Taking risk is natural for some, but in our experience most successful risk takers gradually developed their ability to leave comfort zones and take risk and we’ve asked them to share their experiences and advice below.
Tim Hotchkin
Risk taking is something that I am always working on improving. But I think it has all stemmed from my Dad. From a young age, he instilled in me this urgency to always give something a go. “Having a go” is also a very Australian value that you see taught to most kids growing up in Australia. So I got it from that but especially my Dad. He always encouraged me to try things, no matter if it was a small as tasting a food I don’t think I would like, or joining a sport team even though that sport was not my specialty. Read More>>
Derrick Ingram
I developed my ability to take risks through real-life experience—first as a Division 1 athlete, where high pressure and performance were part of daily life, and later as a young entrepreneur. Competing at that level taught me to trust my training, adapt quickly, and perform under uncertainty. That mindset carried over when I took my first major leap: opening my own shoe store before I even turned 22. Most people saw it as risky—I saw it as necessary growth. Read More>>
Jake Crist
I think I developed the ability to take risk when I was a very young child. I remember being very adventurous and always loved to take risks, big or small!
The bigger the risk, more of an award there is at the end when you succeed!
I’m a professional wrestler, so taking risk is just a thing I do every time I get in a ring, one wrong step or slam my career could be over. The hazards are very real and you never know what could happen. Read More>>
Joshua White
For me taking risk is the only option, no risk no reward. I feel if you want to change your circumstances you have to bet on yourself. When you bet on yourself you’re taking major risk. Understanding that no one is coming to save you and that the ball is in your court. That responsibility is yours to take imperfect action everyday. Always remind yourself that so many people are depending on you. Taking risks becomes easy. I think about my family and the generations to come, it’s way bigger than me and I understand that. Read More>>
David Allen
Risk is inherent when working for yourself. Each project is a calculation: will this benefit me financially, creatively, or both? If the answer is neither, and it doesn’t involve helping a friend, then the answer is usually no. Creative projects are the highest risk because they oftentimes don’t have the same financial backing as, say, a commercial or corporate project, and have the highest likelihood of something going wrong. Read More>>
Krysta
I developed my ability to overcome risk because I don’t just react — I prepare. I’ve been in high-stakes environments from the jump, whether it was launching cannabis businesses in new markets, working with investors, or hosting major events. I assess the situation, calculate the real variables, and trust my instincts backed by experience. Read More>>
Troy Gabrielson
Life is inherently risky, so I think taking risks is unavoidable. At the same time, when we’re scared of something we can be very adept at avoiding it. Some of the things that have been scary for me have evolved over time. As an early example, I found moving away to college when I was 18 to be very stressful; I was starting at a new school in a new state, where I didn’t know anyone. Read More>>
Kersten Davis & Ashley Boggs
Starting Pages of Glass LLC was definitely a risk for us, especially with the mindset that we wanted to take on such a big project within our first year of existing. However, we know how large the reader community is in northwest Ohio and felt we are perfectly situated between some big cities that house a lot of indie authors, creators and bookstores that we wanted to work with. Read More>>
