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.

London James | Content Creator (Foodie)

It is important to take risks, some of my greatest success has come from taking risks. Most people are afraid of the word “NO”. Not me, I love the grind, tell me no 100 times I am going to get a yes somewhere. Walt Disney’s “Disney Land” project was rejected more than 300 times, because he wanted to build an entire world based on a mouse! At a young age he was fired and told he lacked imagination and had no good ideas. His company is now worth 130 Billion dollars. You have to block out the noise and keep your vision in front of you no matter what. The reality is you will fail, we all fail but you only have to get it right one time and your whole life can change. So, take the risk!. Read more>>

Brandi Reed | Director, Cinematographer, Producer

Life is all about taking risk. You have to take risk and sometimes even step outside of your comfort zone to achieve your goals. Regardless of the outcome, you learn from it and move forward. I feel like my entire career I’ve taken a lot of risk, the biggest, leaving a corporate job to start my own company from the ground up. I didn’t know what was going to happen but I was willing to take that chance to be self employed. A lot of people doubted me, but that was only motivation to show them better than I could tell them. Read more>>

Yakira Lynn | Branding Strategist

Risk taking is an action that people are very afraid to take. However, when it came to my life and business, I learned that my biggest accomplishments and opportunities comes from taking risk. I personally do not believe in fear, because it is something that we make up. If the average human was naturally fearless, imagine how many risk takers would be in this world. I also evaluated by biggest inspirations in life a lot, and noticed that they were risk takers, which put them in a light where everyone wish they could be in their position. By noticing that, I was like, “Wait. These are regular people like me. If they are making risk and sacrifices to get what they want, I can do the same thing”. No one stops you from taking large steps in life, but yourself. Once I got that down pack, taking risks became easier and easier. It’s almost natural now. Read more>>

Danny Cruz | Tattoo Artist

The most important factor behind the success of my brand as well as myself is never giving up, and having a solid team around you. The road to success isn’t quick nor is it easy and honestly, I’m still traveling on it but with the security of knowing to never give up, and that everyone at the tables eats. Anything you want in life is going to come with obstacles, you just got to find a way to overcome them and when you do, they don’t seem as big as before. Success has its own meaning to people, mine is simple, go hard everyday and never give up, never quit. 25/8 Life. Read more>>

Sean Randolph | Rewards From Risks

Well if you think about it we all take risks every single day with more than we realize. We take them with our lives by getting inside a car,our finances with our choice of things we purchase,kids with sending them to shcool/Daycare, or outside,ect. Most of us are just used too those kinda risks. But! I know what you mean and If anybody believes in taking extreme risks its me! I believe sometimes taking risk can help us find Reason and further help our reach towards whatever we Want. You Remember last time we had an interview i spoke on some risks i took towards doing music. Ill just say i have no complaints and its all been worth the risks. But with that comes more and more risk you’ll have to take. For me its now more so Faith. I feel like risks is a word with possible room for failure or Regret. When you have full clarity to make that jump you should believe its gonna work out even if its not how you thought it might. Read more>>

Alexis Daughtry | Model, Model Agent, Actress, Entrepreneur

Life is full of risk. The biggest success stories always start off with “betting on yourself,” which could be a major risk. I would not be where I am today if I did not step out on faith and take a risk. The first risk I took in my life/career was going to college. At an early age, becoming a model has always been a passion of mine. However, being a black woman in America, we have a lot of statistics against us. I made it my duty to graduate college and obtain a degree before accomplishing anything in my adult life. While attending college, in my spare time I would do model jobs and photoshoots here and there. I was also a part of my school fashion show committee, where we host/coordinate fashion shows. The experience I had in college gave me the courage to fulfill my dreams once I graduated. After graduation, I became a full-time model and started my own business named “What’s Your Runway.” Our mission and goal are to develop freelance and aspiring model careers. Read more>>

