In our experience, most folks, including ourselves don’t have enough of an understanding of risk and the role it plays in our lives and careers and so we have made a concerted effort as a team to have conversations about risk with our interviewees. We’ve shared some highlights below.

Terri-Leigh Huleis | Interior Designer/BoyMom

The biggest risk I have ever taken was agreeing to marry a boy I’d known for a grand total of 10 days, and then moving from South African to America to be with him. Yep. I was in my very early twenties and I had been drifting along, traveling solo through Europe trying to figure out what I was going to do with my one precious life. We met, completely by chance on a small boat moored off a dock on the little Island of Milos, Greece. I was kicked, hard in the gut, with “knowing” and thought well, what the heck, what have I got to lose. That was 14 years ago and boy we’ve had our ups and downs but I have never looked back. Read more>>

Bruce Ruff | Pro Skier

I say go for it! You never know what you can accomplish if you’re not willing to take a risk. When I was 21 years old, I had the dream of moving from New York to Colorado to become a pro-skier. Forty four years later I am still a professional skier, living out my dream. I left New York with very little money and not knowing where I was going to live or work, I managed to figure it all out and never returned to New York. Skiing everyday and working at night were the catalysts for me to compete on the pro mogul tour for 14 years. I had the opportunity to travel to new places and meet new people. Read more>>

Molly Gallegos | Radio Host and DJ

My mom always told me that if something scared me, that was exactly the thing I needed to be doing. I get scared a lot, but I rarely let it stop me. Any big dream is going to involve risks but to me, if I really want the scary thing, then I gotta be vulnerable and go for it. I try and look at it this way, what’s the worst that can happen? Someone says no, or I don’t get the thing I wanted? Ok, well I already don’t have it so I’m no worse off and at least I tried (another bit of mom wisdom). Read more>>

Adri Maria | Forward Thinker & Continuous Learner

I live by a quote that says My Faith > My Fear. I believe that a path has already been created for me and I have to walk in faith in order to keep going. We risk everything we could ever attain by not risking anything at all. When you come from parents who left their own home countries to pursue endeavors in a country where they didn’t speak the native language and had to build a support system/community on their own – you see risk as an essential part of moving forward in your life and seeking more for yourself. Read more>>

Lindsay Mitchell | Founder & CEO of Vital-Side, PA-C

Everything that was ever worthwhile in my life was a risk. I came from an antiquated system of healthcare that I absolutely loved. I loved working in internal medicine and treating patients. When I started doing this, I knew it was my life’s work. But I quickly found the limitations of western medicine. When I was spending 5-10 minutes a day with my patients with multiple diagnoses and complaints, that’s when I knew I had to make a career change. Read more>>

AJ Rezac | Travel Photographer

In my eyes, risk taking is one of the most important things in life. If you never take risks, you will never leap forward and achieve your dreams. If you want it, go for it! If you always play it safe you will get to the end of the road with regret. Taking smart and calculated risks that seem scary at the time, are always ALWAYS worth it on your path of life. When I was 13 years old, my family and I sold nearly everything we owned and flew to Hawaii with no jobs, no school, and not even a town to settle in. Just my parents, two kids, two dogs, our suitcases, and a place to stay for two weeks. Read more>>

Julie Pomerantz | Personal Coach, yoga teacher, adventurer

Risk-Reward assessment is foundational in my approach to business and to life. The saying “how you do anything is how you do everything” is something I work to live by. To me, life without risk, a life primarily lived in one’s comfort zone, is safe. However, the safety of comfort, without risk means we miss out on discovering, and fulfilling our full potential. Failure is unavoidable when we continually take risks, yet growth is also guaranteed. If I were to avoid risk, I would have continued to work a job for someone else and stay in my comfort zone. When I started “Resolve with Julie” it was a huge risk. Read more>>

Blayne Ippolito | Photographer, Videographer, & Adventurer

The first question that pops in my head when asked this is, “What have I done this week that pushes my level of comfort?”. You see, to me risk is a necessity of life- it’s the absolute uncertainty of what’s to come next- the freefall into the unknown. It makes me feel alive. I could lock myself in a padded room to feel safe, but that level of safety and mental comfort does not allow a life worth living. The question that precedes this is: “Am I truly living?”. The stark reality of this metaphorical scenario is that I would simply be existing. Read more>>

