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.v

Jessie & Ricky | For Jessie | Sticker-maker & Owner of oddloop // For Ricky | Visual Designer

Jessie: Risks, while scary, are definitely a net positive on my life/career. It took me a while to learn that if something scares you, it is probably the direction you should take. Growing up I was extremely risk-averse, and followed a very conventional path, which was “get good grades, go to a good college, and get a good job.” How does one really define a “good job” though? My mindset now is this: if you really want something, take the risk. I don’t believe there are any right or wrong decisions in life as long as you put effort into the decision you’ve made, and learn something from it. Ricky: It may seem like a bit of an obvious answer, but the risk I took was to become a  graphic designer/artist and go to art school and sign myself up to all that that entails. I was lucky to have discovered graphic design late in high school and was able to pivot my interests and career path towards making that happen. I told every club and sport in my high school that I would make their flyers, posters, T-shirts, whatever, for free and some of them actually bit. Read more>>

Gulmakai Saleh | Author & Speaker

I would always think, risk is something that is in the unknown. Whenever there is something in the unknown fear comes in. That fear comes in because one has never tried it. So, I thought why not take a small risk and see how it will go. Therefore I wrote my first book not really making a big commotion about it. Then I notice it wasn’t so bad, let me try a second time. During my second book, I made a big commotion. I continued to my third and fourth books. It is all about one’s mindset that puts us in fear of taking risks. Since I played around with a small risk I learned a lot and improved when I took I bigger risk. Read more>>

Jalyn Nwogu | Digital Artist & Designer

Risk has been an integral part of my life and career. The fact that I decided to go to New York for Computer art, an industry I had zero knowledge of, from my small city of Irving was the biggest risk I’ve ever taken. I had no idea how it was going to play out or if I would succeed, but It was the best decision that I made in my entire life. I struggled with my mental health greatly while I was in college, but in the end, it helped me understand myself a lot better and I was able to push myself to heights I never thought I would be able to do. I consider everything I do as a risk because internally I want to stay in my safe area in fear that I could make a mistake or someone will reject me, but my need to be creative, independent, and unique pushes me to continue to take risks. I think every artist should be taking risks and get out of their comfort zones because that’s when you create or do something amazing, and even if the risk you took didn’t turn out exactly as you wanted, you learned something from it and improved your perspective. Read more>>

Diana Ayala | Home Baker

I always think of the saying “Without risk there is no reward.” I have learned that in order to be successful you have to take risks and “go for it.” There was a time in my life when I felt like my life had no direction. I had graduated with my Bachelor’s degree but I struggled to find a job in my field. I felt sad and wondered if I had chosen the correct path for me. In my feelings of no direction I stumbled across a video tutorial of macarons, I decided to try them out. I thought, “how hard can they be to make?” To my surprise, they were a challenge. I failed a lot in the beginning but I was determined to get them right. One day, I finally got them right! I haven’t stopped making them since. I started posting about them on Instagram and Tik Tok and eventually I had people asking me if I was selling them. Without having a large background in baking or business I decided to start Dayala Treats. I took the risk of putting my degree to the side and pursuing what was making me happy. Read more>>

Anna Glasgow | Empowerment Coach

I think calculated risk is necessary for any type of growth and success. Our lives begin with tons of risk-taking. We try to roll over, sit up, walk, run, ride a bike…etc. The only way we develop is through risks. At some point we learn that taking risks can be painful and should be avoided. The consequence of this thought is stunted growth. But, what we want most is on the other side of that risk. I know that any time I get that scary feeling in my gut, I have to analyze it. If it’s the “oh no, I could die” scary, I avoid it. If it’s the scary feeling when strapping into a rollercoaster, I go for it! This has proven helpful in my life, both personally and professionally. I’ve achieved the things I set out to achieve. I’ve fallen short and learned how to do it better the next time. I love rollercoaster risks and look for them consistently. My success is always on the other side of that risk!. Read more>>

Lauren Lopez | Artist

I believe that risks are inherent to being an artist. Making work is a personal process, and sharing that with the public feels like sharing a piece of my soul. There is potential for so many outcomes – will viewers understand? Care? Hate it? Love it? My work ties back to my own experiences and identity, so I’m exposing myself when I make work. However, I find that the more I dive into my practice, the more I revel in this element of risk. It’s exciting to not know what will happen next! In my installation “I remember in vibrant technicolor brilliance,” I had phones where viewers could listen to me sharing my secrets. Being this vulnerable is extremely intimidating. I work on a project until I know it’s ready, and when I’m at peace with it, I release it into the world. Everyone interacts with art differently, and I have no control over that. With this installation, my vulnerability created an atmosphere of openness and acceptance. Some of the viewers started to share their own secrets – it became something celebrated, to be honest and genuine. I found it’s incredibly freeing to allow myself to be comfortable with the unknown – taking risks is always an adventure. Read more>>

