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.

Erin Mastopietro | Co-Founder

The biggest risk I’ve taken in my life was choosing to start a business with my romantic partner at the time, after just 1 year of dating. Starting a business alone is a huge risk and then adding on the commitment to involve a personal relationship is taking it to the next level. I could not be happier with my choice. The challenge, excitement and freedom of working for myself is beyond any dream job I could have imagined. Working with my now fiance Michael has expanded our relationship in the best way possible. I am grateful for taking a risk that could have easily been dismissed as a crazy idea. Read more>>

Dawn Grabowski | Actor, Writer, Content Creator, Speaker & Producer

Risk has taken an essential role in my life and career. My most notable risk was to come to California. While on vacation here, I decide to stay and build a life for myself working in the entertainment industry. Now, risk continues every time I create & produce my own projects. Of course now, we all share our health and moral risk. Read more>>

Lauren Mary Kim | Professional Stunt Woman

My whole career is about taking risks. As a professional stunt women this is something that’s in the back of your mind everyday. To even become a stunt person you are taking a risk by not taking on a typical career. You have to have full trust In Yourself And know deep down you can do it. Anytime I have a big stunt I have to do I always think about the physical risks and assess the situation. Once that’s in my mind I let it go because if I dwell on the fact I could get hurt than I’ll get in head and be afraid. Then I do a little prayer in my mind before the big gag that I am protected and I visualize the end result as a positive one. Read more>>

Isaac Pelayo | Fine Artist

Risks are the corner stone in every successful entrepreneurial endeavor. Without any risks, big wins would likely not exist. Making a decision that appears to be frightening and career threatening makes the game all more exciting and gratifying. It makes the life of an entrepreneur all the more difficult however, the victory is that much greater. If it were easy then everyone would be victorious. I have had to make many risks and will continue to do so. Some of which include investing large sums of my own money, which at the time seemed like money I shouldn’t have touched. Read more>>

Kayla Perlstein | Business Owner & Social Media Specialist

I believe if you don’t take the risk, you could miss out on something huge. I guess you could say I got to where I am today by taking multiple risks. And I don’t regret any part of my journey. I quit my job in Alabama and moved out to California without a job. I got lucky and landed a job at a talent agency where I worked in the Tour Marketing Department for a year. From there, I went to work for a VIP ticketing company. Within my 5 years of working there, I realized the music industry was not where I wanted to be. I really enjoyed working in marketing and social media, so I decided to start freelancing while I had my full-time job. Read more>>

Matt Musty | Studio & Touring Musician

When I look back at my career thus far, there are a handful of distinct and defining moments that I can credit to having the stones get uncomfortable and take a chance. I’ve packed up in my car and moved to new and unfamiliar cities, I’ve piled into vans full of strangers and I’ve been at border crossings an inch away from spending the night in jail. I’ve lost brakes, blown out tires. I’ve taken jobs for cheap and then gotten paid zero when I was counting on that money. Now that I’m thinking back on it, I’ve also taken jobs for free and paid to do them! Read more>>

Odunayo Majekodunmi | Actress & Writer

I believe Risk taking is a requirement in order to accomplish any Career, Business or Life Goal. It’s impossible to be successful without taking risks. We take small risks everyday naturally has a part of life but in order to Grow, taking major risks is a requirement. I’m constantly taking risks in my Career goals and has I get older I realize that risks are unavoidable. At this stage in my Life, all of my success has been the outcome of being brave enough to take a Risk. Read more>>

Ann Sloan | Fiction Podcast Creator

I think we’re wired from a young age to equate risk with danger and as a result we often spend our lives avoiding risk, playing it safe. No doubt, there are risks we absolutely want to avoid: kind that put our health, body, finances, loved ones, and livelihood in danger are types we want to avoid. But I want to talk about creative risks: the kind of risks that give fulfillment, satisfaction, meaning. If you are a creative person, risk-taking is central to your being. Or it should be. The times in my life when I took a risk: changed a job, moved, pursed a passion — I can say unequivocally that it worked out, to some degree, every single time. Read more>>

Alex Mehra | CEO & Founder

To me risk is a gamble. It’s uncertain and could lead to success or failure. In my mind, risk was the biggest fear factor to overcome. It’s like a big block of uncertainty standing in your way, and it’s up to you on how you choose to get around it. Starting my business was a risk, so many questions arise. How can I survive without the stability from my previous corporate job? How can I convince people to give me work, with not much work to show for? What happens if I run out of my savings money? All of these questions fell under the umbrella of “risk”. Read more>>

Antonio Darwiche | Filmmaker & CEO

When confronted with a challenge, some might feel fearful and understandingly so, however my take on fear is challenge itself, one with obstacles established along the way. I think fear is as natural a feeling as love and happiness, and perhaps a more complex emotion to handle. Taking a risk, in my opinion, is an act of chance whereas you gamble success or instant defeat – BUT the win tends to come with a much higher reward if achieved. My personal and professional story is one that has risk as its core. Taking the easy way out has never been my way. I like to make my own path and I have done so by taking immense risks. Read more>>

