How to Develop an Entrepreneurial Mindset in Any Career

What separates people who act on ideas from those who stay stuck in overthinking?

In this episode of UMBC Mic'd Up, host Dennise Cardona, M.A. ’23, sits down with Shawn Wolf, D.S.L., graduate faculty member in UMBC's Entrepreneurship, Innovation, and Leadership program, to explore the entrepreneurial mindset and why it matters far beyond starting a business.

Shawn shares lessons from his own entrepreneurial journey, discusses the power of curiosity, explains why successful entrepreneurs view failure differently, and offers practical strategies for developing innovative thinking in any career.

Topics discussed include:

• The role of curiosity in entrepreneurship and innovation
• Why failure is a valuable source of learning
• Entrepreneurship vs. intrapreneurship
• Taking calculated risks and navigating uncertainty
• How innovation drives continuous improvement
• Practical habits that help people move from ideas to action
• Why entrepreneurial thinking is especially important during periods of technological change

Whether you're a business owner, a leader, or simply someone looking to solve problems more effectively, this conversation offers practical insights you can apply immediately.

Learn more about UMBC's Entrepreneurship, Innovation, and Leadership program. 

Transcript

Dennise Cardona  00:00:00  
Hey everyone, thanks for tuning in to this episode of UMBC Mic'd Up Podcast. I am Dennise Cardona, your host, and I am here with an instructor in the Graduate Program of Entrepreneurship, Innovation, and Leadership, and that is Shawn Wolf. Shawn, it is fabulous to have you here on the podcast.

Shawn Wolf  00:00:16  
Great to be here, and great to see you again, Dennise.

Dennise Cardona  00:00:19  
Yes, we recorded some sessions earlier in the month, and so it's great to see you too. It's.. I cannot wait to dig into this topic of entrepreneurship and all that that entails. Now, before we get started, can you tell us a little bit about your background and what first drew you to entrepreneurship and innovation.

Shawn Wolf  00:00:41  
Sure, shall I go back to eight year old Shawn? Yes, please. So I'm one of those weird kids that I grew up in a small town, northern central Pennsylvania, and my father was a school teacher, stayed home with us kids, and early on I realized that if I wanted money, I needed to make it myself, and so I had multiple jobs as a young kid. One of the first things I did, I recall, and my mom and I laugh about this still today. I want to say Good Housekeeping was the magazine that she had, and in the back of it I was a probably eight 910 at the oldest and I ordered this box of gift cards and greeting cards and I went door to door throughout the neighborhood selling gift cards so I would take the orders, and then come back, order, you know, Mom would do all the phone call to do the ordering, and and then she would try to drive me around to do my deliveries and collect the money. It was kind of a fun early thing. I was, I was the Fuller Brush man at 14, maybe 15, and our, in our community, and I did a number of things like that as a kid, just because I don't know something about that process of engaging a customer and watching this whole thing of commerce take place, of course. I didn't use that term back then, but I loved, I loved that, all of that. And so, over the years, I've attempted, I've started, and really failed at a bunch of things, a bunch of businesses, and I've started and been successful in a few. And so it's, it's been a lifelong journey for me. 

Dennise Cardona  00:02:43  
And both of those failings and successes teach you valuable lessons. Both of them do.

Shawn Wolf  00:02:48  
Yeah, yeah, for sure. And I suspect in teaching in the entrepreneurial program, this is one of the things that I chat with the customer, with the customers, with the students about, and that is, boy be don't be so sad about your failures, because they are indeed that a point of knowledge, a point of learning, and if you see it that way, it can be that way for you. Yeah, and I'm

Dennise Cardona  00:03:14  
guilty of being one of those people who used to be so fearful of that failure, I try everything to avoid it, and it was painful, because you know when you try to avoid pain, when you try to avoid pain or failure, in this case, it really does stunt, stunt your growth.

Shawn Wolf  00:03:30  
Yeah, yeah, and understandably, right, for most of us, if we start an entrepreneurial thing, it's public, and your friends, your family know that you failed, and so it just feels so, so challenging to the person, you know, that like I'm a failure, not it's a failure, and so the successful entrepreneurs make that transition, they understand that, ah, that was interesting, fascinating, that one didn't work, it didn't work that way, so now what?

Dennise Cardona  00:04:04  
Oh, I love that. It's kind of like putting on a curiosity hat instead of, like, you know, worrying so much and being so serious and rigid about what it is you're about to endeavor on. You instead look at it as a curiosity. Oh, at that, didn't work. That's interesting. Let me dig into that a little bit, yeah, yeah. Now, how would you describe an entrepreneurial mindset to someone who doesn't really think of themselves as an entrepreneur?

