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.

Juanma Salazar | Content Creator / Social Media Expert

I would believe that risk and success go hand in hand, I believe that without risk there is no success, in most of the successful cases of many professionals and artists there have been great risks that they have taken to get where they are. Personally, I took many risks, I studied engineering, a profession for which my family expected me to have a permanent job, in an office doing documents and engineering things, but when I graduated I wanted to risk turning my life around, I wanted to dedicate myself to an artistic work and creative that is the creation of entertainment content to social networks, I risked my last savings to acquire recording equipment and pay for courses to learn how to edit and act professionally. Read more>>

AdrienneRose Gionta | Artist | Curator | VJ

Risk is necessary. I tend to overthink &/or over evaluate decisions but in the times where I have trusted that inner voice or gut instinct…& taken a risk… it has lead me in the right direction. Being an artist is the riskiest thing I feel I could ever do or be. It leaves you completely vulnerable, yet it is the most rewarding & most enlightening adventure. I tried to tiptoe around it most of my life & do the practical/realistic safe work but felt unhappy until I took the plunge into doing & being who I truly am… an artist. Read more>>

De’Nasia Grayson | Owner and CEO

I believe so many people are afraid to take risks simply because of the unknowns and the what ifs. While I feel that it is normal for us all to be a little afraid of failure, we should really try to use that fear as further motivation for us to live out our dreams. When I first created What’s Tea Company there’s a lot of things that went through my head. “Will people like my products?” “Who would I market to and how will I do it?” “Will my products work?” These are some of many questions that haunted me throughout the planning process of my business, However I quickly realized that those small moments of uncertainty had to become the fuel to the fire that would soon become a thriving business. For me the fear of failure couldn’t compete with my drive for success and representation. What’s Tea is more than just a tea company for me, it’s a tea company owned and operated by a Black Queer identifying woman and it was designed to help those who suffer with those same bodily conditions that are dismissed by professional medical practitioners on a day to day basis. Even though creating and running a successful business is one of the hardest most nerve wrecking things I’ve ever done so far, I know that its purpose will outshine all of the hard days and sleepless nights. The risk will always be worth it. Read more>>

Kraig Knight | Marketing, Architecture & Entertainment

Risk has lead Kraig Knight to exciting, precarious, unbelievable, dangerous, amazing, lucrative, industrious, painful and overall unforgettable places, moments and people. Risk has been Kraig’s greatest teacher and has caused him to learn the most wisdom. “It has mostly taught me useful skills and information that enables me to have more insight, intuition and all around first hand experience in a multi faceted universe.” He believes it is true in life and business that everything you want to know is on the other side of fear which is a word directly associated with risk. “There is a risk associated with everything we do. Some things considered risks by others wont appear as a risk to you because subconsciously you are not fearful of the matter at hand. Perhaps this is because you have been conditioned with different norms based on your environment or life experiences. Therefore, you do not look at some things as a risk if you are more prepared for it, until you meet someone else who thinks you’re crazy for going on a blind date which could be something you do every Thursday at 7pm on your hunt for holy matrimony.” Having chosen the risky career path of entrepreneurship has lead Kraig to learn a lot about himself, business structure, business models and business operations. As well as, a lot about people in a wide variety of industries, working on multiple projects. All while magically paying yourself last and others first, sometimes not even paying yourself at all. It can be a lonely road of ups and downs but this risk of entrepreneurship has given Kraig more freedom to work from anywhere based on how his businesses or businesses he sits on the board of operates. This gives him a slightly more enjoyable quality of life than the traditional “9-5ers”, which to Kraig is a trade off for not always paying himself. We can’t talk about risk and not talk about reward. As risky as this may sound to some, the reward is a life of freedom, solving problems for the masses, leaving a legacy and being able to pass something you created down to your heirs that can hopefully withstand the test of time and lay a foundation for them to stand on. Kraig believes all the energy excerpted in a lifetime should not simply dissipate or start over for the new life we bring into this world and he doesn’t even have children yet, but mentally that’s where he has been since a teenager. “I try to break barriers so that my family won’t have to now or in the future.” Kraig once took a risk that he told his parents he could die over but the reward was “worth it”…to him. Yes you heard right! Lol Crazy I know, as the legal matter already involved serious threats. )The reward was an instant shot at legacy, so he took the risk as legacy is something that envokes a feeling of ecstasy just imagining reaching this goal of his in whatever version that is to him. Therefore the trade off was equal as this is his number one goal in life. Kraig’s father said to his mother “talk to your son” and Kraig laughed and got on a plane the next day to the mission to accompany his partners in this risky business venture. “That risk has lead me to learn the most useful pieces of information I have ever learned all in the span of 3 years, absorbing thousands of pages of documents literally and because of our persistence on top of that we arrived at success.” Perfection is impossible so don’t let that stop you from taking the risk of entrepreneurship. No matter what you do something will not align when there are many moving parts which is a reminder we are not fully in control, just try to do your best at all times. Murphy’s law is a popular adage that states that “whatever can go wrong, will go wrong.” Simply put this is another way to say anything is possible if the scenario has multiple possible outcomes. So to eliminate risk would mean eliminating as many possible negative outcomes through preparation, and everything else will fall into place naturally. The excitement in the unknown that leads to an ultimate reward or pain is the fuel that keeps Kraig running and keeps his life interesting. “The reward should always be greater than what you perceive the risk to be. I would say definitely stay in your lane but always push to the edge of that comfort zone because you either win or learn.” The mindset of being driven by the upside of risk more than the fear has opened many doors of opportunity for Kraig as he continues to grow as an entrepreneur. Read more>>

