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.

Fletcher Kasell | Co-Founder / Co-Creative Director

Fashion and most creative fields for that matter are full of risk. Without risk taking, how would we evolve? At Tanner Fletcher, we think about risk as a must. It helps us to learn what works, what doesn’t and helps to form new ideas and trends. Sometimes, risk gets uncomfortable but we like to say, that you either love something or hate something. We are fine with either because it means we’re creating something new that pushes boundaries. We would say that risk is a big part of our design process. We often design crazy, risky things and either edit them down to be more wearable or leave them as is. It all balances out in the end. I don’t think we would be able to design good fashion without taking risks. Read more>>

DeVannah & Vikiah Gardner | Registered Nurses & Wellness Spa Owners

To take risks calls for blind faith. It is a blindfolded journey at times in just trusting God. Our journey will allow us, to process and gain valuable information all while taking note of our experiences. Life is meant to give us situations where failure is the result. It is shaping us. As Les Brown has said, “If can look up, you can get up and try it again”, but from another angle in which success is bound to happen with persistence. As a backstory, iVannah means “Gift from God” it is our mission to execute the task or assignment at hand and steward to our clients where we create a space or environment where clients can have a peace of mind and feel good mentally, spiritually, physically, and emotionally. Read more>>

Risha Ferdinand | Boutique Business Strategist

Everyday we take risks. We take risks in leaving our homes, not knowing if we will return in one piece. We take risk when trying a new meal/dish. We even take risk when hiring UBER placing faith in a total stranger to take us to our destination safely. The risk appetite is what sets people apart. Some folks rather take risks by trusting a stranger to take them to their destination safely instead of investing in their education or business. Risk appetite is influenced by our relationships with money, people and our past. Read more>>

Marlo D. | Artist/Songwriter & “The Difference Maker”

Risk taking is a monumental role when looking a one’s life or career choices. Risk taking is unavoidable! The only choices we have, is how big or how small we want that risk we take to be in the lives we live from day to day. I’ve recently decided to take a new perspective on life. Tomorrow isn’t promise, so today, I’m going to make every risk I take count! Read more>>

Rayshanna Byron | Body Contour Specialist

When it comes to risk, I take them. Life is all about taking risks. You will never know the outcome if you don’t at least try. If you fail, at least you tried and you know what to do differently. If the first plan doesn’t work, come up with another. Do not ever give up. Through out my business, I have taken many risks. Starting my business was a huge risk, but I had the faith that everything would work out. If I would’ve never took that jump, I wouldn’t be where I am now. Read more>>

Brittani Glover | Model, Stylist, and Healing Influencer

When thinking about risk I look at the worse case scenario. In the industry of modeling, there is a lot of “sweat equity” involved, meaning time, effort, and putting in my own work. I travel to model calls and fashion shows, which of course is done on my dime at times. Is it a risk? Could I go out there and they not choose me? Absolutely. Read more>>

Danny Steele | Actor, Coach, Author and CEO

for me, i have discovered the positive effect of thinking of my life as a series of writing myself permission slips – often i told myself a story that i couldn’t do something (which was primarily based in fear), i used to get overwhelmed with all the things i wanted to do creatively – so i gave myself permission to start thinking of living and having a career in the US as a British actor writer and coach. I took a risk and called myself an author before i had a book published, i called myself an actor before i had taking an acting class for example . even though there was risks involved in all of these pursuits, thinking of each one as a series of permission slips that had to be mentally (or physically) written made them easier to break down and work through Read more>>

93Ferro Sergeant Taliaferro Bersiah Martin | Life path 3 Artist to promote change and one day bring world peace by spreading Love and Peace this world needs it!

Life is a risk. So why not risk it doing what you love following your inner child its where your imagination lives! At 28 I was delivered a message to spread and live by. Always know you are enough. Love your self . Control your emotions. Execute your dreams and goals daily. Seek validation in no one but yourself keeping your heart pure. As times get more weary, we must chose to be our own best friend never our own worst enemy its faith over fear anything opposite of faith is fear. and anything opposite of love is evil. The frequency of God(Yahweh) is Love. And anytime you operate in love more positive things are bound to happen in your life energy is real you attract what you are . Read more>>

