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.

Gigi Carballo | Fashion Model & Entrepreneur

I think taking a risk can easily be thought of with a negative connotation, but something that I’ve learned over the course of my life/career is that sometimes taking a “risk” is necessary for growth. By human nature, anything that’s outside of our comfort zone can be considered scary or risky, and we usually avoid these things, but on the other side of our comfort zone/safety-net is the potential to do something great. To be different, to make new choices, and to bring change. In business and in life in general, I think the things that involve risk-taking are usually the most worth it. The important thing is to come to a point of faith in yourself and your capability to take these leaps and trust that whether you fail or succeed, it’s better to have taken the risk and learned from your experience than to settle and wonder “what if.” Personally, as an entrepreneur, I’m taking risks every day. Read more>>

Benjamin Krohn | Co-Owner After Dark Music Management

Risk takes on two facets for us at After Dark, financial and “social.” Financial one is straightforward, are we going to make money on this or not? Social is a bit more complex, i.e. will an artist we are scouting align with our values in the long run or will this new venue provide the right experience. Then of course the two mix constantly and affect our daily decisions. Figuring out which artist to take a risk on that may/may not have experience being in front of a live audience can be just as crucial as deciding how much we want to charge for tickets. The right mixture of these risks often provides the greatest rewards and we strive to really ride that line of risk. Read more>>

Dana Baasiri | Director of Public Relations

I never thought of myself as a risk taker. Generally, the older you get the more fearful you are. While I find myself taking less risks these days, I’ve noticed that they tend to be bigger risks than the ones I took when I was first starting out in my career. I learned the hard way that growth doesn’t come from a place of comfort. Instead, we only grow and learn (in every aspect of our lives) when we do take risks. I realized that no one will push me to take those leaps of faith, so I have had to make a commitment to myself and take accountability when it came to doing so. I’ve also learned that it’s not about the number of risks you take but about taking the right ones (think quality over quantity). Reflecting back on my career, I can say I got here from taking the right risks. Read more>>

Mijhal Daisy Poler | Metalsmith & Jewelry Artist

When I was beginning to fall in love with metalsmithing and jewelry making, I traveled to Mexico, where I dreamed I would find a true master to teach me his ways. I arrived in the beautiful colonial town San Miguel de Allende, and through word of mouth, found Antonio, the silversmith. I quickly realized he didn’t want to teach me how to be a metalsmith, he wanted to “show” me how to make my designs and send me on my way. There was little technique or patience involved, and I knew I couldn’t leave Mexico having only learned under him. One afternoon about town, I stumbled upon an outdoor artisan market and struck up a conversation with a man who was selling his jewelry. Luis was petite, wearing round metal-rimmed glasses, a black velvet vest, a bowler hat, and a thick brass cuff around his wrist. Read more>>

Julie Kim | Acupuncture Physician

I believe taking risks is a necessary part of life.  Of course there are varying levels of risk but everything we have and do in life are the results of the choices we’ve made and will continue to make whether big or small. My original major was biology in undergrad, which would eventually parlay into pre-med. However, I couldn’t shake my desire to pursue a more creative field. I had a strong inclination to move to NYC to pursue a career in fashion. I took a chance and changed my major to fashion and business during my late sophomore year and busted my rear off so I would still graduate ‘on time.’  After college I moved to the Big Apple and it was amazing! It really was all I dreamt of and totally lived it up in NYC for 10 years. After my decade stint, I moved back to Miami along with my corporate fashion job to work remotely and travel to NYC when required. Read more>>

Jennifer Gutschmidt | Entrepreneur

As any entrepreneur knows there is an inherent risk in starting your own business and there is a lot of pressure with that. At the end of the day the success of your venture rests solely with you. The flip side of that is you create your future and when your ‘why’ is solid and you truly believe in your vision nothing is better! I have always been a risk taker in my professional life. My father was an entrepreneur and he instilled an amazing work ethic. MobiPop has absolutely been a risk we have taken a product that really no one else has and introduced it to the market. Read more>>

Toby Gotesman Schneier | Renowned, Highly Exhibited Artist/Painter

Mine has been a career largely DEFINED by risk… I paint Human Suffering, the Human Experience, and the history of certain dark periods of time… Holocaust, Homeless,Slavery, and most recently, HIV/AIDS, … These are not always pretty subject matter, although they do have moments of pure beauty even through the epic pathos…The paintings require a certain brand of brutal honesty in order to appropriately resonate… Although thankfully, there are myriad collectors, museums, galleries who love and appreciate them, I would absolutely qualify the work I do as “RISK” in and of itself. Never easy to look at… Certainly not easy to paint….A footprint, if you will, to mark those periods of time, those ongoing subjects, visually…thru my art…. Read more>>