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.

Marena Bronson | Journalist | Founder & Editor-in-Chief of Fashion and Fandom

I’ve never met anyone who doesn’t want to become successful — whether that’s in their career, their business, or their personal life. Not everyone is willing to step out of their comfort zone and take risks, and I understand that. The comfort zone is familiar, it’s safe, and it doesn’t involve anxiety and fear. I think it’s important to be honest about what we want and how much we really want it, rather than lie to ourselves and make excuses just to stay in our comfort zone. When we are ready to do the hard things, when we are ready to take risks for something we’ve always dreamt about… that’s when we really create the biggest successes in life. Looking back, I can’t think of many decisions I’ve regretted taking a chance, even when the end result wasn’t a “success” in the way I initially visualized it. I have more regrets about NOT taking that proverbial leap of faith even if I wasn’t sure what was on the other side. Yes, incremental changes can happen when you play it safe, but if you want something to be really transformational you need to think big, lean into the fear, and figure out how to deal with it. Read more>>

Kasey Nauton | Conceptual Artist & Designer

Even the act of taking a risk itself feels like it gives me special powers. I think luck might be a universal force, an angel who favors those who strive. For me taking a risk is always a win-win; either I am rewarded for my pain with a victory or a lesson. Tempt your fate and see how generously you are paid back. Sit around in indecision and watch your energy fade. I’ve always chosen to bet on myself, and then double down. Each work I create is a risk, an emotional and physical effort that drains me, but the risk must be taken if I want to hold a new work in my hands. I moved into my first studio a week before I finished art school, two months into the pandemic. I took a shot when the ground was shaking beneath me, and have been rewarded with joyous adventure and a series of lessons from the school of hard knocks. Roll the dice baby. Read more>>

Trudy Moylan | Artist | Photographer | Dreamer

Risk taking to me is the biggest part of being in business for yourself. Personally I have always been able to take risks with out hesitation. I am a person of intuition. I always listen to my own intuition & gut. I get gut feelings on things & just go for it. I don’t really over think or sometimes even think things out. I just know what feels right & do that. I am usually right. When I am wrong I just adjust. I seem to never succeed when I overthink things & ignore my gut feelings. I have an awareness of self that tells me just listen to your gut & go for it. I think when you know yourself & trust yourself you should just try things to see if they work. Usually the reward is worth the risk. Overthinking can lead to stagnancy. Taking risks can lead to breakthroughs & paths you may have never imagined for yourself. Read more>>

Brooklyn Janielle Miller | Licensed Cosmetologist & Wax Specialist

Risks can make or break a career, but without those risks you may never know your full potential. Starting my business has been a gamble from the start. When I decided to finally go out on my own and become a booth renting stylist, in November 2019, I had zero clientele. Somehow, I knew everything would work out and by taking that leap of faith, I am now a Owner of my own brand, Beauty by Brook Jani. Read more>>

Cherie Harrington | Realtor

Thinking back over my lifetime I would say that I am a big risk taker. I risked moving to California from a small town in upstate New York when I was just 19 years old. I saw the dream of living in warmer weather and how that could benefit my life. I took many risks in my 30+ year corporate career that would have scared a lot of people. I moved into departments that I knew nothing about but had a strong passion for. I left in the middle of my corporate career to franchise 3 restaurants that were underperforming and needed a lot of work. I was a single mother with a 5 year old daughter. Some say I failed. I say that I learned more in those 2 years as a franchisee that I could have ever learned staying in my cushy corporate job. Many years later I decided that I had enough of corporate politics and wanted to start my own business…again. It was a huge risk. I was making six figures in a career that I had no passion for. I would leave that to start up a real estate business where I would be paid on commission. Talk about scary! My friends and family told me I was crazy. Read more>>

Gabby Foley | Professional Ballet Dancer

My entire career would have never started in the first place unless I had taken the life changing risk to move away from home at 15 to go to a prestigious ballet school instead of staying in the small town in Nebraska I was from. From that point on every step I’ve made in my career came from taking huge risks. Going to audition for things I never thought I would get in to, moving back and forth across the country more than once a year, and putting myself our there as much as I could to be able to follow my life long dreams. Read more>>

