Risk is the most common topic that comes up in our conversations with entrepreneurs and so each week we ask entrepreneurs to talk to us on the record about how they think about risk.

Jordy Clarke | Photographer

There is always a certain amount of risk when you go into business for yourself because everything comes back on you. When I quit my day job to pursue freelance photography full time, the main concern was ‘Am I going to make enough to survive in one of the most expensive cities in North America?’ Leaving a regular paycheque was scary, but the idea of not trying to follow my dreams and feeling regret was scarier. Luckily my partner is a full time artist and they were very supportive of me and encouraged me to take the leap. Read more>>

Devin Woodall | Spirits Industry and Landscape Photographer

Risks are everywhere in this world and I think that scares people to their very core. I’ve seen it time and time again as the fear of failure stops some from ever doing anything worth a damn! But that fear that comes from taking risks is a power unrivaled in this world. – Believing in something so intensely that you jump headlong into it will always make you a stronger person, win or lose. Read more>>

Brittany Petrick | Acupuncturist & Herbalist

I have always followed the motto of “The bigger the risk, the bigger the reward”. I was a Registered Nurse for about 9 years and a CNA for 7 years before that. Healthcare had always been a huge part of my life and being a nurse had become part of my identity; someone I was very proud to be. So, when I became an acupuncturist, Read more>>

Kailey Nellis | Travel Photographer

I think of risk as an opportunity — an opportunity for growth, adventure, and creativity. Risk has played a huge role in both my life and career. Almost three years ago, I took the risk of moving half way across the country to a city I had visited once. I moved away from everyone I knew and the place where I had begun to grow my photography business. I spent two years there before deciding to take yet another risk by working travel contracts and only knowing where I’ll be living for 13 weeks at a time. Read more>>

Imani & Iman Lee | Owners of Lee’s Luxury Outings

The only way to insure failure is to not try. We see risks as opportunities! They are either going to work out, or not… but if we don’t take them, how will we learn? There has been many instances where we have to go out of our comfort zone and take risks that we may not be comfortable with. What we learned from these experiences was if we weigh the pros and cons and are happy with the potential wins and losses we will make our decision from there. Read more>>

Flavia Bennett | Designer, Metalsmith and Owner of Flavia Bennett Designs

I truly believe you have to take risks in order to get to where other people don’t go. I used to always play it safe. I started to follow my mom’s footsteps and got into med school. I was in my 3rd year when I realized that it wasn’t for me. That’s when I started taking risks. I quit med school and moved to the US to learn metalworking, a college degree that doesn’t exist in Brazil. If it wasn’t for taking risks I wouldn’t have met my husband and had my kids, and I’d be creating some pretty noses and lips instead of jewelry! I feel that taking risks takes practice and it’s a constant exercise of pushing yourself out of your comfort zone. But without it though, the creativity and innovation wouldn’t exist and I would be just another jewelry designer. Read more>>

Zuma Ayriyan | Travel writer/YouTuber.

I feel like my entire life has been about battling my fears and taking risks. Since I was fifteen years old, I wanted to travel and write about different people, places, and cultures. But when time came to choose a career, the fear of uncertainty and failure scared me, and I ended up pursuing a much more conventional career, and became a lawyer. That career choice did not fit me as well as I originally hoped, though, and after a few years of practice, I started thinking about following my dreams. Read more>>

TyLisa Booker | BigSis

I feel like it’s important to take risks. If you don’t take any risks especially when comes to your life/ career your going to regret it in the end. At times it’s the uncertainty that stops one from taking on risks, but I look at it like this: even if things don’t turn out how you imagined at least you took that chance.. grew from it and ultimately became more resilient. Read more>>

Marsha Barron | Artist, Designer, and Business Owner

I am a recovering perfectionist, people-pleaser and peacemaker so everything used to feel like a risk to me. Any decision I made, I wondered who would be offended or disapprove of my choices or if anyone would like me afterwards. Then if someone did not approve of my choices, I would do anything just to keep the peace. I wouldn’t speak up. I would remain quiet and small. That old way of thinking caused me so much unneeded stress. When I used to make art, it needed to be perfect to be good enough to show others. Read more>>

Taryn Quinterri | Tattoo Artist & World Wide Educator

Risk taking has had an impact on my career in many ways. Without taking the risks I took I wouldn’t be where I am today, but also without taking some of the risks I wouldn’t have lost all the money I lost. The point is you have to take risks! You’ll win some, you’ll lose some, but the only regrets a person should have in life are the chances they didn’t take and the decisions they took too long to make. Read more>>

Thaddeus Hornung | Musician

I personally view taking risks as a necessary vehicle for progress. No one ever changed a thing without taking a risk. In my own experience taking risks has granted me the opportunity to work with some of my favorite artists and musicians that I looked up to as a kid. Without taking that leap I never would have had that chance. Read more>>

Armando Nuñez | Entrepreneur

Being a risk taker is one of the most important qualities a human being should have. If you are not willing to take chances on yourself and bet that you will come out on top, then you will never be able to grow and further yourself in life. one of my favorite quotes “You have to take risks. We will only understand the miracle of life fully when we allow the unexpected to happen.” -Paulo Coelho, No one knows what tomorrow will bring so why not bet on your self and face the world head on. Read more>>

Livia Xandersmith | Artist

I wouldn’t call myself a natural risktaker, I’d actually call myself risk-averse. But some risks in life have to be taken to in order to feel fulfilled. No risk equals no reward. In the case of choosing to be an artist, I had to ask myself: What was a bigger risk? The risk of being an artist or the risk of potentially never feeling fulfilled and always wondering what if… Obviously, I chose to be an artist. I could not risk not being able to explore what this career could be and the happiness it could bring me. I take risks all the time, but they are calculated risks. They are risks I spent time and care to consider. Read more>>

Sarah Dugger | Painter, Printer, Muralist

I am a natural risk taker, though not with things like sky diving or down hill skiing. Free falling through the air or careening down a mountain of ice makes my bowels loose just thinking about it. I am partial to risk taking in my chosen field, fine art and textiles. To me, the root of risk taking lies in seeking and understanding truth. I’m not talking about the post-modern, everybody has their own truth, view of truth but the old stand by, the real version of truth. Truths that can’t be argued. There are three truths that I have internalized and have given me the ability to take risks with jobs, projects and relationships even if I’m unsure of my success, Read more>>

Molly Peters | Photographer

In my experience, taking risks is a necessary part of life but one that needs to be approached thoughtfully and strategically. There is no growth, progress, or innovation without some risk. I prefer to take calculated risks in both my life and my career, which allows me to develop my work conscientiously. As a woman and the sole owner of my freelance business, there are risks I need to consider every day. Some are related to my personal safety – I prefer to travel and work alone, and as a photographer, that means I often end up in places where I don’t know anyone, where I am frequently carrying expensive equipment. Read more>>

Dmitry Dolzhanskiy | Commercial and Fine Art Photographer

I see risk taking as an opportunity for growth. Taking risk is experimenting in a way. And experimenting is ultimate form of creation. Taking a risk is getting out of your comfort zone and allowing yourself to experience something new. Taking risk might be scary. It involves a lot of self-work. Working on fear of unknown, fear of failure. And of course, letting go of control. I wouldn’t be who I am today without taking risks. Read more>>