Entrepreneurship often starts long before someone launches a business. It begins with curiosity, a willingness to learn, and a desire to solve problems.
In this episode of UMBC Mic’d Up, host Dennise Cardona, M.A., ’23, speaks with Shawn Wolf, D.S.L., Graduate Faculty in UMBC’s Entrepreneurship, Innovation, and Leadership program. Together, they explore the entrepreneurial mindset, the role of curiosity in innovation, and practical ways anyone can develop entrepreneurial thinking.
The Early Experiences That Shaped an Entrepreneur
Dennise: What first drew you to entrepreneurship and innovation?
Shawn Wolf: Entrepreneurship started early for me. My father taught school, and I quickly realized that if I wanted spending money, I needed to earn it myself.
As a child, I sold greeting cards door-to-door throughout my neighborhood. Later, I became the local Fuller Brush salesperson. I enjoyed interacting with customers and watching commerce happen in real time.
Over the years, I started several businesses. Some succeeded, and others failed. Each experience taught valuable lessons. Entrepreneurship has truly been a lifelong journey.
Dennise: Both successes and failures teach valuable lessons.
Shawn: Absolutely. I often remind students that failure provides knowledge and learning. When you view it that way, failure becomes a valuable part of growth.
Why Failure Fuels Entrepreneurial Growth
Dennise: I used to fear failure and tried everything possible to avoid it. Looking back, that mindset limited my growth.
Shawn: Many people feel that way. Entrepreneurial efforts often happen publicly. Friends and family see the outcomes, which makes failure feel personal.
Successful entrepreneurs learn an important distinction. They stop saying, “I am a failure,” and instead say, “That approach failed.” They become curious about the result and ask what they can learn next.
Dennise: That sounds like putting on a curiosity hat instead of approaching everything with fear and rigidity.
Shawn: Exactly. Curiosity creates space for learning and improvement.
Why Curiosity Drives an Entrepreneurial Mindset
Dennise: How would you describe an entrepreneurial mindset to someone who does not consider themselves an entrepreneur?
Shawn: Curiosity sits at the center of entrepreneurship. Successful entrepreneurs notice pain points and friction points in the world. They constantly ask, “How could this work better?”
That curiosity leads to exploration, experimentation, and learning. The entrepreneurs who succeed continue pushing boundaries. They try new approaches and learn from outcomes.
The best word I can use to describe an entrepreneurial mindset is curiosity.
Asking Better Questions Sparks Innovation
Dennise: Do better questions help create curiosity?
Shawn: Absolutely. Researchers and thought leaders have written extensively about the power of questions. Questions help us think differently.
My graduate mentor challenged me to read far outside my normal interests. He encouraged me to explore magazines and subjects unrelated to my field. That process exposed me to new perspectives and unexpected connections.
Entrepreneurs benefit from doing the same thing. Looking beyond familiar spaces often sparks innovation.
Dennise: That reminds me of advice from Tony Robbins. He encourages people to ask, “What’s great about this problem?” That question forces your mind to search for possibilities.
Shawn: That connects well with leadership expert Ben Zander’s approach. When something does not go as planned, he suggests pausing and saying, “How fascinating.”
That simple phrase shifts your mindset from frustration to curiosity. It helps you explore possibilities instead of focusing on disappointment.
Entrepreneurial Thinking Beyond Business Ownership
Dennise: Is entrepreneurial thinking valuable for people who never plan to start a business?
Shawn: Without question.
I spent many years leading a manufacturing company where we practiced lean principles. One of the core concepts within lean is continuous improvement.
Continuous improvement asks a simple question: “How can we do this better?”
That question reflects the entrepreneurial spirit. It encourages people to improve processes, solve problems, and create better outcomes.
Everyone benefits from thinking this way.
We also discuss intrapreneurship in our program. Intrapreneurs innovate within existing organizations. They may not own the company, but they create positive change from within.
That mindset creates tremendous value.
Dennise: Organizations that encourage innovation and intrapreneurship often bring out the best in people.
Shawn: I completely agree.
Developing Confidence Through Calculated Risks
Dennise: Some people seem comfortable with risk while others struggle with uncertainty. Can people develop that mindset over time?
Shawn: Yes, they can.
Many people assume entrepreneurs love risk. In reality, successful entrepreneurs usually take calculated risks.
They become more comfortable with uncertainty because they experiment, learn, and adapt. They try things. Some efforts succeed, and others fail.
Everyone can become more comfortable with risk by starting small. Try something new. Observe the outcome. Reflect on how it felt.
Risk-taking is a learnable skill.
Entrepreneurship Education and Real-World Experience
Dennise: How much of entrepreneurship comes from experience versus formal education?
Shawn: Both matter.
Formal education provides frameworks, tools, and ways of thinking that many people never encounter otherwise.
For example, students learn how to experiment thoughtfully. They learn how to assess financial impact, evaluate customer needs, and approach innovation strategically.
Many people think innovation only applies to products. In reality, innovation can improve systems, processes, customer experiences, pricing models, and much more.
Education helps people see opportunities they might otherwise miss.
At the same time, experience teaches resilience, adaptability, and confidence. The strongest entrepreneurs often combine both.
Innovation Leadership During Uncertain Times
Dennise: Why does entrepreneurial thinking become even more important during periods of uncertainty and rapid technological change?
Shawn: During uncertain times, people often shrink their thinking. They become cautious and focus on protecting what they already have.
Entrepreneurs respond differently.
They ask, “How might we solve this problem?” They look for opportunities to create value and help others.
Technology provides a great example. Entrepreneurs who embrace new tools often discover innovative ways to serve customers.
I see this with artificial intelligence. Entrepreneurs who actively learn and experiment with AI position themselves for future success.
Entrepreneurship helps people remain open, adaptable, and solution-focused during change.
Moving From Overthinking to Action
Dennise: What separates people who act on ideas from people who remain stuck in overthinking?
Shawn: Action.
One of my favorite quotes is, “Action is eloquence.”
Entrepreneurs understand that setbacks provide information. They do not treat failures as permanent. In fact, they view them as data points.
They stay curious, keep learning, and continue moving forward.
Action creates momentum. Momentum creates learning. Learning creates growth.
Daily Habits That Build an Entrepreneurial Mindset
Dennise: What practical step can listeners take today to develop a stronger entrepreneurial mindset?
Shawn: I recommend two habits.
First, carry a simple question with you throughout the day: “How could this be done better?”
When you focus on that question, opportunities for improvement appear everywhere.
Second, keep a journal.
At the end of each day, write down what you noticed. Record problems, inefficiencies, and ideas. Ask yourself why certain systems work better than others.
Over time, patterns emerge. You begin making connections that previously went unnoticed.
My mentor encouraged me to read outside my normal interests for the same reason. Exposure to different ideas helps you discover new solutions.
Stay curious. Ask better questions. Pay attention to the world around you.
That is how entrepreneurial thinking grows.
Final Thoughts on Developing an Entrepreneurial Mindset
An entrepreneurial mindset extends far beyond starting a business. It begins with curiosity, grows through experimentation, and strengthens through continuous learning. Whether you work within an organization, lead a team, or pursue your own venture, entrepreneurial thinking helps you identify opportunities, solve problems, and adapt to change.
As Shawn Wolf explains, the key often lies in asking better questions and remaining open to new possibilities. Small daily habits, such as journaling observations and looking for ways to improve systems, can transform how you approach challenges and opportunities.
Interested in learning more about UMBC’s Entrepreneurship, Innovation, and Leadership program? Explore the program and discover how entrepreneurial thinking can help you create meaningful impact in your career and community.