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.

CIRE B | Visual Artist + Owner Of Cire B Studios

As a visual artist, risk-taking fuels my creativity and pushes me to explore new techniques, styles, and concepts. It’s the backbone of innovation in my work, leading to breakthroughs and original creations. Without taking risks, my art would become stagnant and predictable. However, calculated risks allow me to push boundaries while still maintaining a strong foundation in my craft. Ultimately I find that the GREATER the risk the GREATER the REWARD! Read more>>

Lindsay Dills | Media Composer & Violinist

Risk taking is such an interesting part of the human experience. We wrestle with the anxiety of putting ourselves out there with the potential to fail or playing it safe with the potential for regret. In my own story, I have tried to live my life after some advice my father gave me. He shared with me that it was important to reach for the highest stars in whatever dreams I wanted to achieve, because even if I jumped and didn’t reach the farthest one- I would be closer to my dream than if I had aimed lower than what I truly desired. Read more>>

Bea McCormick | Artist

It’s kind of funny, and perfect, that I’m answering this question at this point in time – I recently put in my 2 weeks at my day job in order to have more time and space for my art practice. The moment I decided to leave the job, I felt simultaneously that it was a risk, a crux of my decision making for my adult life, and that I could not have made a different decision. As I become more and more aware of the economic ramifications of quitting a secure, almost full-time position, to pursue art, the feeling of exhilaration grows, as does my overt awareness of my personal monetary and social security. It feels like a risk because I gain a huge amount of responsibility not only for my personal welfare, but also towards my practice and work. I have a responsibility to make that decision count, to make art worthwhile of mine and others’ time & awareness. It was, to me at least, a necessary risk, one that I couldn’t skirt if I actually, tangibly, want to invest in art as the thing that I do, the thing I’m committed to. Read more>>

 John Karyus | Actor

As an actor, everything I have done from day one is some sort of risk. The idea to pursue it in the first place was definitely a risk. Read more>>

Maria A. de Hollanda | Independent Marketing Communications Consultant

Risk-taking is integral to professional growth, requiring individuals to navigate uncertainty while weighing potential rewards and setbacks. By embracing risk, individuals can propel themselves forward, uncover untapped potential, and foster innovation. Calculated risks contribute to professional growth, resilience, and the development of essential skills like adaptability and resourcefulness. Read more>>

KOOMASAE The Revolutionary | Artist

Risk to Reward; Cause and Effect. These are dualities in life that are inevitable! Although we do get a chance and a choice each day we wake. Through my own experiences I have learned that taking the “risk” which feels intuitive with my divine calling brings about great reward. In Today’s world we have become feens for instant gratification, the hit of dopamine or serotonin. As one of my great brother’s says, “Patience Pays.” Read more>>

Kendall Goodman | Songwriter

Taking risks has been the most pivotal thing that’s gotten me where I am as a songwriter. Sending that one song to that one person that might just listen to it could give it a life off the hard drive, pitching song ideas to an artist or their team, or even posting silly videos and putting my music out there could catch the right attention. All of those risks have been met with acceptance and rejection in my experience. plus, both responses helped me move the needle in some way. Read more>>

Ian Donlon | Entrepreneur, Mentor, & Philanthropist

Risk taking is something that has definitely played a pivotal role in my own life and the lives of others who I have seen create what they want in any area of life. Read more>>

Alex Hernandez | Cultural storyteller. Videographer and photographer.

