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.

TU Leonardo Antinori & Giorgi Antinori | Artists & Music Duo

The way we see it, risk is always involved in life and business and is something that we should be ok assessing and taking at most times. In the worst case if it doesn’t work out after taking the risk at least you learn from it, so you really can’t lose. If you think about it, everytime you get on a plane you risk going down but how often do you actually go down? Most often you do reach your destination. Same in life, with diligence, persistence hope and passion the risks you take usually get you there. The risk of putting your art out there in the face of being rejected or not appreciated is nothing compared to the journey you’d miss out on if you don’t take the risk to begin with. We feel the art and the true passion for something will ultimately find it’s audience. We’ve had to take many risks in our life together and in our career. Read more>>

Lauren Leonelli and Jenifer Golden | Podcast Hosts

We’ve always known the world of entertainment is risky, however we’ve never let it stop us. We would have an idea and take it one step at a time, pushing forward to our next goal, and pivoting if need be. Read more>>

Celina Lee Surniak | Fight/Violence Choreographer

“Risk taking” is a very weighted statement and has many perceptions and connotations of what it entails and stands for. Often, it comes with a negative or frivolous perception. I view it more as a necessary evolution in order to reach a goal, position, and/or ultimate state of being. It is my firm belief that if you are reaching for what you want and crave, moving outside your comfort zone is absolutely necessary. Creating a difference in your world, even if it is a small portion of what encompasses your entire existence, comes from a beautiful and terrifying shift out of the comfort zone that is embedded within your life. Change is difficult and terrifying. But, I have found it absolutely crucial in how I approach my everyday life and career thus far. Without my willingness to adapt and change my approach as needed, I would not be able to grow and evolve in my own life. Read more>>

Ranay Daye Orton | Founder & CEO

We take a risk by walking across the street, driving in our car, eating a piece of chicken so we might as well take the risks that will put us in a better position to live a full, purposeful life. To sum it up, we take the biggest risk by not choosing to take more risks. The reason most people don’t take more risks is due to the fear of failing, but the reality is that failure and success are not mutually exclusive. You can’t have one without the other so you have to go through “failures”, or I like to call them learning experiences, to get to the highest level of success for yourself, PERIOD. The biggest “risk” of my career was leaving the “security” of my sales position with an amazing Fortune 500 company to fully pursue and execute my business, Glow by Daye. Read more>>

Denise Poole | Actress & Entrepreneur

I’ve always been one to jump without looking. In hindsight, this may not be what I recommend everyone to do, but I am where I am today because I took risks. I’m not afraid to learn the hard way if it means I can live my life the way I choose to. I carve my own path and never let anyone stop me from taking a risk. One of the biggest risks I took was immigrating to the US. I fought for years to live and work here freely. If I didn’t take that risk of failure, then I would not have this company today. Big risk = big rewards, and what is more exciting than that?! Read more>>

Akvile DeFazio | President & Social Media Advertising Specialist

When it comes to taking risks, I weight my outcomes and decide whether I can accept the status quo or if I go forward with taking the risk, it can possibly improve my situation, I can learn something new, acquire a new hobby, develop a new relationship, experience living somewhere new, or find success for my business. Before I proceed, I do also assess the risk versus the reward. Is it worth it if it works out well? I look at my life as a whole as an opportunity to continuously test as it is, after all, an optimization worthy experience. My mottos is that you should try something, be it with work or other areas of life and it if doesn’t work out, then there is no shame in that as you tried and now you know for certain. After all, more often than not, you can revert or take a different path going forward. Read more>>

Elliott Nes | Artist

I consider risk taking a requirement in both my life and career. What is there to gain if you’re not willing to try something new? I’d say somewhere between 75%-85% of my creations I’m trying something new that could ruin the whole thing – that’s how I feel I have the chance to get better. If I always made the same type of thing it would lose all interest in it. I think the same goes for life – if I’m not willing to go out and try something new, how will I ever grow and learn? So, to answer I really feel like I owe everything I’ve accomplished to being willing to take a risk. Read more>>