Dannyel Carranza | Senior Director of Content – Atlanta FaZe & Atlanta Reign

I think risk is pretty synonymous with success; and that it’s necessary to take risks to advance your career and your life as a whole. As for myself, the risk of dropping out of university led to my whole career. I left tradition and comfort to chase a crazy dream and to try to do something that I love. In hindsight, it was a huge risk to ditch school at 19 years old, but knowing where it got me, I wouldn’t change a thing. I’m 23 – turning 24 in August – living in a different country than I was born, working many kid’s dream job and having fun doing it. Taking risks led to this. Read more>>

Trinity Hewling | Aspiring Hair Artist

In my experience, risks are beautiful. There’s always that worry of the possibility of something going totally left but at the same time there’s that voice telling you “just do it.” I love that. It’s like the soul speaking. If the risk you take ends up falling through, you almost always gain wisdom for a new approach or a completely new perspective. Either way, in the end you’ll be standing in the right direction. Read more>>

Javan Wallace | Music Producer, Singer, Musician

When I think about taking risks, I think about sacrifices of certain things that are also a necessity in my life such as work, school, etc. However, I manage to put my career above that and put more of my time into my craft and perfect it. The role that taking risk has played in my life is a very important role. It has shown me that if you don’t take that step in order to see what’s next in your career path, you may never know what it is. Read more>>

Stanton Marshall | Graphic Designer & Branding Specialist

Taking risks plays a major role in my career. I took the risk of quitting my job and going full force with my business. Then after doing so, I took more of a risk and opened a brick & mortar. That was terrifying but exciting. Read more>>

Arischa Conner | Actor and Audiobook Narrator

I believe that risks are necessary in everyone’s life. If you believe that you have the talent to do something that others may or may not believe in, you have to believe enough in yourself, your ability and your work ethic and know that you can be successful. But remember, faith without works is dead. You have got to work hard to achieve your goal, there is no way around that. I decided that I wanted to pursue my dream of being a full time working actor. I did not want to look back over my life and wonder if I could have, or should have taken that risk. Read more>>

Joenesha Hardman | Event Stylist

I’d consider myself somewhat adventurous and I don’t mind taking risks as long as it is something I really want to do. I’m also very analytical and logical thinking so even if I do take a risk, chances are I’ve given it a lot of thought. I think that risks are a very necessary thing and very little progress or growth happens without them. This year I’ve taken a lot of risks with my career, interests, and personal life and it has stretched me in so many ways. But it has also allowed me to go after the things I want with much more confidence and drive. Read more>>

Ayanna McNeill | Author & Editor, Certified Life Coach, Writing Coach

One of my personal mantras in life is “You’ll miss one hundred percent of the shots you don’t take.” Success requires risks, calculated risks that helps you find opportunity for growth and to learn lessons. In business you have to have the gall to bet on yourself, It takes confidence to believe in yourself, and taking actionable steps towards securing your success. When I started Harriet Returned, there was a million reasons why starting a business was too risky. However only one reason trumped all of those internal fears, I believed in myself. My company’s motto is “The Cost of Freedom is Faith!” Read more>>

Alex Beano | Radiant Family Records

Ive took a lot of risk that I probably shouldn’t have but thats the thing with risk, You gotta know that its a 50% chance things might not work out like you planned it. I can definitely say i’m a risk taker but you have to be one in the music industry or you’ll probably not see the results u want. Read more>>

Jay White | Serial Entrepreneur and Author

My life has been fashioned to go through the weeds. I realize there is a stark difference between the seen path and the unseen path. I’ve found The Divine and met the absolute most remarkable people in the weeds. The weeds are less traveled and there is so much abundance there but few have the faith to charter it. The way I see it, If we’re not taking risks we’re not really living………. We’re merely existing! Read more>>

Naomi Ibañez | Nail artist & Nail Supply Store Owner

Having the courage to take risks plays a major role in becoming an entrepreneur, & the risk that I have taken over the past two years have led me to becoming the owner of two business at only the age of 20. In my personal experience, I took the risk at the age of 18 to quit my job, & drop out of college to commence my career as a nail artist, & to most recently launching my own brand of nail essentials (nail charms, nail tips, tools & more.) Read more>>

Chloe Mihacevich | Dancer & Actress

I feel like I’ve always been a risk taker. I think you have to in the life that I want to live. Having your dream career be to pursue professional dance and acting is nothing short of a risk. The entertainment industry is very different than most jobs. You’re practically always unemployed until you’re employed again. It’s constantly waiting for auditions, auditioning, hoping you book the job and if you do, having (if you’re lucky) a decent paycheck to last you a month or two, and then you’re back to waiting. There’s no guaranteed money in the business and no guaranteed employment. Especially when you’re first starting out (like me). Read more>>