Risk for me is something I was always taking without realizing it. Both of my parents to a risk to leave their home country of Mexico to start a new life here young age. as I grew up, both of my parents took bigger risk in order to bet our lives on here. I ended up moving to Mexico and going to middle school there. I came back to start high school here and finish it. Both of those moves were risk I had taken without fully understanding what it could’ve led to. I look back, and I’m very thankful for taking those risk as it advanced my understanding and knowledge of both lives in the US in Mexico. as I got older, I fell in love with my passion of photography and videography. Four years ago, I had my daughter. And I asked myself can I take one more risk in order to pursue this passion and make it into a career. it was a hard decision as I Still have responsibilities that would not stop even with this financial and career change risk. If I can at least say I’ve tried it and show my daughter and family that we are allowed to take risk and potentially see the life we want then I’m going to take it. I am on month number five of going full-time with my photography and videography as I left my career of five years in the automotive world. Read more>>

Sean Flores | Self taught artist

Taking risks is very necessary when trying to get to the next level. I took the risk to quit my day job and went full fledge with art. Never looked back since. If it wasn’t for my risk taking I’d still be working a 9-5 Read more>>

Maddox Haberdasher | Fashion Designer & Philanthropist

When it comes to risk, there are two mantra that I try to live by: Fortune Favors the Bold and No Risk, No Reward. I served as a paramedic in the US Army for 11 years and these two mantras have worked for me time and time again. Read more>>

Andrea Cabrera Jakucs | CEO, Psychotherapist, & Speaker

I wouldn’t be where I am today if I didn’t take a risk. Life is all about risk-taking to get ahead and get better so do it. If you don’t take a risk, you may miss out on life or have regrets. Go to therapy, do online dating, apply for that job, ask for that raise…take a risk, Don’t live in fear. Celebrate failure. Read more>>

Sang Eun | Artist

Risk taking to me is the same thing as accepting it. My type of risk taking is to put my trust on the idea with a bit of that…psychological tension that comes from my expectations. And, whether that expectation comes true or not, I always find it more interesting about the process of risk taking. To think about what “Risk” is important to me. Why do I feel risky for further action? If I’m being hesitant, why hesitant? what is so important about it? Why do I put value in this? Then, I finally allow myself to think more rationally about the situation and take a step back for a moment to see from a wider angle. Read more>>

Chaewon Suh | Filmmaker & Photographer

I remember one of the professors at Chapman said this in our orientation week, “Comfort zone is where your dream goes to die.” I try to think risk is opportunity to grow. As much as I put myself in a risk, in a discomforting situation, it means I’m leading to somewhere. I’ve made several choices in my life based on this view and it only made me move forward. Read more>>

Toni Blackman | U.S. Hip Hop Ambassador

For me, risk-taking has been an intrinsic part of the journey—a testament to the audacity of dreams and – I don’t like the word anymore but resilience. Leaving home at 17 with just $300, a few suitcases and a trunk, and an unwavering determination to pursue my dreams at Howard University was perhaps the boldest risk I’ve taken. It was a leap of faith into the unknown. I was fueled by passion and a burning desire for something better and bigger than I had known in my life. Read more>>

315CASH | Hip Hop / Rap Artist

As I said on the hook of my most recent single release “Risks” I’d rather take the risk then play it safe because sometimes if you want the reward, you have to take the risk. All depends on if you are willing to bet it all on yourself when it’s crunch time. If you don’t take the chance you might never know all possible outcomes. Read more>>

Roxanne Engstrom | Founder & Storyteller Hawa Images

Risk IS life. If we do not risk we live small. Living in alignment and taking shaky and messy action towards your goals will mean risk but that is the ONLY way you will grow in skills and confidence to evolve and realize a meaningful, healed, connected, purposeful life. Read more>>

Mario Cabral | CERTIFIED FINANCIAL PLANNER™

Ever since I could remember, I’ve been all about taking risks. This wasn’t just some phase or a fleeting interest; it’s been a core part of who I am, deeply rooted in my upbringing and experiences. Growing up, whether it was going one-on-one in basketball, video games, or strategizing in Monopoly, I was always down to gamble, put it all on the line and had no problem putting money up as well. Monopoly, especially, hit different. It taught me early on that navigating tight spots and making bold moves was key to coming out on top. I can still recall almost hitting rock bottom in the game, time and again, because I went all in on properties and upgrades. But even when I had to liquidate most of my assets, that one major hotel flipped my situation completely, teaching me two critical life lessons: never lose hope, and embracing risk is essential for major wins. Read more>>

