Risk is the most common topic that comes up in our conversations with entrepreneurs and so each week we ask entrepreneurs to talk to us on the record about how they think about risk.

Dana Sokolowski | Director, Writer, Choreographer

These last 2 years have been about the commitment you make when you take a risk. You may not see the fruits of that risk until years later, depending on how you define success. When you make that bet on yourself, you open yourself up to the possibility of seeing it, of experiencing it. It scares me far more to not take the risks and find myself with only myself to blame for the options I have before me. When I take the risk, I sleep better at night. Read more>>

Erinn Cottman | School Leadersip Coach & Education Consultant

I’ve always been fairly calculated when it has come to my career. When I decided to leave my job of 11 years to pursue entrepreneurship, while I weighed all of the risks, I took a bet on my expertise, knowledge, and hustle. As the saying goes, there is no reward in life without risk. As I close the chapter on my first year of full-time entrepreneurship, risk has allowed me to increase my impact in the education space, as well as live a fuller life. Read more>>

Garfield Peart | Architect & Diversity, Equity and Inclusion Advocate

Nelson Mandela once said, “there is no passion to be found in playing small and settling for a life that is less than you are capable of living”. Risk is the ability to step out on faith without a parachute or a soft place to land to become the person you were meant to be, live your best life, and contribute to the world as only you can. – I am a 50-year-old career architect and project manager with over 25 years of experience. I have managed over $700 million in federal, state, and municipal projects. In my latest position, I was a Program Management Officer for the City of Atlanta, working under the Mayor’s office, managing over $60 million dollars in construction projects all over the city, and making over six figures and year. Read more>>

Mark Price | Pro Pickleball Coach

I left the dusty streets of Kathmandu, Nepal and flew over the beautiful snow capped Himalayan mountains on a flight to Hong Kong. I had never been to Asia before but was excited to arrive in this modern city with a dream to continue my coaching journey. The risk paid off, one month later I was working for the largest sports coaching company in Hong Kong travelling from the New territories to Kowloon as well as all over Hong Kong Island. Read more>>

Aaron Davis | Real Estate Entrepreneur

One way that I like to view risk is by looking at how my life could turn out if I don’t take the risk, and also how my life could look if I do take the risk. Since becoming a full time entrepreneur I had to take some pretty big risk, and I had to weigh the pros and cons of each situation. If the reward is greater than the risk than I’m going to go for it. Risk taking has played a tremendous role in my personal life/ and in my career. I moved to a new state shortly after graduating college, without having a secure job in place. That was risky at that point in my life, but I felt led to leave at that time and it worked out well for me. Read more>>

Lisa Irving | Education Content Creator

Every risk is a chance to learn. Despite the fact that I am a definite introvert, I have found myself taking some big risks over the past few years. Right after earning my bachelor’s degree, I moved from Florida to DC with my now-husband. I didn’t know when or if I would find my first teaching job in the few weeks before school started, but I did. After one year in the classroom, I decided to interview for a gifted program coordinator position. I didn’t know if I would be taken seriously, but I got the job. After our wedding, I persuaded my husband to start a debt-free journey with me. Being so young with so much in front of us, committing to debt freedom was a huge change. Read more>>

Symoné B. Beez” | Investor

When I think about risks and decision making I always think about them in terms of Expected Value (EV). EV is a poker term that can either have a positive or negative outcome. In my life, I have taken what many people consider major risks. I decided to leave the United States and move to Japan at the age of 23 to further my career as an Overseas Government Contractor. This allowed me to double my income and live tax free which boosted the amount of money that I could invest every month. Making this one decision allowed me to continue to advance my career and invest aggressively which lead to me retiring from corporate at age 29. Read more>>

Frank Rossi | Co-0wner & Producer

Starting any business is a risk. We cannot fear failure. Wayne Gretzky said, “You miss 100% of the shots you do not take.” Sometimes you have to risk it all if you truly believe and feel passionate. This is true in both our lives and careers. We understand that sometimes you have to fail in order to succeed and that’s ok. But if you try your best and let your love of the art drive you, and you stay humble through the process, the passion will show in your work and people will connect. You will never know unless you try Read more>>

