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.

Sacred Thomas | Influencer & Video Production Business Owner

I think taking risks are a must when it comes to living a fulfilled life. Nothing in life worth doing comes without risks. Whether you’re deciding on college or starting a business at some point you have to trust your gut and take that leap of faith. I had a party bus business before I got into filmmaking. A year in I completely left that party bus business and went all in with video production during covid. I made that decision to go all in because of the love of video and not the money. That ended up being one of the best decisions of my life. Read more>>

Jarian Wade | Head of Compensation, Square

The bigger the risk, the bigger the reward! I have always viewed risk as a stepping stone to greatness and it’s been one of the common themes in my life and the life of those I admire. I believe that every decision you make, every opportunity presented to you will have some level of risk involved. The earlier you figure out how to cope with and/or manage risk, the sooner you will reach your true potential. Read more>>

Tasj-Mari Myers | Entrepreneur & Photographer

Risk is everything in my career. Each time I decide to invest in my business, whether it be time or money, it is a decision to go against the grain and pave my own path. It’s far more comfortable to have a traditional job with a fixed income, but being an entrepreneur and doing photography is my passion. If I hadn’t taken a leap of faith, I wouldn’t be where I am today. Read more>>

Krystal Harriott | Holistic Doula and Herbal Family Planning Educator

When I think of risk, I think about taking a chance. When you do something you have never done before, or expose yourself outside of your comfort zone. Studying holistic birth work and educating birthing rights, I knew I was taking a risk by offering the public a non-hormonal herbal birth control lubricant. Read more>>

Rickelle Felton | Entrepreneur & Podcast Host of GRL

Anytime you present a new business or concept to the world you’re taking a risk. You’re revealing and exposing a part of you that people may or may not support. You’re taking a financial risk just as much as a personal risk. I’ve never been afraid to take a risk. The biggest regrets and failures lie in things undone and unsaid. Investing in something can be a scary thing. You’re putting your money where your passion is. Read more>>

Zoriae Dixon | Braider

I look at taking a risk like a challenge and I love challenging myself. Taking risk has impacted my business tremendously. I took my first risk when I quit my job but I knew that I could do hair. So that’s exactly what I did. I did not have a huge clientele base at the time but I was motivated and determined to take it to the next level. Taking that one risk opened many opportunities for my business. I knew the pros and cons when I took that risk but I did not want to look back and regret not doing what I had a passion for. Read more>>

The Messenger | Singer|Rapper|Songwriter

One of the key words in the definition of risk is “expose”. Without taking a risk, you won’t be able to expose yourself to the success. I’ve been taking risks all of my life soley because I’ve always believed in my talents that I’ve been blessed with. By taking each risk, I take a chance on getting closer to reaching my goals in life. All success comes with some form of risk. If you want it, you’ll go for it. Read more>>

Quanisha Gindraw | CEO of Divine Jewel Entertainment

Taking risk means to me strength. I say strength because if I don’t do it, I will never know if I can achieve it. The strength shows I got what it takes and willing to take sacrifices. Taking risk has played a major part in my career and life. Since I started Divine Jewel Entertainment, it been all about business and sacrificing my personal life for business life for two years straight. Personal life could of been a whole lot better, but me knowing if I take this risk – it’ll be worth it all at the end. So I continue to show my strength and sacrifice! Read more>>

Bria Moore | IT Technician & Entrepreneur

Taking risks have played a major role in my life/career. In fact, if I hadn’t taken one specific risk in particular I wouldn’t be as far ahead as I am. I think that risks are influential. Risk exposes you to a preview of greater possibilities. I understand the concept of taking risks. I take them proudly because I am being led to do certain things, which means that I will succeed by committing to something that may not necessarily make the most sense. Risks showcase your faith. Read more>>

Michael Butler | Actor, Artist

I love taking healthy risk . Taking Risk has award me with many opportunities that’s have opened other doors , I would definitely have to be honest and say I’ve taking some risk that haven’t played in mya favor also, but it’s apart of life and I embrace it. Read more>>

