My Unlikely Journey Towards Entrepreneurship

I Never Meant to Be an Entrepreneur

If you had asked sixth-grade me whether I would one day run not one but two businesses, I would have been caught between laughing at the absurdity of that idea and panicking in my little introvert heart. 

In my mind, “entrepreneur” meant selling fundraiser fruit door-to-door or awkwardly asking neighbors to buy coupon books for band trips. It meant pitching. It meant convincing. It meant being salesy. And I hated it.

I was shy. I blushed when I got called on in class. I associated entrepreneurship with a kind of boldness that didn’t feel like me. So somewhere along the way, I quietly decided: that’s not who I am.

And yet, here we are.

The Clues Were There Early

When I look back at my childhood now, I see a big sister who took her role seriously. I see a creative kid who loved drawing horses and reading Nancy Drew books. I see an avid journaler, someone who processed life through words and longs for deep conversations. I also see a girl who felt most alive outside, whether that was vacationing with my family or exploring made-up worlds in my backyard.

What I didn’t understand then is that entrepreneurship isn’t primarily about pitching products. It’s about paying attention to what brings you alive and building something around that aliveness.

The First Career That Taught Me More Than I Expected

After high school, I studied elementary education at the University of Northern Iowa. Teaching made sense for me. I loved explaining ideas clearly. I loved helping young humans understand something new and watching that lightbulb moment happen. There was something deeply life-giving about nurturing curiosity and creating engaging experiences.

But five years in, I found myself sitting on the floor of my classroom after school, exhausted in a way that felt heavier than “end of a long day” tired. It wasn’t the students. It was everything surrounding the actual teaching—the constant changes, the mounting expectations, the pressure that made me feel like a first-year teacher five years in a row. I was in my late twenties and already burned out.

For a long time, I tried to deny that reality. I switched schools. I told myself it was just a rough year. I reminded myself how important teaching is—because it is important. But eventually I had to face something harder: my students deserved a teacher who wasn’t running on fumes. And I deserved a life that didn’t feel like survival.

The Question That Changed Everything

Around that time, a close friend asked me a question that shifted everything. Instead of asking, “So what are you going to do next?” she asked, “What makes you feel most alive?”

It was such a simple question, but it cut through all the noise.

When I sat with it, the answers came quickly. I felt alive when I traveled and explored new places. I felt alive when I was creating—writing especially, which had quietly become my lifeline during those heavier teaching years. And I felt alive in deep, one-on-one conversations, the kind where you lose track of time because you’re talking about something that actually matters.

Instead of trying to architect a perfect five-year plan, I decided to experiment. What would it look like, even temporarily, to build a season of life around those three things?

The Eight-Month Experiment That Became a Turning Point

That decision led to about eight months of what I lovingly call my quarter-life crisis. Throughout 2016, I traveled along the West Coast. I house-sat, connecting with people who needed someone to watch their pets and water their plants while they were away for weeks at a time. I spent time in Australia on my own. I asked people to coffee. I followed curiosity instead of certainty.

To support myself, I dipped my toes into freelance writing. People often ask how you go from third-grade teacher to marketing, as if that’s an impossible leap. But the skills were more transferable than you might think. Teaching is, at its core, about taking complex ideas and making them accessible to people with short attention spans. Marketing is not so different. You’re clarifying a message, distilling what matters, and communicating it in a way that resonates.

One small freelance blog post turned into website copy. Website copy turned into branding projects. Branding projects turned into strategy work. Without ever formally deciding to “become an entrepreneur,” I found myself building something. Slowly and steadily, through referrals, coffee meetings, networking events, and a willingness to keep learning, that freelance experiment grew into what is now Illuminated Marketing.

Two Businesses, One Common Thread

Today, I lead two intertwined businesses.

Illuminated Marketing is a boutique agency partnering with nonprofits, service-based businesses, tribal organizations, and economic development initiatives—organizations that care deeply about their communities. We help them clarify their message and tell their story so their work can have a greater ripple effect.

Allie Jones Consulting grew from the same place, but it focuses more directly on leadership development. I help people lead themselves well through self-awareness, lead others well through healthy culture and communication, and lead the work well with clarity and strategy. Burnout shaped my story, and now I feel deeply committed to helping leaders build workplaces where burnout isn’t inevitable.

