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.

Grant Terzakis | Actor & Photographer

Risks suck. They force us to be vulnerable and that is downright horrifying. But that really is the beauty of taking a risk. As blissful as it may sound to live your life fully protected by the status quo, living a life without taking any risks, especially as an entrepreneur and an artist, will leave you treading water until the end of time. A lot of people talk about how they took a big risk and it paid off and led to their success. While I love a feel-good success story as much as the next guy, this paints a romantic and unrealistic view of risk taking that makes it seem like its always going to work out. It warps our perception into thinking that if we “just go for it,” everything will fall into place. In most cases it wont. We end up crashing and burning. We feel dumb for taking the risk in the first place. We are vulnerable. Read more>>

Karla Espino | Filmmaker & Photographer

Risk-taking is absolutely necessary for growth, no matter how big or small. It’s played a huge role in my life but especially at 18 when I decided to move 500 miles away from everything and everyone I knew. What’s funny is that at the time I didn’t really understand what I was risking, I just knew in my gut it had to be done. And that is the same feeling I look for today when deciding which risks are worth taking. Sometimes it can be disabling to take the leap but intuition is everything and what it comes down to is that the biggest risk of all is not listening to the ideas that visit me everyday. Of course it’s easier said than done and there is always a chance of failure, but every moment is a learning experience. Read more>>

Justine Miller | Ayurvedic Lifestyle Educator & Yoga Instructor

I’ve always been one to make sure I do the things that scare me. From writing for my college newspaper, to moving to Iowa for an AmeriCorps program, to trying out for the wildland firefighting team, operating a chainsaw, sharing my struggles with strangers, swimming in the Pacific Ocean, ending a relationship, opening up to a new relationship, and moving across the country. Each time I’ve done something considered risky, I’ve been rewarded with a deeper sense of self, courage, and the reminder that I can always change my mind and start again. As risk relates to my work, as an entrepreneur, I’ve had to bet on myself more. It sometimes feels like the greatest practice, working for myself. I’m accountable to myself and that can expose some of my shadow work on worthiness. Read more>>

Brian Bonanno | Photographer

Risk taking is not easy, if anything, I still am working on taking risks. When I am out doing photography or taking on gigs, I acknowledge that mistakes could happen, you just have to not be afraid of making them. I find the same goes with any form of art, I am also a musician and I got back into taking piano lessons over the past year. Although I tend to mess up sometimes, it would not lead me to my goal if I do not practice. Any new skill or opportunity that you dive into is a risk that you are taking. Read more>>

Irene “La Sentío” | Professional Flamenco Dancer & Teacher

As an artist I think risk must be part of our lives on a daily basis. If you don’t leave your comfort zone you will never know where you can get to. Art in itself is risk. It is commitment to yourself. It is challenge. Personally, I wouldn’t be the person I am today if I wouldn’t have risked everything by leaving Italy and moving to Seville with the only purpose to become a professional flamenco dancer. I was so determined because I needed to express myself and I found in flamenco the perfect channel to do it: flamenco is my therapy. Read more>>

Jose Andres Cortes | Photographer, Cinematographer & Film Colorist

I believe risk is that “something” that makes you advance in life. Risk is about listening your instinct and no matter how low or high it is the risk you’re taking, you just won’t be the same after it. I was someone very reluctant to it. Always tried to play “safe” and conformed myself with the kind of life I was living at the moment, it was just easier. However, my passion grew stronger and ended up making me leaving the comfort and steadiness of my job and hometown to start a fresh new life in a new country to follow my passion and work into what I love. The result? The greatest decision I’ve made in my life so far. Read more>>

Pejmon Noori | CPO (Chief Pickle Officer) & Co-Founder

If I have learned anything it is that the risk of not taking one outweighs the risk of taking too many. Being a small business owner is a big risk in itself. However, it is the risks taken during the daily decision making process that generate the biggest uncertainty. I have been both an employee in a large company and now a small business owner and risk analysis and decision making has been the most significant learning experience for me. When part of a large corporation the majority of decisions are made at the top tier of management, with every employee underneath left to implement said decisions. As a small business owner, every single decision is left up to me, which means every decision I make has some degree of risk to it. Whether it be product related or budgetary decisions, every time a decision needs to be made, there will be some sort of risk attached to it. Read more>>

