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.

Kate Welch | Co-Owner & Marketing Director/Professional Puppy Wrangler

These days, both Corey and myself are generally risk averse. Calculated risks are necessary to move forward in life and to create the life that you want for yourself, so we are willing to make them, but not without a safety net. The biggest risk I have made in my life was moving to Arizona. I’m originally from Michigan and moved here in 2014 because I felt stuck. I graduated from Grand Valley State University in that beautiful time where jobs were sparse, particularly for a new graduate with a photography degree. Read more>>

Cyndi Hardy | Photographer, Painter and Digital Artist

I think most business owners are risk takers or need to be willing to take risks sometimes. Taking risks can give you the opportunity to propel forward in your life or business if things go well or failures from risk give you a chance to learn from what doesn’t work. If you start thinking of your failures as learning mistakes instead of complete disasters, then risk taking becomes less scary. Not taking risks makes us become more stagnant and becoming more stagnant is the death of a business. Ultimately, taking risks is how we learn, grow and live. Read more>>

Mahna Ghafori | Travel Photographer

Taking a risk has been game changing for my travel photography business. I took a risk in May of 2021 when I decided to take an unpaid leave of absence from my corporate job to pursue my travel photography passion. It was a terrifying choice to leave the secure, known path and dive in to making my own business work. I had no business background or mentors in the business space at the time. From diving in and pursuing the riskier path, I’ve experienced my dreams coming true, a life of fulfillment, service, and opportunities more than I could have imagined. Just from taking a risk. If there’s something inside you that you feel pulled towards, don’t silence that voice. Take the leap. Follow your heart. Read more>>

GAELLE BUSWEL | singer, songwriter and guitarist

Taking risks gets things done. It is often a good thing. In a job like mine, artist, you have to take some all the time. People often think that the opportunities that present themselves are luck, but often they are the result of many risks and sacrifices taken upstream. Whenever I took risks, like saying no to other projects in parallel to defend my independent project or said no to certain musical productions, it was beneficial. It was not the easiest path, but my determination helped me to make this or that choice and take risks. Sometimes taking risks is scary, because we always know what we are leaving or what we are losing but we do not know where it will lead us and if it will work. But often taking risks make us stronger, allows us to recover in the event of failure, or to better structure ourselves. Read more>>

Donna Ruthruff | Photographer of Lightning and other beautiful moments

As a lighting photographer, it’s all about risk. If you’re not willing for a certain degree of risk, this would not be for you. The question comes to play when I ask myself “How much risk am I willing to take?” In every storm, I weigh the risks. “Should I leave now? Is it safe to stay in this position?” “How close is the lightning and what is my comfort zone?” For me, sometimes, pushing the boundaries is where the excitement lies. Every lightning photographer and storm chaser knows what the risks are, being struck by lightning, hail damage or stuck in a wash. But without any risk, there is no adventure and there is no adrenaline rush and ultimately, there is no lightning photography. Read more>>

Robert Rodriguez | Managing Partner of Vantage Realty and Home Loans

Growing up in a lower middle class household I believe it gave me a superpower. Yes I did not go without meals, or without a roof over my head but we had alot of other struggles that most families that I knew had. We would have to avoid the bill collectors over the phone, listen to my single mother argue with my father about money. Going out to dinner meant Mcdonalds, having clothes on lay away, hand me downs, wearing payless shoes that were remincenent of addidas having 4 stripes not 3 and being made fun of them. Read more>>

Taylor Miller | Freelance Digital Artist | Media Producer and River Guide

I took a huge risk in leaving my career as a teacher three years ago to pursue being a full time artist and river guide. Ever since taking that leap, risk has not gone away, in fact it has increased in my day to day life. Things are always changing. At this time in my life I am most grateful for my riskiest decisions. I’m so grateful that I get to create, explore, and share stories for a living. I would not be able to do these things comfortably without the kindness and support of my community (who are also a bunch of risk takers). Read more>>

Ellie Paget | Luxury Vacation Rental Management

I feel whole heartedly that risk is about the level of trust you carry with your intuition. With that said, HomeSlice Stays embodies “a home within you, wherever YOU are.” That “home” is as cluttered or organized as you so choose. If you can’t follow your intuition and trust in it to make calculated risks, calculated being measured and weighed, then you are making reckless risks. With our service and product we deliver to our clients, it’s grounded by our level of attention to making these temporary homes for some feel like a new found place to rejuvenate and rediscover. Read more>>

Jean Hanson | Co-Owner of Realign Your Life Wellness Center featuring the Harmonic Egg, Higher Guidance Life Coach

By nature, I’m not much of a risk-taker. But I learned a lot about how to take calculated risks from my husband. We went into business together the year we got married, and he quickly set out to invest in equipment for the business. It put me into a bit of a panic because I looked at the investment as a large amount of money that we didn’t have. He looked at it as a way to generate a large income that would pay for itself quickly. He was right. Read more>>

Elizabeth von Isser | Film and voice actor, jewelry designer and fine artist

Over my adult life, people have told me they think I’m a risk taker – that I’m ‘brave’. But I’ve always considered ‘risk taking’ to have a bit of a negative connotation and have never seen myself in that way. I prefer to think of myself as someone who is willing to try something new, try something that excites or interests me — someone who is willing to try and fail, rather than not try at all. Read more>>

Sydney Joz | Social Media Agency Owner

Risk is essential in business. It’s the terrifying change that is necessary for growth whether it ends up working in your favor or not. If it works in your favor, instant growth! If it doesn’t, then you learn something from it and that in itself is value! Read more>>

Krystle Robinson-Hershey | Owner of Sage & Elm Apothecary

I believe that risk allow you to be vulnerable and experience a decision in a way like never before. I am a risk taker with opportunity, as well as in business. In my life and career I feel taking calculated risk has been the best decision even when difficult. There have been advances, jobs, travel and so many new experiences because I took a risk that many wondered why or how it would work. I believed that the next step would lead to something bigger. I never want to look back and see a bunch of “should have, would have “so I try to push life forward. Read more>>