Clara de la Fuente | Acrylic and watercolor artist

.When I was 24 I moved to the US from Spain. On an early morning of November, I got an email offering me an internship in the US. Five minutes later, I emailed back accepting it. I had no clue where in the US I was going, and honestly I didn’t care. To me it was a no brainier; you only get these chances once in life. After the initial hype, I was like: oh my, am I moving into another continent?!?! It was a mixture of excitement and fear. However, that was the most pivotal point in my life. Read more>>

Rachy Raxx | Photographer & Entrepreneur

I remember when I was younger my OG’s would tell me “within this one life you have if their is anything you want out of it there will always be risk involved so come to terms with it.” If you truly want it you will do whatever to get it but understand that it won’t always go your way, even now mentally, if i cant accept that and do what needs to be done you’ll always be stagnant and THAT is what causes me more stress then any bad outcome that came from me trying to elevate my brand or business. Read more>>

Rebecca Antrim | Professional Photographer

I believe taking risks is a good thing because you never know what could be without pushing yourself beyond your comfort zone. It is when we are uncomfortable that we learn and grow. For these reasons, I consider myself a calculated risk taker. I begin by thinking about what I want to accomplish and then consider the rewards and potential consequences of my actions. Sometimes, it takes a lot of self-talk to push myself outside of my comfort zone. Even though things don’t usually turn out as we plan, I know that taking calculated risks will pay off. Read more>>

Fai A. | Effective Communication Consultant and Content Creator.

“The irony is that we attempt to disown our difficult stories to appear more whole or more acceptable, but our wholeness—even our wholeheartedness—actually depends on the integration of all of our experiences, including the falls.” Bernie Brown I think that the greatest risk an individual can take is being Vulnerable, is being honest about your story. Speaking your unfiltered truth, and by doing this I learned that the truth becomes your most powerful weapon. Its not only your shield and armor, its also your bow and arrow. Read more>>

Beau Allen Collins | Artist & Actor

I have always loved Ai Wei Wei’s quote, “If you don’t act, the danger becomes stronger.” I love taking risks. For me, if there is anything I am even remotely interested in, I will try. I do fail – I fail often – but the failure is always within the task or opportunity at hand. Never have I felt that I’ve failed myself, or that the journey wasn’t worth the outcome. Read more>>

Destiny Harris | Inspiring Entrepreneur

I believe that taking risks is essential to being successful. I love to go by the statement “without risk, there are no rewards”. Taking risks has played a significant role in my life and career. If I didn’t take the risk to start my business, there wouldn’t be a Charismatic Cosmetics. Starting my own business was definitely one of the biggest risks I’ve taken in my life. I didn’t have a blueprint to anything, I was just learning as I went. I am still learning now, but I’ve definitely learned from my mistakes. Read more>>

Gvijin Films | Film Director, Cinematographer

Ive always felt like an outsider, like I didn’t fit in just right, so i had to take a risk on myself to prove that people like myself can do what we want without having to go down the traditional route, I believe if you want something you have take it, There are risks in everything we do, just make the best out of each opportunity. Read more>>

Melissa Rojas | Lifestyle Influencer

In the last 2 years, I have taken more risks than ever before. I believe that life is meant to be lived through adventure. I was recently blessed with becoming a locally certified teacher in my home town and taking this position mid-year was a considerable risk and step in the right direction. Read more>>

Rebecca Anuru, LMSW, MPH | Founder of Dream Keep Consulting

I think growing up as a Hood Black girl fighting to survive was a big risk in and of itself! Being grown now and trying to balance being traumatized, healing, and constantly aiming for thriving in an unjust world definitely makes me realize how much of an accomplishment it is just to be Black and alive. I have always wanted to be a container of safe space, a soft place for people to land so creating Dream Keep was honestly second nature. If I’ve always been risking my life, why not dream as big as possible and protect those dreams? Read more>>

Westin Gaspard | Sr. Analyst | Creative | Entrepreneur

Risk taking is essential to your growth and development as a person. Instead of running away from it, I find myself going towards it. I noticed that many people will run away from taking chances especially when they present any type of risk. So many of us ultimately are afraid of “failing”. However, the greatest opportunities arise when you stop playing it safe. Read more>>