Samantha Auster | Artist & Entrepreneur

I believe that the best things that happen in life happen as the result of stepping outside of our comfort zones. Far to often we are afraid to try the unknown for fear of failing. When in reality even if you fail, it is still a step forward towards your goal which is always going to be a success. I truly believe the more risks you take in life, and the more you put yourself out there the happier you will be. Nobody gets out of life alive so we may as well take all the chances we can! My biggest fear in life is to be on my death bed regretting all the opportunities and risks I was to afraid to take. Read more>>

Ruth Catchen | Realtor, Realtor Trainer and Educator

Risk taking: how do you think about risk, what role has taking risks played in your life/career? Ever since I was a small child I focused on doing whatever I chose to do and being the best. Call it impossible, excellence serves as my core mission. At the same time, I realize that there is always someone better, someone to motivate me to go a little bit further. Read more>>

Ryan Hughes | Freelance artist

I believe life is best experienced when one is willing to take risks. Personally, risk taking has been helpful for the sake of new experiences, accomplishments, and interesting stories to tell. Taking risks has also been an integral element of my path as an artist, all the way from experimenting with mediums to being part of shows. In fact, I believe it’s an inherent aspect of the artistic process. Read more>>

Tara Nalty | Salon Owner, Mom, Partner, Daughter, Friend, Tired

As far as taking risks… I feel like I’ve done it my whole life, and it’s guided me along my path. I don’t necessarily look at it as “taking risks” though, I look at it as following my heart. Taking risks is crucial to my personal happiness. My business is my heart and soul, and I feel that it’s worse to NOT take risks… if you don’t risk, you deny your heart’s calling, and you’ll regret it. Everything that I have in my life that I love, I got from being risky. Read more>>

Natalee Newsom | Real Estate Broker – Entrepreneur

Live fearlessly. Be courageous. Take chances. You will never know if you don’t try! I’m a risk taker, always have been. Big or small. I lean toward the big risks maybe more so than others do, but if you don’t try, how are you to know if your idea could ever work? I have moved across the country, away from my comfort zone, to take a risk, not knowing if it would work. I started businesses, not knowing if it would work. Hard work and dedication are the only reasons I am here and still striving forward today. If you treat failure like its not an option, it wont be! Read more>>

Annie Pieper | Education Director at Cottonwood Center for the Arts, artist

I suspect that the first impression I give people is “nice” and “accommodating”, but risk-taking has created and defined success in the arc of my life, both personally and professionally. Even though it’s been terrifying, I’ve said “yes” to a lot of crazy-sounding opportunities, and almost every one has resulted in making me a better human and a better artist. I moved in with my now-husband after losing a game of pool (to him). I took a job gold leafing the dome of San Francisco City Hall with zero prior experience (I’m an expert now). Read more>>

Meredith Waller | Licensed Therapist, Anxiety + ADHD Specialist

My relationship with risk has really shifted over the past several years. I mean, I specialize in anxiety for a reason, and as a life-long worrier I have avoided risk at all costs. However, I’ve learned that being uncomfortable does not mean that I’m unsafe, and a lot of the best decisions I’ve made have required me to take risks. Ultimately, I think taking risks is required for growth- putting ourselves out there for new relationships, leaving the comfort of a job/situation for our happiness, allowing time to learn new things, and so on. The key seems to be acknowledging that there are risks to staying in our little bubble of comfort, too- the risk of not achieving our full potential, of not finding joy, of not experiencing life fully. It’s all a choice. Read more>>

Mia Anderson | Photographer and Creator

When it comes to risk taking, it can be hard to measure the amount of risk to the amount of success it can bring. But the fact is that sometimes you just have to take the risk or you’ll never know what amazing things you could accomplish! I jumped into professional photography and its been great! I turned a small profit in my first year which is crazy! Plus the work is very rewarding and I like making people happy! Some risk pays off, you just have to decide whether you’re willing to see it through to the end. Read more>>

Ryan Waters | Owner – Mountain Professionals

Though I am a professional adventurer and guide who has been in and around lots of real risks in my career, there is a specific decision I made that sticks out for me regarding taking risks in life… which now pertains to my business directly and where it led me. I worked as a geologist after college for a few years in consulting. I loved the work for the most part because I had a good mix of field work and office work, with a bit of domestic travel mixed in. Read more>>