Anthony Jones, II, Esq. | Trial Lawyer

Years ago, while vacationing in Florida, I purchased a mug that states, “Life begins at the end of your comfort zone.” I still drink out of that mug every morning. It serves as a reminder to me that being uncomfortable means I’m growing and learning. Growth is what risk taking is all about. As an attorney, it is very easy to get complacent, and complacency eventually breeds contempt. I don’t shy away from risks. My assistant and I often joke about me being the first to have to do something at my firm, whether it be a new legal issue or a new client request. I embrace being the first to ever try something. So much of life is unpredictable so we should never let our careers become predictable. I often find that the times when I think outside of the box are the times when I am most rewarded. Read more>>

Mii G | Nail Salon Owner

I feel you’ll never reach your highest potential if you fear taking risk. I see risk as having that mustard seed of faith in the unseen trusting and believing it shall come to life. Doing nails was definitely a risk I had never did nails in my life and I taught myself so I was definitely stepping out into the unknown. Read more>>

Troy Faruk | Actor, Musician, Stuntman, Creator

Risk taking has been one of the most important, and essential factors contributing to my success in life and my career. Choosing a career as an artist and creative in itself was a risk. Every level of advancement and success I’ve experienced has been the direct result of taking a risk. As a kid I always dreamed of becoming an entertainer. I wanted to do the cool things I saw in movies. I wanted to play complex characters, and be apart of the story. I wanted to make music and impact people the way my favorite artists impacted me. Growing up in a small city in the south, I never really saw a path to make that dream come true. So I did the only thing I could do to keep the dream alive. I used my imagination to develop my creative side. I taught myself how to write lyrics and create songs when I was 11. Most importantly I took education seriously to be an above average student. Read more>>

Brandy Janell | Credit COach and Financial Strategist

There is no reward without great risk. We always hear that saying. I can’t tell you how real it becomes once you decide to be an entreprenuer. An even bigger risk being a full time one. You don’t risk you don’t eat. You have to show up and take accountability for self, your image, your brand and your clients every day just to make sure you are able to keep the lights on. You take risks from having terrible weeks and amazing weeks in revenue. Most people are very quick to throw in the towel after one day of frustration. You have to risk people, places, money, sometimes even comfortability to reap from risks sometimes. Read more>>

Kelli Laneé | Creative Architect

I absolutely love taking risk in my life personally and professionally. I believe risk what make you it shows your strength and weakness and where to be build off what ever your fears are , that’s what make risking take so thrilling . Even being an artist we risk take are whole career even if we have a sense of direction to go we take risk in believing in our vision and rather it work as we expect or don’t we didn’t it so that the success of taking the risk. Read more>>

Hunter Hutcheson | Writer/Director, Founder of Classic Distractions

I think taking risks is vital for any artist or entrepreneur. There’s always a bit of inherent risk when trying to create something new. I also think it’s important to consider the risk of staying too comfortable: if you don’t push yourself you’ll most likely never create your best work. To me, that risk is scarier than going for it and failing. Of course, there’s some balance required here: I’m not saying people should empty their bank account and go all out on an idea. But give some thought to the risk of playing it safe as well. One good example of this risk balance is in surfing. If you’re too far ahead of the wave breaking, the ride is way too easy and will fizzle out quickly. If you’re too close to it, you might get stomped on and washed away. The best rides are found just ahead of the break: where you’re being challenged but can also see a clear way to the end of the wave. That is the fine line between chaos and order, and you don’t want too much of either. Read more>>

LaKisha Greenwade | Innovator, Tech Founder & Business Innovation Coach

Risk is essential for growth and exposure. The question is “Do you have enough wisdom to know when and how to take risks? ” In the financial world, customer personas are defined based on their risk acceptance: risk averse, risk loving and risk neutral. It is important to assess how you view risk and how you respond to risk before you are presented with an opportunity to decide to move forward with one. I would not be where I am today if I had not taken risks to love the life I dreamed of, including turning down key positions to choose a flexible lifestyle while building a global wearable tech ecosystem. In my second book, Rejection to Reward, I discuss risks taken to attend graduate school, transition from private sector to government, higher education, and ultimately tech. I did not use the same risk formula for all my life changing decisions but I did allow the concept of timing to help me make decisions that have not only impacted my life for good, but other diverse innovators and leaders. Read more>>

