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.

Analuisa | Small Jewelry Business Owner

Taking risks has been crucial to the success of my business. Starting Amoriana Jewelry in itself was a risk. but I’d rather take that risk and fail than to never have tried at all. Even though it is much easier to play it safe, no growth or progress can come from that comfortable space. Read more>>

Daniela Vianna | Co-Founder & CEO of Ephemeris, Inc.

I would rather bet the house than live by a stable payroll. And this is what made me get to where I am. One day I realized I was unemployable. Not because I lacked skills or reliability. I was unemployable because I couldn’t stand the ceiling. Knowing that I was going to make x amount of dollars – every month; to perform the same tasks – every day; in order to make a soulless corporation succeed, was killing me slowly. But breaking the ceiling comes at the cost of diving into the unknown. Read more>>

Pablo Rammsy | Tattooer

there are many risks and sometimes we have to leave our comfort zone, it is a job and like any job where you don’t know if you will do well or not, effort and dedication are very important and many times you have to put aside the things that we like them, to be able to evolve and continue learning and growing in our profession but an old proverb says when you find a job you love you won’t have to work anymore Read more>>

Jordan Kownacki | Mixed Media/Epoxy Resin Artist & Entrepreneur

I’d say risk has played quite the role in my life and career… in the way that it hasn’t stopped me whatsoever. I don’t think I’ve ever really been the timid type in giving something my all and risking the loss or letdown from failing. It’s part of who I am, and with that quality, I’ve grown exponentially as an Artist. It’s a large reason as to why I am where I am in terms of my artwork… I definitely have the scars and stories to prove it! You can watch all the tutorials you want, listen to different advice from people all over the world, tread lightly and try to narrow everything down to a science in trying to get the result you want. Read more>>

Nicholas Richman | Director, Producer and Writer

“If you want it, go for it. Take a risk. Don’t always play it safe or you’ll die wondering.” If there’s one thing I’ve learned, life can be as boring or as exciting as you make it. What joy is there in life if you don’t take risks? I know it sounds corny but I truly believe that. I couldn’t imagine where I’d be today if I played it safe, one thing’s for certain, I would not have accomplished anything in my career that I have thus far. Screw playing it safe, we only get one shot at life, right? So what better way to learn to swim than by stripping off the floaties and diving in the deep end. Read more>>

Dr. Kelly Wilson | Dean, High Tech High Graduate School of Education

When we started the High Tech High Graduate School of Education (GSE) in 2007, we were the first in the nation to emerge out of, and be fully embedded within, a network of innovative, project-based learning K-12 schools. While linking the preparation of teachers and leaders to the reality of K-12 schools seems obvious now, and aligns with the residency model medical schools have employed for over a century, at the time we were truly pioneers in this space. Read more>>

Tessa McFionn | Author

Wow. Well, I am a true believer in the idea that fortune favors the bold. Being willing enough to stand up in front of the world and say, “Hey, I wrote this. What do you think?” takes a lot of guts. Deciding to be an indie author is definitely a scary prospect. When I first began writing, I had never imagined that I would be doing it all on my own. Finding editors, cover designers, formatting the book itself. Each time I put out a book, it’s a risk. Is the timing right? Is it what people will want to read? Then there’s the marketing. It’s daunting and I am constantly needing to remind myself that journeys are always made up of one risky step after the next. Read more>>

Jennifer Diaz | Licensed Esthetician and Educator

Risk taking was something that I usually stayed clear from when I was younger. I always played it safe and worked jobs that were seen as responsible and steady. I always had a great interest in art, beauty and health but never saw it as a tangible career. My goal was to always be self efficient and I thought I could only do that with traditional careers. I worked hard and wanted to be the best possible as well as dependable but I saw a different perspective of life as I got older. Read more>>

Sandy Huffaker | Photojournalist

In my line of work “Risk Taking” takes on a bit of a different meaning. When I go out on photo shoots in perilous situations such as wildfires, riots, hurricanes, etc.. I have to make time to prepare and have the proper equipment, and in many cases, knowledge of the situation I am about to enter. For instance, if a fire breaks out in the back country, I have to make sure I have the necessary fire gear(Nomex suit, helmet, goggles face mask, etc..), plenty of water, battery chargers, communications systems, safety gear and always have a clear path to escape if fire surrounds you. Read more>>

Christina Bamaca | REALTOR® at Keller Williams Realty(San Diego County)

Risk is the biggest factor in my career. I am a Realtor. We do not get an hourly wage or salary. We have to build our brand from the ground up. We hang our licenses with the brokerage we feel will give us the best chance at success, but it is essentially our business. Becoming a Realtor or Real Estate Agent is an investment, and a heavy risk. You get out of it what you put into it, and I put my all into it. This isn’t just another job, it is who you are. That is how you can recognize the best in my field. You know them as Realtors. Read more>>

Alexandra Duffy | CEO, HIVE33

Take the Risk & Destroy Your Comfort Zone Comfortability is a paradox. Often, we measure the concept of comfort with happiness, but in the case of our careers and lifestyle choices, comfort is often a suppressor for growth and satisfaction. There is a saying the U.S. military uses, and that is “complacency kills”. Vigilance and taking risks are the ingredients to combat the vulnerability of stagnation. Read more>>

Natasha Patel | Visual Artist

Risk is essential for me in order to push myself past my boundaries and comfort zone to truly grow. If you told me 3 years ago that I would have coaches and mentors guiding me in my life and career, I would have laughed. Seeking out help in the form of a coach or mentor in your industry is definitely a financial risk for a lot of people, but the value add you get from professional expertise pays itself back in full in no time. Read more>>

Mini Palmer | Life Coach

To me, risk taking is the courage to live in the mystery of the unknown. To open yourself to new ways of thinking and being. Having the courage to make decisions from an inner place of knowing what you feel called to, even if external conditions are not supporting your choice, this is what creates space for innovation and growth. Read more>>

Robert Tyler | Entertainment Industry (screenwriter/actor)

you can not get ahead without risk… however… I was offered 5 opportunities to move to southern California From Napa Valley… 1. Assistant Director on a Major Motion Picture… San Diego… with free rent included, 2. Run a tv station in Hemet free rent included… (i googled Hemet and highest crime rate in the Nation.. so no to that.) 3. Fly to Dubai as camera man on music tour for music videos documentary. (this shut down due to Covid ) 4. Run a television station in Palmdale CA. (they are still waiting on grant) etc. Read more>>

Domenic Fuqua | Curve Model

I truly think , like is built on risk . Often I find myself weighing out options on “ what’s the worst that can come from this “ . Risk can bring fear of uncertainty but risk also cuts out your comfort zone and brings more opportunities Read more>>