Shawn Wolf  00:04:34  
So, you already introduced one of the key words, and that is curiosity. An entrepreneur, in my mind, most entrepreneurs who are successful are very curious about, let's call it, pain points and/or friction points in the world, and they notice things, and they say, How could that be done better? How might I do something better there? The sense of curiosity is probably one of the. Guess one of the most important and valuable aspects of successful entrepreneurs is they're curious and they're willing to then go explore, exploring, experimenting, trying things, and failing at things. You know that that whole process, that cycle is where I see entrepreneurs who succeed, I do some entrepreneurial coaching along the way, and the ones who succeed the most are the ones who are willing to continue to push that envelope a little bit, try new things, and learn along the way, and they recognize that the customers will do what they do. You can't force them to do what you want them to do, and when you, when you're willing to just look at it that way, gives you a lot more of a space. So, the easiest, the best word around it is curiosity.

Dennise Cardona  00:05:59  
Yeah, and again, speaking of curiosity, I might argue, do you think that it's true that to maybe spark that curiosity for listeners who are like, well, how do I get curious about something that maybe it's really the quality of the question that you're asking yourself.

Shawn Wolf  00:06:16  
Yeah, there's been a lot written lately, last 10 years around the power of questions and our ability to think by asking questions, even thinking on our own, but asking questions in a particular industry that are outside of what the norm is a great way to do that. I remember my mentor in my grad work, Dr. Harold Howard. He was, he's, he's, he's passed since, but he was my mentor when I was at Eastern University, and he would, he forced me, required me to read way outside of my normal reading, and literally go buy magazines that were outside of my field and of my sense of interest, and this was what he was after, is that that sense of seeing the world through a different pair of eyes and having a sense of asking questions about how that might connect to that and how these things overlap and that was one of the most interesting things. Interesting parts of his mentorship of me was forcing me to think outside of my norm, and I think entrepreneurs, there's value in business people who start businesses to make sure they do that.

Dennise Cardona  00:07:41  
That's powerful, so So, Tony Robbins, you know, motivational person, somebody who's like, you know, just really great at what he does. I remember taking some of his courses, and one of the things that stuck out, that stood out to me was he said, ask yourself, when you're challenged by something, what's great about this problem, and that has helped me so much in my life. Just, what is great about this situation right now? Even if it doesn't feel great, you have to, your brain is going to go on a hunt, it's going to seek that answer and do whatever it can do to find an answer to that question. So, yeah, pointing it in that kind of direction, like what is great about this versus, oh my god, I failed.

Shawn Wolf  00:08:23  
So you're reminding me of so Ben Zander. He wrote a couple of books, I think The Art of Possibility was one of them, but I remember first seeing a video that he put out on leadership, and one of the things, very similarly, one of the things that he said is when something go doesn't go your way, pause and say how fascinating, and I love his intentionalities. You have to say it that way, how fascinating, because what it does is it pushes your mind into curiosity, and it allows you to think differently about this was my expected end result. This was the my expected outcome, and it went very differently. And if I say how fascinating with that kind of intentionality, it allows me to become curious. I think there's real value in that, and certainly, Tony Robbins has been a tremendous entrepreneur that we can all learn from, and his, his drive toward asking better questions. Love it,

Dennise Cardona  00:09:31  
Love it. Yeah, love it too. Do you think that entrepreneurial thinking is valuable, even for those people who never plan to start a business, and why?

Shawn Wolf  00:09:43  
Yeah, really good question, Dennise. I would say I ran a manufacturing company for about 16 years, and we practiced what we used to call lean manufacturing. Now it's simply called lean because we implement it in. Lots of different types of organizations, not just manufacturing. One of the core tenets of lean is Kaizen, or continuous improvement. And if we think about continuous improvement, we've got to be asking ourselves, where is the entrepreneurial spirit in that, which is what I believe is true. The entrepreneurial spirit says, How can we do that better? And continuous improvement is always asking. We've created this, let's call it a process. We've created this process. The process is working well. We're really happy about it. Immediately you start asking, How can we improve it? And I think that's the entrepreneurial part of the entrepreneurial spirit, so yeah, I think all people benefit from having a little bit of that entrepreneurial spirit that is always asking, how can it be better, how could we do it better, and what is my part in that. I think that allows everybody in every organization to make some of that entrepreneurial kind of spirit stay alive and be alive within organizations, we will often in the classroom here in our program talk about intrapreneurship, which of course is somebody in an organization that might not be the decision maker around big things, but they can innovate and be an entrepreneur inside. We call it intrapreneurship, really valuable to think that way. I believe,

