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.

Glady Dalton | Brand & Business Photographer

To take a risk is to expose yourself. Possibly exposing your weaknesses, but it can also expose your strengths. I’ll give it to you straight, I quit my full time job and took all my money to travel around Europe for 30 days. I came back broke and determined to make my side hustle photography business my full time job. That was in 2016. Taking a risk like that isn’t something I’d recommend. However, if I didn’t do that I definitely wouldn’t be where I am now. That applies to both my life and my career as a brand and business photographer. A risk like that showed me it was possible to travel. Possible to try new things. Possible to fail and still succeed. Possible to change course. Up until then, I had done all the “right things”. I did everything I was supposed to, I followed the logical path and I dreaded where that got me. I was so confused as to when I was supposed to feel happy about any of it. Read more>>

Low Valentino | Artist

When you take the same path all the time you start to know what to expect. But you don’t get to see anything new. But if you step out and try something new, there is at least a chance you will find an even better path. In my case, I used to think that my art wasn’t good enough to show anyone so I wouldn’t. Then one day my mom told me that she had got me into my first art show. And I was horrified. I had no idea how people would react to my art. But it went well. And I’ve been doing them ever since. And I learn something new from each show that helps me to improve my art and presentation. Read more>>

Jessica Luis | Hairstylist & Owner of The Blowout Babe

With much thought, I weigh my options by making a list and I question everything. I’m not a risk taker by any means & I do well by planning and calculating. At the age of 30, I can honestly say that i have already taken the biggest risk of a lifetime. Mid-February I was let go from my place of employment. A week later, I opened a salon in the uncertain times of a pandemic. Being a business owner is not an easy path, it’s definitely risky. But the reward is far greater than you could ever imagine. I was presented a negative situation that I turned into a positive opportunity. I’m a firm believer in that when the universe speaks, you need to quiet your mind & listen. Read more>>

Sarah Jack | Performing Artist

I view risk as a necessity in my life. You can set up as many dominoes as you want and measure out the pathways, the distance, but there is always the chance they won’t fall the way you plan. I often approach risk with calculation and trust. If it doesn’t work, make an assessment, adapt, try again or change gears. I wouldn’t be where I am if I didn’t take risks. “Embarrassment is the cost of entry. If you aren’t willing to look like a foolish beginner, you’ll never become a graceful master.” (Sourabh). Read more>>

Adrian Perez | Entrepreneurs, Chef & Actor

We tend to attach the feelings of fear, the unknown, and failure when it comes to the idea of risk. We amplify those thoughts over ones of reward, payoff and success. Up until I was about 30 years old my life was very linear, one action after another leading to outcomes that I was already raised to believe, taught to think and forewarned about. Just months after I left my job of 11 years to start my own business, I was dumped and left with nothing but a suitcase and my knife kit. I had five dollars in my bank account and opted for living out of my Jeep so I could rent a commercial kitchen space. I had never faced adversity, felt hungry, or been homeless. I thought all the hard work Id put in up to that point would pay off one day so it had to be worth the risk. Plus, when you have nothing left to your name, you stop defining yourself by material things. So when you have nothing left to lose, that’s when taking risks is twice as exciting. People also don’t take risks because the fear of failure, and failure is a misunderstood and under appreciated perspective. Read more>>

Janelle Mack | Singer / Songwriter

I used to think taking risk was thinking outside the box and trying to be as different as you possibly could in this industry but I was wrong. Everyone as an individual has something so special to contribute to whatever it is that they do and there’s a lane specifically for your differences. Once I realized and applied this to my music career it put into perspective that standing in who I am was the true risk taking. No matter how awkward , how my edges laid or who featured on my tracks. What defines Janelle Mack is my ability to be myself in my art knowing what I have to offer to the music world is more than good enough. Ever since I changed my perspective on risk taking I never back down from anything that I want. If theres someone I want to work with… I tell them. Its helped to trust myself and my personal creative process a lot more. Read more>>

Jazmine Lemons | Entrepreneur

Risk to me plays a huge roll in my life because, without taking risks I wouldn’t have come as far as I have in my career and personal life. Every achievement I’ve had came from calculated risks such as becoming an entrepreneur and successfully starting my Real estate and Clothing line from the ground up. If you are an aspiring entrepreneur my advice to you would be, “take that risk”. You will thank yourself in the end. Read more>>

Courtney Bonds | Singer-Songwriter

I believe that taking risks is simply a part of living life to the fullest. No one gets any further by playing the game safely so I choose to live by a quote from David Bowie that always resonates with me while creating: “Always go a little further into the water than you feel you’re capable of being in. Go a little bit out of your depth. And when you don’t feel that your feet are quite touching the bottom, you’re just about in the right place to do something exciting.” As an artist, I fully understand that I’ve entered into a world where only the risk-takers thrive. I am a leader and I am an entrepreneur, which naturally means that stepping out of my depth comes with this career’s trajectory. Furthermore, failure is always an option, but more importantly, learning from said failures is the goal. I’ll encourage anyone to take risks to truly experience life. Read more>>