Mathan Cephas | Model, Artist, Entrepreneur, King

Through my experience in life, I have learned RISKS and moving out of my comfort zone into the unknown is a huge part of achieving greatness. I’m all about taking chances and calculated risks. A favorite quote of mine from George Lucas reminds me to “Always remember our focus determines our reality.” In life if you want to succeed, we must pursue it fully with unfettered determination. My career path has shown me that the world is incredibly competitive and our choices can come with an incredible amount of risks. Thomas Jefferson taught us a phrase that still rings true today, “With great risk comes great reward.” I encourage you, as readers, to give it your all. Ambitiously, take those leaps of faith, leave your fear of ‘Risks’ behind. Read more>>

THEARTISTJADE | Visual and Performing Artist

I think risk is beneficial to both my career and life. Whether good, bad or indifferent the risks I’ve taken have made me more courageous and knowledgeable. Read more>>

Dominique Doe | Veteran, Realtor, Accountant, Tax Preparer, Book keeper, Business/ Personal Credit advisor and Business/ Spiritual Coach

When I think of risk I think about my transition from a small town in Georgia called Claxton to Atlanta. Prior to taking this risk I experienced a few devastating years that lead me into a mental institution for attempting suicide. After I spent a few weeks in Saint Simons mental Hospital, I discover that my best option for my mental health and my three kids would be a different environment. Read more>>

Adrian Dalsus | Musician at heart, Marketer by profession, Teacher by vocation

When you start a business or dedicate yourself to being a Creator, suddenly you start hearing this word all the time. Deep down, you know that giving up your 9-5 job to dedicate yourself to developing your own brand is a risk. But it’s not until you make the decision that you understand what this means: There is no room for failure, you have to make things right. My first takeaway from this is that you need to create a space of safety within your own risk. Read more>>

Shynesha Howard | CEO

I think calculated risk is absolutely necessary. I only said calculated because that’s just how I am lol. When it comes to risk, I quit my full-time job to pursue full-time entrepreneurship with no backup plan. My backup plan was that my original plan had to work. I remained positive throughout the process. Every day, I would get up as if I was getting ready for work. Then, I’d go sit at my desk and “clock in” at 8. I treated my business exactly like a job. Read more>>

Amina Sahovic | CEO of Glossy and Bossy G&B, LLC. / Pursuing Creative Director

Risk taking is huge for me. I believe I have always been the type of person to just go for what I want. If an idea/ thought is consuming my mind, that must mean it is meant for me to pursue it. There are risks you must be logical about, but I would rather make it happen for myself than regret not doing so later. Glossy and Bossy in itself was a risk. Being a Junior in high school, I did not know anything about running a business so I was entering a gray area, Read more>>

Sicarah Lashay | Host, Photographer & Videographer

I think risks are great because you never know what the outcome may be unless you give it a try. When I was 21 I would go to concert venues and bring my camera, say I am media and get into the event even though I didn’t have a press pass. This method did not work all the time but nevertheless I still made it into some pretty cool events. I knew I could get footage outside the venue and maybe even catch a few fan reactions regardless of if I made it into the event or not. Read more>>

Chanel Douglas | Jeweler & CEO

Life is full of risk. I feel like you can’t get very far in life if you don’t take risk. I worked at a job that I hated very much and I was very afraid to take a leap of faith. I worked as a cashier and owned my own business on the side, I always seem to put my job before my business. Finally one day I was let go from that job and I was forced to take a risk and invest in my business full-time. After risking it all and believing in my business I made my first six figures. If I would have never had faith and believed in taking risk I would have been stuck where I didn’t want to be and that was working on someone else’s job. Read more>>

Alexis Hallum | Personal Trainer & Freelance Model

I believe risks are meant to be taken. Life isn’t written out for us to follow step by step. There are always going to be choices and decisions we have to make and some of those may be risky. Risks aren’t a negative thing. It’s highly favored in my eyes. You will get nowhere in life living in your comfort zone. In order to explore what else is out there for you, you have to take risks, you have to fail a few times and you have to keep learning and educating yourself to be better than you were yesterday. Taking risks has put me in a much better position of being more open minded and knowledgable. Read more>>

Capusine Clemons | Personal Chef & Caterer

Risks are a good thing, provided they are taken in an intelligent way. During the pandemic, I decided to resign from my full-time job in order to better grow our catering business. The journey has had its challenges. However, my husband/business partner fully maintains our household, while I focus on the business. Read more>>

