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.

Shirley Martinez | Teacher and Plus Size Model

“You can not swim to new horizons until you have the courage to lose sight of the shore.” This quote from William Faulkner spoke to my life in many occasions. I was born and raised in the small Caribbean island of Puerto Rico. My childhood was not filled with extravagant gifts and trips but it was definitely full of laughter. Even though we didn’t have a lot, being able to listen to my father’s crazy youth stories while we drank a delicious “chocolatito caliente”, seeing the ocean of stars that lit up our balcony when the electric lights went out and feeling the intense rush of hiding between plantain trees while hearing my primo’s footsteps getting closer while we were playing hide and go seek, filled my heart with joy. Familia was everything to me! Read more>>

Rogers Healy | Owner / CEO, Rogers Healy Companies

In both life and business, I’m a firm believer that you won’t get anywhere exciting without signing onto some risk. It can be a scary and daunting thing no doubt, but ultimately in order to find yourself at a place of earned happiness and respect, you have to have the guts to embark on the unknown. Time in and time out I’m going to bet on myself – that’s just the kind of person I am and how I operate. The decision to pursue real estate and put myself out there is just one example of how I’ve wagered money, time and reputation in the name of drive. Read more>>

Imagine Renovations – Luis & Isabel Gachuzo | Owners/General Contractors

Risks are opportunities waiting to be discovered by those brave enough to embark on such journeys. I know, I know. You can almost taste the coffee from the mug this statement is written on. This sentiment is motivational, idealistic, even romantic, but to us who have lived the literal meaning of that sentence, it holds real and heavy weight. Luis and I have taken a lot of risks for our lives, both professionally and personally, but the truth is, risk-taking is our heritage. Risk, for us, is a constant companion, one that has traveled with us through many generations, various terrains, and ever-manifesting political barriers. It’s just been a matter of whether we will allow that risk to terrorize us or motivate us. Read more>>

Adeline Rock | Wedding & Engagement Photographer

I think everything making my business worth doing or even anything in this life wouldn’t be anything of substance or quality without risk. There’s a quote I love: “God placed the best things in life on the other side of fear.” I try my absolute best to live my life by this because I’ve never heard anything of higher truth. Taking risks, like side-stepping college, having enough confidence in myself to run a business without a true backup plan, or even making the first large investment in my business, is exactly what has led me to the amazing business I get to run today. Read more>>

Jason Stallings | Artist

My post-art school career has been all about risk-taking. Though at that point it’s been quite a while. When I got to the end of my time at SCAD, I had a portfolio that I would call a bit too “safe.” I was pushed to get better in regards to my drawing skills. That definitely proved to be an asset in the long run, but I had let certain influences poison the well of my creative process. I loved studying Illustration. It provided me with a lot of structure and challenges. However, I had to push against all of the rules I had learned in school about what it meant to make art effectively. I have a lot of respect for artists who are masters of simplicity, but what made sense to me was finding order in complete visual chaos. I got out of college just before the great recession. Read more>>

Bethany Anderson | Speaker | Spiritual Coach | Story Artist

Risk is an adventure. Without risk-takers, our world never sees progression. Read more>>

Bethany Powell | Stationer, Calligrapher and Artist

I’ve never been great at taking risks. I’m a very planner-oriented girl, and when things don’t go according to my plan (as things most often don’t), anxiety creeps in. So the fact that I’ve taken more risks than I can count during the course of owning my business is absolutely crazy. But without all of the risks I’ve taken, I wouldn’t be where I am today. Cheesy? Maybe. But it’s so true. One risk stands out among the rest. It’s a beautiful story and one that I’m always so giddy to share. During the first 3 years of getting my business off the ground, I had many many side jobs to help with cash flow. One of those jobs was a nanny job. This was seriously the best arrangement I could’ve asked for. I got to watch the sweetest baby girl a couple days a week, and during her nap times, I was able to answer emails! Read more>>

Stephanie Blair | Professional Organizer

After working as a teacher for ten years, I decided to take the leap of faith and pursue organizing full-time. I had some incredibly loyal clients and the belief that I would just make it work. I’ll never forget the moment I resigned and the subsequent phone call to my disbelieving husband. It was a tad impulsive, but I do not regret the decision for even one second. I believe that there are times in life when you just need to jump and do what you feel called to do. I feel blessed to call this my full-time job and am thankful that I listened to the call to do it. Read more>>