Bianca Bee | CEO of BFF Cosmetics Company & Author

Taking risks is extremely important because you don’t ever want to say to yourself “I wish I would’ve done this or that” as you get older. I believe that we never make mistakes, we just learn lessons. So even if that risk seemed like a failure or too big, it never was a failure because at least you tried and didn’t give up on yourself. I’m a firm believer in taking risks and it has played a major role in my journey of life. My first risk was moving to LA from Detroit at 17. I was alone, no family, no friends, and I just did it. After now living here for 10 years, it was the best decision I made. Some family & friends thought it was too expensive, though I wouldn’t last here and I did. I’ve worked for some major television networks and if I didn’t take that risk I wouldn’t be where I am today. I am always betting on myself and I think others should do the same. Read more>>

Terry Spain | CEO/Terry Spain Consulting

Taking a risk is huge for me, One of the biggest risks that I took was joining the U.S. Navy. Because of that initial risk, I was able to have a successful career in the military and after retirement, I was able to use what I learned and applied it to my business. Read more>>

Lorna Finn | Blogger, Model, PCOS Advocate, & Consultant

Honestly, I feel that risk taking is an ideal that if you want to be successful, you have to learn to accept. There is no safe way to be successful. Sure there may be more reliable ways to make a living, such as becoming a doctor, lawyer, or a teacher, but that doesn’t guarantee happiness or that one will feel they have reached success. I truly believe that one thing that you’re the most afraid of that is attached to the largest risk is what is the destiny you are meant to fulfill. For me personally, my greatest risk was moving 1,000 miles away from my family to start my life and career in the Washington D.C. area. I had to literally figure my life out at the age of 24, learn how to lease an apartment, adapt to the cost of living, and figure out my identity and career aspirations. There were a ton of tears, but ten years later I sit in my career and most recently began my entrepreneurial journey into Federal Contracts and Consulting. Read more>>

Adrienne Whelan | Yoga Teacher & Studio Owner

Taking risk is exactly how I got here. If I had listened to other peoples fears or doubts about my goals or dreams I would have never made it here. Some times taking risk for me has meant ignoring logic and trusting my intuition. It is scary but when you know you are meant to do something, you have to trust it, no matter how other people feel or how “out of reach” it might seem, it is meant for you. I left another life and career behind to follow through with my passion to teach meditation and yoga, some days are very challenging, I have never once regretted it. It was worth the risk. Read more>>

Philip Buchanan | Owner of Phil’s Remodeling & Peachstate Pad Airbnbs

If you want to be exceptional, you HAVE to take risks. My success all started with a major risk: I did everything I could to save up $10,000 to buy an Airbnb property. I simultaneously quit my office job and started a flooring business (which later became a full remodeling business). The key factor to risk-taking, though, is to have calculated risks. For example, if you want to become a successful musician, don’t just quit your job so you can make as much music as possible; you still need to be able to fund that career path; you need to have the money for instruments, branding, marketing, recording sessions, etc. My advice (especially to young people) is to work extremely hard, devise a well-thought-out plan, and take a calculated risk to give your plan a high chance of succeeding. In addition to that, set up “safety nets” to make sure you don’t end up completely broke and helpless if part of your plan does not work out because, trust me, not everything will go as planned. Read more>>

Taylor Howard | CEO and Designer of Sinclair

Risk is necessary. Many of my decisions have been made on risk taking. The biggest risk I’ve ever taken is stepping out on faith and moving to Atlanta by myself at 19, and it was the best decision I ever made. I never looked back because it was also necessary for my brand. I take risks on my business everyday, because I know whatever’s meant to be will be and I know one good decision could change your life forever for the better. I’ll never stop taking risks. You have to take risk to get greater results. Read more>>

