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.

Kat Parks | Yoga & Face Yoga Instructor

When I was just 13 years old, my parents made the huge decision to move our family from Miami, Florida to a tiny town in Washington state 3,500 miles away — despite all our family being located in Miami, my dad having a successful business there, and my brother and myself being in the middle of our teenage years. People thought they were crazy (myself included!), but the move turned out to be incredibly positive for all of our family. This was my greatest firsthand experience with risk-taking, and although my 13-year-old self wouldn’t believe it, I am grateful that my parents showed me that it’s okay to do “crazy” things! Read more>>

Lee Davenport | Artist

When considering risks, I ask myself, “Is the risk worth it?” Often I’ll compare pros and cons for help deciding the matter. However, something that I found to have significant weight in determining if taking a chance is worth it is also asking if now is the best time for it? For instance, one of the biggest risks I ended up undertaking in my life was deciding to become a full time artist. Looking at the pros and cons, it was fairly balanced, with the lure of success being just as tantalizing as the threat of failure. Read more>>

Anissa Buckley | Founder, b-untethered

Taking risks is critical to growth and optimal personal success in life. To take risk means to step out onto a limb that might crack at any moment. Of course, there are gradations to risk. Calculated risk means you’ve evaluated all of the possible negative and positive outcomes and know that you can live with either of them. Risk without some level of analysis is a form of adrenaline that some people thrive on. For me, I’ve taken both types of risk in my life. Read more>>

Steve and Noelle McGarvey | Travelers

We would describe ourselves as fairly risk adverse in our careers and finances. In 2016 a major health issue allowed us the opportunity to view our lives in a different manner. The drive for success is still present, but our willingness for risk has increased dramatically. After all, we all end up dead at some point! Read more>>

Barbara Weigand | Arts & Music Manager, Graphic Designer, Songwriter

I’m an artist and I’ve always been one. If I worried about taking risks, I could never be that, at least not full time. Simply being a full time artist is a huge risk, which is why most people don’t make that choice. “Even worse” my husband is a full time musician and that’s all he’s ever done. So the beauty is we are both dedicated to living a creative life, and the downside is “we are both dedicated to living a creative life.” Truthfully, I don’t consider that a downside at all and we’ve always made it work, but it does take some focus. Read more>>

Gary Hershorn | Photographer

When I look back on my career as a photographer, I would say risk-taking played a huge part in my development from the very beginning. When I started, I had an awesome mentor who instilled in me the idea that I needed to know exactly what I had to achieve when I went out to take photographs of news events but that accomplishing that sometimes would involve taking chances to get the best picture. I was never afraid to take a risk in where to stand or what lens to use as I was supremely confident that if something happened in front of me, Read more>>

Duda Gribogy | Makeup Artist

Since when I was a little kid my mother has thought me how important is to take risks, she always told me to be brave and that nothing can substitute experience. So when I was only 14 years old I started my makeup business, I didn’t have too many products to use or experience, but I had to much passion about how makeup can transform woman’s self esteem. Read more>>

Hoyt McGarity | President, 8AM Golf

I have always been a believer in taking risks, but calculated risks. I think everyone who starts a business, who has an entrepreneurial spirit, knows how to take risks. My whole career in, in fact, is an exercise in risk-taking, and there were no guarantees. I started as a caddy when I was twelve, then earned a golf scholarship to Lynn University, then shifted to business — taking more than a few risks to get my business running. Read more>>

Laurel Olotoa | Fine Art Photographer & Entrepreneur

By definition risk is “a situation involving exposure to danger.” by this definition I wouldn’t say I have put myself in “danger.” However, I believe that “calculated risk” has everything to do with growing ones business, No successful entrepreneur will say that they, at some point didn’t “put it all on the line” to move forward or further their careers. Sometimes you just have to jump into the deep end and quit doubting yourself. For me, that meant jumping into a career that may be heavily saturated and spending the money & time to better my skills. 10 years ago this meant buying a 2nd home and flipping it. Read more>>