Brandon Perryman | Actor/Writer/Brand Ambassador

Grind and Go Get it is a the Main Goal. No Excuses Read more>>

Ty Norwood Jr. | Actor & Producer

Risks are very necessary especially in terms of an individuals growth. Risk is a big part of my career as an actor! Moving to Atlanta from Philadelphia was not an easy decision and I tried to calculate everything as much as I could but truthfully you’re never 100 percent ready. Sometimes you just have to jump. You’ll either fly or hit the ground either way you’re already doing something many can’t say they’re willing to do. Read more>>

Sonya Pfeiffer | Criminal Defense & Civil Rights Attorney, Owner of Elder Gallery of Contemporary Art, Co-host of Abuse of Power on Audible, Proud Mama

I have always thought about risk the way T.S. Eliot described it: “Only those who will risk going too far can possibly find out how far one can go.” Back when I was a kid, maybe around age eleven or twelve, I read that quote from my quote-a-day calendar that was all the rage at the time. I tore the page out and taped it up on my wall. The quote embodies everything I believe about risk: it’s exciting, it’s the only way to know your limits, or any limits, and only those who are willing to take risks will reap the benefit of doing so. Read more>>

Dustin Lee | Business Owner & Physical Therapist

My view of risk has constantly evolved throughout the course of my life and professional career. The younger version of me looked at risk as a way to escape. I left my hometown, family, and friends after my parents divorced to start school at Colorado State University (CSU) – a city and state with which I had zero connection. Leaving everything behind and starting fresh was appealing but it came with the risk of potentially leaving everything I loved and not enjoying my decision. Two years into earning my degree at CSU, my understanding of risk changed again, as I recognized an opportunity for growth in the degree field I wanted to pursue – kinesiology. Read more>>

Diana Visser-Gregory | REALTOR® & Actor

I think Risk is important in everyone’s life and careers. For me it’s being able to take the risk to giving up a weekly paycheck and benefits to achieve the direction of my life. I control when I work and how much work I take on. Not having to work the traditional 9-5 hours and allowing myself the flexibility to work on my other passions is huge for my mindset. My life now adays consists of being a REALTOR® for over 20 years now, my acting career and activism roles. Read more>>

Alejandro Amorosi | Music Producer

In the music scene, risks take a big part in how far you make it and how much you accomplish. I haven’t reached my full potential yet but i have accomplished enough to say that how ever much time and effort you put in to what you do, you’ll have a successful outcome with that subject. Secondly nothing comes overnight, late nights and hard work are the steps for success. Read more>>

Nichole Walker | APC, NCC

When I think about risk, I have always considered myself very conservative. Always playing it safe! If I’m being totally honest, it was rooted in fear. Fear of loss, fear of failure, fear of what others would think or say, etc. FEAR! As I’ve grown older and wiser and continue to become more confident in myself, I can say I’ve been more open to taking more risk. Read more>>

Kayla Wright | Children’s Boutique Owner

No risk, no reward! Starting my own business was a huge risk. Being that I was the first in my family to start a business with an LLC, I was scared out of my mind! I truly had no idea if I would be wasting my time, wasting my money, wasting my ideas.. but I took the risk. Taking risks are worth it with a plan of execution. Taking risks on my business has not only helped me with my personal development, but has also motivated others to face their fears. Life is short! Do it and give it all you’ve got! Read more>>

ohdollynetworks@gmail.com 462874677 | Actress & Founder of OhdDollynetworks

By taking a risk, you are facing the fear of the unknown. As an actress I always struggled with balancing financial stability and being able pursue my acting career. Being an actress is expensive, keeping headshots up to date, paying for subscriptions, classes, networking events, even the paying for gym memberships took keep up your image. Taking risk plays a major role in my life, it exposes my true faith and survival skills. It has shown me that a lot of the times our biggest opportunities are just on the other side that risk we need to take. Read more>>

