Making It Without Losing It: Wisdom for Speakers & Entrepreneurs with Jess Ekstrom

On this episode of Adventures in Business, Amani and Mandi sit down with Jess Ekstrom, founder of Headbands of Hope and Mic Drop Workshop, Forbes Top Rated speaker, and best-selling author of Making It Without Losing It. This is a refreshingly encouraging episode about success, ambition, and redefining “making it.” Read on to learn Jess’s story of successfully founding two businesses, how entrepreneurs can break out of analysis paralysis and take action, and what will actually grow your speaking business. 

Meet Jess Ekstrom

Jess is the Founder of Headbands of Hope and Mic Drop Workshop, and a Forbes Top Rated Speaker. Her motivational, edge-of-your-seat storytelling and infectious energy is a refreshing experience for audiences looking to improve their culture, purpose-building, and fulfillment.

Jess Ekstrom’s Early Entrepreneurial Spirit

At just 12 years old, Jess Ekstrom was already experimenting with business – selling toys online, learning customer service the hard way, and even taking a loss when shipping costs wiped out her profits.

Her idea for Headbands of Hope didn’t come from a lightning bolt moment – it came from frustration. While interning at Make-A-Wish, Jess realized that kids losing their hair to chemotherapy were given wigs or hats… but not headbands.

So she asked a question most people wouldn’t act on: “Why doesn’t this exist?” And instead of waiting for someone else to solve it, she built it.

Turning Storytelling Into a Business

Before she ever became a professional speaker, Jess was just trying to get the word out. She started by asking college professors for five minutes before class to share her story (with headbands literally tucked inside her blazer).

Eventually, she realized that people didn’t just want her story; they wanted what they could learn from it. When she moved from telling to teaching, her speaking became a scalable business… and ultimately led to the founding of her company, Mic Drop Workshop, where she now helps other women find their voice and step onto the stage.

Redefining “Making It”

With the upcoming release of her new book, Making It Without Losing It, we had to ask Jess: What does making it actually look like? 

Jess challenges the idea that “making it” is a fixed destination. For her, what felt like success 10 years ago looks different today. At one point, Jess thought “making it” meant having a Netflix show. Now? She wants flexibility, time, and a life that actually feels good.

The Ambition Trap

Jess Ekstrom drops this truth bomb: Ambition can make you feel like you’re always behind. Like there’s always another goal: a bigger business, a better title, a new milestone.

Jess calls this the “ambition gap” – the space between where you are and where you want to be. And if you’re not careful, that gap can steal your joy. Her challenge to listeners is to stay ambitious – but don’t let ambition convince you you’re not enough.

Why People Don’t Take Action

Why do so many people learn… but never actually do? Jess doesn’t sugarcoat it. The biggest misconception is that they should take action once they feel confident. But the truth is that confidence comes after action. 

That means waiting until you feel “ready” is basically a guaranteed way to stay stuck.

It also gives way to analysis paralysis – learning all the things and avoiding action due to perfectionism or not feeling “ready.” Jess has worked with hundreds of thousands of women through Mic Drop Workshop, and she’s seen the pattern over and over again.

So instead of trying to create perfection, focus on creating the “first version.” Jess also offers another practical tip: commit publicly (like booking a talk), do the prep work, and use that deadline to create accountability for action. 

For Speakers: What Actually Grows Your Business

Jess also drops some real talk for anyone building a speaking business.

1. Stop selling topics and start selling outcomes

Nobody hires “a leadership speaker.” They hire someone who creates a result. Figure out the practical takeaways your talks will offer, and sell yourself on those. 

2. Master one talk instead of reinventing the wheel

You don’t need 10 different talks. You need one really good one that works. 

3. Other speakers are not your competition

They’re your referral network. When one speaker gets booked, they can’t come back next year. So who do they recommend? The people in their circle.

What Makes Mic Drop Workshop Different

With so many “become a speaker” programs out there… what actually makes Mic Drop Workshop different?

Jess broke it down:

• It’s built specifically to get more women on paid stages

• It blends storytelling and real business strategy

• It focuses on turning personal experiences into audience value

• It’s deeply community-driven (referrals, connections, opportunities)

But one of the biggest differentiators? The person teaching it is still actively doing it.

Resources Mentioned

🔗 Pre-order Making It Without Losing It and get your free Success Fingerprint

🔗 Learn more about Mic Drop Workshop

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