Dennise Cardona  00:11:31  
Yeah, and it's such a wonderful thing to be able to.. it's such a gift, I would say, when you're part of an organization that actually encourages that type of innovation and intrapreneurship, entrepreneurship type of thought, it just brings out the best in people, and yeah, so it's I will say working for UMBC, I find that is so true, it just brings people to the table in a different mindset, and for those listeners who are in that kind of position where you can encourage that kind of process. It's just to me, it's advantageous. Yeah, for sure. Yeah, now some people seem comfortable taking risks and or navigating uncertainty, while others really do tend to struggle with it. Can you, can that mindset be developed over time to be able to take that risk and feel somewhat comfortable with it? 

Shawn Wolf  00:12:28  
For sure. The funny thing that I find in our program, as I talk to students about this whole thing, is that the world seems to think that entrepreneurs are just awesome risk takers, not true. In fact, I would - I would call most successful entrepreneurs educated risk takers, calculated risk takers. They are more comfortable with risk, mostly because they've tried and failed, and tried and failed. They're willing to take to do experiments, those kinds of things, so I think everybody can learn to be, to be a little bit more of a risk taker, but you have to be willing to start, and I've always encouraged our students, in particular, to start small, try, try some stuff, and when it fails, ask yourself, How did that feel? What does that feel like? And can I do more of that? Of course, over time you can. And so, yeah, the risk-taking thing, I think some people may be born with a little bit more of that willingness and capability, or maybe they, it was nurtured in their families a little bit more than some of us. But overall, it's a very learned, it's a learnable capability to take risks and learn from that risk. So, yeah, I think it's learnable.

Dennise Cardona  00:13:50  
Yeah, well, that's good news for those folks who shy away from it. How much of entrepreneurship is learned through experience versus formal education.

Shawn Wolf  00:14:03  
Well, we're here talking about an educational program, so I must say that there's great value in higher education around entrepreneurship, for sure. However, I do think there are some people that have a bent that way, as I mentioned earlier, either through their own natural personality or through nurturing in their family. What I've found in our program, as I teach entrepreneurship, is I'm opening eyes to things like how do you do experimentation, how do you try things from a calculated way, and then how do you think about the financial impact of the experiment? How do you think about the impact to your customers on these experiments and whatnot? So, I think the formal education opens people's eyes to ways. Of looking at how you run a business, in particular innovation. I just finished teaching the diffusion of innovation in our program, and when we look at innovation, way too many people think it's simply innovation around a product, when reality is it can be in a very innovation around systems, around processes, around how we deliver to our customers, how we charge our customer. There's so many ways that we can do innovation, and so that's what the formal educational process does, is we provide a whole way of thinking that's different than what the average person would land on, and so that's important part. Then there's also the natural tendency to try things, the natural competitiveness, that natural joy of succeeding in something, and how the energy is built along the way. So I think both are valuable, and yet there's no doubt that the formal education process drives and brings out some of that stuff that some people might have latent in them that just hasn't come out yet, so we provide some of that in the educational process.

Dennise Cardona  00:16:15  
Yeah, and you know, I know going through a program at UMBC myself, a graduate program, one of the greatest benefits of that is, as an entrepreneur, sometimes you feel like you're just an island on your own, right? You don't have, maybe you're not, you don't have those resources available, and you're trying to do it all on your own. And one of the things that I found in being part of a cohort, and being part, and having relationships, working relationships with my professors, and the mentorship that comes with it is like you just said, it's kind of like that professor or that mentor that challenged you to think beyond the scope of where you're comfortable, because I think when we're on our own, sometimes we tend to go towards comfort, at least I do, and it's those people who push you beyond that comfort zone, I think it's really where that growth comes from and the knowledge that you need in order to push forward and innovate. Yeah, for sure. Yeah, now in periods of economic uncertainty or rapid technical technological change, which of course we're experiencing as a society, why does entrepreneurial thinking become even more important

