Breaking free from the metaphorical boxes that confine us is a universal struggle – one that bestselling author and successful real estate entrepreneur Betsy Pepine knows intimately. In a recent conversation, she shared her journey of discovering and dismantling these confining structures in her own life and business, offering profound insights for entrepreneurs facing similar challenges.

I’ve got two dogs sitting beside me. They never, ever wonder if they’re going to fail at something. You know they’re going to go chase a squirrel today. They’re not worried about if they’re going to fail or not. They don’t have that. This is all human based.

Betsy’s journey began with an uncomfortable realization: despite her outward success as a business owner with thriving companies and a wonderful family, she felt deeply discontent. This admission didn’t come easily. “I didn’t feel like I had the right to be unhappy,” she explained, acknowledging her privileged position compared to many others in the world. This internal conflict – the gap between external success and internal fulfilment – is something many entrepreneurs quietly struggle with behind their carefully curated professional personas.

Through extensive self-exploration involving journaling, meditation, yoga, therapy, and various healing modalities, Betsy identified a pattern: she felt confined by expectations – from family, society, industry norms, religion, gender roles, and even her own internal standards. She brilliantly compared this feeling to an Amazon mattress delivered in a seemingly impossible box: “I felt like I was that mattress in that box, yet to be opened, and just not being able to be and live my true potential.” This powerful metaphor captures what countless business owners experience – compression of their authentic selves to fit prescribed roles and expectations.

The real estate industry, like many others, operates within rigid boxes of traditional thinking. Betsy demonstrated entrepreneurial innovation by creating salaried agent positions in an industry dominated by commission-based models. This unconventional approach solved a significant problem – allowing talented individuals who couldn’t weather the commission rollercoaster to enter and succeed in real estate. “It’s pretty unheard of in our industry,” she noted, explaining how this shift created valuable options for agents at different career stages.

For business owners struggling to break free from confining boxes, Betsy identified three primary fears that keep us trapped: fear of failure, fear of change, and fear of loss. Her approach to dismantling these fears offers practical wisdom. On failure, she observes that it’s a human construct – “Dogs never, ever wonder if they’re going to fail at something. They’re going to go chase a squirrel today. They’re not worried about if they’re going to fail or not.” This perspective liberates us to see supposed failures simply as pivot points and learning opportunities.

To overcome resistance to change, Betsy intentionally builds her “discomfort muscle” daily. She maintains a habit tracker that includes exposing herself to something new or uncomfortable each day – even something as simple as taking a cold shower. This practice of intentional discomfort prepares her to handle bigger changes with greater resilience. For entrepreneurs, cultivating this ability to embrace discomfort is essential for innovation and growth.

Finally, she acknowledges the legitimate fear of loss – whether of status, social connection, or financial security. Her practical approach includes setting aside ego concerns, understanding that relationships naturally evolve (and some necessarily end), and recognizing that today’s gig economy offers more flexibility for career transitions than ever before. These insights provide a roadmap for entrepreneurs feeling trapped in roles or business models that no longer serve their authentic vision.

Breaking out of boxes requires first recognizing that you’re in one. “You can’t get out of a box you’re not aware that you’re in,” Betsy wisely noted. This awareness, coupled with intentional strategies to address our underlying fears, creates the path toward authentic entrepreneurship and leadership – where both business success and personal fulfilment become possible.

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