Brian Lambert | Musician Artist

Measuring risks is everything in running a business and most especially in being an artist. On one hand, I want to take as many low risk /high reward activities as possible. These activities allow me the potential to hit that home run. In recording that means experimenting. What if try this effect? What if I try this approach? Try it and if it doesn’t work, I’ve learned something. When it does work I’ve found some magic. In art feeling like something is a risk means I am probably getting down to something that really matters. When it doesn’t feel like I’m out on the edge then it probably isn’t going to have an impact emotionally. In big decisions the risk boils down to the question, “How will I feel about myself if I don’t take this risk?” I get one shot at life, I think. Read more>>

Hilly Holsonback | Artist

To be an artist is to take risks. To create takes courage. I’ve always centered my practice around risk-taking. With my career as a multi-media artist, I examine the order in which things are done. Understanding there is no right way has given me the freedom to move around in realms I should have no business existing in. That’s the wonderful thing about risk-taking… to jump into mediums unknown is to work against your better judgment. Let these very risks inform the medium in which you are familiar. My photo work has evolved by decorating it with these outsider experiences. Something as simple as changing the roles of your tools can feel risky but lead to a burst of new ideas. Read more>>

Abenaa Adjei | Independent Consultant, Digital Products + CEO & Founder of Basics et al + Owner of

I see risk-taking as a spectrum. On one end of the spectrum you have the risk-adverse, and on the other end you have the aficionados. I used to be risk-adverse, but over time I have gradually dialed it up and currently reside comfortably in the middle. The risks I take are approached with a cautious disposition, but I’m still challenging myself to try new things and get comfortable failing rather than not trying at all. Read more>>

Jeffrey Mason | Entrepreneur, Author & Podcaster

Risk is part of life and central to entrepreneurship. In business it is important to calculate the risk versus reward. Is the view at the top of your goal worth the climb? Failure is also part of the risk vs. reward equation. In my opinion, the best lessons of life are found in failure. What may look and feel like defeat might be an opportunity in disguise. I failed in my first two attempts to start companies. Mt third attempt worked and the business is now 14 years old. Without embracing risk I would not be where I am. Read more>>

Reuben Lael | Singer/Songwriter & Activist

Each risk you take naturally sharpens your talent. I learned young and quickly in all aspects of my career to not let emotions sway you from playing to your strengths. Mom always encouraged me to never let weaknesses hold me back when faced with good opportunities in life. Stay ready!  Trusting the unknown is not easy. It takes faith, and faith in yourself! Doing the math and counting the cost is always step #1. Fear is natural but when you got what it takes… go for it! Read more>>

Karen Chatham | Artist of the Wild Horses

Risk taking in art (and life) is always an adventure that enriches my life whether it ends well or not. All risks result in learning experiences for me but most of them are life changing. For example: I was very determined to get from Texas to NW Colorado to see the wild horses with my own eyes and photograph them for future paintings, so I took the chance and traveled alone. I slept in my car for two nights and thankfully, a friend who knew the area and the horses met me there and took me to where the horses like to hang out. It was so exhilarating that I planned another trip this past summer with another artist friend. I contacted wild horse photographer friends and they met us in Utah and in Wyoming to take us out to photograph the horses. Read more>>

Jenny-Rebekah Miller | Photographer

I think starting your own business is a risk, along with every decision made after that. Most decisions will directly effect your business. It’s easy to work for someone else with a guaranteed paycheck. My husband helped me decide that doing this business my own way was what wanted. I love the fact that I will either succeed or fail depending on myself and how much I’m willing to put into this. Read more>>

Tom Lail | Entrepreneur & Artist

Risk is necessary to design the life people day dream about having. Taking calculated risks to get what you desire, seems to be the only way to make things happen. Before I opened my Management Company and my Fitness gym, I would ask myself over and over again, can I live without these things in my life? If the answer was no, I can’t live without them, I would purse them relentlessly. Taking any risks financially, emotionally and spiritually to achieve opening the businesses, and becoming successful in them was the driving force. Risks equal rewards. Read more>>

