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.

Heather Kuhl | Licensed Psychologist and Marriage and Family Therapist

I must admit, I am not a fan of taking risks. In fact, like most people, I prefer to feel comfortable. However, life taught me an important lesson about risk and it is one that has significantly changed my perspective. My dream was always to have a private practice where I could specialize in conducting psychological evaluations and carry a small case load of therapy clients; however, the idea of having this as my sole source of income terrified me. In 2013, I decided to secure a full-time position working at a substance abuse treatment program which was always a passion but also a comfort of mine. I told myself I would maintain this job while I built my practice. While I was able to pick up a few therapy and testing clients throughout the years, I was so tired after working my full-time job, I had no energy to grow my practice. In 2018, when the treatment center I was at closed suddenly and laid off all the employees, this was the push I needed. I was too fearful to take the leap of faith on my own, so life decided to give me a shove. I learned that by taking that leap of faith, I finally had the time and motivation to dedicate to myself and my practice. Read more>>

Rosh Rebel | Artiste

Risks are necessary in moving forward, in growing overall. I have no problems taking them. I just ensure I get into risk-management mode where I get to look at the pros and cons and how a risk could really play a huge part in my moving forward. It’s either a success or a valuable lesson.A true dreamer has to take risks. Read more>>

Martina Marcet | Filmmaker

When talking about risks, I feel like some people see them as something scary and they can be. But in my opinion, they are something essential in life in order to move forward and experience things whether good or bad. I for one, would not be doing what I do if I hadn’t taken the risk of moving to another country by myself at the age of 18 to pursue filmmaking. When talking about film, something I’ve always been told, is to not be afraid to take risks and make the movie I want, without being afraid of what others might think. After all, every great movie, has gone through some kind of scrutiny at some point but they wouldn’t be as great or iconic if their creators hadn’t taken the risks of making them. Read more>>

Nikki Gal | Graphic Designer

What do you think of when you hear the word, risk? Does it scare you or empower you? Does it give you goosebumps or make your heart race? You’re probably thinking the word “risk” can only make you feel one emotion over the other, but in my life I have felt both fear and empowerment when I hear the word risk. Risks are always going to be present no matter what the circumstances are in your life, and even in your career life. As an artist, risk taking plays a huge inevitable role in my everyday life. When I first started as an artist, I was scared. I didn’t know what was going to come my way, what opportunities would surface, or even how to run a professional company. I had a lot of doubts. I would think to myself, “Where do I even start?” “Is this the right career path for me?” “Am I talented enough in my own craft?” “Will I even get work/commissions?” “Who will see my art?” Wing it. That’s what I did. I winged it. Some people would say hold off, you’re not ready. Or, take some time off and maybe you’ll think about it differently. Read more>>

Karen Bennett | COAST CEO & Founder

All new businesses are a risk but when you have opportunities backed by knowledge and experience the risk is greatly diminished. I took the risk a long time ago when I left Chicago for an opportunity that presented itself in New York City with a prestigious trade show. While I was there I learned everything I could to better my knowledge in the fashion industry. Years later when I left, I again risked everything and started COAST Fashion Trade Show. With only an American Express credit card and faith I went out and started my own trade show. I had developed a lot of strong relationships through my attention to detail and always responding to exhibitors’ questions and needs. They knew my standards and taste were on par with theirs. I started to fill a void in the regional marketplace. Taking this risk was the best thing I’ve ever done. The risk was compounded by my being a single mother with 3 children to support. I used that fear to push myself to provide for my kids. The risk paid it’s self off I’ve been in business now 14 years and I love what I do. I believe that you must take that risk to better yourself and your career. Everything in life has a risk but this was one decision I was happy I made. Read more>>

Judica Salmon | Founder/CEO & Writer

I think every risk is worth taking especially if it can potentially work towards your benefit. I haven’t always thought this way…Growing up in a strict and conservative household had groomed me to ignore risks and greatly fear the repercussions if I took them. However, entering into adulthood starting with college, I noticed that without ever taking risks I was left with a very mundane/predictable life, no friends, and a lack of opportunities and anticipated experiences. Now, I take more risks after calculating and concluding that it will help me excel in some way or just for fun. Read more>>

Laura Sgroi | Certified Coach, Bilingual Speaker, Author of “In Our Thirties”

Risk is the ever-present possibility of failure and success. I have never played it safe in my life or my career, therefore it has always been there. From taking first steps and making first moves, to moving from the Dominican Republic where I was born and raised to the United States to pursue my professional dreams, to reconnecting online and starting a long-distance relationship with an old flame who later became my now husband, to writing “In Our Thirties” in my second language, to betting on natural fertility and a medication free birth and changing my career for the third time in my thirties, my biggest goals have involved a considerable risk. Being alive is a risk, to love is a risk, to go for what you want is a risk. As the saying goes: Do it anyway. Read more>>

Lindsay Tobias | Certified Holistic Health Coach and Owner of Keep Your Plants On, LLC.

