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.

Mike Thom | Dallas Food Bloggers

I think the most important impact I’ve had on my kids would be teaching them to take risks & believe in themselves. Dream big and go for it! We live in a world of opportunity, yet surrounded by negativity. People might not see nor understand your vision and you can’t wait on circumstances to give you permission. Plan, execute, and stay focused! Also, have the discipline to finish what you started. These very principles helped me start my own business and will push you towards your destiny! – Mike Thom. Read more>>

Ekua Anyanful | Certified Financial Planner & Investment Adviser Representative

I perceive risk as the ability to assume and navigate the psychology that involves uncertainty about the effects and implications of an activity or outcome. I do not associate risk with danger, negativity or an undesirable consequence. This is simply because of the fact that I always focus on the reward component of assuming some risk. By so doing, I was able to leave a corporate position where by I was an employee to start my own private practice as a Financial Adviser. It was not easy, especially the first two years, but my mantra is “Keep your Eyes on the Price” In this case the price was the reward of independence, flexibility, business ownership and freedom. As a business owner you have to assume the right amount of risk that will ensure business growth and continuity. Some are measurable but others are not. I couldn’t allow fear to cripple me because of potential exposure to harm or loss but rather I weighed the pros and cons of any action and determined if it is worth taking. Read more>>

Terrelle Wallace | Personal Trainer & Doctoral Candidate of Physical Therapy

I am a huge advocate for strategic risk taking. I say strategic because I think its important to weigh out the the pros and cons if something doesn’t go as planned. When it came to me starting Wallace I can honestly say I would have from the beginning quit my full time job and put 100% of my time into making it better…if I wasn’t married. So instead of quitting my full time job I took a pay cut so that I’d be better able to manage my time and mental energy. I still took a risk by taking the pay cut and Wallace Wellness still managed to grow. Timing and planning is everything when it comes to taking risks. I will continue to take risks and I’m sure Wallace Wellness will continue to grow as I do so. Plan ahead and take the leap!. Read more>>

Tara Pearson | Hairstylist

If there is even a slight chance at getting something that makes you happy, risk it. Life is too short and happiness is too rare. All my life I have been what most would call a “risk taker” sometimes they have been on the disastrous side of risks, but I’ve always learned something none the less. As I’ve gotten older I’ve learned to take more smart, calculated risks. Like quitting my banking job after 9 years of the corporate world to finally chase my dream of being a full time stylist. I took the leap of faith and left the job that made me financially comfortable but miserable otherwise, all to jump head first into 2 part time jobs making half of much and working every day. I took the risk on MYSELF, I knew I could hustle and create the dream life of being my own boss and having creative freedom, and doing something that fulfilled me and made me proud to do. Taking risks requires a lot of blind trust in most cases, nothing is really guaranteed. However you have to trust your instincts. Read more>>

Marcus Dickerson | Writer/Author

I believe that risk is necessary. A person cannot live without taking some type of risk in their life and I have decided that the only way to live is by undertaking some small risk everyday. I used to be an extremely pragmatic person and always made very calculated decisions regarding everything in my life. I was doing fine professionally, but one day I realized that I truly wasn’t living the life I wanted to live, rather I was living the life I was conditioned to live. I was numbing myself to the monotony of working a job that I couldn’t stand, because I thought that was how society functioned and I’m so thankful that I broke myself from the shackles of complacency. My biggest risk was to strike out from the corporate world and pursue my passion of writing. I made a plan of writing a book and within six months of leaving that job, i had self-published my first book and I’m currently working on my second. Through taking charge of my own life I had finally discovered how beautiful life was when you live it on your own terms and I learned that lesson simply by taking a risk. Read more>>

Kyla Dailey Alfaro | Jewelry/Accessory Business Owner

When anyone hears the word “risk”, we automatically think negatively or positively about taking risks. Our minds go to failing or all the “what if” questions. In every area of life, risks must be taken and we either fail and learn from our risks or they could be the best, life-changing risks that has ever happened to us. I believe risks and taking risks are needed and important in our lives. For me, I stepped out and took a risk to start my own small business and it was the best “risk” I’ve ever taken. I stepped out of my comfort zone and tried something I thought I could never do. All the “what if” questions entered my mind; “what if no one buys from me?”, “what if I fail and I have to shut my business down?”, “what if I don’t make any money?”, “what if I create things I love and everyone else hates them and makes fun of me?” Every negative question I could think out entered my mind but I didn’t dwell on them. Read more>>

