Building Confidence, Community & Possibility: Lessons from My Conversation with Jeremy Hahn

Where Purpose Meets Possibility
When you talk to someone like Jeremy Hahn, you quickly realise he’s not just teaching entrepreneurship, he’s teaching kids how to believe in possibility again. In our conversation, Jeremy shared stories that ranged from five-year-olds running lemonade empires to teenagers signing supply contracts with gas stations. But more than the impressive stats or wild success stories, what stood out most was his commitment to building confidence, community, and purpose in young people long before the “real world” ever tries to shrink their dreams.

For Jeremy, adventure isn’t just climbing mountains or taking big trips. It’s “capturing life,” staying awake to the spark, pushing against routine, and choosing curiosity over comfort. That’s the lens he brings to everything he builds: from turning abandoned schools into thriving community hubs, to helping kids create their own micro-businesses, to redefining what’s possible for families, neighbourhoods, and entire generations.

His work reminded me that adventure and purpose aren’t things you wait for. They’re things you cultivate, one brave step at a time.

Reimagining What Young People Are Capable Of

It’s common to hear adults talk about “preparing kids for the future,” but Jeremy’s approach flips the script, he prepares kids to create the future.

Through the Young Entrepreneurs Showcase and the new Young Entrepreneurs Academy, kids ages five to twenty-five learn the fundamentals of business through hands-on experience: building products, designing branding, practicing pitches, and selling directly to customers in community markets that feel like mini Shark Tanks.

But behind the business skills lies something deeper:
They’re learning they can do hard things, often much earlier than anyone expects.

One of Jeremy’s favourite stories (and mine) is about a girl who started with a simple lemonade stand at age five. Today, at seven, she’s producing nearly 90 gallons of lemonade a week, fully branded, fully confident, and fully lit up by her own sense of capability.

Then there’s the fifteen-year-old making six figures.
And another student licensing her basement for commercial food production.
And yet another who went from being too scared to speak in front of a panel… to confidently selling her products, negotiating deals, and calling business owners directly.

These aren’t just “cute kid stories.”
They’re proof that when the environment invites growth, young people step into it.

It’s easy to forget this as adults and even easier to underestimate ourselves.

Fear Is the Roadblock… Until It Isn’t

Every entrepreneur knows fear. Jeremy sees it every day, in adults and in kids.
But the way he coaches them through it is refreshingly simple:

Start small. Speak your idea out loud. Share it with someone safe. Let your confidence grow through action.

There’s no forcing, no pressure, no “sink or swim.”
Just intentional exposure, repetition, and support.

We also talked about adults sharing their dreams with the wrong people, those who unintentionally squash possibility because they can’t imagine that level of growth. Jeremy teaches his students (and now us) the same lesson:

Protect your dream.
Share it with people who want to help you build it, not bury it.

That’s why kids thrive in his program, they’re surrounded by peers, mentors, bankers, and business owners who all show up with one message:

“Your dream is welcome here.”

Imagine if more adults heard that.

The Power of Community: Entrepreneurship as Connection

One of the most striking parts of Jeremy’s work is its deeply community-oriented nature.
He doesn’t just develop young entrepreneurs; he develops entire ecosystems around them.

Local bankers attend sessions.
Business owners mentor the kids.
Families rally around the events.
Neighbourhoods revive.
Disconnected worlds collide for the better.

And often, the biggest transformation happens between the kids themselves.

In one touching example, a girl who said she had “no friends” because she felt different at school finally found her people, other young entrepreneurs who understood her passion, encouraged her ideas, and celebrated her wins.

It’s a reminder many adults need:

Entrepreneurship is not meant to be done alone.
If you want to grow, find (or create) the community that helps you rise.

Turning Old Spaces Into New Opportunity

Jeremy has a habit of turning forgotten buildings into vibrant hubs of possibility.

He’s transformed abandoned schools into maker spaces, commercial kitchens, after-school academies, coffee shops, restaurants, boutique hotels, and more. These aren’t vanity projects, they’re community engines, places where people learn skills, discover purpose, build confidence, and reconnect with what they’re capable of.

And it all started with one giant leap of faith.

Jeremy left a stable salaried job, kids at home, full responsibilities, no financial safety net, to step into the unknown with nothing but conviction and a vision.
What got him through it wasn’t certainty.
It was courage.

His boss, rather than shutting him down, became his first donor.

A reminder for all of us:
Sometimes the support you need only appears after you take the uncomfortable step.

Seeing Life Through a Different Lens

One of the most unique things Jeremy shared was his “death date” countdown timer—an idea that might sound dark at first, but is actually profoundly grounding.

He uses it not to fear the end, but to honour the time he has left.
To stay awake.
To stay intentional.
To stay connected to what matters.

That timer fuels his life plan: year-by-year visions, adventures, goals, and the kind of life he wants to build with, and for, his family.

It’s an approach rooted in a simple truth:

Life is short when you live it on autopilot.
Life is expansive when you choose it deliberately.

Helping Others Find Their Own Direction

Whether he's guiding kids through drawing their first business plan, coaching teens to pitch with confidence, or reminding adults to stop letting fear choke out possibility, Jeremy’s core message echoes something powerful:

You don’t have to know the whole path.
You just have to take the next step.

It’s not about grand gestures or perfectly mapped roadmaps.
It’s about everyday courage, curiosity, and willingness to try.

For anyone feeling stuck, overwhelmed, or unsure where to begin, this is the takeaway:

Start small.
Be consistent.
Let community hold you.
And don’t wait for permission to pursue the life you want.

A Few Questions to Reflect On

As you think about Jeremy’s story, consider:

• What “small step” have you been avoiding because you’re waiting to feel ready?

• Where could you invite more community, mentorship, or support into your journey?

• What dream feels “too big,” and how could you break it down into a first step that feels doable?

• And maybe the most important:
  What kind of life would you build if fear wasn’t steering the wheel?

Meet Jeremy Hahn

Jeremy Hahn is a community builder, entrepreneur, and storyteller with a passion for helping people turn big dreams into real-world impact. As Founder and President of Living Adventure and the Young Entrepreneurs Showcase, Jeremy equips young people and families with the tools, confidence, and opportunities to launch their own ventures and strengthen their communities.

With more than 40 years of experience in education and non-profit leadership, including serving as Executive Director for multiple organizations, Jeremy has led projects that revitalize neighbourhoods, create economic opportunity, and inspire the next generation of changemakers. He is also the author of Make Me Believe, a book about faith, perseverance, and finding the best possible way to live.

A father of five boys (three through adoption), Jeremy brings his love for adventure, storytelling, and hands-on learning into everything he does, whether it’s launching a new community initiative, mentoring young entrepreneurs, or heading out on a family fishing trip.

Connect with Jeremy:
https://www.linkedin.com/in/jeremyhahn1/
https://www.facebook.com/jeremy.hahn.9
https://www.instagram.com/jeremyhahn1/