Braden Daniels | Leadership Strategist & Mentor @ Lead Like a Magician

In my Lead Like a Magician Leadership and Creativity workshops I talk extensively about The Three Sirens of Fear. In Greek mythology, a siren’s enchanting ballad would lure sailors toward their peril by crashing their boats into the rocks or by compelling them to leap into the ocean. Symbolically, these three Sirens represent Temptation, Desire, and Risk. The siren of risk sings the verses of self-criticism. It is a disempowering habit of expressing adverse, disapproving comments, or judgments against oneself. This inner voice focuses your attention on the risk that you aren’t good enough, you don’t know enough, your competition is better than you, and no one cares what you have to say anyway. This siren song enters your ears and goes deep into your being, attacking your credibility and eroding your confidence. Read more>>

J.D. Moore | Visual Artist

I think risks are immediately associated with one or multiple fears. I have for a long time now thought about fear as an emotion that should not be ignored or mitigated, rather felt and then redirected. Risk taking in my life has helped me evolve and mature as a person and as an artist. I am often times met with the challenge of venturing into uncharted territory that requires me to face some insecurities. When I was younger, those uncharted territories were driving on the highway for the first time or talking to a girl I liked. Presently, these new terrains are exhibiting my artwork in large, public venues in the form of murals. The risks I have already taken and overcome has been simply executing and completing my first pieces, not knowing what challenges would arise for it to come out as intended. Read more>>

Zan Truluck | Visual Artist, Clothing Designer & Creative Consultant

I learned about risk early. I’m from an urban East Coast environment and you’re hardwired early on to scan your environment for risks/threats and learn how to mitigate them. You might be 8 years old on the subway alone and need to figure out how to get home and avoid any interactions that might not allow you to make it there in one piece. So I guess I’ve always thought of risk in the context of avoiding any potential harm and when that harm is unavoidable, lessening the blow. That’s where calculated risk comes in. I’m ultra-logical. Often times to a fault. But it serves me well in business because I won’t assume any risk without forecasting potential countermeasures. We can’t plan for everything, but I know there are a couple life maxims that have helped me navigate risk and seek opportunity. Read more>>

Christian Hoyle | Director of Creative and Digital

Everything in life is a risk. I’ve always been one to jump into risky situations head on. It doesn’t mean that I’m not terrified of the risks, I just prefer to try and fail rather than live a life filled with “what if’s”. Risk is meant to push us forward as creatives. A safe place is not conducive to the best creative thinking. Now, I’m not saying we should sit on train tracks to come up with the next big idea; but we have to get out of our bubbles to see and understand who we’re communicating with. This is the way the best ideas are created. One of the biggest risks that I ever took in my young adult life was after my father unexpectedly passed away in my junior year of college, leaving me financially and emotionally high and dry. My father was a strong figure in my life. His influence on me reverberates to this day. Read more>>

Jack Charles | Singer/songwriter & Performer

Fear is there to be faced. When you run from fear it has already possessed you. Art in general has been culturally pigeonholed as a risky endeavor. Therefore, to become the artist is one of the greatest acts of courage. It comes down to one question: will you follow the fear that risk ignites and bury the artist? My answer is absolutely not. Read more>>

Matthew & Andrew Reyna | Filmmaker Duo

As filmmaker’s we have made all sorts risks and choices that have lead to great opportunities, and some that really didn’t go anywhere, some we even regretted. But when we came up with the idea to create our own documentary series we really jumped in feet first right into the unknown. Making a documentary series on our own definitely carries plenty of risks, especially with the type of subjects we cover. The series is very different than any other docu-series we know of. It’s really dark, weird, strange, even disturbing & funny at times, yet it’s what we want to create. But you still have the questions every artist has: Will people respond well to this episode, will they be interested in it? Early on there definitely was some concern on making 20+ minute videos for a platform like Youtube which, at least in the past, has historically specialized in short form or fast paced content. Read more>>

Mariah Jackson | Reiki Practitioner

Taking a risk is like diving into an ocean. You’re unsure about what you may encounter. You don’t know enough. Will this risk be successful or will it lead to failure? But that’s also the beautiful part about taking the risk. You truly don’t know what may happen. Consequently, when you think about the negative outcome more than the positive outcome, that’s exactly what will manifest until your life. When creating Sync’d Life, I had to take a risk to reprogram my mind and step out of my comfort zone. I listened intently to my intuition and allowed my desire to push me towards a more purposeful life. Once your desire is rooted in something, taking the risk is easy. Read more>>