Caitlyn Mims | Actress

Risk. If you say that word to a group of people everyone will react different. Myself 6 years ago would have been disclosed by anything that had to do with how I defined risk. The more I grew up the more I realized every decision requires risk. If you stay in bed all day you risk hurting your relationships. If you don’t drive to that opportunity you risk losing the next one. The more I caught onto the idea that comfort doesn’t keep you from risk but rather let’s you soak it in it the more I began living life. I had to face some fears, and the risks got bigger but so did the rewards. The more I was willing to challenge myself the more I was growing. It’s paid off and now I am a casting coordinator for an acting studio. If you have a dream but you are scared of the risks that it will take to get there just think of the risks that will come into effect if you don’t even try. You are capable my friend. Today is your day. Read more>>

Evan Wheeler | Entrepreneur, Activist, Philanthropist

I believe risk taking is one of the most important falsely stigmatized negative in business. I say that because risk is always attached to growth whether the risk is success or fail because you earn either way in a failure you’ve earn experience what not to do again & where to reinforce bug in a success you earn more money, exposure, and confidence. Risk has played a major role in my life putting myself out there in the business world because to walk away from traditionalwork the 9-5 comfort in with life trains & personal life as well as far as networking and allowing other people in my space/brain trust. Read more>>

LaVonna Jackson | Owner of Royal V Room

I come from a family of successful entrepreneurs and understand the importance of embracing risk to advance and expand your personal horizons. To begin with you have to understand that sometimes risk pay off and sometimes they don’t, however you will never know if you never take a chance. I honestly believe that you only regret the risk that you didn’t take, particularly when it’s something that you’re passionate about or strongly believe in. Looking back, I can recall switching careers and starting several businesses during times when my life was pretty comfortable and financially stable. If it’s something I’m passionate about, I am going to pursue it because the “what if’s” would bother me more than a failed try. This is how I felt when I made the decision to invest a good portion of my savings into the Royal V Room. Read more>>

Lawrence Johnson | Coffee Lover & Roaster

I think risk taking is probably one of the most difficult things to handle as an entrepreneur. It can be difficult at times navigating risk taking. However, taking risks in the business world is essential. I think my first successful business (Helix Cleaning Services) was a bit of a risk upfront when I started it a few years ago after leaving my corporate job. However, through time I developed a solid business model based off recurring revenue and this has really helped diminish risk from within my entrepreneurial ventures. Terminus Coffee, my most recent business venture, has been a lot of fun getting off the ground and has not been as risky because of how stable my first business has been through the years. I basically used capital from my first business to launch the coffee roasting business. It has been a really fun and exciting process!. Read more>>

Sean Anthony Baker | Creative Artist.

I think Taking Risks is a part of our everyday lives; small or big we do it more often than we realize. My belief in taking risks empowered me to experience life, truly live it. It pushed me to make a seemingly impossible dream come true. I wouldn’t be where I am today in Life or career if I didn’t make an effort to “Risk It All” Read more>>

Ashlee Maltbia-Burgess | Creative

Taking risks can be very scary. But that’s what I love about it, The unknown has so much beauty in it. Taking risks has caused me to live a less fearful life. I’ve had moments where I took a risk and failed, but I learned from it. I’ve also had moments where I’ve taken a risk and come out on top. You can’t own your own business and not be willing to take a risk it will never work out. You’ll miss 100% of the shots you don’t take. Read more>>

Patricia Murray | Vegan Chef & Food Creator

Without risk, the business wouldn’t be where it is today, right? This new stage is due to me feeling trapped and unsatisfied at my full-time job. After some planning- I finally quit that job in June 2020. I decided to push through my fears and re-introduce my vegan brand. I mean as they say, ” you don’t know unless you try!”. Read more>>

