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.

Jack Cusumano | Independent Animator

I’m actually extremely risk-averse! I’m pretty great at catastrophizing and identifying all the possible ways in which something can go wrong, and often only make a move once I’ve gone over something 1,000 different times in my head and am relatively certain I’ve accounted for everything. That said, I’m also easily bored by things that are predictable and cliche, and really excited by new, unexpected and surprising ideas, so there can be a frustrating stale-mate between those two sides of me sometimes. Ultimately it’s usually the times in life where external circumstances really push me that I go out on a limb and try something risky. Read more>>

Dany Anka | Luthier, or Guitar Maker

I view risk as an essential element in my craft. Embracing innovation, trying new techniques, and taking on challenging projects have not only fueled my passion but also led to continuous growth and satisfied clients. Adapting to change and overcoming challenges through calculated risks has been instrumental in shaping my successful career as a craftsman in guitar making. Read more>>

Leigh Brooklyn | Multidisciplinary Artist

I think everything in life is a risk. You’re always risking something no matter what you do. Even doing nothing is a risk. You risk possibly losing an opportunity. I will always take risks on my career, on getting my name out there, on approaching someone or some place like a gallery. If I don’t ask the answer is always “No” so I always ask and give myself a chance. I don’t get embarrassed or too disheartened if they say No, I take it as a “Not right now”. People can change their mind over time. So it’s important to put yourself out there to give yourself a shot. Read more>>

Adham Ossama | Screenwriter

I think of risk as an opportunity to grow, learn, and explore new possibilities. I believe that taking risks is essential for achieving my goals and fulfilling my potential. That said, Risk taking can also have negative consequences, such as physical, emotional, or financial harm. Therefore, it is important to take calculated risks, which means weighing the pros and cons, assessing the likelihood and severity of the outcomes, and preparing for the possible scenarios. Taking calculated risks can help you minimize the downside and maximize the upside of risk taking. Read more>>