Felicia Nykaza | Blogger-Creator & Advocate

At first I really didn’t think of my blogging as risky. I was just naturally sharing some elements of our lives. The world we live in is changing, evolving, my kiddo is now a teen, topics of motherhood and my worldview broaden with it, but as time went by I started to notice having some kind of push back. A sudden drop in numbers, a little more hate comments/messages needing to be moderated. And it has been just because I have a stance or addressing Human Rights topics, such as LGBTQ+ related was kind of shocking to some. I guess I was always viewed as a “Mommy Blogger” and for some reason it’s that typecasting is viewed like certain subjects such as those are off limits. Like moms or women aren’t entitled to want better. Want change. Want the world to be safe and educated for their reasons. I was shocked. Honestly, I hate to think of what I do as “brave” or “risk-taking,” but as I’ve grown, as the “Ello Felicia” Brand and Blog as grown my eyes are open. Read more>>

Dahlia Strong | Women’s Clothing Retail

Risk has to do with danger, navigating into the unknown, yet I always had a deep belief in my taste and my gut instincts, but that being said, venturing out on your own always has the deep element of risk, but that’s how life shows up when you become an entrepreneur. We all start out a bit scared, but I say do it anyway!! One needs to crack the egg shell to get the yolk out. Read more>>

Toby Ogden | Photographer and Surfboard Company Owner

When we started Culture Supply we were just trying to fill a void. We were selling some expensive surfboards for my stepdad who is Mike Hynson from the cult classic surf movie “The Endless Summer”. Mike makes amazing surfboards and they are expensive as they should be. We found that we were turning away a lot of people because they were looking for a better price. We then decided to start our side brand and call it Culture Supply Co. We would make surfboards and offer at a fair price but we did not cut any corners. We make the boards with the same materials and the same manufacturing that every board you see out there in surf shops and whatnot. We never intended our board company to turn into anything except just selling a few here and there. We are now 5 years into our business of selling surfboards under our own brand and the risks we have taken have been just 1 after another. We were selling our boards out of a storage shed for many years. Found an empty warehouse in Oceanside where we are today and just decided to take the risk of building out a showroom. Read more>>

JM Balbuena | Commercial Cannabis Consultant, Author, Navy Veteran & Entrepreneur

Taking risks is scary, whether you go against the grain on a creative piece to be displayed in front of a crowd of strangers or taking the leap to quit the rat race in pursuit of your promising business ideas. Most people tend to avoid risks whenever possible, because inaction is frequently safer than taking action, but what most successful people have in common is that they got to where they are because they were willing to take risks no one else was “crazy” enough to take. I believe taking risks is super intimidating, especially for new entrepreneurs. But it’s more convoluted than just “doing something that might go wrong.” It is impossible to start your own venture without a high metabolism for risk. Matched with resilience, intelligence, and a dose of intentional luck, high risk tolerance has the potential to lead you to greatness. On the other hand, low risk tolerance can keep you stuck in patterns that will leave you unfulfilled as you watch others take the leaps and dives you dream of, while you remain in your comfort zone. Read more>>

Raquel Miller | Professional Boxer, Clothing Company Founder, Non Profit Organization Co Founder

I live by the motto no risk no reward! I honestly believe in order to grow and get to new levels you have to be willing to take risk and get comfortable being uncomfortable. Its the only way to grow! Risk taking is how I became a boxer, i wanted to challenge myself to see how Id do in a real boxing match. It was scary yet empowering and it made me fall in love with the sport while changing my life for the better in so many ways. Read more>>

Emily Silva Hockstra | Author & Spiritual Life Coach

Risks are opportunities for growth and insight. There have been many times when I wasn’t sure how things would pan out, but decided to try anyway. Not every launch will be successful. The risk in trying is that you may get rejected. When this happens, I ask myself “What is the lesson here?” and ” How can I grow from this?” When we view “failure” as a catalyst for growth, amazing things can happen. Without risk, my life would be less adventurous. I’ve quit jobs, traveled without plans and started a business…all included some element of risk. I named my company Soul’s Adventures because I believe our soul’s nudge us to take these leaps, even when we aren’t sure where they will lead. When we ignore these soulful nudges, they usually persist. When we heed to their call, it’s amazing what transpires. Read more>>

Kris Angell | Researcher & Entrepreneur

Risks, when you run your own business, are about hopes and dreams. Hopes that your ideas, and hard work building towards them, come to fruition. Dreams of the next idea. The next adventure. I use risk as a game changer for myself and my business. Read more>>

Kathy Gomez | Hairdresser- Color & Extension Specialist

Life’s all about taking risks, right? I can’t help but chuckle and smile a little when I look back at this past year because it was nothing but risk after risk and trusting my gut that it will all work out. I was presented with the opportunity to leave my commission job that had security and consistency to go off on my own and start my own business during a world pandemic. It is the biggest risk I’ve taken career wise and I wouldn’t look back. Fortunately, through hard work and determination things have worked out thus far. It changed my life for the better and allowed me to have freedom to determine my own success. Personally I think taking risk is what life is about. It typically works out and if it doesn’t then we learn, we grow, and we move on wiser and more prepared for lifes next risk. If we go through life fearful of what might or might not happen we can only blame ourselves for being in the same place a year from now. Read more>>