Karin Liljegren | Principal & Founder

Taking risk = evolving and moving forward. Risk is essential to growth. The greater the risk, the bigger the growth. Failure with risk is also part of our growth. I quit a wonderful job of 15 years that I loved to start my own company in the middle of the Great Recession in 2009. I was also recently divorced and a new part time single parent. This was my greatest risk and my greatest reward. 10 years later my business is thriving with almost 40 employees. Read more>>

Bernadette Capulong | CEO & Founder

I believe risk is necessary, especially if you want to achieve big things. Starting my own business at the height of the 2008 Recession, was a massive risk. Yet, had I not taken this risk, BC Design Haus wouldn’t be where it is today. Even being a small business in this current crisis poses its own risks. However, I find moments like these to be defining and powerful. These high pressure scenarios can define who you are, and currently, they’re defining me, my team, and BC Design Haus in spectacular ways. Read more>>

Michele Guzy, C.Ht. | Hypnotherapist & Mind Coach

International author, Brene Brown asks, “What’s the greater risk? Letting go of what people think or letting go of how I feel, what I believe and who I am?” Risk is an innate part of being human. It is with us every second of the day, from the moment we are born, until the time of our transition. Every time you drive your car, fall in love, start a new job or make an investment, you take a risk. Any and all of which could have positive or negative consequences in life. To risk is to face your fears. And, as the Nike slogan says, “Just Do It”. Risk comes from one of the most powerful mindsets a person can have and it can open doors to surprising new adventures. Learning how to navigate the challenge of taking risks has been a big accomplishment in my own life. Read more>>

Christina LaRocca | Musician & Entrepreneur

They say risk equals reward, which is true, but so is the opposite. I believe the key is being prepared for both in life and your career. I have done some very risky things in my career. Like driving thousands of miles around Europe on my own for three weeks while on tour. Or when I decided to quit my job at a great talent agency and lost my health insurance to pursue becoming a full time musician. There was also that time I dropped everything and relocated to Los Angeles and moved in with someone I had only been long distance dating. Well, the good news is, I didn’t crash on the autobahn or get kidnapped in Europe, nor did I ever regret leaving that toxic job, and that long distance boyfriend? He recently became my husband. My advice? Look for the signs. REALLY listen to your head and your heart. If something DOESN’T feel right in the depths of your soul, then DON’T do it. Read more>>

Maxine Roediger | Performer

I think my life wouldn‘t have turned out the way it did if I hadn’t taken a risk. It started with my family leaving our home town and moving away to a completely different country without even speaking the language. We were all very scared and worried because it was a huge risk. No one ever knew how it was going to turn out. But isn‘t that what risk-taking means? You just don‘t know the outcome. After some pretty good experiences, I thought that risk-taking always ended well, but obviously, it didn’t many times. I had to go through many ups and downs, to finally realize that risk-taking, requires a lot of bravery and authenticity. Without that, I wouldn‘t be where I am today. Being an actress drags me out of my comfort zone every single day and I always have the need to take more risks, because, without risk, there is comfort, and comfort just means to stay exactly where you are, without moving one tiny bit. Read more>>

Stephen Cofield, Jr. | American Actor & Producer

I’ve had a pretty difficult go at taking risks early on — especially the two biggest ones that have shaped me for who and where I am today. I’ve always wanted to pursue a professional acting career but I was afraid to take the risk. I had just graduated from college, ended up with a really good (but) flexible job and thought.. that was it. It wasn’t until I understood that there was more to life than what I did at a cubicle for 40 hours a week. With the influence of close loved ones and the desire to get the most out of a career, I decided to pursue the journey there with acting. That was risk number one, believing that this idea was attainable. Now it meant that seeds will be planted to take the next big risk — which is leaving the 9-5 life to pursue acting full time. This move wouldn’t come for another 12 years surprisingly. Read more>>

Ali Wigart | Designer & Product Developer

As I reflect on my professional career, I’m a bit flummoxed by the juxtaposition of how I apply myself in the office versus my personal life. When it comes to work (and historically school) I am calculated, prepared, buttoned-up and, some may say, even serious (ahh!). However, at home and in the company of my community I am spontaneous, outlandish and boast a strong sense of personal, often risk-taking style. I don’t find these opposing selves to be a weakness but I do believe it has forced me to have to work extra hard to find equilibrium. My biggest take away on this bumpy ride of interpersonal growth is that I’ve learned I need to be more fluid and a bigger risk-taker at work. I need to remind myself that the confident, go-with-the-flow persona I identify outside of work exists; And she needs to show up at the office sometimes too. Read more>>