Elvis Murry | Hip Hop Artist

Risks are needed progression. There is no success story without some risk being taken. Taking a chance or shot in the dark will do more than just waiting for your situation to change. Long as you aren’t risking your life or freedom, I’m all for risks. As for me, I try calculate my risks as much as I can, though there time where you have to put it all on the line to elevate. Read more>>

Julia Severance | Content Creator, Blogger and Entrepreneur

Learning how to take risk in work and life is a valuable skill set that many individuals overlook. It helps define a good leader and more importantly an entrepreneur. It highlights individualism and it is a critical factor to growth in any aspect of life. As a senior in high school, my first risk was starting my blog. I had no idea what I was doing nor did I know where to start. Failure, embarrassment and hardship lurked around every corner. However, that was the best risk I could ever take because I gained prosperity, confidence, and growth. Not only did I develop skills in content creating, I worked toward marketing, branding and communication regarding my passion for self development. I took a risk that changed how I perceive the world and the opportunities around me. That first risk lead me to a handful more of successful risk that ultimately lead to doors opening. Not every risk is going to successful, but every risk will come with valuable information and experience that will help you transform yourself and your business to the next level. Read more>>

Isabella Garofanelli | Miami based wellness-centric luxury travel and lifestyle content producer

For me, I almost always think about risk as “What if?” Not just the obvious “what if” I take a risk and it goes bad, but what if I don’t take the risk? What do I potentially lose? Is that opportunity the one that makes the difference? I guess in a way its FOMO isn’t it? That’s “Fear of Missing Out” in case you didn’t know. Now there have been plenty of times that I’ve taken a risk only to have it bite me in the proverbial butt but I like to think about that pretty well known quote by Robin Sharma about there are no mistakes, only lessons and opportunities to grow., Let’s just say I’ve grown… On the other hand, but for the risks I’ve taken, I would have never left that comfortable job in a multi-national media company. I would have never thought that my voice was worth hearing. It was only after taking serious risks that I look back and say, what was I so afraid of? Why didn’t I use my voice earlier? I’m so glad I took the risks I did and turned those into opportunities that have literally taken me around the world. I’m nor reckless, but to be successful you can’t be risk averse either. What’s that saying? Ph yeah, “Ships in harbor are safe, but that is not what ships are built for.” I want to use my ship to go around this beautiful crazy world and I know thanks to my lessons, I am willing to take risks that help me to where I want to be. Read more>>