Briittani K | Singer Songwriter/ Actress

Risk for some may be scary but for others it’s a thrill. I’ve always been a risk taker/rebel, going against the grain while expecting a great outcome. I tend to hear “I can’t believe you did that, I would’ve never” or “You’re crazy”. I believe taking a risk is vital, necessary. Taking a risk can shape you, strip you from fear and bring new insight. Risk taking for me has brought many beautiful experiences in my personal life and career. When I sit back and reflect on the benefits received from one small or big risk, Read more>>

Rebekah Pierce | Hair Stylist, Salon Owner & Risk Taker

I had been working as a stylst for many years and loved the freedom of expression I experienced through my guests. After a few years, while that was satisfying, I really wanted more. When it comes to risk taking, I had a little experience. Certainly moving from Southern California to Georgia to start over was a risk and as I looked back I viisualized how that and other events had turned out. I realized I could take a risk and while it was rocky on occation I had learned to focus and pull through. The use of visulization has been a huge help to me when I comes to taking risks. Read more>>

Thomas Crosse | Owner | Design | Builder

Without taking a leap of faith, there is little growth in bringing a vision for business to life. Develop a plan and run it by other successful business owners for advice or constructive review. Work the plan, expect some mistakes, when mistakes arise, correct them and develop a process or plan to avoid making it again. If you’re fearful, sometimes you need to use that energy to focus on driving your plan. The plan won’t happen if you don’t risk giving up or phasing out of your current job. Read more>>

Cortney Morris | Personal Chef & Event Planner

The way that I see the world is…. We as people take risk everyday that we wake up and leave our homes. There’s no way to predict from second to second of life if you will get to see another second of life once you are out in the world. What is the difference in that and taking risk to do something that you feel may help you grow, progress, or elevate from your current circumstances? Read more>>

Deja Iman | Photographer & Creative Director

I feel as though risk taking is very important in not just business, but everyday life! Risk is necessary in order to grow. However, I feel as though the risk should not be so substantial that it can very well ruin a business and/or self in the process. Risk taking has played a major role in my life/career in the aspect that it is a constant reminder that it is chess not checkers… meaning work smarter not harder. Read more>>

Taraneika Brady, M.Ed, LMT | Biology Instructor & Licensed Massage Therapist

I have always been a risk taker, especially if I foresee the benefits of taking the risk. My most recent risk taking adventure has catapulted me into my next level and created a foundation for my future. I left my teaching career of 6 years and enrolled in massage therapy school. After graduation, I hit the ground running and opened my own Spa while going back to the classroom to supplement my new business venture. Read more>>

Hollis Hildebrand-Mills | Artist

Risk taking is an intrinsic part of being an artist. When I have created work, I find that displaying it in front of people is a risk because the art work is personal. Applying to juried exhibitions and approaching galleries is also a risk because I have a fear of rejection. But I get a thrill out of taking the risk and the thrill outweighs the fear. I always feel that an artist should aim for the highest level in the art world. I found that’s where my success has come from. When I do succeed after taking a risk, there is another fear that pops up, creating work again on the same level that earned me the original success. So risk and fear and success go together. Read more>>

Taromi Lourdes Joseph | Award Winning Actress, Writer, Director and Producer

I’ve always been a risk taker to some degree. As far back as I can remember, school days, I was engaging in some activity or having ideas about some activity that the ‘average’ person may not be interested in. As an adult, I’ve been called crazy for some things I have said or done, outside the norm, but I rather be crazy than be the ‘average’ person who stays in one place-mentally, physically, emotionally, socially, career wise. I have embraced risk. Read more>>

Mckennah Laurel | Makeup Artist & Esthetician

I believe at some point in life, it’s important to take on risks. Taking risks have played a big role in a lot of the people and opportunities I’ve come across. I’m an avid believer that everything happens for a reason but your decision depicts how a risk can serve or hurt you. Throughout life experiences, you’ll learn how to decide what risks are worth taking. Becoming a beauty professional and following my dream in becoming a makeup artist was a risk worth taking. In the early stages, Read more>>

SkyQuajus Turner | Photographer + Visual Artist

I can honestly say that risk taking has played a key role in my success. I feel like a lot of times when I was in the beginning stages of photography I’d be afraid of myself as an artist. Not because of my talent but simply because of how far my talent would take me. We don’t truly realize but we hinder ourselves from success due to lack of confidence as well as lack of trust within ourselves to make the first step and walk through doors we may be scared to walk through. Read more>>