When I zoom out, what strikes me most is this: everything I do today traces back to the things that made me feel alive as a child. Creativity. Adventure. Deep conversation. I didn’t set out with a master plan to run two businesses. I set out to build a life aligned with joy and meaning. The businesses grew as a byproduct of that alignment.

What I Wish I’d Known About Entrepreneurship Sooner

When people think of entrepreneurship, the images are usually loud: Shark Tank pitches, venture capital, tech startups, “hustle culture,” and flashy success stories. That version of entrepreneurship exists, but it’s not the only version. If it’s the only story we tell, a lot of people will assume they’re not cut out for it—especially people who are naturally relational, service-oriented, creative, or quietly ambitious.

Here are a few things I wish someone had told me earlier.

• Entrepreneurship is bigger than startups and products.

  There is a whole world of service-based entrepreneurship that doesn’t get as much attention, but it is deeply real. Starting a business can look like offering a skill that solves a meaningful problem, building relationships, and doing excellent work consistently. It can look like consulting, coaching, design, writing, facilitation, therapy, trades, or any number of service paths. If you’ve ever felt drawn to helping people with a skill you have, that impulse may be closer to entrepreneurship than you realize.

  
  

• Your childhood joys are data, not distractions.

  The things that absorbed you as a child often point to your natural wiring. The projects you got lost in, the games you created, the stories you wrote, the things you loved organizing or building—those aren’t random. They’re clues. If you’re trying to figure out your career direction or explore business ideas, it’s worth asking what you used to do for fun before you learned to be “practical.”

  
  

• Work will always have hard parts, but it doesn’t have to feel soul-draining.

  I reject the belief that work is supposed to be miserable. Yes, every path comes with challenges. Elizabeth Gilbert calls them “shit sandwiches,” and her point is that every job includes something you don’t love—you just have to choose which hard parts you’re willing to live with. Teaching had beautiful moments for me, but the overall system left me depleted. The hard parts weren’t balanced by enough life-giving energy. In entrepreneurship, the hard parts are real, but they’re often in service of something you chose, and that changes everything.

  
  

• Look for arrows, not answers.

  When I left teaching, I wanted certainty. I wanted a perfect plan. What I got instead were small arrows pointing me towards the next right step. A thought-provoking conversation, a freelance project, a new connection. Those arrows added up. Most people don’t get a full map. They get a tug in the right direction. If you’re waiting until you feel 100% confident, you may stay stuck. But if you take one small step and pay attention to what it teaches you, you’ll gather the clarity you need.

  
  

• Try things in small, low-risk ways before you commit.

  One of the hidden gifts of the gig economy is that it lets you experiment. I could take one writing job, finish it, get paid, and learn something without signing my life away. That same approach can apply to all sorts of ideas: a one-off project, a small pilot offer, a short internship, a freelance contract, even volunteering in a space you’re curious about. Experiments give you data. Data builds confidence.

  
  

• Knowing your strengths (and weaknesses) is a business strategy.

  One of the most freeing lessons in entrepreneurship is realizing you don’t have to be good at everything. Knowing what you’re naturally good at helps you build around it. Knowing what drains you helps you plan for support. This is why I love tools like Working Genius, because they help you understand where you thrive in the process of work and where you’ll need partnership. Some of the best growth in my business came from collaborating with people whose strengths complement mine, whether that was an employee, a mentor, a peer, or a friend who could see my blind spots.

  
  

• The most sustainable businesses are rooted in alignment.

  There’s a quote by Frederick Buechner that says the place you’re called to is where your deep gladness and the world’s deep hunger meet. The most enduring work tends to come when your joy intersects with real need. For me, that intersection looks like helping people and communities move from surviving to thriving through clear communication, strong leadership, and stories that matter.

  
  

A Different Picture of What It Means to Be an Entrepreneur

It was several years into my business that I realized I was an entrepreneur. It just didn’t look like what younger me assumed it had to look like.

It looks like wayfinding. It looks like building relationships and learning as I go. It looks like creativity and strategy and helping people get clear. It looks like taking a risk that feels worth it because it’s connected to something meaningful.

If you’re in a season of trying to figure out what’s next, whether that’s starting a business, changing careers, or simply choosing a direction, my hope is that you’ll give yourself permission to loosen your grip on the “right” path and pay closer attention to the arrows.

Follow what makes you feel most alive. Try something small. Learn what it teaches you. Repeat.

That’s how it started for me. And honestly, that’s how it still works.