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.

Noelle Ramsay | Actress & Jewelry Maker

Risks are everywhere in life no matter what path you go down. Improving your mindset and increasing your knowledge, however, can decrease any amount of risk. You have to take chances if you want great things to come out of this life. One thing to really hone down on is your mindset. I needed to make sure I was in the right headspace. I needed to make sure I was doing this for all of the right reasons. In doing so, it prevented me from ever giving up. Read more>>

Karla Korn | Photographer

I would rather look back and regret what I did do, not what I didn’t do. I’m the kind of person that needs to experience the outcome of my decisions to make more educated decisions in the future. If it’s all theoretical, you never truly know the payout. That way my experiences compound on itself to make a portfolio of better decisions instead of just daydreaming about what could have been. There was a whole list of risks I took as a business owner, where to advertise, how to connect to people in the industry…etc. Read more>>

Kristina Lopez Adduci | Founder & CEO of House of Puff

As a second-generation American, risk-taking is in my DNA. My great grandparents, escaped the Spanish inquisition by migrating to the Canary Islands and then to Puerto Rico. My grandparents were both entrepreneurs in their own right. My grandmother opened her own boutique selling her own designs near Delancey St. and my grandfather sold furniture in the Bronx. My mother, sold real estate until the age of 35 when you decided to become a physician. Read more>>

Lisa Snyder | Co-Founder of Tokeativity, The Global Feminist Community for Active Cannabis Culture

When my parents died from cancer 5 years apart, I decided to put life’s pleasures and passions on the front burner. It became clear to me as a 20-something that our time is precious and how we spend it here matters deeply. There is no reason why we can’t live our lives to the fullest. Read more>>

Jessica de Vreeze | Artist

It is a very interesting and fundamental question. Risk and taking risks can be viewed from many perspectives, depending on what matters the most to you. In a sense, I’ve always taken risks in my career. I have changed my profession from being a lawyer to becoming a professional artist. I embraced who I truly was. Read more>>

Ben Everden | Photographer & Head Creative

Architectural model maker, internationally acclaimed jeweler, global marketing manager for major surf and auto companies, as well as, a content creator for a new generation. Through the many careers I’ve had, it feels like I’ve lived different lives. Not one of my many careers came easily, and I don’t think I would have been as good at each if it hadn’t been for the ones I’d previously had.
To me, taking risks is the difference between staying with something you find mundane or something that doesn’t give you the opportunities you want and being able to move forward creatively and have a sense of self-achievement and self-worth. Read more>>

Frank Brunner | Personality, Music Producer, and Content Creator

I can’t understand a reality (World) without risk. RIsk is indivisible from life. In my opinion. The perspective of risk is another thing entirely. Focusing on the risk of “things” stalls a person or organization into activity. Fear, another 4 letter word, along with words like can’t and others, can pigeonhole the motivation to “carry out a deed”. How does one manifest their future? Don’t risk what you can’t afford. Don’t risk worrying a meteor could pelt you in the mush while collecting the mail. Read more>>

Cynthia Mondeaux | REALTOR®

The bigger the risk, the greater the reward! I come from a generation of 5 strong women who are all risk takers! My grandmother is 94 years old, a great-great-grandmother who is not afraid to go outside alone and try to confront a snake in her front yard! My granddaughter is 17 months, she holds my finger and shows me exactly where she wants to go, go, go (in her own words)! Read more>>

Karra Janatiss | Founder & CEO

Any type of “risk” is scary! But, you know what they say, ” if your dreams don’t scare you, they aren’t big enough”! As an Entrepreneur, you HAVE to be willing to take risks. Majority of the time, our only regret is not taking the risk sooner! Taking a risk at quitting my job & focusing on my business was the first step towards any success I saw for my future. I knew that if I wanted to start a business, I couldn’t do it while working a full time job. Read more>>

Michael Weiskopf | Musician, songwriter, performer.

Someone once said that “It’s the experiences that you want but don’t go for that you remember more than what you have actually done”. While not a universal truth for me, it does have great resonance. I learned early on that every day brings some degree of risk and most we don’t pay much attention to or give a lot of thought. The big risks in life are the ones that involve great levels of personal failure or fears that need to be faced. Read more>>

Hydeeah “Notcommon” Johnson | Filmmaker

I think you can’t truly succeed in life without risk. The sacrifice is needed and it’s inevitable but when you know it’s the right choice you will feel it. Read more>>

Trinity Auberry | Model

At one point in my career I was playing it very safe. And in doing so I became comfortable. The problem with staying complacent, you don’t grow, you don’t allow yourself to see improvement. And due to not seeing anything different I slowly wanted to give up modeling. I am taking a risk now in my career, not only continuing to pursue it but moving to a different state. This is the most uncomfortable decision I am making EVER! But when you have a dream, a vision, don’t let your comfort zone cause you not to go for it. It’s not going to be easy but it is worth it. Can’t no longer play small when I serve a big God! Can I get an amen?! Read more>>