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.

Brady Lukas | Rapper, Influencer stage name Burr. Our group is 6IX4EVER

Taking risks is something we have naturally always done. Right from the moment we started this journey we took risks and it was all crucial to get us where we are today. We had to jump over serious financial hurdles along the way and talk to people influential when we were stuck on things and it is a lot of pressure. At the end of the day though if we had never stepped foot in that interview with Alan Cross due to our own fear we would miss out big time. You always want to take risks, even if it turns out to be one of your failures.. It will work itself out in your favour some way or another. – Brady Read more>>

Jett Wilder | Actor-Performer

A friend of mine recently talked about a perception of risk I really liked (Thanks Phillip!). It was the idea that if we knew that after a set number of failures, we were guaranteed to succeed, we would run to begin failing. If we knew that after 100 fails, we would succeed, we would try to fail 100 times as fast as we could to get to our goal. It really resonated with me and re-shaped my perception of failure from what most of us view failure to be, which is a loss or a set back, to just another step and place to gather data and feedback and GROW on our way to achieving our goals. This way of thinking makes me more excited to take risks. Failure seems more and more like a construct, because can we ever truly fail? I think it can be a choice. And if we choose to keep going, to keep pushing forward, failure is never actually a reality or a result. It’s just a step. Read more>>

Joe Clarke | Filmmaker

Just like everything, risk is relative. I’m lactose intolerant, so drinking a large chocolate milkshake from Steak ‘N Shake is taking a risk. Moving to Los Angeles to try and break into the film industry was a risk. The entertainment business is one of the toughest and most challenging career paths to take. At the same time, I think risk is an inherent part of living. With the future unknown, potentially every decision we make is a risk. Read more>>


MEAGAN AYRES-ELIEFF: When it comes to risks I think we are all often afraid to lose or be faced with danger but I do believe that when you take risks in life or business this is what pushes you forward into the future — allowing you to really excel in life. For me, going against what may have been what is called the “normal” thing to do or what is on “trend” has always paid off. From a young age, I always wanted to do extreme and extravagant things. Read more>>

Sylvio Martins | Actor & Writer

I have a complicated relationship with risk. 9 out of 10 times, I’ll willingly run towards risk because I believe that the greatest rewards and sweetest satisfaction come from taking risks in life. However, I am also a very anxious person by nature, so I often place lots of pressure on myself (more than I probably should) to beat the odds. But I also believe taking risks is a sign of tenacity and self-awareness. You believe in yourself and know what you are truly capable of, so you place a bet on your dreams and aspirations. It’s a very powerful experience and even if you fail, you can say that you came out stronger on the other side. Read more>>

Tide Eye | Psychedelic Rock Band

Risk played a pivotal role in my life and upbringing. I’ve always found great joy in taking leaps of faith as long as you believe in what you are doing. I like to think of risks as a catalyst and a motivation to keep progressing and moving forward. Taking a risk should feel terrifying yet exciting, it’s what brings about change in your life and allows you to truly be who you are. Ironically enough, I decided that 2020 was going to be the year of risks for me personally and boy was I in for a surprise. Nobody was prepared for the world to shut down and I was definitely one of them. But instead of leaning into doubt and accepting defeat, I muscled the motivation to pick myself up and keep moving forward. Read more>>

Esnavi | Recording Artist & Entrepreneur

I’m a risk taker. I thrive off of taking risks because I’m not afraid of failure. I think the only way to seek limitless possibilities is to take some sort of risk. I wouldn’t be where I am today without risk taking. I’m a Top 40 Urban A/C Recording Artist turned organic skincare formulator, with a successful skincare brand…it took a lot of risk taking to get here. Read more>>

Gaby Torres | Founder and CEO

To succeed in business, you can’t avoid taking risks. You need to take risks in the face of doubt and fear. There’s a Spanish saying that goes: “El que no arriesga no gana,” the person who never risks anything never wins anything. That’s what I say to myself if I ever start to feel scared about making a big decision. Risks drag me out of my comfort zone and force me to grow. I have been comfortable in some positions. I became good at them until they became easy. When things become easy for too long, I start to lose my drive. Read more>>