Allison Epstein | Reiki Healer, Soul Advocate & Speech Therapist

The phone rang, it was my manager. “You’ve run out of time,” she said. “You need to report back to work or else we will consider your lack of attendance job abandonment.” When COVID hit, I was working the daily 9-5 grind as a medical speech therapist at a rehab hospital. There was no work from home option, as I was considered an essential worker, but I also had a young daughter now at home because of school closures. I had to make a choice and both involved risks. Should I stay at my secure job, or leave for good and risk financial instability? Intuitively, I felt it was the opening I had been dreaming of – I could finally have autonomy over my schedule, spend more time with my daughter, and have the ability to invest 100% of my energy into my newly established Reiki healing business “Soul Advocate.” I remember taking a deep breath on the phone when I told her I had to leave. Read more>>

Roy Vongtama | Actor, Doctor, Producer & Writer

I think I have taken a lot of risks, but since I have been living the life of actor/doctor for about 15 years now, it’s doesn’t have the same feeling of risk it once had. For me, where the risks lie becomes clearer when I talk with my friends. When I speak to my doctor friends, they often envy the freedom I have being an actor, and they don’t dwell on the financial risks I took to make it happen. When I talk to actors, they see the safety I left behind when I decided not to practice full time medicine- I think they inherently empathize how risky this career choice is. Read more>>

Brette Genzel-Derman, Psy.D | Clinical Psychologist & CEO

Being willing to take risks has everything to do with the success of my company, Innovative Group Psychotherapy, Inc. As a psychologist with no business training, it seemed daunting to start a business. However, after seeing Sonic Highways – HBO’s documentary profiling the Foo Fighter’s journey to create their 2014 album – I found myself on the brink of an innovative therapeutic discovery. The series profiles Dave Grohl, the band’s lead singer and former drummer of Nirvana, interviewing talented musicians across the country as inspiration for his album. Feeling passionate about the concept put forth in the series, which used interviews as the back drop for unique lyrical creations, I developed a therapeutic songwriting curriculum. Since I was using his idea, I took a giant risk and reached out to Dave Grohl. Of course, I never thought a rock star would respond to me. But I had nothing to lose. Read more>>

Amy Smith | Artist

Risk taking is important to everyone especially artists. I tend to make decisions based on my goals and what’s going to make me the happiest. I’ve had to make a couple scary decisions and pivots in my life. They were all really hard to make but ultimately they ended up being the best decisions. I don’t shy away from taking risks. I try to only consider how I honestly feel about the risk or decision. Knowing what might block you or what your natural excuses will be is helpful. Knowing yourself as much as possible will help you make those tough decisions. Read more>>

Kevin Loucks | International Concert Artist & Arts Entrepreneur

Few words elicit such polarizing emotional reactions as the word “risk”. Some individuals will immediately associate it with a sort of reckless bet, something that is perhaps motivated by explicit greed. Others will see it as a golden opportunity to better a strategic position for themselves and those around them. In both cases, the word requires an absolute willingness to explore and embrace something that is unknown; a commitment that has the power to transform this feeling of fear into something much more productive. There is also an inherent learning opportunity built in to risk-taking that rewards those that are willing to embrace it. This process for me – a blend of research and information gathering, flexibility in the way that I approach my goals, and hopeful aspiration – has led to some of the most successful outcomes I have seen in my peer group. Read more>>

Matthew Schildkret | Creator

The risk of living everyday… That’s something isn’t it? My life, my career, why even label them? Where do you live? Where do your co-workers live? Who do your kids go to school with? When I look inside myself about the risks I take, within the circles that I roam? Sometimes the risks are bodily, sometimes they are romantic. The risk in what I do, is what I do. I have been making scarfs, ascots, shawls, bandanas, pocket squares, and handkerchiefs since 2012. I’d define the decision to go from the Obama White House to making scarves in Venice Beach a huge ‘Life’ risk. Life is meant to be lived, shared, loved, created. I live to create. Any time I make a choice I create my reality. Late Sunday Afternoon is my reality. Read more>>