Christopher Lardner | Real Estate Advisor

Risk is something I’m fortunately able to do more than others. I’m 26, no kids, no wife, and I’m able to take risks on a daily. I’m able to quit my jobs and take the leap into the entrepreneurial world. My most recent risks were quitting my job and taking on real estate full time. Read more>>

Federico Uribe | Sculpture hand craftmaker

Talent is not something that some people have added to their personality, it is just the lack of fear Taking risk is the standard for a creative artist. I challenge myself permanently on new materials and new way of building Read more>>

Jaclyn Sklaver | Licensed Integrative Sports Nutritionist

Taking risks is how I have reached the point that I am at now with my business. I left my life in NYC to take an internship in Atlanta working with NFL Draft prep. I decided to stay in Atlanta to grow my network and start my business. Two years later I moved back to NYC and in 2020 I took a contract in Fort Lauderdale, once again working with NFL Draft prep. When COVID-19 hit I decided to take the biggest risk ever, for the first time in my life I gave up my home in NYC.  Today I’m living in Miami with offices in NYC and Miami. I travel often to Atlanta and NYC for clients and my business has been growing despite the challenges of the pandemic over the past year. I’ve spent many days uncomfortable, alone and focused solely on my career but I believe that taking risks is how we grow. Read more>>

JANNELY ESPINAL | Fashion Journalist

Before taking a risk, I always answer this question: Will I regret not taking the risk? If the answer is yes, I go for it. Life is full of daily risks and you need to be willing to master the art of decision-making. Whether it is changing careers or letting go of a relationship, I always try to follow my gut. If something in my life feels stressful and affecting my mental health, I immediately know I need to make shifts and changes. During my late 20s, I changed careers, zip codes, and relationships, knowing there would be risks. In the end, it was all worth it. Risking a salary, the comfort of your place, or the stability of a job, sometimes is necessary to move forward to your true destiny. Read more>>

Kassandra Timothe | Political Candidate for North Miami City Council District 2

I am someone who is not a risk taker. I do not like to gamble or invest is risky stocks (only conversative IRA’s). In personal life and career and I am the same, very conservative and non risky. But in 2020, I decided to risk it all. Every year in my planner I would write, it’s time to take risks Kassandra. Start the business. host that event, jump out on faith. And I did just that. I jumped out of the boat and started walking on water. I left my job in the midst of a pandemic to run for office in North Miami. Read more>>

Stephanie Lopez | Graphic Designer

I love taking risks, they might not always be easy to make but I know that amazing things can happen when you just go for it! Personally, taking risks has helped me grow out of my comfort zone, especially when it has come to changing careers. Going full time with my business, A Design In Between, and not going back to bartending was a big risk financially but a risk I had to make for my future. I knew growing a business was not going to be easy but it was going to be worth it and most importantly say I took the risk of going after my dreams. Taking risks will leave you surprised at how much you are truly capable of. I think that if you strongly feel passionate about something it is worth taking risks for it. Read more>>

Iva Ballou | Certified Cleft Confidence Coach and Motivational Speaker

Being a risk-taker is often defined as a person who is willing to do things that involve danger or risk to achieve a goal. When I left my corporate job in DC to start Realsophisticatedjoy (RSJ), I had no idea what I was doing or what RSJ would look like. I easily could have stayed at my job, with my comfortable pay and apartment. Doing what I was doing, traveling and twirling in the wind. I could have done Realsophisticatedjoy as a side hustle. But I had to bet on myself and see what would happen if I fully committed myself to RSJ. Because I knew there was something more significant at stake than my current comfort level. With Realsophisticatedjoy, it is bigger than achieving a goal. Every speech I give or group coaching session that I facilitate, I do it all nervous and scared! But, I know that the message and helping someone rewrite their life’s pain far greater than any case of nerves. That is how I have always approached life. So, yes, I may be a risk-taker or wild, but one also has to say she lived in her Realsophisticatedjoy! Read more>>

Symone Rodney Diamond Fedrick | Symone – Event Planner & Chef. Diamond – Event Coordinator