Shawn Wolf  00:17:20  
in uncertain times, we tend to shrink. Most of us, we tend to go, you know, come back to our base. We tend to hoard. We tend to, you know, kind of shrink our thinking. Entrepreneurship says nope, nope, not now. Let's do this. And when we open ourselves to how might we solve problems here, how might we address this issue in a creative way, in a way that is useful to society, useful to the marketplace. We haven't, we have much more of a, we have a much better opportunity to actually solve problems and be a part of it when we allow ourselves to think that way, and I think that's what entrepreneurship, classic entrepreneur, would naturally go, "huh, that's interesting, let's let's try this, as opposed to shrinking and closing in, which is the natural thing in uncertain times, and particularly when we're looking at right now the impact of technological change. An entrepreneur can say, Oh, how could I use that in my business? I noticed in the entrepreneurs that I work with closely, the ones who have embraced AI, they're the ones who are winning now, and I suspect will win in the future, because they've embraced the learning, the change, the growth, even if they're uncomfortable with tech, with that, some of the technology, they have figured out how to embrace it, so that they can provide new solutions for their customers, and really address societal issues with it. So, I think that's what entrepreneurship brings to this table of the times of uncertainty and the times of technological advances. Yeah, and

Dennise Cardona  00:19:21  
I would think that an entrepreneurial mindset is even more important because of those changes that we're experiencing. Yeah, for sure. Now, what habits or mindsets tend to separate people who act on ideas from people who stay stuck in overthinking?

Shawn Wolf  00:19:40  
Action is eloquence. I forget who said it, but is one of the, one of the great philosophers, I think, said action is eloquence. The entrepreneurial mindset points us to action, and it's very easy to treat failure. Or as permanent when reality is it's just a data point and there's there are times in our lives and our lives when we but I think it's valuable for us to recognize stuff's going to happen what do we do about it what does this mean to me now and how do I know I get beyond the struggles of today, and how do I stay curious, stay open, you know, all of those kinds of things.

Dennise Cardona  00:20:29  
Well, you know, this kind of brings me to like a closing question that would bridge to this, is if listeners wanted to know, like, hmm, I want to start developing a more entrepreneurial mindset today. What's a practical step that they could take, so that they could get in full, like inform their thinking, or create a new habit that will actually help them be become more entrepreneurial?

Shawn Wolf  00:20:59  
Two big things that I recommend for our students, one is, if you need to write it down, pick it up, take a write it out on post it, and carry it with you, and frequently throughout the day ask, How could that be done better? Now, here's, here's the challenge, you find it everywhere when you start looking for it, when, when in, as I mentioned earlier, about lean, one of the key tenets of lean is the elimination of waste, wasted steps, wasted processes, standing in line too long, you know, all of those kinds of things. So, when you start to see waste, you see it everywhere. Same thing with this, if you, if you have a question on a post-it that says, How could that be improved, and you then live your day, you see that everywhere. And so I think there's real value if you want to be an entrepreneur. Simply start with those kinds of questions. The second thing that I recommend for our students, and I think anybody who is really serious about considering how could I be an entrepreneur is then also have a journal at the end of the day write down the things you noticed, the spots where you said why has somebody not come up with a product to do that, why, why is it that when I go to this restaurant or this fast food place, I stand in line for 10 to 15 minutes every time, and this one seems to get it done like this. Why? What? And when we start asking those questions, and then at the end of the day, journal, we start to see things happen, we start to make connections, and as I mentioned earlier, my mentor challenged me to read outside of my norm, particularly magazines, magazine articles way outside of my, my norm. What I was, what he asked, what he was wanting me to do, and what I saw really valuable was I started to make connections that I would not have made. I'm not a mechanical person. I read Popular Mechanics for like six months. I found very interesting things the way mechanics were putting things together that I could do in the human side of things. I studied leadership for a long time, and so the human experience bringing things together very similar to some of the mechanical and so I think there's real value, be curious throughout your day, constantly looking for how might that be done better, and then take some notes, journal at the end of the day around what you're noticing over time, I think you'll start to create for yourself that entrepreneurial mindset that is always looking for how do we make things better.

Dennise Cardona  00:23:50  
Wow, thank you so much for sharing that. That's really great advice, and I'm going to actually take you up on that, because it's, yeah, that was very practical, very easy to implement into Wednesday, so thank you so much for that. Yeah, my pleasure. Yeah, thanks so much for sharing your insights with us today. It's been so valuable. I really liked this conversation. I have so many takeaways that I'm going to reflect on after this in a journal, so thank you for that. And really appreciate all of our listeners for tuning into this episode of UMBC Mic'd Up Podcast. If you would like to learn more about our offerings, click the link in the show notes. Thank you so much. Thank you.