Kristy DeWitz | Real Estate Mogul

One thing I’ve leaned over the past few years is if you never take risks you can’t level up. If you’re afraid to fail it will keep your butt glued to the floor. Moving outside your comfort zone takes guts and we all dislike being uncomfortable. Wether it’s in relationships, exercise, jobs, this same principal applies for all areas of life. To say we took huge risks is an understatement. Without risk and without failure their is no reward. It can be terrifying to take such leaps of faith especially with 3 little kids. You have to take a massive step outside your comfort zone to begin to change your circumstances. We weren’t lucky. I took risks and worked INCREDIBLY hard to get to where we are today. Read more>>

David Monreal | Music Artist and Videographer

Risks are everything in life. I firmly believe that life without risk is a waste. If I didn’t take risks I wouldn’t be where I am today. To be honest I don’t know where I’d be without taking chances. You have to fail forward and be okay with failure knowing it’s going to happen all the time in life. That is how you succeed. Read more>>

Cheryl Magellen | Artist, Creator, Consultant

Risk represents being vulnerable and once there is a confession as to being an artist, there is immediate judgment. Growing up, not only was it unfashionable for young girls to be groomed to be anything but a wife and mother, any kind of entrepreneurial effort made toward autonomy was shunned. Add to that something as frivolous as pursuing a career in art and I could forget about being taken seriously. Ever. I was a dreamer. I was unrealistic. I was a bohemian. I was irresponsible–all the titles that have labeled artists for decades. Read more>>

Kimberly Villa | Fitness Coach and owner of FitFX Fitness

I think in order to achieve something great you have to step out of your comfort zone and take risks. In my experience as an entrepreneur taking risk comes with the territory, and often requires a lot of trial and error along with incredible dedication no matter the pitfalls that may come. At the end of the day taking those risks ultimately lead me to my purpose and something I will forever be grateful for. Read more>>

Shawna Jones | Licensed Massage Therapists

Risk has played a huge part in where I am today. I took a chance one day and answered the phone that led me to attend massage school here in the valley. I toured the school on a Friday, signed up and did orientation on Saturday and started school on Monday. All of this involved risk, I took a chance with no job prospects, no place to stay, a new city, and not knowing anyone. Read more>>

Diana Dorel Gutierrez | Real Estate Agent & Relationship Coach

With every new endeavor there is an element of risk. Anything can happen-there are unlimited possibilities, but if you never take a risk and venture beyond what you know, you miss out on all the awesome surprises, up-levels and growth. For me, I’ve learned to reframe risk as a necessary step to the creative process. There’s a difference between just blindly jumping into a new path from a space of fear or anxiety….and consciously jumping from a grounded space. Whether it is starting a new business, taking the next step in my relationship or even embarking on a new hobby, I trust my intuition and when it says it’s time to jump, I listen! To me, that is authentic risk taking. Read more>>

Robert A. Lane | Mindset & Health Coach

Risk involves facing your fears, getting out of your comfort zone and having the confidence to believe in yourself. Sounds easy, right? I was a shy introverted kid growing up and there were many times I was too scared to go for things I wanted. Maybe it was all those “should haves” and “if onlys” that finally got me out of my shell. Read more>>

Stef w/ an F | City of the Weak (Band) + HXTEFUL (Custom Clothing)

Risk taking is obviously a very scary thing. No one likes to think that something they’ve invested their time or money in could potentially fail. But I like to think about each risk as it’s own potential reward / potential failure situation. I’m always a ‘worst case scenario” kind of person which really ensures that I’m prepared for any situation. “What’s the absolute WORST thing that could happen, & how do I make sure that doesn’t happen even if everything goes wrong?” Assessing the entire situation & trying to bring that risk of failure down, or at least being able to live with yourself if you do crash & burn, makes you feel so much more prepared to take on anything. Read more>>