Hayley Sawyer | Dried Flower Florist & Bouquet Preserver

There is a saying out there that quickly sums this up for me: “I would rather live a life of ‘oh wells’ than ‘what ifs’.” Risks are a necessary evil to this crazy thing we call life, and there is absolutely no way I would be this far into my flower career if it wasn’t for taking risks. The first risk I took was just talking about my flower art to my tattoo artist at the time, which sounds so silly to say. I had casually mentioned that I press and frame flowers, and she immediately asked me if I wanted to sell my work out of her new tattoo shop. I still remember that moment so clearly too, because I had never even sold my work to anyone and I felt like I might have made a mistake just mentioning it. But my weird flower art was a perfect fit for a tattoo shop, and it quickly showed me that I might have a unique niche. The second risk came very shortly after that when I had a dear friend ask me to preserve her bridal bouquet. Read more>>

Dara Carter | Artist & Creative

100% of things you don’t try but it is important to know what the healthy risks are,and it takes intuition to know what risks to take. Leaving college and deciding to be an artist was a really big risk for me.I come from a family of high achievers, and music was an uncharted path in my household. Deciding to take a different path was a big risk for me, but one I was willing to take because of my passion for my music and support from my family and colleagues that help hold me up. Taking that risk and many others has allowed me to know what my boundaries are, opened up to experiences that I wouldn’t have otherwise, and realize my strength and persistence. How to know whether to keep going or give up: I always know to keep going as long as I have a vision. I’ve realized the time to give up is if you no longer can see what the goal is—long term. Read more>>

Loren O’Brien | Writer, Director, Filmmaker

We’ve all heard the phrase: ‘without risk, there is no reward, no victory without effort, no battle won without risk’. And it’s not thrown around for no reason: risk is the first step towards the pursuit of happiness. So in order to discover true success: you need to jump in the deep end and do that thing you can’t stop thinking about. Get out of your comfort zone, take the brave step and embrace the uncertainty. It is worth it, I promise. I’m a natural risk-taker. People tell me ‘they admire my confidence’, although the insecure part of me thinks they’re calling me ugly, but that’s beside the point. I understand it’s easy for me to tell you to take risks, but hear me out. Every single risk I have taken has moved me forward in some capacity. Whether it’s towards a better career path, better relationships, better art, or even better health & lifestyle. I’ll give you an example: London, 2017. I was doing pretty good. Read more>>

Randy Mcknight | Fashion stylist/ Creative Director

When I hear the word risk, it makes me think about what I could lose and what I could gain. I use to be so afraid to take risk. I always use to think why chance something I have going on for something else that I dream of having also. But that’s the thing about risk, you never know what the outcome could be if you don’t take them. For myself I took a major risk concerning my fashion styling career. I remember working a job that I really didn’t like. And to top it off I was working third shirt. I had an opportunity to be the wardrobe stylist for a film. I had to choose between taking this opportunity or continuing staying in my place of comfort. I prayed really hard and asked God to give me a sign. And he did just that, things continue to come at me left and right. So I made the decision to leave my job and work on the film. Since then my career has catapult to new heights! So many doors have opened for me because I allowed the world to see what I could do. Read more>>

Lib Aubuchon | writer + Personal Brand Strategist

Risk-taking is an essential part of being in business for yourself. For most of us, the choice to become an entrepreneur implies a healthy amount of risk. Will Rogers (look him up, kids!) is credited with saying “Go out on a limb — that’s where the fruit is” and I wholeheartedly co-sign that saying. Before tacking any new goal, I think it’s worthwhile to think through your own comfort with risk and maybe nudge yourself gently past it. Read more>>

Marcia Polite | Model and Entertainer

I feel like life is one big risk within itself if you ask me . Life is so unpredictable that at anytime life can change in a instant for you . So if your contemplating something I say definitely go for it ! For me I know for a fact I took a huge risk moving from New Jersey to Atlanta Georgia by myself. That move definitely taught myself that sometimes you gotta risk it all and take that leap of faith. Read more>>