Anton van Vuuren | Owner and Chef of Anton’s Meat and Eat

Risks are a vital part of my life, have helped me with my current business and with my travel here to America. Making business decisions go hand in hand with taking risks. Every time you make a business decision you risk everything you have built. Opening a business puts everything you have at risk. If you are risk adverse, being in your own business may not be for you. Read more>>

Khristophe | Multidisciplinary Creative

Risks taking is essential to the growth & development of a person’s life/career. You will always experience risky situations when entering into a new stage of life. These situations exploits a person’s true character and makes them aware of their edge. It is easy for someone to manipulate their character when they are in a circumstance favorable to them, but how you react to adversity and uncomfortable situations defines who you truly are. My whole life and career is predicated by risk taking and knowing not every risk comes with the intended reward. Read more>>

Haley Burkhead | CEO of Recurring Profit

There are so many variables to risk. I think being an entrepreneur in general is a risk. For me, I use data to help me make decisions, so no decision is made without having data and calculation behind it. So even with taking risks, I use tons of data to inform my final decision before it is made so that I am making the most calculated risk possible. Risks don’t seem so scary when you have tons of information and data to back up your final decision. Risk has taken a huge role in both my career and in my personal life. Like I said, being an entrepreneur in general is a risk. There is no guaranteed paycheck that comes with being an entrepreneur, there is no guaranteed success. In my personal life, risk has also played a huge role. I retired my husband, letting go of the security of his stable income. That was a major risk for our personal lives, but so worth it. I also decided to move states in order to move somewhere where I felt that my business could thrive better. Read more>>

Bianca Massaro | Entrepreneur & Social Worker

I believe that life is about taking risks. You will never know how good you are at something if you never take that leap of faith and just do it. Essentially, you will never know who will be blessed by your leap of faith. In 2019, I decided to take the leap of faith and share my business to the public. It was extremely scary and something that was totally out of my comfort zone but since doing so, I have received tons of messages from people all over America sharing with me their gratefulness for my products and company. This encourages me to keep going hard for my customers and continue to take risks. Read more>>

Julius Gordon | Songwriter & Vocal Coach

I am the ultimate risk taker now lol! I wasn’t always that way though. I kind of got forced into it out of necessity and sheer anger honestly. I’ve never had situations where I was given opportunities so any opportunity I had I had to create. I would get so furious with the powers that be for not putting me in positions that I felt I deserved and say “well forget them I’ll create my own and it’ll be way better lol!” That kind of created this fearlessness in me and I began feeling like I can do anything! So now my default is simply to take the risk! To create the space that I want to operate in and do it my way and if it doesn’t workout, I’ll learn from that and take that into the next risky endeavor. As a result of that I’ve created this life and career model that I thrive in!. Read more>>

Ty Higby | Luxury Wedding Videographer + Colorist

In starting my own business, there were certain risks involved, including quitting my full-time job and investing in camera gear that was not particularly cheap. At the time of me making this decision, I received a lot of criticism from family and friends. Although this criticism came from a good place – one of trying to help me – I had a vivid picture of what I could achieve, and I had to be true to myself and pursue my passion. One of my favorite parts of that time was: even though I had not made a single wedding video, I knew I would do anything possible to become the best in the industry. I would give the most value, and do the most I possible could for every bride + groom I interacted with. This philosophy of giving more value than you could ever receive back from the couple has paid some incredible dividends. I’ve had the chance to become a preferred vendor at some of the biggest venues in DFW, including The Castle at Rockwall, The French Farmhouse and Knotting Hill Place. Read more>>

Isaiah Wilson | Founder & CEO of The Pickle Plug | Commercial Real Estate Broker

The best things in life are on the other side of fear or whatever Will Smith said. I naturally gravitate towards a challenge even when I am not looking for it. This has changed my perspective in life and in my career when it comes to the many challenges one may face. When taking a risk, I approach each challenge with an understanding that I am trying to take it from a challenge to a window of opportunity and from there to a success. Read more>>

