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.

Desirae Hosley | Community Organizer and Enthusiast

Risk taking is a motivator for myself. I have lived most of my life either people pleasing or looking for validation from those around me that I assumed would be giving me the right advice in my life. Instead I would feel myself being placed in the same cycle of failure or being in someone else’s shadow. After my life had a change that would turn my path into me not fearing what could be next; I began taking all kinds of risk because I believed I had nothing to lose. I stick by the saying that “NO’s” don’t hurt and I that has been the fuel that I needed to accomplish the goals that I have been able to accomplish thus far. I take risks as challenges that I need in my life and if I don’t “challenge” myself I will would either be burnt out or not feel fulfilled in my life. I continue to push through and accept what being a risk-taker has to offer. Read more>>

Saionara Frederick | Business Owner/ Nail Technician

Risk is something that we should take in most situations. In my situation, I worked in a factory for 10 years working 50 plus hours a week but, I knew my dreams were not in the factory. My dreams were to go back to school to get license as a nail technician and opening my own business. I was scared and worried to leave a job that I worked for so long to take a risk in following my dream but I never gave up. I`ve been licensed for 3 years, I worked for a salon briefly, then went on my own a year after my business expanded and now I own a successful salon and run it with an amazing team. I kept moving forwards even when things got difficult because I believed that if I didn`t take that risk I might’ve have regret it in the future. Read more>>

Toi Arnold | Fashion Designer & Entrepreneur

Risk play a huge role in decision making, when you aren’t taking a risk you will know or expect the outcome. Though when you choose to take a risk you don’t know the outcome(s) only the what-ifs. Due to me taking risk, I became a Fashion Designer & entrepreneur which I am thankful for the risk each day. In some ways it is true, “no risk, no reward” but when taking risk sometimes you have to work harder to see what the risk was worth. Read more>>

Edward Carignan | Producing Artistic Director, Short North Stage

I have always found that taking responsible risks can pay off. Being a former actor/director in NYC, I learned quickly how much you have to put yourself out there to be successful. The few times where roads diverged and I had to make a choice about something major- listening to my intuition has always guided me in the right direction. Read more>>

Tracy Baranauskas | Life Coach for Women & Author

You cannot get anywhere in life without taking risks. As a life coach, this is an important perspective that I help my clients develop because no human has ever accomplished anything great from the confines of their comfort zone. Read more>>

Tanya Kaiser | Director and Owner

Calculated risks are an important distinction when considering a risk. It’s about assessing the uncertainties and making informed decisions. For me, risk-taking has been pivotal in shaping my life and career. It’s been a balancing act between caution and courage, where calculated risks have often led to some of my most significant achievements. Read more>>