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.

Donna Bates | Painter & Artist

Looking back, I think my whole life has been about taking risks! Growing up in the 50’s and 60’s there were not a lot of jobs available for women. My Mother wanted me to become a Secretary, but I knew that was not for me. After being a struggling musician, I went on to work as a commercial illustrator and 3D Artist for over 20 years. Somehow that evolved into a career in painting. Where usually people transition from Traditional to Digital, I went the other way. Not playing it safe, I have created my own mash-up style of urban, tough-chic, edgy, fresh, strong, and independent humans or “BadAsses”. Read more>>

Tony Testa | Choreographer

There’s a difference between taking risks for instant gratification and taking risks for a bigger picture. In the latter, you can’t really “fail,” bc a risk taken either teaches you or graduates you. You win some, you learn some. Read more>>

Lenka Wallace | Skincare Consultant & Beauty Coach

As a fearless Aries, I love taking a risk on myself! The way I see it is that there are all these fantastic opportunities waiting for us to explore, and sometimes also lessons that we need to learn. Either way, we gain from each experience, and we grow. What usually stops us from going for it are our fears. In my experience, fear comes from not knowing what will happen or how the potential situation will play out. It occurs in the future, which does not exist yet. I think it’s pointless to worry about something that may or may not happen. If we don’t put ourselves out there and if we don’t try we will never know whether or not it was worth it. Read more>>

Ngozi Bolin | Founder

You must take risks. Without risks we cannot test our capabilities and grow. It was a risk for me to come to the United States in the first place. I had already finished law school and was en route to be a very well paid lawyer given my family background and connections. I was also on my way to living in a society that did not put a premium on the value of women, at that time. It would be comfortable, pampered and opulent life, but I felt a different calling. That risk took me to New York where I had a very successful law carrier with published cases. Read more>>

Jordan Jeppe | Founder & CEO

Risk taking is fundamentally tied to my role as an entrepreneur, a title I never thought I would wear. See, I passed studying entrepreneurship and I actually avoided it while in Business school. A deep fear of failure lied within me from my personal experiences growing up and witnessing our family business collapse. It wasn’t until I lived in Los Angeles, waitressing full-time and managing social media accounts on the side, that I fully owned being an entrepreneur. My first real risk in this role was recognizing and owning it. Read more>>

Saharai Álvarez | Profesional Makeup Artist & Permanent Makeup Specialist

When we think about risk taking, most of the time we tend to step back because of the fear of doing something new and step out of our comfort zone. This fear can stop us to do whatever it takes to make our dreams or set of goals a reality. Before I became a profesional makeup artist and a permanent makeup specialist, I was a lead teacher in early childhood education for around 15 years. I had a good job that I was good at, a job that provided me with financial stability and good benefits. Read more>>

Carrie Walker | Artist

I’ve always been a sensitive woman. When I was younger I was even worse! I grew up with a step Dad who’s an action packed kind of guy! He loves adventure and doing dare devilish things! For me, although I love my step Dad, this was a nightmare! He’d try to get me to learn things that I was just too scared to do. Like dirt bike riding, waterskiing, snowboarding and skateboarding… Needless to say after many tears, as an adult I learned to take risks even when I was afraid. I’m grateful my Dad raised me this way, even though at the time it was difficult. Read more>>

Elizabeth Orleans | Ceramic Sculptor & Installation Artist

I realized I was an artist when I was in College. I decided to get a BFA (and later an MFA) with a focus in Ceramics. That was the first of many risks. It was never a thought or option once that light bulb went off in my head that I needed to express myself in a visual manner. I did not enjoy making pottery but loved creating sculptures and installations. This was the next risk as potters make utilitarian objects that people are more likely to buy. Being an artist is not like other jobs where working hard always equals compensation for your time. Read more>>

Silvano Barba | Handcrafted Leather Goods & Accessories Owner

I would say I’m a calculated risk taker. To start and run your own business like we do, risk taking is just part of the deal that comes with it. Which in part, the risk taking extends to your life choices as well. If you want a business to be successful, it has to be one with your life. We try to be as calculated as possible with career/life decisions, but if we take risk and they don’t work out, we have to be open to adapt to changes at all time. If we would have never taken the risk of quitting our day job to start our business, we wouldn’t be where we are today. Read more>>

Hayley Samartin | Photographer and Actress

You have to take risks – I only have the life I have because of taking risks! I am always trying new things and seeing where it leads me. Moving to LA 10 years ago was a huge risk as I knew no one and I remember thinking as my plane took off ‘what AM I doing??’ Leaving all my family and friends behind on a whim felt pretty crazy at the time, but I’ve actually been reflecting on it a lot recently and my life has changed exponentially since that day and all for the better. I originally moved here for my acting career and while I still do that. Read more>>

Julianne Barbas | Blogger & Digital Creative

For as long as I can remember, I’ve never been terribly averse to risk. When I was a child, I embraced a lot of challenging activities that involved heights. As a young teenager, I ventured to Australia + New Zealand with an ambassador organization for 3 weeks. By the time I was 19, I started to travel internationally alone. Taking risks and pushing myself through discomfort over the years allowed me to witness my own capabilities time and time again. Of course, there were also countless moments where I came face to face with failure — but I saw these as opportunities to collect valuable lessons that ultimately would aid in my growth. Read more>>