Kenneth Cohen | Media Specialist

A risk is really just an opportunity. While I feel like taking risks is essential, I value managing the risk more. Not all risks are equal and sometimes they are not even known early own but learning and preparation can be buffers. As a media specialist, my process to understanding lighting is similar to the process of taking risks in my life. Read more>>

Ty Hunt | Director, Producer, CEO

Filmmaking is inherently risky, now matter how much planning, money, foresight, whatever you put into your project. At the end of the day, there’s always something that pops up outside of your control that forces you to adjust your plan to accommodate. The crazy thing is, even in “stable” jobs (you know, the ones that people always tell you to have a backup plan for in case this crazy, unrealistic plan doesn’t work out…), even in those jobs, there’s a risk. Read more>>

Jillian Smith | Realtor + Real Estate Investor

Risky behavior is what tends to set apart those that can achieve their dreams from those who only realize them during sleeping hours. I’ve made many risks professionally and personally. In the past 10 years I’ve moved across the country 5 times. Each time not knowing a soul in the town I was moving to. Most people thought I was crazy being a single mom of four young kids and starting a business purely based on commission. Read more>>

Torrey McDowell | Singer/Songwriter/Music Business

It is “easy” to stay where you are comfortable. Familiarity and routine can offer comfort, but there is typically very little growth in those spaces. For years, I stayed in places that made me feel safe until I realized I wouldn’t ever be able to build the life I wanted there. Taking risks has played a vital role in getting me to where I am now. I had to make the choice to just go for it and once I did that, a job, new home, friends, and opportunities just started showing up. Read more>>

Cyrus Nelson | Mixed Media Artist

Life presents us all with choices, some riskier than others. The decision to dedicate all of my time and energy into being an independent artist not only requires risk taking but more importantly resiliency to battle the storms. After being furloughed and eventually terminated from my corporate job due to the pandemic I decided to take a leap of faith and exclusively focus on my art. Read more>>

Shelby Peterson | Online Fitness + Nutrition Coach

Risk taking can be incredibly daunting, but I think that learning to get comfortable with being uncomfortable, like taking a risk knowing you may fail, is how you have growth. I took a risk leaving my in person coaching job, where I was offered to run a department, to step into my current role as an Assistant Coach for Level TEN Coaching, with no clients. I knew it would be a risk, but it was one I felt was worth taking, and here I am 2 years later, thriving and loving the decision I made! Read more>>

Andrew Bernadine | Personal & Private Chef

Taking risks is a necessary part of growth. It demands something of you that will ultimately make you better wiser, and stronger. Becoming a more in tune, decision maker along the journey. Taking a risk defines the leap-start of my career, choosing the pursuit of my own culinary passions, over the wholesome vision my family had for me. But the goal is always worth the risk. I know that my success and my happiness, is all they’ve ever really wanted for me. Read more>>

Madam Dixie | The Superstar

When you believe in yourself you can’t be scared to take risks. Risks in your career shows your hungry and dedication to your craft. Never be scared to bet on yourself. I’ve had family/friends say I couldn’t rap and should stick to my day job, but this is my passion and they don’t determine my destiny. One of the biggest risks I took is putting my entire work check into my WWS music video. Read more>>

Courtney Gardner | Owner of Basic Where!?! Boutique

I read “Think and Grow Rich” & listened to seminars from Bob Proctor and I have come to the conclusion the are two outcome. You take the risk or you don’t. You will always wonder what would’ve happened if you took the risk. Taking a calculated risk is always a good thing in my opinion, it will work or it will not and a lesson was learned of what didn’t work. Read more>>

Antar Tidwell | Engineer, Music Executive, investor, & Entrepreneur

I feel as though risk taking plays a key role into future progression, and setting yourself apart from your competition. However, I try my hardest to research as much as possible which in return increases my potential for success. I would definitely say that I take calculated risks for sure. Read more>>