Grace Goen | Filmmaker

Risk is all about reward versus failure. What is challenging is the fear that pokes its head out along the way. When I think about risks I always go back to myself as a kid when everything was new and scary. I wasn’t good at school but I wanted to be so bad. I sat in the back and I never asked any questions in front of the class; I was petrified everyone would know I didn’t understand the lesson. I got so behind and eventually, my classmates saw my low test scores while the teacher was handing out papers. Something clicked that day for me and I decided that I was going to do what was best for me to succeed and if people knew I was struggling that’s ok! I’m still doing better than I would have been and I deserved to give myself the space to try my best. Obviously, business endeavors are much more complex but I think you have to bring the same energy to the table. It helps tremendously to have the outlook that you are going to do something because you want to do it and that’s it. Read more>>

Rickale West | Visual Artist

I appreciate this question for one primary reason, that is I have never been a big risk taker. I had always believed in playing it safe until i was a faced with two choices. It was either take the risk to go all in on this art business or wait around to see if I sink or swim without ever even trying. Risk taking for me at this point has been scary yet the most exciting time of my life. I have been able to share my art, and my message with many people because I decided to take a risk. The mission for this brand would be impossible to complete if it were not for stepping out on faith and taking the risk. As I know things will get even riskier, I hope to be able to impact so many more people with my work. Read more>>

Moji Karimi | Carbon-Negative Entrepreneur

Risk is related to having a vision for what the future is going to look like. Basically, you are making a bet on that and become part of the process to create that future. The risk comes into play since there are other factors involved that may create a different future than what you envisioned. I’ve always embraced calculated risk-taking to create the future that I envision. At Cemvita, that’d a future where humans live in harmony with nature. A future where humans deploy nature-inspired technology to reverse climate change. That’s the Cemvita vision and we are determined to play our part to make it happen. Read more>>

Vera Taku | CEO and Creative Director of V’etta Creations Event Company

Business = Risk, if you’re not a risk taker then you’re not ready for business. My entire business is based on risk taking, there’s no guarantee of a return when you do an investment in our industry, but you have to do it . Recently I made another big risky investment for the company and indeed it was risky, I recently imported wedding furniture for the first time from out of the country and didn’t know what all came with that, it cost me so much out of pocket without me knowing if it would even come in on time for my event, of which it didn’t, it came in the same day of the event and there was no way to make use of it….. did I cry? Yes, was I frustrated? Yes, was I stressed? Yes,……. But at the end of it all I pulled through pulled some strings and made it happen for the client. That’s Business, I took a big risk and now just waiting with faith that I will see my return. Will I do it all over again ? Yes because it’s worth it. Read more>>

Bri Morrison | Certified Lash Tech/ Instructor & Master Brow Artist

Honestly , taking the risk to quit what you know is guaranteed to do your own thing is scary! I stepped out on faith even with being scared and knew at minimum God is a provider. I knew my hustle & work ethic would take me far. Taking the risk is the best thing I have ever done! It’s played the biggest role in my life thus far because everything in my life has changed for the better since I decided to bet on myself! Sometimes you just have to have faith and put some work behind your prayers. Read more>>

Ilse Calderon | Venture Capital Investor

Hmm this is a broad question; but, I associate risk with context. Risk is always relative and subjective to one’s environment. While I do not think I have the luxury of an infinite, guaranteed safety net, I still think of myself as more of a risk taker than someone that is risk averse. For me, thinking about risk brings up opportunity cost: what am I missing out on by taking this risk? Is timing on my side? Also, as an investor, I often use an investment risk analysis when considering a personal risk, I think, does this risk’s upsides outweigh the downsides? If so, then I probably take it. As I think about my career and where I want to be in the coming years/future, I am definitely open to taking risks if it means getting closer to my long term vision. Read more>>

Sha’Na “Shay” Smith | Founder/Director/Artist/Visionary

I read somewhere that everything is a manifestation of our thoughts/beliefs, and every thought/belief is an affirmation in so many ways. I look at risk the same way. Everything is a risk. Staying at the job that is only paying the bills but killing my spirit is just as much a risk as taking that leap on faith. If it’s in my heart to try and I don’t, I run the risk of never knowing. Apart of me feels new to faith based living, but there’s also a larger part of me that knows I’ve come this far by faith, hard decisions, and a few mental breakdowns. The risk & the choice to walk in what my spirit is drawn to with as little concern as possible has brought me so much closer to my higher power. A truly personal power. I don’t always call myself an artist/creative. I’m a being. Human, being. Being is a risk. We’re conditioned to do. Creating is a doing, but what I create are extensions of my being. If I didn’t realize that for myself I’d still be running around trying to realize someone else’s dream. Read more>>