By far, the topic that comes up most in our conversations with entrepreneurs and creatives is risk. We’ve had conversations about risks that worked out and risks that did not. We’ve seen eyes light eye sharing about career-trajectory changing risks as well as folks sigh about the risks they wish they had taken. Below, we’ve selected and shared some of those thoughtful conversations.

Alexander Ruwe | Artist, Entertainer & Band Leader

Risk is necessary for artists and leaders of any industry. The nature of our work demands that we push our crafts or our teams or our organizations in order to pursue new opportunities. I know that I am in a good place with myself and my work when I feel slightly overwhelmed and exhausted. Too much of this and it becomes a distraction — I become unable to think and organize and execute, and my decision making becomes cloudy. Read more>>

Penelope Gomes | Civil engineer

Taking risks marks a change in you, many times we are victorious by taking risks and sometimes things do not turn out as expected. But it is always better to say try. In my case, I take the risk of emigrating to the United States and founding my own company, which today makes me immensely happy to have done so. Read more>>

Oxana Rumyantseva | Owner Of Shapemode LLC weight loss program

I love risk, I always open to try something new. It gives you opportunities, each step from comfort zone extends the range of possibility of the success. I was absolutely destroyed after my divorce, alone with 4 kids with 0 child support. So it was a choice: stay there and cry or risk and start new business. Read more>>

Josephine Kostick | Owner

Taking risks is very important in all aspects of your life, whether it be with your business, relationships or any other area. Even if you fail by taking a risk, you will never question and wonder what would have happened if you did it. Failure is the best teacher, and all successful people have failed at something at some point in their life. If you are deciding whether or not to take a risk, look at the situation and consider the absolute thing that could possibly happen. Read more>>

Tianna Guy | Elite International Boxer & Business Owner

Initially I avoided risks at all cost. Since I am a huge perfectionist, it I felt like I wouldn’t execute something in the most perfect manner I’ll shy away from it. Through me becoming an athlete (Elite International Boxer) and business owner I realized that risks are crucial to development. Risks doesn’t always mean you’ll be successful but one thing that is guaranteed is lessons. You will learn, then that situation another time around would seem even less riskier. Due to the fact that you’ve learned from your unsuccessful risk. Read more>>

Jenny Dalio | CEO/Founder of Live Deeply

I was part of a beautiful group in college that met weekly to talk about lived experiences. Within the group, there was a moderator that would often interrupt us and say, “Risk yourselves more! Share what’s really going on for you! Jugatela!,” which in Argentina means, “get in the arena and risk playing for real.” We took his advice and started saying what we were actually feeling or struggling with and it was transformational. I noticed that when someone shared honestly, everyone else put their guard down. I started trying it myself and realized it helped me create more genuine relationships. This excitement in the face of social risk continues to serve me to this day. Read more>>

Lacey Byrd | Entrepreneur

Life is partially about know which risks to take and when. It’s an inevitable part of the journey to success. I think all successful entrepreneurs have that in common. We are natural risk takers. But it’s about taking calculated risk. Read more>>