How Entrepreneurially Thinking Leads to Eliminating Business Boundaries

“Think like an entrepreneur!” they say. And we try our hardest to do exactly that. But how does an entrepreneur really think? Every single business, startup, enterprise, and non-profit is unique. Surely there is more than one way to be entrepreneurial? There is. In fact, the more time I spend with business owners from a variety of industries, backgrounds, and experiences, the more I realize that entrepreneurially thinking is less about doing things a specific way and more about pushing past the boundaries of business, life, and self.

It was this process of stepping outside my own comfort zone that led me to embark on the journey of Entrepreneurially Thinking, the podcast I host with the great Dr. Cheryl Watkins-Moore. We have the privilege of speaking weekly with entrepreneurs who are challenging the status quo in business both in St. Louis and across the country. 

But every person we interview has had to walk the tightrope of eliminating the boundaries that bind them, whether boundaries of race, gender, industry, or self-confidence. What does it really mean to think like an entrepreneur? Here are just a few of the many things I’ve learned from my own process with Entrepreneurially Thinking.  

Manage Risk

When it comes to being an entrepreneur, taking risks is one of the most common things we discuss. There is a reason for that. While risk looks different for everyone, choosing to build something that has never been built before is risky. That’s why I subscribe to the belief that entrepreneurs are talented at managing risk portfolios, a concept Adam Grant explains in his book Originals. While choosing to take a risk in one area of their lives successful entrepreneurs tend to play it safe in other ways.

In one of our most recent Entrepreneurially Thinking episodes, Cheryl and I spoke with Sucheta Bhide, the owner of the Resplendent Crow, a vintage furniture business in University City, Missouri. Sucheta shared her perspective on risk when defining entrepreneurial thinking by saying, “You have one life to live. Chase your dreams, and if it doesn’t work out, you can always do something else.” 

However, how Sucheta chased her dreams is the epitome of a risk management approach to entrepreneurship. She worked full-time running a cleaning business while pursuing her furniture restoration gig on the side. As the furniture business grew, she carefully chose her moment to take the leap. This is not unlike acclaimed director Ava DuVernay who made her first three films while working full time as a publicist. In essence, successful entrepreneurs find ways to de-risk their ventures rather than throwing caution to the wind. 

By managing which risks we take and when, we decrease the likelihood that our venture will fail, increase the chance for long-term sustainability, and increase our hireability if/when we should we ever wish to go back to working for someone else. Who wouldn’t want to work with someone who can think outside the box, take on the challenges of running a business, and navigate the daily risks of entrepreneurship? 

Overcome Self-Doubt

If you’re like me, you likely struggle with self-doubt, at least occasionally. When it comes to taking on new ideas, new clients, or simply the more overwhelming tasks of your business you wonder, am I up to this challenge? I know I do. 

I discuss this briefly in my post about how Entrepreneurially Thinking got started. When Cheryl and I were approached with the idea of doing a podcast, I felt myself being pushed way beyond my comfort zone. I wondered, will my skills really translate? Do I really have something to offer in this space?

When I’m at my best in these moments of self-doubt, I tell myself and others to look for evidence of past successes,  tangible examples of their capability, competence, and resourcefulness. That evidence is far more reliable and indicative of future results than any story of doubt you can tell yourself. 

When we started the podcast, Cheryl and I had been working together already. We had evidence of our individual abilities as well as our dynamic as a team—and our combined passion to advance racial and gender equity in the world of business and entrepreneurship. While self-doubt could have easily sideswiped us and derailed the project before it began, we told ourselves a different story—the story of past successes, future goals, and evidence-based inspiration. 

As the initial fear of stepping out into the unknown wore off, and the podcast took flight, I realized that by overcoming self-doubt, I had reset the boundaries of what I once considered comfortable, safe, and “me.”  

Be Authentic

One thing every one of our interviewees has in common—which is also one of the things that makes them unique—is their willingness to be authentic. Authenticity goes beyond how we present ourselves to those around us, it is also the inner working of being true to ourselves. 

By choosing to be authentic, we are choosing to admit who we are, what we want to accomplish, and how we plan to get there. It is this honesty with ourselves that allows us to be honest with our clients and build trust with those we serve. 

This is what entrepreneurially thinking means to internationally renowned artist Cbabi Bayoc. Even before he knew that his pursuit as an independent artist was, in fact, a deep dive into entrepreneurship, his overarching value was to authentically share himself with the world in every piece he created. 

Cbabi’s approach opened up a world of opportunity to him, from an album cover for Prince to children’s books and even community and school murals that in turn encourage students to explore their own dreams. Authenticity drove him to completely crash through the boundaries that confine the world of art and business, especially art that, like his, is bold, powerful, and challenges the systems of race, fatherhood, inequality. 

What Boundaries Can You Eliminate With Entrepreneurially Thinking? 

Entrepreneurially thinking looks different for everyone we interview on the podcast. While there are threads of commonalities—like managing risk, overcoming doubt, and being authentic—what that looks like in practice changes from entrepreneur to entrepreneur. And so it is for you, as well. 

What does entrepreneurially thinking mean for you? And what boundaries in business, life, and self-awareness do you want to overcome? Wherever you are on your journey of business, consider the ways you can challenge yourself and your growth as an entrepreneur to think differently, push through barriers, and accomplish something new. 

And check out our podcast! We share weekly encouraging stories and interviews with business owners and entrepreneurs just like you.