Chandra Nicole Lever | Wine entrepreneur

If you want it, go for it. Take a risk! Don’t always play it safe. You’ll always be wondering, “What if”. Life’s too short and happiness is very important! In my career taking risks has giving me more courage to face the uncertainty. I’ve grown through the process and become more ambitious and confident. Along with building key qualities such as self-belief, humility, bravery and the willingness to learn. As an entrepreneur if you take a risk you will see the reward eventually. Read more>>

JaMeyah “Lowkeey” Moore | KeeyRagz CEO, & Artist Development

You have your pros and your cons, when it comes to risk but its well worth it! “If you dont try, how will you ever know?” I live and breathe by that motto! Taking risk, because you know it wont happen overnight. I truly feel, the best part about taking a risk is the accomplishment that becomes apart of it. It feels great going hard for yourself. Read more>>

Yvoire Whittaker | Strategy Consultant

If you google the definition of risk, it defines risk as “a situation involving exposure to danger, harm, or loss”, which, to me, is an incomplete definition. Now, what you define as danger, harm or loss is what determines your response to how you take risk. To me, risk can be measured with the same yardstick that measures opportunity – they go hand in hand. In economics, the Risk Return Trade Off means that higher risk is associated with greater probability of high return and lower risk with a greater probability of smaller return. This is how I prefer to look at what risk means to me and in doing so, realize that a failure is a return that teaches me something. If I don’t learn from my failures and see it as a way to change direction or propel me forward, I am just failing in a black hole. In a similar vein, risk involves being comfortable with managing ambiguity and strategizing around imperfection. Read more>>

Victoria Ricalde | Violinist, Pianist, and Songwriter

I’m a musician who frequently performs solo gigs, which means I have to pitch myself to venue owners and booking agents in order to get jobs. Every time I do, there’s a risk that the person will say they have no openings, or they’re looking for a different genre, or that I’m welcome to play but the only pay will be tips. There’s an even bigger risk that the person I reach out to by phone or email will simply never respond. Each time this happens—and it happens often—I experience a sting of rejection. That fear of rejection is a huge part of why self-employed folks don’t get their businesses off the ground. It is so hard to overcome the fear of self-promotion because we are afraid we might get viewed as pushy, or annoying, or that we might get flat-out told that we’re not wanted. But I’ve learned from people who have been in the business longer than me to reframe my thinking about that risk. If I believe in what I have to offer, then when I extend that offer to others, I’m giving them the opportunity to receive something good. Read more>>

Rob Gs Aka Lucky | Rob Gs Aka Lucky

Risk To Me Is Very Important. Risk Is what helps make you and your success. every thing i do and did involved risk far as chasing my dreams and learning new things. Taking the risk of failing when learning and performing music. Taking risk far as quitting my job to not only pursue music but also to start up my own studio business and go full throttle. It was scary and hard but it was worth it now im making way more than i made at my job and im more proud of myself than ever. If you wanna get far in life its a must you take risk and fail that leads to success. Read more>>

Tegan Broadwater | Creative Entrepreneur

Risk is always relative to one’s responsibility for others. But, if your “others” are cool enough to support your tendency for risk, then go for it. Your ultimate happiness becomes contagious to others and it breeds determination within yourself. Once you take the leap, there is no turning back. For me, that has been the key to pushing through crazy difficulties. Don’t have an out. Just hunker down and push through. It will make for an interesting life at the very least. Read more>>

Rufina Lao | Entrepreneur, Online Boutique Owner

Risk to me is exposing yourself, or putting yourself, in a situation where there could be potential loss or danger. I decided to start my online boutique during one of the riskiest times our economy has ever seen, the pandemic. So many people were losing everything including their lives, but I felt like there was no better time for me to throw myself out there and follow my dream. Before the pandemic I worked a 9-5 that was 95% travel so I had no free time to work on my dream of starting my own online boutique. Once the pandemic hit I was unable to travel for work so I had nothing but free time. That’s when I hit the ground running and started Empyreal the Label. I had my site up and running by December. That same month I was faced with the choice of going back to my 9-5 traveling full time and pushing off my boutique that I had just launched or staying home and focusing on growing my business. I decided to keep on taking risks and stay home, and I am thankful that I did. Read more>>