Ken Steimle | Artist & Teacher

My life has taken many twists and turns. Moving across the country from NY to AZ was a huge risk. Forgoing art college out of high school was another risk. My life was unconventional and filled with hard work. I learned art techniques and how paint works by spending countless hours in the studio. I went to college as an adult taking twelve credits a semester while working full time. My wife at this time gave birth to a baby boy Milo Venn Steimle who was born two months early at two pounds eleven ounces. Milo was in the NICU for a month and each day after work I would drive to the hospital with my school books in hand and spend time with him. Countless hours in the NICU with my son Milo changed my life. It gave me a new and fresh perspective on how I saw the world. Read more>>

Jennifer Walton | Entrepreneur & Professional Violinist

The vast majority of my career has involved a great deal of risk taking. Apparently, there is a risk taking gene and I am sure that I have it. I have always reached out to people, expecting that I may get no answer at all and then when I do get a response, I am quite pleased. When I reach out for a job that I think might be unattainable and end up getting it, I feel very satisfied. It makes me want to continue taking risk to provide work not only for myself but for hundreds of other people. Read more>>

Misha Crosby | Filmmaker

When I was a kid one of the best pieces of parenting I received was that I was always encouraged to try and follow what made me happy as a career. This isn’t always easy of course and being practical when it comes to surviving in a place like LA, thousands of miles away from any family or support can be very challenging. I believe that you’re most valuable commodity is your time, and risking that on things that don’t serve you well can be very hindering. There’s definitely been a learning process on that for me and I’ve be forced to be more and more efficient with how I spend it as my responsibilities have grown. Years ago I saw Jim Carey speak about how his father could have been a wonderful comedian, but he made a more conservative choice and got a safe job as an accountant. Read more>>

Andy Striker | Owner

Take a risk without fear !You can’t lose what you never had, when you have it hold on tight! If I did not take risks I feel I would have done myself a dis service in not making the most out of the gifts i have received. Read more>>

Wara Pornkulwat | Director of Photography

Risk taking is necessary in my career, especially in career development. As a DP, I was starting out as a camera assistant until I felt I really want to make some changes in my life. To pursue what I really want I took a risk of quitting my job and was getting no job at all as a DP at the beginning. However, it paid off in the end and I’m now going in the way I always wanted. Read more>>

Stefanie Templeton | Owner & Teacher

The Merriam-Webster Dictionary describes “risk,” as, “to expose to hazard or danger.” When I think about risk, I usually do not think about it in terms of physical hazard or danger as most of the risks I have taken have seemingly been existential in their implementation. I have consistently been someone who weighs my risks and plans accordingly. This doesn’t include the time I went sky diving in New Zealand over Mt. Cook during that lone backpacking trip I took after my father passed away in 2002. When planning for a career as an artist, I chose not to go to an art school as I preferred to immerse myself into a community of people on various career paths. That’s what I told myself. Read more>>

Sarah Stone | Art Maker

I left a job on the East Coast for a possibility of doing something different, maybe better, on the West Coast. I had no knowledge of LA, 2.5 contacts, no place to live, no job prospects, just a desire to make a big change and see where it took me. The take-away for me was, I made a difficult leap and didn’t fall flat on my face. In fact, I made friends, found work and built a career. When I feel intimidated about trying something new, or letting go of old habits that are no longer productive, I remind myself that “risk” is just another word for trying something new. Being an artist requires overcoming shyness, being an outgoing introvert, dealing with frequent rejection, making complex business decisions, stretching out of comfort zones and trying new things all the time. The old shark analogy: gotta keep moving. Read more>>

Danny Star | Founder & CEO

Risk taking has formed the foundation for my career. It was the origin. After the recession, the car dealership business was done. I knew I had to do something. Creating Website Depot was a risk worth taking. More than that, it was a start. Too often I feel, people realize that just “keeping on” is a risk in and of itself. To try and ride out the recession without switching careers may have seemed like “the safer bet,” but really, it was the opposite. Since then, taking informed risks, backed by research and following intuition, has helped in business and life. Read more>>

Tony Rockliff | MultiMedia Producer

I think taking risks is a vital part of career growth, and every upsurge in my life has been preceded by taking at least one pretty wild risk – doing something that caused others to say (literally), “You’re nuts!” https://tonyrockliff.com/how-to-not-break-into-the-music-business/ tells the story of a few of these in my life. It details how I escaped from Jesuit boarding school in the middle of the night, formed a band with gang-members, flew to Beirut and lived through a war there, and then talked my way into a recording studio job that led to my career as a music producer. Another time, right at the start of the Internet, I built a massive web community in 3D multi-user Virtual Reality – at the time when modems were super-slow, and when what we were attempting was considered beyond impossible. Read more>>