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.

Sasha Brown | Artist and Hair Stylist

There can be two different types of risk. One is defined in the dictionary as exposure to danger, harm, or loss. The other one you should always be open to, because it can provide possible positive consequences. Some people view risk as something to be feared or avoided, but in life I’ve learned that you cannot grow without taking any risks. It can present unexpected opportunities for personal success. We have to constantly step out of our comfort zone or else we’d be stagnant. Read more>>

Kelli Wassom | Fine Artist & Art Educator

A few years ago a friend said, “If you never ask, the answer is always no. But, if you take the chance, the answer could be yes!” I wouldn’t consider myself a jump out of an airplane type of risk taker, but I don’t let fear or worry hold me back from trying something new. So many career turns and wonderful surprises have developed because of my willingness to push out of my comfort zone. Taking risks has been something that has not only helped my business grow, but has also helped my creative process. Read more>>

Brandon Rose | Chief Executive Officer

I think about risk the same as I think about opportunity. The larger the risk, the increased opportunity to learn and grow, which is ultimately moving in the right direction. I find many people don’t take risks because of the fear of failure, but in failure is where the opportunity to learn and get better come from. I love the quote by Thomas Watson “If you want to increase your success rate, double your failure rate.” Everyone is at different points in their life, and on different paths to who they want to be. Read more>>

Thomas Crosson | Entrepreneur

I am a firm believer that in order to achieve anything great, risk is always involved. It doesn’t matter if you are trying to be a YouTuber or a doctor or raising capital for a startup, risk is always present and can cause a lot of people to change paths or stop pursuing their dreams. Risk comes in many shapes and sizes and looks different in various scenarios. For example if you are trying to start your own YouTube channel there is minimal financial risk. Read more>>

Tiana Clewis | Financial Lifestyle Coach

My training as an accountant makes me naturally seek to avoid to risk, so it has taken me a lot of work to overcome that inclination. It wasn’t until I looked back at my life that I realized I have always taken risks without even realizing it. Auditioning for a school choir was a reputational risk. Working at Six Flags as a teenager, checking bags with unknown contents, was a safety risk. Going to college in Washington D.C., even with the full scholarship, was a social risk (culture shock, anyone?). Read more>>