Michelle Solis | Dancer, Model, Human Being

Once I became a dreamer I became a risk taker. But before I was a dreamer I was a worrier and didn’t enjoy the thought of taking leaps of faith. Now, I depend on those leaps and the trust I have in myself. I would not be where I am right now without the leaps I’ve taken. Before I decided to dance professionally I studied writing simply because I was fearful of the dance industry simply because it is so difficult to succeed. To be a paid dancer isn’t impossible but the thought of failing was so daunting to me that I shyed away and stuck with a career I knew I could be inevitably hired. Once I discovered how much I loved dance I realized I couldn’t do anything else in my life and I wouldn’t wanna do anything else in my life besides dancing. My epiphany allowed me to accomplished my dreams and accomplish goals I was too scared to even reach for. Now I’m grabbing it all without any regret. Read more>>

Brian Blindauer | Landscape Photographer

I think inherently photography has a lot of risk on its own. It’s a very competitive business and to succeed you have to put a lot of time, effort and money out with sometimes very little payoff. But with landscape photography itself there’s a lot more risk that is associated with being out in nature and trying to get the best pictures. I know for myself I can be out in the middle of nowhere with no service in search of a hidden spot for beautiful pictures. I never know what can happen out there, but I go out in hopes to get unique pictures that will set me apart from everyone else. Sometimes the risk doesn’t pay off, but sometimes it pays off very well. Most recently I was in New Mexico with a few photographers. We were deep in the Navajo Nation in probably one of the most remote places I’ve ever been. As we arrived there was a huge storm coming in. We started hiking and as we were about a mile in on our hike the storm started dumping heavy rain on us. Read more>>

Jane Kusuma | Owner of Jovietajane Creative Studio | Illustrator, Designer & Letterer

I am quite a risk-averse person. I grew up in a very strict household that is heavily focused on stable career path and practical planning. But the few times I’ve mustered up the courage to take considerable risks in my life, it has definitely paid off. A big risk I took in my personal life was to move from Dallas, TX to Seattle, WA with nothing lined up and I was relying heavily on my savings, which, *thankfully* mitigated a lot of the stress of risk-taking. Recently, the biggest risk I’ve taken in my career is to leave a very stable job I was growing increasingly unhappy in to start my own business in late 2019. I did the same thing I did before, I made sure I saved up enough money to buy myself a little breathing room financially. I’m definitely glad that I did before leaping off because 2020 was quite an unstable year to be running a brand new business. Nevertheless, I am beyond glad I took the risk! The role taking risks has played in my life have been quite astounding. In 2020 alone, I have learned work-life balance in a way that is very healthy for my mental health. Read more>>

Katherine Carrion | Artist and Entrepenuer

Risk-taking is so very important to the process of being an Artist and an Entrepreneur, investing in ourselves and believing in ourselves is important when taking a risk. It is the only way to lead ourselves down a path of self-discovery and ultimately success. I recognize and acknowledge that the ability to take risks in a career choice is a privilege and many artists are privileged to spend time doing what they love with the hope and goal that it can become a career but this is also part of the risk. It takes so much confidence and courage to do this, but with any risk we will either be met with rewards or lessons, both are valuable. Read more>>

Bronwyn Ison | Entrepreneur, Director Of Communications, Spokesperson, Speaker, Editor, Yoga Enthusiast & Mom to Teen Girls!

When it comes to risk taking I’ve always done so responsibly. A well thought out plan, executed the best to your ability, is still considered a risk. Each risk taken is a lesson to be learned, good or bad. The idea is to be prepared for either outcome. I’ve come to recognize each risk I’ve taken has required a multitude of things; passion, love, faith, diligence, hard-work and how does it benefit others. While your list may differ, without passion and a love for what you do, you will likely struggle because your heart isn’t fulfilled. In 2013, I opened a brick and mortar yoga studio on a shoestring budget. Essentially, I had no money but I had a love and passion for the practice and I knew I could help others achieve health and wellness. Successfully, I owned and operated my studio, Evolve Yoga, for eight years. From my brick and mortar I founded,, a subscription platform for yoga enthusiasts. While I loved my practice I knew I wanted to return to my roots of Broadcast Journalism. Read more>>