Jeffrey Ramos | Filmmaker & Strategist

Risk is all about sacrifice. When I think of risk I think about getting my butt whooped at chess and asking out a girl. Risk is necessary for you to win a game of chess and when you ask out a girl, you run into the possibility of being rejected with life threatening embarrassment. With risk, it can go either way. When things go wrong you have to acknowledge it and move on. I know my computer can beat me at chess, but it can’t survive a round of kickboxing with me. It’s the idea that you could be wrong and you must consider the cost of that. Living life to the fullest often requires making well thought out decisions, so we usually are afraid of the ones that can potentially hurt us. Hurt our pride, egos, reputation. Risk has been a predominant part of my life. I pride myself on coming up with original and sometimes outlandish ideas. Read more>>

Elena Shahnaian | Founder & CEO

Risks are crucial for growth! I wouldn’t be where I am today if I didn’t believe in risks. I believe that taking risks allow us to challenge and grow ourselves in areas that we’d normally settle into comfortable routines. I took a risk transitioning from a corporate environment to leading a non-profit organization. That very big risk, that was based on a sense of leading or calling into an unknown direction, allowed me to start something that would fill a void: to serve a population of women who desperately needed the tools and resources to feel confident in embracing their new lives. Some risks can be calculated and others based on a deep feeling or ‘hunch’ that can lead to life changing outcomes. At Two Wings, taking risks is part of our organizational DNA. Everyone from staff and volunteers to participants is encouraged to think bold and take risks. Read more>>

Kristen Lem | Writer & Web Designer

I am probably the most calculated risk taker I know. Like many people, I am afraid of it. But also, like most people I’ve experienced big rewards from big risks. I view risk as 50% preparation and 50% self-awareness. Preparation is the easy part to define. A risk can feel less scary if you plan for as many known variables as possible. Of course, there’s always going to be unexpected obstacles and you will without a doubt learn to navigate them. But the other half of this process that’s been the most helpful is knowing myself. What I mean by that is knowing myself enough to say how stressful a particular risk is going to be on me, and how much will that stress hinder me from executing my plan. For example, when I started my business I knew I needed to be at 100% in order to do this well. Read more>>

Megan Duffy | Actor & Filmmaker

I worked with an acting coach years ago who gave me the best advice: Leap and the net will appear. While it’s important to look at the bigger picture and not be so naive as to not consider what could go wrong, along with what could go right, if you aren’t taking chances, you’re not going to grow as an artist or as a person. Every single one of my biggest career successes happened because I stepped outside my usual box and took risk. Read more>>

Ci Ci Foster | Entrepreneur & Filmmaker

I’ve always been somewhat of a risk taker growing up, but I didn’t start to really feel super comfortable with the unknown until I opened my studio. I realized that great achievement involves great risk. Throughout my spiritual growth I’ve become more comfortable with risks. I usually set an intention and don’t worry about failing because I understand that all of life is really a learning lesson. And more people are afraid of failing because they are super concerned with what other people would say about them. As soon as I gave up that mindset and embodied living for MY purpose, and not giving a damn about what people say or think, I started to fly! Read more>>

Marija Macesic | Project Manager & A Lifestyle Coach

Risk is part of any decision making. As soon as I accepted that, all my decisions seemed easier to make. I am also very versed with working around risk, given that in my full time professional career as a Project Manager, I had to quickly learn how to manage risks on day to day basis. I like considering how can present risks help me stir a decision to a comfortable solution. Read more>>