Jasmine Scruggs | Professional Makeup Artist & Creative Director

This is a great question! Risk taking is what got me to where I’am today! I think life is all about taking a risk. You’ll never know the outcome of something until you do. I took some losses don’t get me wrong but big wins came out of taking those risks as well. I learned so much through it all! & most importantly it helped me grow as a business owner. Read more>>

Dr. Stephanie Iglesias |

I believe risk is something entrepreneurs take often, it’s the biggest part of making it from one level to the next. On a personal level, the biggest risk I have taken is telling my deepest and darkest truth in my personal life story. I have exposed myself at the deepest level. For others, they will either love you for it or hate you. Read more>>

Livisha Renee | Actress

I have learned that taking a risk in life versus if you’re is your career any kind of us in life take the risk because you never know what can happen take a risk can always change your life taking a risk for me if I didn’t take this risk to want to be an actress and you know step out of my shell of being on the camera screen how would I know how far this could take me I still don’t know how far I can take me but I took a risk to step out on faith and I’m still taking a rest till this day. Taking risks of scary but long as you walk out on faith and keep your vision follow your path everything will be fine Read more>>

jerald robinson | Artist/Educator/Entrepreneur

You can’t be an entrepreneur if you’re not willing to take risks. It’s just part of the life. To really make it, you h have to be willing to take risks that others aren’t willing to take. So I guess I was just built to be an entrepreneur because I’ve always taken big risks to get where in needed to go. It has put me ahead of some of my peers because I have no fear of risks or failure. Those two go hand in hand as part of the success story. Read more>>

Arielle King | Environmental Educator

To me, taking risks means stepping outside of your comfort zone and/or taking an unconventional path. That’s what I’ve been doing my whole life. Very early on my parents instilled in me the notion that nobody is better than me, and that I’m not better than anyone else. That lesson has allowed me to confidently create my own path regardless of naysayers’ opinions or the paths other people have taken. Read more>>

Krys Bond & Kass Armenti | Founders & Owners of Kitsch & Keen Collective

While we have a healthy view of taking risks, doing so can be scary. Failure is never fun. However we recognize that doing so could also result in growth. It’s never easy to take a leap of faith but in our case it has proved to be rewarding. We started out with our focus being our subscription boxes and we were and are content. But we recognize an opportunity when we see one. Read more>>

Ebonie Brown | Owner of Heaven Jewels Boutique

Life is about taking risks! If you never take the risk, how will you ever know the outcome! I took a big risk and started my business. I have invested and sacrifice a lot, but I kn0w it will be so rewarding in the future. Read more>>

Tara Dew | Model, Art Historian, Artist and Alchemist

To me, life without taking risks is settling and truly doesn’t make life sound fun for me. Risks set a fire underneath you that catapult you into places and moments you’d only dreamed of being in. Life hasn’t always dealt me the easiest hand of cards to play with, so taking risks is something I had to do for survival. If I didn’t take risks for myself, I wouldn’t be where I am today. Read more>>

Rocco Lapaire | Acrobat, Juggler, Cirque Performer

When I finished college/military I was offered a job in IT (Information Technology). I had always expected that that would be the kind of job I would work for the rest of my life, but I turned it down to try my hand at being a professional acrobat. Read more>>

Michelle Necole | Influencer

Risk taking goes with anything you do in life. You have to be willing to take risk and be prepared to fail nothing is ever just a cake walk. But knowing the risk and the ability to tackle each that makes a person. Read more>>

Chris & Ch’nese Pittman | Tour Company Owners

Risk taking has been central to our launching Fiesta Tour Puerto Rico (FTPR). Chris, Ch’nese and Christopher packed up and moved to Puerto Rico leaving behind family, friends and livelihood. We believed in our vision and had faith that we could manifest our dreams. Without taking such a risk, we would not be where we are today. Read more>>

Autumn Thomas | Mrs. Defy Gravity, Entrepreneur & Mentor

I am all about taking risks! To be honest, just stepping into full-time entrepreneurship was a “risk”. I left a comfortable job with good benefits for the uncertainty of being my own boss. But my advice is this, whatever scares you, do it! You will never reach your full potential if you operate solely within your own comfort zone. Read more>>