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.

Chelsea Kephart | DesertBalloon Designer and Owner

I have not always been a risk taker until last year when my husband and I decided to move across the country from Buffalo, NY to Tucson, AZ with our two young sons. Our life was starting to feel monotonous and we realized that that was not the life we wanted to live. Read more>>

Don Hurzeler | Retired executive, owner of Kua Bay Publishing, co-owner of Lava Light Galleries, Inc, photographer and author.

I’ve made my entire professional career by understanding and managing risk. I was the Chief Underwriting Officer for one of the largest commercial insurance companies in North America and then became CEO/President of one of their businesses. There is tremendous opportunity in risk. Read more>>

Jessica Weaver | Wealth Advisors, Best Selling Author, and Founder of the Women’s Wealth Boutique

Risk is all apart of life, and not taking a risk is the biggest risk of all. To me, risk is about growth and without growth we become complacent, bored, and stuck. I joined the financial industry over 12 years ago when I began my work as a financial advisor in my father’s firm. Read more>>

Bri Zie | Wire Wrap Artist & Jeweler

Risk taking is essential to growth, and present in every aspect of the human experience. Personally, I view risks as opportunities. For a long period of my life, I was afraid of taking risks more than anything. Afraid of failing. Afraid of not meeting the expectations of others or myself. Read more>>

Sara Muckenhaupt | Bartender, Art Model, Real Estate Agent

It’s been easy for me to take risks. I have always been more of an “act now, think later” type of person, where I will seize an opportunity and then figure out the rest once the ball is rolling. Read more>>

Lauren Lerner | Founder + Principal Designer of Living with Lolo

Someone once told me that I should do one thing everyday that scares me. It is the scary things that push you outside of your comfort zone and challenge you to be the best version you can be. I truly believe that having confidence in yourself and following your intuition is crucial in growing both personally and professionally. Read more>>

Pauline Thomas | Principlal Designer & Owner at Studio Artise

Risk is an element in nearly every decision a small business owner makes. It is solely the action of taking calculated risks that transitioned me from being an employee to being an employer. I come from a long line of entrepreneurs so it was a natural progression for me to start my own business. Read more>>

JOE SULPY | Customer car builder, designer, metal shaper and teacher of metal shaping

I’ve never been one to follow the pack. So building custom cars and motorcycles is a perfect fit for me. Everyday I get to create and push myself to think outside of the box. When you are trying to reinvent yourself everyday, pushing the boundaries of your skills, you are constantly trying to do something that has never been seen before. Read more>>

Victoria Dowers | Traveler & Content Creator

Risks are exciting. Whether the risk results in a win or loss, it brings experience that helps propel me forward. The risk must be calculated, of course, but nonetheless, taken. Taking risks is the reason for my advancement. Whether it’s been a change in my career, a major last-minute travel move or a monetary risk, it has always brought the value of experience. Read more>>

Jessie Thompson | Artist | Graphic Designer | Dreamer

Not to be cliche, but ‘risk it for the biscuit’ came from some people, somewhere that probably had a life experience of risking to gain. Sometimes the wheel doesn’t need to be reinvented and we can learn from these people and their mistakes and successes of the past Read more>>