In our experience, most folks, including ourselves don’t have enough of an understanding of risk and the role it plays in our lives and careers and so we have made a concerted effort as a team to have conversations about risk with our interviewees. We’ve shared some highlights below.

Dara Green | CEO, Founder Seaside Staffing Company

My entire life’s journey has been all about risk taking, ever since I was a kid. I think it is just part of my DNA! I would not have had the opportunities that I have had, especially the ones that have pushed me and challenged me in my growth, in business and as an individual. If you jump, there is always a 50/50 chance of landing on your feet, but you have to be willing to jump… Read more>>

Jennifer Barnes | CEO & Accountant

Personally, I think people are born with a certain risk tolerance that can only be slightly modified. I have always been a risk taker. I take chances that others probably wouldn’t. On a DISC scale, my C which is your risk tolerance was a 14 out of 100 about five years ago but recently it went down even more to a 7 out of 100. That is exceptionally low for someone in the field of accounting and HR! I can share some stories about the risks I have taken and the payoffs that ensued. I’ve now started two companies at 41 years of age and both of them required me to take some substantial risk. The good thing is that both ventures turned out enormously successful and I am blessed to own 100% of company #2! Read more>>

Samantha Harris | Business Mentor & Marketing Strategist

Risk was the foundation on which I built this business, so I fully expect that during any season of growth, I’ll need to consider risk in order to level-up. When I started my agency, I left my only guaranteed income, on literally a hope and a prayer. It worked out & I was able to replace my income from my full-time job within a week of being in business. I took that as a major sign that I was following the right path. When it was time to open my membership community, I really wasn’t sure how it was going to work out. But I took the risk the night before launch to completely switch to the most robust platform for hosting memberships that was available. If I was going to do it, I was going to do it ALL the way. That risk paid off too, and we were able to scale to 100 members in our first 5 months! Read more>>

Margit Whitlock AIA | Principal and Creative Director

Every entrepreneur is a risk taker. We invasion and process differently then those that do not chose to take on the challenge of owning your own business. In owning your own business, you ware all the hats! marketing, development, HR, client and project management to produce a viable set of contract documents. Architecture and Design excellence are the ultimate goal both without a strong staff culture and financial management to foster growth there is no true business success. The risk is worth the effort to me and has been a driving factor in the last 28 years of creating a strong business. Read more>>

Joshua Dunn | Interior design, Choreographer and Writer

Life without risk is life not fully lived. I believe that my relationship to risk can be summed up in one word…. balance. within my early years I felt like risk had to be the main ingredient for all new discoveries, opportunities and goals. I was wrong! Risk comes from wisdom and genuine achievement. once I accepted this reality, my relationship to it shifted drastically. I started to way the pros and cons of the risk presented. In my experience genuine risk is not something we add but something we find and not all risk is worth it. However, the risk that is, could change your life forever. The most recent risk that transformed me for the good was this year. I was living at my family home in a transitional period post first stay at home order additionally, post me leaving new york after a 8 year stay. Read more>>

Carleen Carrasco | Carleen Carrasco / Fine Artist , Graphic Designer & Narrative Illustrator

During my adult life journey I’ve often found myself in search of my life’s purpose. I’ve reflected on where I’ve been at different life challenges and the risks taken over the years, and where to go next? Why do so many artists/creatives always seem to stay on the straight path to making a living and career from their gifted craft? I admire them and wonder how life delivered different roads for everyone? Then in 2014, I experienced a massive corporate restructure layoff. I had always pursued the office management careers to survive and climbed the corporate ladders too many times. However, each time, I wasn’t fulfilling my artistic drive that was still stirring deep inside me since my youth. Was it too late as an adult? The layoff provided a small severance check, and I thought this is it! Read more>>

Erika Guilherme Flores | Brigadeiro Maker

I always believed that my appetite for risk wasn’t very considerable. However, the day I decided to come to another country on my own, I was open minded to another culture. I had to learn the language, different habits and customs, and that day my perspective started to change. With a financial advisor background, I always knew that taking risks can be a way to achieve better results, but it is not always easy to take risks and be okay at the end of the day. Moving to another country was already a big move for me, but I knew I could always go back. Opening my own business in another country was the biggest risk I’ve ever taken in my professional career. Even though it might be the way to freedom, it is also scary and challenging, and you will only know if it is worth it or not if you do it. Read more>>