Sam Sirmons | Radio Producer & Personality

When it comes to risk taking, I feel like my career is based on it 100%. I don’t like the safe way, the way that’s the masses take. I want to be the underdog and do something that’s never done. I came from a small city in Indiana. The only urban station I had growing up was an hour away, so I wasn’t even really exposed to radio to have been my first love. But, once I found it during my junior year at Ball State, realized that I wanted to do it as a career, I started branching out, reaching out to anyone I could. And even as connected as I thought I was at the time, nothing came from it. But, I go to my bestfriend’s undergrad graduation at Alabama A&M and his sister is dating a sales executive at an Atlanta radio station. He suggests that I intern at his station, I apply when I make it back to Indiana, and patiently wait. The day of my commencement, I finally get the call that I can be a summer intern. Read more>>

Kelsey Muse | Recording Artist & Songwriter

My curiosity and willingness to never quit often put me in these situations. Each time, I learned to not associate a risk with negative results. When facing fears head on, your mindset can change how you handle your success as a creative. Taking risks and making unconventional choices put me in positions that surprised me, impressed me more than, disappointing me. I elevated more in my career because of my risks. Read more>>

Myteshia Russell | Urban Graphic & Web Developer

Taking a risk has played the biggest role to me. Because in summer 2019 when I began designing, I quit my only job and began to design and focus on learning tools and things I needed to know about being the best designer I could be. I used to offer free designs to people locally just to get the attention of the city and surrounding areas. Even though I didn’t know the length that my business would go. I am very proud to have made that choice to do such and create my company. Read more>>

Lawrence Henderson | CEO, BOSS, LLC

This is a fun question for someone like myself. As a former U.S. Army Officer I see “risk” as being a matter of perspective. To put it plainly I think about risk in a very extreme way. To make something worth taking a risk on I weigh the risks to my life being taken, me loosing a limb, or me loosing my eye sight. See I told you it was extreme. Due to this extreme way of seeing risk I have rarely come up against something that makes me shake in my proverbial boots. The role taking risks has played out in my life has allowed me to view it as a filter and connection to doing what I was put here on earth to do. Any thing that is not aligned with my purpose means I am placing myself in harms way. Taking on my entrepreneurial journey was not a matter of thinking that I just wanted to it was in alignment with what was next for me. So quitting my job albeit scary, it paled in comparison to staying in a position that devalued who I was and what I was supposed to be doing. Read more>>

Corianna Bradford | Photographer and Clothing Designer

Taking risks in certain situations could sometimes be good. Especially when you own your own business your going to always have to take risks. If you take that one risk in your life regarding your career or business you never know where in life that could possibly lead you. Starting my photography business I was afraid to go above and beyond because I personally didn’t know whether who would support me and who wouldn’t until one day I picked up my camera and just started snapping shots. It was random places like nature, a downtown skyline etc. I posted them and now everyone loves to book with me. Read more>>

Tokyo Trendz | DJ, Producer, Tastemaker, & Creative

I highly believe in taking calculated risk because nothing great has ever come from remaining stagnant in my experiences. I think of risk based off the possible outcomes of an action and if I can accept the outcome going good or bad then I do it. A big part of my life/career has been associated with taking risk ranging from moving out of my hometown to reestablish myself in a new environment, going to new places alone to network and establish connections with people in my industry, quitting jobs to bet on myself, and other various things. Read more>>

Naimah Elmore | Talent Manger & Co-Owner of Alicia’s Coffee

I mostly risked investing in others some risk were successful but most weren’t. I felt it would push their music career a little better. Doing this set me back multiple times financially and mentality times but I wanted to help. This process taught me to invest in yourself more and that’s what I started to do. I learned that the biggest risk in life is betting on yourself. Read more>>

Beleshia “Lyrical” Mcculley | Manager, Label Owner & Motivational Speaker

For me I actually stepped out on faith about 12 years ago. I left my corporate America Job of being a case manager and started working in the music business. Taking that risk allowed me freedom and a closer trusting relationship with God. It’s been challenging to say the least but well worth it in the end. My success has created hope for others who are scared to have some type of hope that if I did it. They can as well. Read more>>