The Society of Alternative Entrepreneurs

When Katherine climbed into a caravan instead of climbing the corporate ladder, she was staging a quiet rebellion against everything we've been conditioned to believe about success.

In this episode of Art is the New Wall Street, I sat down with the founder of The Society of Alternative Entrepreneurs, Katherine Pomfret who walked away from her global head of marketing position to pursue what the corporate world might otherwise call "impractical dreams": makership, creative writing, van-life, hospitality, and community building.

The Corporate Hamster Wheel

Remember when you were a kid and adults would ask what you wanted to be when you grew up? I bet none of us answered "exhausted, unfulfilled, and living for the weekend."

Yet here we are.

Katherine's story mirrors what so many of us feel in our bones. That gnawing sense that something fundamental is broken in how we've structured work and success. She entered marketing thinking it would be a practical way to apply her creative skills (I'm vigorously nodding over here), only to discover that corporate creativity is often just repackaging someone else's vision to sell more stuff people don't need.

Success meant bigger title, bigger paycheck, bigger burnout. Sound familiar?

Alternative Entrepreneurship

The Society of Alternative Entrepreneurship rejects the false binary that you must choose between financial stability and fulfilling work.

This isn't about glorifying poverty or embracing struggle as some badge of artistic honor. It's about recognizing that there are multiple paths to creating a life worth living, and most of them don't involve fluorescent lighting and performance reviews.

When Katherine talks about alternative entrepreneurialism, she talks about using your unique gifts and talents that align with your core values. It's entrepreneurship that serves life, not the other way around.

The Society itself functions as a community where members can uncover and develop their talents, share resources, and support each other in generating income outside of traditional employment structures. It's built on the radical idea that what brings us joy and ease, rather than what is externally validated and expected of us, should guide how we choose to spend our working lives.

Om Mani Padme Hum

Mantra in Tibetan Buddhism, meaning "Hail to the Jewel in the Lotus" representing the path to enlightenment through the union of wisdom and compassion.

The Illusion of Safety and Security

Katherine tells us that our perception of a corporate safety net is a bit of an illusion. With AI reshaping entire industries overnight and companies treating loyalty as a one-way street, the "safe" corporate job might be the riskiest bet of all. You're one reorganization, one market shift, one new technology away from becoming redundant. Choosing yourself, betting on yourself is bold and brave.

So the question isn't "Can you afford to take the risk?" but rather "Can you afford not to?" It takes a lot to make a shift. It's not overnight.

Instead of quick fixes or burnout-inducing hustle culture, Alternative Entrepreneurs respond sensitively to evolving needs and building something that lasts.

Reconnecting With Your Original Programming

One of the most powerful moments in our conversation came when Katherine described how she rediscovered her childhood passions, the things she loved before the world told her what she should love.

This isn't woo-woo stuff. It's about stripping away the conditioning and asking yourself what lights you up. For Katherine, that's things like:

• Walking in nature without an agenda

• Creating with her hands

• Building community spaces

• Embracing slow, intentional living

When you reconnect with what lights you up, you often find that your gifts can be viable paths to supporting yourself in ways that the corporate world never imagined possible.

Touching Grass

Katherine shared how integral reconnecting with nature has been to her journey. She lives in a caravan by a lake. During our conversation, she described what can happen when you just get outside and take a walk without your phone, without a podcast or music, without any agenda beyond being present. This practice of deliberately unplugging has become a cornerstone of Katherine's alternative entrepreneurial philosophy. The society was actually originally named Unplugged Ambition.

A Manifesto for Living Differently

The Society of Alternative Entrepreneurs challenges conventional definitions of success and work. Katherine has developed a manifesto that outlines principles like:

• Generating income from your unique gifts and talents without shame

• Building multiple income streams rather than relying on a single employer

• Valuing creative practice and time in nature

• Measuring success beyond financial metrics

• Consciously delivering benefit to all community members and the world at large

What makes this approach revolutionary is its rejection of the grow-at-all-costs mentality that dominates traditional entrepreneurship. Instead, Katherine advocates for businesses that serve both the creator and the community. We're talking sustainable movements built on authentic connection rather than exploitation.

Your Permission Slip to Bet On Yourself

If you've been waiting for a sign to make a change, consider this it. Katherine reminds us that the most meaningful transitions often begin with a simple acknowledgment: This isn't working anymore.

Whether you're contemplating a complete career overhaul or just seeking ways to bring more of your authentic self into your current work, the principles of alternative entrepreneurship offer a roadmap back home to yourself.

As we wrapped our conversation, Katherine emphasized that this journey isn't about having all the answers upfront. It's about taking one step, then another, toward a life that feels more aligned with who you truly are.

And isn't that what art has always been about? Showing us what's possible when we dare to imagine something different?

Until next time, keep creating, keep questioning, and remember: when the world keeps demanding productivity, your creativity, rest, and play is an act of rebellion.

Listen to the full episode with Katherine Pomfret on Spotify or Apple Podcasts. Learn more about the Society of Alternative Entrepreneurs and read their full manifesto. New episodes of Art is the New Wall Street drop monthly. Subscribe so you don't miss our next conversation about creativity, purpose, and redefining success on your own terms.