Manuel Ruiz | Author, Computer Geek and p/t Musician

Risk taking played a major role in helping me build two different careers and also set an example that I’ve been able to pass along to my family. The first big risk I took actually led me to the DFW area. During college, I worked as a “computer guy” for the school district in my hometown in South Texas while I completed my degree in Math/Computer Science. Once I graduated, I was offered an additional half-day position as a high school math teacher, which I did for almost two years. It was a low-risk and comfortable decision since I was already working there, but my desire was to work in the high-tech computer field. I chose to leave family and friends and landed a job in Irving, which is also where my son was born. The job allowed be to learn and thrive in the corporate world, but my wife and I wanted to raise our son closer to family, so after 3 years, I took another big risk and we moved to Central Texas where we’ve been ever since. Read more>>

Katie Henry | Charcuterie Designer

I HATE taking risks! If I could just stay in my own little world, my own little comfort zone, I would be perfectly happy. But I would also stay stagnant, unchallenged and would definitely be unfulfilled. While I do value comfort and security, I also value growing as a person, helping others and seeing what God does when my faith is completely in Him. That’s the best part. In this business, I’ve been forced to take a ton of risks. Every single time, I think to myself, “I can’t do this. It’s too much. There is just NO way.” And sometimes, there really isn’t. So when it’s all said and done and it actually does happen, I know that it was only because of God..not me. So yes, risks are super scary. But without them, I wouldn’t be nearly as blessed as I am today. For that, I am incredibly grateful. Read more>>

Tracie Graves | Integrative Body-Worker and Coach

Risk has been an integral part of my success throughout my life! I feel taking risks helps expand personal boundaries in amazing ways and helps build both experience and adaptability. I believe these two attributes makes you stronger and able to achieve more in life. Every risk move I have made has expanded both my brand and my career in phenomenal new ways. A couple of memorable leaps I have taken are, revamping my technique from hands on bodywork only to a unique blend of bodywork (somatic integration) and tantric/spiritual coaching. Anther leap for me was choosing to leave a comfortable job/contract space due to lack of personal growth. These leaps keep my life and work from feeling stifled and stuck and help life feel more exciting and fresh, I love working with my clients to help them lean more into taking such risks and expand their own horizons. It makes my heart soar to see myself and others take off in new expansive directions. You never know what awaits unless you are brave enough to forge new horizons. Read more>>

Brionne | Female Emcee, Songwriter, & Hip-Hop Enthusiast

Risk has played a factor in my life since…well I can’t remember when. I have a tattoo on my right thigh that says “rebellion leads.” When I was in college I fell in love with this Sociology of Deviancy course. I always felt attracted to rebellious behavior, thought, doing the opposite of the norm. I’ve learned that’s a risk in itself, not adhering to what is taught or believed. I’ve always set out to believe my own ideals. If I mess up, or fall astray that’s fine, because it has always been my lesson to learn. I guess me being the eldest child plays a part in that. I have always had to make the mistakes first, and teach the lesson to either myself/others after. In my career risk can sometimes be effective or ineffective. I’ve always believed in having the power of time by my side. As long as I’m still growing in my craft I will take this risks, because I have the time to learn after them. Recently, I’ve had to take a hard, long risk with myself. Read more>>

Arlena Bessard, LMT | Massage Therapist

I believe taking a risk is quite pivotal to a person’s realization of some of their biggest blessings and successes. This is coming from an individual who didn’t ‘live’ for most of her life. Risk taking was out of the question in my younger years, I merely existed. Now I actively practice taking deep dives that scare me, lol! Recently, I expanded my business from my small hometown to The DFW area. That was a huge leap and I’m loving every minute of it. There’s always something you will really love as a result of leaping even if you have to do it afraid. Read more>>

Dominique Jones | Owner of Jam Box Fitness & Events and DAQ’s Luxury Daiquiri Lounge

I have been a risk taker my entire life. Mainly because my mother really created an environment that made me feel safe if I fell flat on my face. I always knew she had my back and that is I believe the foundation of taking risk. Knowing if you fail it’s okay. As I got older that peace came from faith in God. Risk taking is a talent I believe because you have to know when a risk makes sense. Risk and faith work hand and hand once you have done all you can to stack the odds in your favor ie hard work and research you have to just do it! As you get older and have more responsibility such as myself with my daughter you are more careful about taking risk because you have more to loose and if you fail it effects more than just you. Read more>>