Damon Jones | Automotive Manufacturer

You have to have a budget in business, otherwise you won’t be sustainable! In business I manage my finances using cost benefit analysis. The systematic approach to understanding the cost versus the benefits of various different options with the final output outlining the best approach to achieve your particular goal whilst saving on your investment. I also have a business spend tracker which records everything I spend each day vs my monthly budget allowance. Personally my spend tactics are very different. Whilst I do consider cost vs benefit more often than not my decision is based on me buying something I personally just like from a style perspective which has no bearing on the cost but is aligned with ‘my look’. I wear my personality on my outside and I work on the premise that every day you should wake up and be the best version of yourself, and consider every day to be an interview. Read more>>

Chloe Perrier | Jazz Singer & Actress

I believe that I can’t move forward without taking risks.  I wouldn’t be where I am, if I hadn’t taken any risks. The biggest risk I took was moving to NYC. I was comfortable in Paris, working regularly as an actress and a singer, but something was missing so I had to take a risk to make a change. I arrived with my visa & microphone without speaking the language, and a year later, after some English classes and adventures, I was already making a living as a singer in NYC at the best venues, and at the fanciest private parties. 10 years ago I would never have imagined living and making a career in the US!  As an actress and a singer, if you don’t take risks, nothing happens. Even in the choices you make within your art. Without risks, art can be boring. Read more>>

Eyelid Kid | Musician & Actor

I was just talking to my friends about how important risk-taking is for an artist’s growth… Looking back on my career as a musician/actor I’ve been able to pinpoint a handful of risks that I’ve taken that define Eyelid Kid’s story. From an early age, I’ve neglected just about everything else in my life except for music and meaningful relationships. It took time, but I realized the risk I was taking by not preparing for the traditional route of; College — Degree — Job — Family. Instead, I poured my time and resources post-highschool into musical gear and midwest tours. By the time I was 23 I had performed twice as an official SXSW artist, joined a local music label, and relocated to LA. Through pursuing a career in music and acting I’ve learned first hand that the greater risk you take the higher reward you receive. I’ve learned that it’s an artist’s job to venture down unknown paths in order to bring new perspectives to our collective lens. Read more>>

Kemisha Edwards | Day Care Owner & Philanthropist

Taking risks is always scary but definitely necessary for my growth. I am now a self-sufficient business owner due to taking risks and betting on myself. Read more>>

Tm Gratkowski | Visual Artist

With risk comes failure, so you have to learn how to embrace the failures as part of your process, it’s kind of like learning how to be comfortable being uncomfortable. For me, risk has always been an opportunity to step outside of my comfort zone to learn or experience something new. Being comfortable with the unfamiliar and the unknown allows me to gather new information, process it, and then come up with a new skill set to execute a new idea. As an artist If it doesn’t involve some kind of risk it’s probably not worth doing, so every choice or decision I’ve ever made involves some kind of risk. The process of taking risks as an artist also allows me a way to get to a more unique place of discovery within the work. I believe it’s a great way to set yourself apart from what others are doing and follow your own vision. Read more>>

Natalie Avalos | Hand Lettering Artist

I really think risk taking is a habit you need to get comfortable with when owning a business or working full time freelance. Taking risks can be super scary but the rewards can be really big! I can’t say how many times I’ve failed when taking risks but I’ve also succeeded largely because of risk taking. I would say risk taking definitely comes with the entrepreneurial terrority. You gotta get comfortable with it. You’ll soon realize it’s part of the process and it’s also what helps you succeed! Read more>>

Ana Esperanza Dominguez | Model, Artist & Activist

Risks for me have a parallel correlation to faith. When I think about the definition of risk-taking, I immediately associate my life to be the personification of a risk. I look at risks as the blocks that build the cornerstone of the beautiful greatness in which we are destined for. Taking risks can be very frightening and it definitely doesn’t happen easily, by any means. It is that moment of truth where I refuse to let the fear of striking out, keep me from playing the game! I have been taking risks for as long as I could remember. I grew up with a mother who ingrained that fear was a choice not an option. She raised me to look fear in the face and move past it, even when it felt dreadful. Overcoming fear was the only option. I am so thankful for the way my mom raised me to navigate through life and push past the barriers that lie ahead. Read more>>