Taking risks are so, so important when you have a small business. When you want to get started with your business you’re normally in a situation where you have all the time and ideas to begin making things happen, but not the money. Majority of small business owners are people who still rely on a paycheck and have other responsibilities. And even if you are financially stable, you may genuinely be scared of taking that step that could change your life. Because in the beginning you never know if the risk will be for better or worse. Though sometimes it seems like it won’t be worth it, we believe you taking that risk when you feel it’s right is so important. It will either be a blessing or a lesson. Read more>>

Andgelita Laguerre | Artist/Creative/Designer

I believe that every major decision we make in our lives brings risks. When I first had the idea of starting my own business, I delayed the process for a long time due to the unknowns. But later, I realized that if we paralyze ourselves due to the unknown, then we will never make any progress in life; this was the thought process that I kept in mind when I started Grand Rising Creative Crafts. Being creative comes with a lot of risks, and the complexity lies in trusting the process as you go. The most epic project I created comes from taking risks. Risk is like a double-edged sword. There is no guarantee that the results will lead to a favorable outcome. But I would rather take the risk than live a life full of regrets with what-ifs. Grand Rising Creative Crafts would have still been an idea to this day if I never took the risk of starting it. A vision is just a vision until you are bold enough to make it a reality. Read more>>

Faith Renee | R&B artist and Song-writer

Risk taking is essential in becoming an artist. Finding a balance between taking risk and staying true to myself as an artist is my biggest struggle. However, finding new styles and methods of branding myself via photo shoots and genre of music has been rewarding and has pushed me to see myself in a more radiant light. Read more>>

Bruklyn | Writer & Director

I have this theory that when people think of taking risks they immediately consider all of the bad things that can happen. When in reality, we all live with some level of risk every day. Nothing we do is 100% safe. If this year has taught me anything, it’s that nothing in this life will ensure you 100% security. You have to be uncomfortable to learn, to grow and get to where you want to be. I think knowing that makes it easier to take risks. You eventually learn that the worst thing you can be is be complacent with how things are going in your life. Change is necessary. Change is fulfilling. And to bring about that change, you have to take risks. With. me, I’ve always known the film industry is where I wanted to be. However, I struggled with fitting into everyone else’s expectations of who I am and what I’m going to do with my life. I fell into that belief that I had to play it safe because everyone else around me was doing that. Go to college, get a degree in something that will provide you with a stable job. That’s the status quo nowadays. I did exactly that and at the end of the day, I found myself dissatisfied with my life. While all of my friends were so ecstatic to be landing internships with businesses that could help with their careers, I found myself repulsed by the idea of having a 9-5 job. I found myself not giving it my all. I was just coasting by. I applied to New York Film Academy on a whim. I got accepted a week later and with only $2,500 in my pocket and not a lot of time to find a job or an apartment, I moved to Miami, Florida. It’s been hard and challenging. I’ve had to sleep on friend’s couches. I would go to school in the morning, work until night, sometimes I’d have to go on a film set and be up until 12 in the morning. Do it all over again. I was working so much, but I wouldn’t change my decision. That risk I took to go to film school and be in Miami brought me closer to my dream. I’m an award winning director because of that risk. I may not be where Spike Lee or Issa Rae are yet, but I’m making movies. I’ve met people who I call my family. I’m one step closer to where I want to be. Nobody looks amazing at the start of their journey unless they’re born into it. There is always going to be challenges in life. There’s always going to be hardship. At least when it comes to the risks, you know you’ll come out of it with a significant upgrade. The downside is almost nonexistent. Read more>>

Alex Lopez aka Friks84 | Creative Director and Artist

Risk plays a huge roll on how your life unfolds. So many are scared to leap into their purpose. Most are scarred of failure, others are making excuses to prolong they’re actions because of distractions. The true fear shouldn’t be in the risk, but in the regret. We get one life, and we all have to work. Turn your passion into your day to day grind. Thats the definition. of success. Read more>>

EMILIO APONTESIERRAPARETTI | A.KA: APONTESIERRA. Multidisciplinary Artist and Guidance Counselor