Joe Guerrero | Photographer

When I think about risk, I think about how people hold back from how they truly feel about themselves. People tend to care what others think and because of that, they live dangerously. However, when a certain individual takes the risk on loving themselves first, they see life from a different perspective. Taking the risk of putting yourself first will only lead to a smaller circle of family and friends. Taking the risk on speaking your mind will only trigger people who can’t handle constructed criticism and lastly, taking the risk to sacrifice everything you worked so hard for something that may or may not be. Read more>>

Ronnel Ricardo Parham | Actor, Writer, Producer & Creator

Risks are motivation to me. One of my favorite quotes ever, I came across this when I was a teenager is “Failure is not a risk, it’s motivation.” This quote stuck with me because at the time, the last thing I wanted with my life was to be a failure. Since then, I’ve realized that failure is apart of life. It’s not your end all be all. In fact, failing is a good thing. I’ve taken many risks in my life and failed at some and accomplished others. So, to say the least, risks have become a big part of my life. If it wasn’t for me taking risks, I probably wouldn’t be at the point where people are interested in interviewing me. I probably wouldn’t be an actor. Read more>>

Joey Grace | Singer, Songwriter & Music Producer

Over the past two years I have started taking bigger risks in my music career. The biggest risk I took was filming my Beautiful Storm music video, where I was completely naked and body painted! It was a risk to go completely solo as a musician, learn how to produce my own songs, learn how to edit music videos, learn how to make a website, fund my projects myself, and basically 100% advocate for what I want to accomplish. When you are able to get to the point where you simply don’t care what people think of you, it is incredibly freeing because you are making your art in a way that is true to you, instead of trying to fit into what’s currently “cool”. Read more>>

Arye Campos | Actress

I believe that risk taking is one of the biggest factors of my success. I think as humans we naturally want to stay safe and in our “bubble”, but 99% of the time our success happens outside of our comfort zone, and if allow ourselves to be uncomfortable and still push forward, that’s when the real magic can happens. When I moved to the US, we had no idea how we were going to live, we didn’t have a house, my mom didn’t have a job, I barely spoke English, but my mom still pushed thru and go us into a school, found us a home and go her self a job. I followed that same path when I decided to move to take the leap to move to Los Angeles after college. Read more>>

Bia Jurema | Director & Editor

You don’t have to jump out of a plane or scale a mountain to be a risk taker – Falling in love is risky. Following a dream shared by many is risky. Starting a life in a city where you don’t know anyone’s name, taking credit for the writing you usually post anonymously, forgiving someone who’s wronged you in the past – risks are implicit to a precarious life. It’s the risks we take everyday that serve to expand our character and in turn, push us forward. Read more>>

Gavin Michael Booth | Filmmaker

Risk is everything in life and career. Taking the plunge to ask the girl of my dreams on that first date, deciding “I’m going to make my first film”, reaching out to someone that could change your life even if there’s a good chance they’ll say no. As they say without risk there is no reward. It is absolutely true. I would be nowhere in my personal life and my career without taking huge swings. It is always risky but what do you have to lose? You at least will know you tried and can never be haunted by the What If demons down the road. One example in my career is that I used to sneak into concerts with a fake media pass. This was back home, when I lived next to Detroit. Read more>>

Karina Frederico | Actress

Taking a risk is worthwhile, as you are obliged to leave your comfort zone. It gives you one more challenge and when you overcome you see that it is worth it. Carmen De La Frederica was one of the most challenging roles I have played so far, because due to her problems with alcohol, it was my first role where I had to stay in lingerie on stage and dance, besides that I created the scene’s choreography. Read more>>

Shaleea Venney | Best Selling Author, Speaker & PodCast Host

My entire career is a risk. It takes courage and perseverance to go against societal norms. Society says we’re supposed to go to school, get a job, and retire from that job after having spent your life doing it. It doesn’t matter if you are fulfilled or if you even like the job. You just wake up and show up for work daily. You’d have to be a little crazy to risk the security that comes with a 9-5 to chase your dream. It’s a huge risk. What if people laugh at you? What if no one supports you? What if you can’t make any money? The odds that you will fail seem insurmountable. I had all of those thoughts and fears until I realized one thing: God will not give you the desire to do something that he will not see you through. Read more>>

Andy Nguyen | Serial Restauranteur

Taking a risk is the courage to face your fears. The tension of being uncomfortable creates something beautiful. Risk has played a major role in my entrepreneurial career. I did things that I felt were right. Not what anyone told of me what to do. If I didn’t take the risk of dropping out of school. I wouldn’t be in the position I am today. If I didn’t take the risk of jumping into other industries, I wouldn’t know what I was capable of. Taking risks has now become apart of who I am. I’m just calculating my risks a bit more these days. Read more>>

Charles Southward | Founder & Master BBQ Chef

Risk taking to me is a leap of faith. When I truly believe in something I will not loose faith or belief that what I desire will manifest itself in time, my job is not to give up. Read more>>