Shih-Chun Hsiao | Editor/Director

The greatest risk I’ve taken was leaving my stable engineering job to plunge into the unpredictable world of filmmaking. In 2018, at 28 years old, I held a leading engineering position at Schlumberger, overseeing crews and conducting wireline surveys—a satisfying role. Yet, my passion for filmmaking, lingering since college, had gone unfulfilled. Read more>>

Angeline Brunk | Fashion Designer, Entrepreneur

2 years ago I was working for a couturier in Seattle that I had been at for 13 years but I started to feel deeply unsettled and unhappy – not because of specific reasons at this company but because I knew I needed a change. I suspected I might for some time but always felt the risk was too big and I didn’t know where to begin. I also didnt know if I could stay in Seattle as there were no other job opportunities at other fashion brands at this level so I thought, now is the time to take a risk and see what other cities have to offer. And while you’re looking, you might as well explore all the parts of the world that really call to you. So I contemplated and prayed for a few weeks and then decided to take the plunge and sell everything I owned and move in 2 months. Read more>>

Daniel Troia | Filmmaker

I believe that many of our greatest accomplishments won’t happen unless we take a risk. Personally, the biggest risk I ever took was deciding to ride my bike across America without bringing any food or money with me. I felt nervous and scared before I started the journey but the experiences that happened on that trip changed my life. Read more>>

Michael Alvarez | Business Strategist, Founder, Educator, Executive Leader, Innovator/Originator, and Personal Advisor/Coach.

There is song by Kenny Rogers, called “The Gambler”. I heard this as a teenager, and have been a song-writer throughout my life. One refrain says “You’ve got to know when to hold them, know when to fold them, know when to walk away, know when to run. You never count your money, when your sitting at the table, there will be time enough to count up, when the dealing is done”. I love its succinctness and clarity – explaining (metaphorically) that in life, we all have to assess our ‘hand’ (situation), and do the best we can with the situation we are in to try to make it a winner. The proper amount of investment (i.e., time, money, and/or energy) that is worth expending must be carefully calculated. Read more>>

Starr Callahan | Multi-Disciplinary Artist: Designer, Stylist & Photographer

Being true to yourself and craft should always be in the front of your mind when creating, but I advise my fellow creatives to inquire more about the opportunities that are outside of their norm or set timeline. In the occasion where people see me in a space that I had not originally put myself, are the times that changed my life, career and perspective about my art. Now, you know in your gut when things are not right for you. I am not advising to go against that, but every time I have been slightly uncomfortable yet still intrigued, has made me grow stylistically and technically. I can honestly say that every leap of faith has paid off in one way or another. My advice with risk taking is to not seek an immediate reward. Read more>>

Ivan Giang | Sushi chef

I think risk is like a storybook about your journey in life an example would be Me meeting a girl in Los Angeles that came from Japan we dated for 6 years then soon after she moved back to Japan and ask would I like to move to Japan with her i told her I’m willing to move to Japan for 6 months to see how I adapt before making a decision. After 6 months of me being in Japan thing started going down hill with our relationship we ended up parting ways it was very difficult for us cause the bond we had for 6 year but I never regretted taking the risk and moving to Japan I learn a lot about the culture/ food and was able to reflect on myself. Soon after I return back to the states I was dealing with the aftermath of the split I had no motivation to create food or do anything at all then one day I was talking to my friends they help me find a way to slowly step foot back in the chef world again it was scary to take that leap of faith but if it wasn’t for me taking a risk I wouldn’t be where I am now sharing this chapter in my life. It goes to show never fear the unknown learn how to embrace the fear and risk it all better to have risk things in life then to have regret of the what if no one can predict the future or what will happen in the end of the tunnel sometimes you just have to keep pushing forward. Read more>>