Randolph Simmons | Actor, Model, & Entrepreneur

Taking risk has played a major role in my life. Growing up I had fear that if I failed it meant I was a failure. However, by taking risk you will learn to overcome your fears. You will likely begin to care less about what people think and less about what could go wrong, which is a powerful shift in thinking. “I think if you risk nothing, you risk everything.” -Geena Davis Read more>>

Rachel Griner | Founder and CEO, Brave Nu Ventures

Risk is the defining force in my career. I’ve always been guided by my curiosity. That means I start with a question and learn as I go. I worked in PR for a few years right out of college and I got to lead the IBM Healthcare account for Ketchum. It was all about how IBM is entering this new space, and I became fascinated with how markets evolve. How can a business adapt to serve an evolving market? Read more>>

Adam Guard | Full Time Dreamer

Well it’s an apt time to talk about risk. I just left my well paying day job in commercial real estate to become a full time entrepreneur or as I like to say…a full time dreamer. The risk is huge, I am recently married and bought a house 6 months ago so I have some large responsibilities that I need to be able to take care of. But overall what I want to say about risk is that it’s all about the reason and approach. You can’t just jump out of an airplane with the dream of surviving. Read more>>

Lily Hagen | CEO & Founder of Lingo Plaza

I think life is about taking risks. From relationships to businesses, we’re all taking risks in one way or another. Before we founded Lingo Plaza, we saw and experienced the pain points of Language and Cultural education. It was an opportunity to either wait and hope for someone to solve this issue, or take a risk and do it ourselves. It was a big risk, and there were a lot of unknown, but if we wouldn’t have taken the risk, we would never learned how our solution is enabling families to embrace the hispanic culture, heritage languages and have genuine cross-cultural connections. Read more>>

Dr. Eddie Connor | Empowerment Speaker & Best-Selling Author

The saying goes, “An entrepreneur is someone who jumps off a cliff and builds a plane on the way down without a parachute.” Undoubtedly, it’s a big risk to reap the rewards but you can’t reap the rewards without taking the risk. If you want to aspire higher and reach new levels, you have to take a leap of faith. Personally, for me to shift from full-time educator and professor to full-time entrepreneur was totally risky. Creating something from nothing, betting on myself, and beating the odds was undoubtedly risky but all the more rewarding. Read more>>

Gregory Linder | Video Producer & Marketing Specialist

One thing I’ve learned from a young age until this very moment is that taking risk are a part of life. Anyone who’s successful or seen success had to take risk to get there. I have a corporate background which means I’ve worked a job in my career, this means that for me to become a fulltime entrepreneur I had to leave the comfort of my job. Which gave me a steady paycheck and healthcare options to creating these things on my own. Taking calculated risk play a major part in my career growth because has an entrepreneur you’re taking risk every day. From business opportunities to purchasing items that will help benefit your business is all a risk. Read more>>

Raeven King | Photographer

I have taken a health amount of risks in my life. As a former overseas basketball player I took a risk leaving my salary job at the time to pursue a career in Switzerland and although, I had a decent season it didn’t lead to a spot on another club.. The experience of doing what I love was invaluable. Which leads me to my present day career. I left New York in 2019 and moved to Atlanta. Outside of my family I didn’t really know anybody here. With no network I began what I like to call my “3rd career” as a Photographer. People would ask me what I do and I would say just that I am Photographer, At that point I hadn’t had any clients or anything. Reward of starting my own business out ways the risk. Read more>>

Cam Hay | Artist

I think of risk as chance. Youll never know what you’ll accomplish if you dont take risk. Risk taking has lead me many different places in life as far as business partners and even intimate relationships. Some failed some and some succeeded, but you’ll never know unless you try. At this point in my life, I’m taking a risk towards healing. My healing process is risky because I may lose fans, friends and even intimate relationships while healing and becoming whole with myself again. But I know it would be appreciated in the long run through my music. Read more>>

Jalessa Montaque | Digital Finesser, Dir. of Photography, Producer, and NOMAD

Oooooh—risk has been the theme of my life in multiple aspects. When it comes to stepping into my identity 100%, my creativity, my relationships, and my growth. When I think of risk, it’s a part of me. There isn’t one individual that knows me who wouldn’t associate me as a big risk-taker. It allows me to break but it will enable me to mold myself and fall into opportunities and experiences. A lot of the time, especially recently, taking risks feels a bit more tricky, you know? I guess it falls in line with stepping into adulthood, you have “more to lose”. Read more>>