I think that life is a series of calculated risk and uninspected risk-taking events that everyone has to live throughout the course of their life. I know that I risk everything, every day of my live without knowing it. In the course of my life I have learned the importance of taking risks. Living my life in my native Colombia as a closeted gay man, I was risking to loss my soul. I was living in the closet because the risk of stigma, discrimination and ongoing violence that LGBT+ face daily just because we love another human being, because we express ourselves in a different way, and because LGBT+ people we risk our life just because we show our real colors. WOLA, a leading research and advocacy organization advancing human rights in the Americas mentioned in an article that Lesbian, gay, bisexual, transgender, and intersex Colombians have been granted momentous protections over the past two decades, but on paper, the country has one of the strongest legal frameworks in Latin America defending the rights of LGBT+ people; however, in practice these protections are rarely enforced. After Brazil, Colombia is perhaps the most dangerous country in the Americas for LGBT+ people. So, When I moved to U.S. in 2002 seeking political asylum, I decided to take the risk to be not just a non-English Speaker Colombian immigrant seeking political asylum in Florida, but to live my life as an openly gay man who will made his way as a multidisciplinary artist. One thing that has helped me to advance in my multidisciplinary artistic career has been the risk that I take every time there is an Artist Call Notification or Open Call to Artists. I always evaluate the risks before applying to these calls, and knowing that anything can happened, I take the risk to be rejected for not being good enough for the call or to be accepted and celebrated as one of the best applicant Artist. I always follow my favorite poem which is “Traveler there is not road” by Antonio Machado. As Machado mention in this part of the poem: “Traveler there is not road, you make your own path as you walk…” I am taking the risk of build my own destiny in my own risks. I started my Art business scared of what people would think about me walking between different careers paths from Theater Actor and writer, Fishing Engineer and Environmental planner in Colombia to a Guidance Counselor and Public Health Practitioner in the field of Sexual Health and HIV prevention in U.S. Walking into a world where thousands of artist are fighting to stablish their niche, there was me as a public speaker of social and health issues of my Latinx community and showing people my own paper manipulation fine art technique. I was scared of every risks piled in my asylum path and now I am walking my path as the Husband of Dr. Robert Paretti and embracing the risks that comes with different accomplishments from risk-taking decisions such as being one of the 15 Latin hero’s from The Sun sentinel. Or the risks from being one of the 8 Hispanic Gay men featured in the Spanish version of Start Talking. Stop HIV, a national public health video production by The Center for Disease Control and Prevention of the U.S. Also, the risks that come with being selected by the Favorite Poem Project out of 800 submissions from Florida. My paths were documented in a video by Poetry Foundation, Boston University, and Library of Congress. The Video belongs to the Favorite Poem Project which is a compiling of 50 videos documentary showcasing Americans reading and speaking personally about poetry. There is me taking my own risk and reading Machado poem. Currently I am looking to jump into the risks that I am discovering after been awarded as one of the 15 artist of the commons project: 15 artists. 15 Spaces by the COVID-19 Artist relief program of the City of West Palm Beach. COVIDA, my first ever public art piece was created and born during this risky times of COVID-19. She is a mixed media sculpture generated by the risk that I embraced when participating in a call for public art without having experience in this art field. Read more>>

Matt Stabile | Producing Artistic Director, Theatre Lab, the professional resident company of FAU

I think too many people associate a negative connotation with “risk”. Getting comfortable with Risk is really just getting comfortable with the unknown. If this last year has taught us anything, it’s that, even when we think we have it all “under control”, there’s actually very little that is within our control. Every time you try something new – truly new – you’re taking a risk. But those are usually the most enjoyable parts of life – at the very least, they are the times you learn the most. I guess the negative associated with risk is the possibility of failure. But we’ve all failed. At a million things. The question is whether you view failure as a stopping point, or as an opportunity to improve and be better. Our theatre is dedicated to new work. So…every show is a risk. We don’t have recognizable titles – “sure-fire” hits. What we do have is a commitment to our audience that no matter what we do, we’re going to do our absolute best with it. That’s what keeps them coming back – even when they don’t know what the show might be. Read more>>