Risk was the ultimate four letter word in my head. Because risk never meant reward, risk always meant FAILURE. Two years ago, my new years resolution was to fail. To become comfortable with failing, because failure was a necessary step for success. I started by doing “one big ask” a week. I would go for something that terrified me. Asking a world renowned author on my podcast, ask a corporation for a wellness initiative, ask to host a ballin’ event. If you are comfortable with being told no, you strengthen the muscle of asking, of confidence. Every big jump in my career came from this practice. Read more>>

Bairi | Aka “Bairi The Siren” | Singer/Songwriter/Artist

I think risk is INCREDIBLY important in life, as long as it’s backed by good intention and thought. Whenever I didn’t just do something because of fear of the unknown, I more than likely regretted that decision. I’m also a Sagittarius so it’s unsettling not to take risks (; In all seriousness, my career is a testament to walking by faith and taking risks despite the fear of unknown, as well as the societal pressure not to take risks and be an artist. 2012-2017: I started college with suppressed dreams of singing even though I had done it my whole life. Where I’m from, it just didn’t make sense to be an artist. I aimlessly maneuvered, first wanting to be a music therapist, then an English teacher. It was only until I took a risk and moved from Hershey, PA to New York with my then boyfriend and really no other family or support (my parents were very worried) that I realized that my dreams were possible. Soon after, I started recording music. I graduated with a degree in Arts Management but spent most of my college years making music. 2017-2019: I went back home for two years and worked as a server, hearing day in and day out that I should get a real job. Read more>>

Mendy DOS SANTOS | Business Owner

I think that risk taking is part of a successful life and business. I moved from France 2 years and a half ago with my family. That’s a big risk I took in order to offer them a better quality of life. That means, I also took risks when I took over my business, to learn more and make a difference with competitors to make everyone happy. Risks are part of my life and my business and without risks, I think we can’t become better every day and make big successes. Read more>>

Heidi Ferguson | Vintage Shop Owner

I think risk taking has played a crucial role throughout my life. I have always been the different one in social settings and in school. I tend to just go for things that appeal to me as opposed to really thinking it through. To me taking risks is exciting and throughout life it has lead me to many different possibilities that I do not think would have happened if I was over analytical and afraid of doing something different. It definitely played a role in opening my business and in turn recently expanding my business. That was super risky during Covid, but we rolled the dice and went for it. Read more>>

Marianela Manzanilla | Photographer

I believe that risks are crucial in life, they force us to step out of our comfort zone whether is in our personal life or career. I think I have been taking risks ever since I was 14 or 15, pursuing an artistic career is not something that is common where I come from, and around that time of my life I already knew I wanted to be a photographer, I didn’t know how I was going to make it happen but I did, I took a risk leaving my home country, Venezuela, to pursue my passion and I have found myself taking more of these as life keeps throwing them at me. Risks force us to make decisions, act, and think about all of the factors and variables of it. The passion and energy you give towards your decision making are what’s going to make a difference in them. I try to always embark on these situations with a positive attitude and with an “I’ve got this” state of mind. In the photography world, we always find ourselves with risks, it could be that the weather is not ideal the day of your shoot, or even when you’re going to explore your conceptual side of your work. Read more>>

Ervince Louis | Musical Artist

I always make sure to have a fall back plan, don’t get me wrong I do believe that I will be successful in my career but I have daughter and other dependents, this pandemic showed me that even with an amazing plan I have to have another source of income. Long story short I learned that taking risks is important in an entrepreneurial lifestyle but to make sure I have a plan in case something unpredictable happens. Read more>>

Melba Pearson | Criminal/Civil Rights Attorney & Activist

No risk, no reward – that’s how I perceive life. Many times, people see taking a risk as a bad thing. You should not be reckless – but must be willing to take a calculated risk. Risks push us out of our comfort zone. Look at any major decision — weigh out the pros and the cons. If it makes sense and feels right – go for it! Folks have approached me after I announced my run for Miami-Dade State Attorney last year with “what if you lose? Isn’t it a big risk?”. I would always respond “but what if I win?”. Although I did not win the office, I know my campaign, while a risk for me personally, brought to the forefront critical issues that so many communities had been concerned about. To me, elevating the discussion is a win — for the people. Read more>>

Dion Kerr | Artist, Musician

I always wanted to make music or art that resonates with a deep level of spirituality. It feels like a risk to make something without the influence of other people telling you what or what not to do. I have taken risks by making the choices I have taken in my art and career. In this industry there can be a lot of opinions about what you are doing, I try to ignore all of that noise and continue to create honest work that speaks to myself. I have never created something that was only made to seek fame or notoriety. I feel blessed to have the opportunities that have come to me out of staying true to what I believe in and at the end of the day I feel good about that. I think you can be recognized for what you do even if it may not be mainstream or what is trending. If you stay true to yourself and don’t let these things phase you out of your work; you can find peace in the process. “Success” is an illusion; I hope to inspire people to create for a reason and not for what the industry standards or social platforms are telling them. Read more>>

Erik Duijsens | Freelance Photographer

Too many people risk is perceived of having a negative outcome, when in reality taking risks has brought fourth an extremely good outcome. Taking risks has played a very important role in my life. I recently took the risk of moving across the globe to Europe, in the middle of the COVID pandemic. Everyone thought I was crazy that things would not go well. I took the chance and said why not? At the end of the day life is about taking the risks that no one is willing to do. Read more>>