catalyst for change. 

Q & A

Josh:
When growing up, who influenced or inspired you?

Jess:
My dad is an entrepreneur, but growing up I never thought I was going to be one. But through him, I started thinking about the world through a lens of fixing. All these problems, all these things I wanted done differently weren’t someone else’s problem – they could be mine to solve.

Josh: 
What was your big break?

Jess:
It’s really the accumulation of all the small things.

Big breaks are just fancy words for all the small moments that got you to where you are.

And so I try to encourage people not to just look for the big break. I ask, what are the small things that you can do every day?

I think for me and for Headbands of Hope, a lot of our success – and this is probably the opposite of what you’ll hear about someone else’s story – was not about succinct strategy or this grand plan of how we were going to take over the world. But a lot of it was about throwing darts.

Aim high and throw stuff out there and see what sticks.

Josh:
How’s your vision for the organization changed over time with these incremental successes?

Jess:
I’ve never had a five-year plan. I’ve had visions of how I want to feel, rather than what I want to do.

I think to myself, how can I do things that accomplish that feeling? And one of the things that’s really changed over the past few years is this thought leadership space I entered into after I started Headbands of Hope. I started to get asked to speak at universities and colleges, and that was really when I uncovered this fire within me of using storytelling to create change.

Josh:
What were some of the biggest barriers you had to overcome as a woman which then inspired you to be an advocate for women in the workplace?

Jess:
I think one of the biggest barriers was one that I created myself. It was this belief that it’s not my turn, and this mindset that anyone who’s working with me is doing me a favor. I wasn’t taking myself seriously as a businesswoman.

So many people called Headbands of Hope a school project, and I just let them do that. I didn’t say no, this isn’t a school project, this is a business that I’m starting, and now it’s a multi-million dollar business. 

I felt like I was at the bottom of the totem pole because I think there’s a long line of history that has made women feel like that. It starts with us and how we choose to see ourselves.

Josh:
What would you say to young girls that want to follow in your footsteps and pursue their passions?

Jess:

I want young girls and people of all ages to realize that the best place to begin is where you are.

I truly believe that the people who do something, people that make it or become successful, it’s not because of their grand plans or their skills or background. It’s their rooted belief in what could be and their courage to just take the first step.

I want to qualify people for where they are at now, and not make them feel like they have to arrive somewhere else. Because I couldn’t even spell entrepreneur when I started Headbands of Hope, I’m living proof of that. 

To hear the full interview with Jess, listen here:

To learn more about Jess’s initiatives, please visit:
https://www.headbandsofhope.com/
https://jessekstrom.com/

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Shoshana Friedman
Shoshana's background in product and user experience gives her writing a focus on the human aspect of the business and technology landscapes. Her unique UX angle allows her to assess the digital era in a way that is both practical and insightful.