Travis & Candice Hill | Premier Inspections- Professional Home Inspector & Marketing Director

In business as in life, sometimes you touch the hot stove to realize what hot means. We have learned throughout the business that you have to protect yourself. When I started out, I had pipe dreams of blindly trusting people that work for me because when I was looking to become an inspector, no one would quickly hire me. I told myself I was gonna start a company that took people who wanted to inspect and make them an inspector and provide them with a job. At this point in time, I now realize, why companies have non compete contracts. It’s taken me over ten years of slowly building the business and creating relationships with wonderful people to realize what is was those other companies were trying to protect. My biggest advice to anyone starting their own business is to have another source of income, a lawyer you can trust and take it very slow for at least the first 3 years. Read more>>

Ron and Star Nelson | Chief Servants & Mission Mobilizers

I think risk is tied to one’s faith or lack their of. In our case, it was our spiritual growth that led the way. Meaning, God revealed Himself and so directed our path the more we grew closer to Him. We began, and more specifically, I (Ron) became more intimate, and wanted more of Christ in my life. I would tell those who would ask that I met Christ at age 16, but did not come to know Him until age 30. After many trails and tribulations, God was teach me (us) o depend on and to trust Him. When we did, our journey really took off. I (Ron) started growing into the man, husband, father, and child of God I was created to be (Still a work in progress). So when the risk appeared, we were ready. We stepped out on faith and left very lucrative careers to pursue our passion for missions. After nearly 18 years in law enforcement and closing out a career as a US Postal Inspector, I (Ron) took a tremendous risk, I walked away from the job. Read more>>

Miguel Noyola | Record Producer and Mixer

I think if you want to get anywhere you will eventually have to take a risk. I personally think the best risk you can take is on yourself. They always talk about the bigger the risk the greater reward but you can also minimize the fall off by taking ownership of certain areas in your life. One of the biggest things that I can’t recommend enough is setting yourself up for financial success. Small businesses usually can’t survive due to being strapped for cash or having to say yes to every client because they financially haven’t set the groundwork. When it comes to risk and reward be confident in taking risks when you have the groundwork to also sustain the falls. Read more>>

Jamesha Bodwell | Professional Interior Designer

“taking risks” is to most people is having faith to me. I’ve always lived by “you never know until you try.” And I’ve never allowed fear to deter me from my goals. By having that mindset, I’ve been able to accomplish just about everything I’ve set out to do. I have had challenges, but I believe I’ve succeeded because I’ve always been persistent and not afraid to fail, because I know I’ll always get back up and try again. Read more>>

Mara Duryea | Author of The Monsters and Demons Fantasy Series

If you’re going to take a risk, you need the faith to believe that it will work. In this way, risk is not a gamble, although the outcomes love to be insane.I took a risk when I became a writer, because writing is not the “normal” career. It isn’t a guarantee. I wanted to be a writer so bad that I took a jump. It felt like I was leaping off of a tower and confident that I wouldn’t go splat at the bottom, but would sprout wings and fly. I didn’t have a lot of support. I had people telling me I needed to make beds over at the hotel, people saying I’d never get a job after a certain period, people looking down on me for the path that I chose, others saying I might never be published, and I’d also get discouraging comments from other writers who said that the bulk of us would never be anything special. We would only be the rabble and only a lucky few would make it. Read more>>

Ashley/Ashley Smith/McDaniel | Owner & Aesthetic practitioner & Salon Manager, color specialist and makeup artist (A. McDaniel)

We’ve been best friends since high school, and have always been outgoing people. But, the fear of failure held us back from making our dreams a reality. It wasn’t until we decided to take the risk, during a global pandemic to open a salon. We knew we were done letting fear control our destiny, and knew there could be great loss or great reward. Fortunately, the reward has shown that taking risks are far better than not giving in to your fears. It’s always better to try and fail, then not try at all. We don’t look at failures as a bad thing, but a learning experience! We learned risks are so worth it and stepping out of our comfort zones was the way to grow and succeed! If it doesn’t scare the heck out of you, you’re doing something wrong. We are so thankful we decided to take the risk when we did, and the outcome has been more fulfilling than we could have ever imagined! And work is never work when you absolutely love what you do and get to work with your best friend everyday! We both play a different role in the salon. Read more>>