Giovanna Gonzalez | Financial Educator at The First Gen Mentor

I haven’t taken much risks in life until recently. This last June, I quit my stable corporate job for the unknown. I resigned from my job because I felt I needed time away from the hamster wheel and “do me”. All my life I’ve done what I was supposed to do. I went to college, Got the stable job. Paid off my student debt. And I wanted to feel what it felt like to have complete control of my time and pursue things that mattered to me. By having the space to explore personal interests, I was able to start my own business doing what I love. I’m thankful I had the opportunity to explore this side of me because the work I do now is much more meaningful. Read more>>

Tyler Armstrong | Photographer

Risk taking can be extremely beneficial. I’m still working on being comfortable with taking risks. Being comfortable feels safe but with that comes little growth or personal discovery. Read more>>

SUMMER RYAN | Aesthetician/Business Owner

The short definition of risk is the possibility of loss or injury. If you look at that definition there is nothing in this world that you cannot apply that to. There is nothing in your life that is not already risky. So the way that I have always looked at taking risks was it is inevitable so why not go out and try something, at least this way I get some control over what I am willing to lose. People have always told me that they think I am fearless. “Oh I cannot do what you did you are fearless”, is something I hear quite often. Read more>>

Ysabel Chavez | Founder and Creator of Global Dream Team

I suppose you could say I’m a bit of a risk-taker. I definitely don’t like to go down traditional paths and I like to create my own path. You could say going all in on my projects and businesses is a risk if I’m currently making less than a more traditional job or it is a risk when they say “90% of businesses fail”. For me – I love working hard, investing my time and energy into something I am passionate about, starting things up from the ground up and seeing them grow. So in my eyes – I think the bigger risk would be not doing what you want to do in life, and letting that time pass you by. After working at a job straight after college that scared me that my life would become a 9-5 behind a computer screen – I knew I needed a change and it was in my power to create the life I want. Read more>>

Jermaine Hopkins | Brand Owner | Director of Happiness | Visual Story Teller: Brotherly Sole [Bly Sole]

When people think of risk they automatically assume of the negatives of the risks. Risk is a 50/50 chance to some and it has to work or it has to work to others. I’m on the side of “it has to work or it has to work”. Jump out of your comfort zone and stay true and consistent to what you’re risking for. Study, plan and execute and it’s not so much of a risk anymore. The risk factor is just starting and stepping out of your normal, once your out of that phase it’s totally on you. Read more>>

TJ Harris | Podcaster, Mental Health Professional

I think risk is always a part of trying to start something new, as far as this podcast journey the whole thing is kind of based on risk lol. Just deciding to do something we found interesting and figuring it out along the way. I’d say the same thing with life, there’s always an element of risk when you try something new or go for something better. Read more>>

Bryan Michael Nunez | Actor, Writer & Digital Content Creator

I think about risk every day. Whether you’re grinding hard at what you’re really trying to achieve or you’re letting negativity make you still, you’re risking it. That being said, I’d rather work hard and ignore anyone or anything that doesn’t support or believe in me rather than risk my mental health, my happiness, my success because I did nothing at all. Risk brings us reward and I think deep down we all like a little risk, a little competition, that feeling of accomplishment. Every single da and every audition is a risk for me in this industry. Read more>>

Philice LeBow | Entrepreneur/Small Business Owner

I find the concept of risk fascinating. It can bury you or give you wings to fly. It inspires the gamut of emotions – fear, loathing, excitement, love etc. – depending on the time and the circumstance. It’s also fluid… it evolves as we evolve, shaped by life experiences. Earlier on in my life, my appetite for risk played out very differently personally vs. professionally based on those experiences, and lucky for me, is still evolving! Read more>>