Elyn Kazarian | Creative Director | Designer | Broadcaster

The way that I think about taking risks is no different than when I think about how I would feel if I don’t try something new that I’m interested in; Would I regret it if I don’t try? Even if the outcome doesn’t go my way, would I ask myself in the future, “what if”? Ultimately, I would much rather live with the failure of having tried, than the regret of having not tried. And who knows, maybe you actually don’t end up failing and finding something that you’re actually good at! Read more>>

Kiara James | Event Designer

In 2018, my parents had an intimate vowel renewal celebrating their marriage. I took on the task of creating a balloon arch for the alter with no experience at all. Orchid Creative Hub (Orchid Balloons) is a product of faith and risks. I took a risk by quitting my corporate jobs to become an entrepreneur. I took a risk by expanding my offerings from just balloons to floral arrangements, custom backdrops, stage design, digital mock ups and more. Read more>>

tahj | Music Artist & Creative Entrepreneur

It is interesting when I think about risk-taking because although I think it’s necessary to discover and achieve artistically, it is a definite privilege to be able to take risks in the first place. My parents grew up in a generation where stability was the priority — meaning, having a stable job that provides a steady income is most important to gain financial freedom and eventually generational wealth. I think I’ve just never really bought into that idea. Of course, my goals are also generational wealth, but I decided pretty early on that I was not going to settle for anything I did not have a passion and sustained interest in. That (mixed with my general aversion to authority and undiagnosed ADHD) meant that I would need to be doing something remote to allow autonomy over my schedule (life) and/or something creative to keep my mind engaged. Read more>>

Shivashish Ahuja | Cinematographer

I firmly believe that cultivating a willingness to take risks is essential for achieving success. The journey to success is often defined by one’s appetite for daring ventures and bold decisions. Read more>>

Stefani Peter | Visual Artist | Entrepreneur

I took a lot of risks in my life, personal, financial, and professional risks. Not all of them I calculated carefully going ahead. Most of the time I made decisions in a split second and was always proud of my gut feeling. I am an optimist and fundamentally believe, that everything will end well. In my professional life I took a risky leap from spending my life in the security of a German teaching job to fulfilling my dream of becoming a freelance artist. I was already 29 years old. It was a great decision. I was successful quickly and was awarded two Fine Arts Grants with 36. I travelled the world to show my art and while being in Canada as visiting artist at Malaspina Printmaker Society in Vancouver, I met a guy. He worked in Film and TV as an Art Director who suggested to start a business renting art to Hollywood North’s Film Industry. Read more>>

Dajah Dorn | Singer, Songwriter, & Model

My ultimate life goal has always been to be free. I don’t like feeling restrained in any way and learned at an early age to be free you have to push through fears or generalizations by taking risks. Everything I’ve done in my life and career, from going to the military after high school to moving from Florida to New York to persue music and modeling, has been a risk. Something I say all the time is: “I play the long game, but I’ll take a risk at any moment.” Read more>>

Matt Rosenblum | Coffee Roaster

Greatness has never been achieved without a certain level of risk involved. In what feels like a lifetime ago I was in search of security. Young and hungry, I dipped my toes in the corporate world and quickly realized I am not built to sit behind a desk 9 hours a day. My roots and heart have always been in a fast paced environment where you feed off the heat, pressure, and challenges of tackling a new goal everyday, always looking to better yourself in the process. I’ve spent the last decade battling risk around every corner, especially as a business owner. Business or otherwise, accomplishing any goal or dream involves getting out of the comfort zone and stepping up to the plate to take a few swings. Read more>>

Nathan Hemmens | Entrepreneur

When you’re taking risks, you first assess if you need to: Is the risk more than the reward? Once you know the answer to that, assuming the reward is greater than the risk, you want to map out a plan. If you’re going down a road you’ve never been down before, it’s always great to ask for directions from someone who has. Understanding this has played a vital role in my life because risk assessment is an important part of being an entrepreneur. Read more>>