Soneakqua J. White | Author, Speaker, Mental Strength Strategist

I’m confident with calculated risks and I take them often. I would not have left my comfy, but unfulfilling job if I hadn’t been willing to take a risk in going out on my own. I put myself out there even farther when I published my first novel in 2017, which was very risky. I never considered myself an author until after my fifth publication. Now, I’m established as such. I believe that if you won’t take risks you’ll never find out what you can ultimately accomplish. Read more>>

TAJAI JONES | Health and Beauty Cosmetic Line/ Mua

I’ve always been a risk taker, I love a challenge! I think that taking risks are important for our growth. If I take a risk and I don’t succeed like I expect to, I always learn a valuable lesson I can use moving forward. You’ll never know how far you can soar if you don’t. Read more>>

Stephanie Giddens | Founder & Executive Director

Anyone who has watched me from the outside for the last 10 years would laugh if they heard me say “I’m not a risk-taker,” because I’m not. I like to go the the same restaurants, order the same thing, and drive there and back on the most direct and predictable route. Safe. Secure. Predictable. In the regular, every day routine of life, I’m pretty boring. Ask my kids – my husband brings the fun and spontaneity…I bring the rules and consistency. But when I decide to go big, I go really big. I get out there and chase something hard, full of conviction and no regrets. Like the time I helped launch Polished ( to help connect young professional women to each other to explore faith together. No one was doing something like it, and we saw a need, so we went for it! It was a pretty big risk. Three years into that project, my husband and I decided to move to East Africa and start a social enterprise that empowered women. Read more>>

Kellen Daniel | Manager, Sneaker Politics Dallas

Without risk, there really is no reward. Personally, I wouldn’t be here talking to you right now if I didn’t take a chance on myself and my friend taking a chance on myself and Ryan to open our Dallas location. I just believed so much in everything we have going as a company, that I put all my chips in and went for it. The best decision I’ve made in my life was taking this risk. Ryan: It’s risky to drink with us!!! Hahaha, in all seriousness, we wouldn’t be here without taking that risk, that’s how the company started. That’s how myself and Kellen got here. That’s how Derek got this far. In our business, everything is a risk. Read more>>

Lucero Echevarria | Make up Artist

When I think about risks, I think about a challenge. A challenge that simply put just has to be overcome. I feel if you don’t want or feel like you need to take a risk , then you’ll never know if you reached your full potential or even discovered something new and amazing. Yes, risks could have bad consequences but you shouldn’t let the negative “what if’s “ stop you if the benefits could be reaping. I always felt that hard work really does pay off and if you had to trust your gut and take some risks along the way well then it’s all part of making your dream a reality then it’s all worth it. Read more>>

Rick Campbell | Photographer | Creative Director

Risks have played a major role in my life/career. I broke free of corporate advertising 21 years ago and never looked back. I believe if you want to achieve your goals in life, you have to be willing to take risks. I’m very methodical in my risk-taking, but without taking the risks, I wouldn’t be where I am today. If you are going to walk the tightrope, you have to be willing to do it without the net. Read more>>

Khadijah Karriem | Actress, Writer, Producer & Entrepreneur

Risks are something I have taken over and over again in my life. I have always believed that nothing ventured, nothing gained. Now, I don’t mean risk my life or others lives and definitely not my children’s life, but if the risk can potentially catapult me into another level of greatness, then I am always willing to take that risk. Every great decision I have ever made to further my career or balance my life or live my passions, started with me taking that first risky step. See, most of the time it’s called a risk because the out-come is unknown. The fear of the unknown is what stops most people. I can’t say I don’t have fear when I am at the threshold of a risky decision, but what I have more than anything is faith in God. If the decision is going to help me be better or can help people or is putting me in alignment with my divine purpose, then I know God will not let me fall. Read more>>

Cameron Smith | Professional Landscaper

Bigger the risk the bigger the reward. We have taken some heavy losses and some large gains because of risk. I personally process risk by a number of factors. Will there be underground piping I am unaware of? Sometimes the soil I’m digging on is clay and I can barely dig 1 foot down. I literally just got done dealing with a home that had almost a solid layer of concrete, it felt like, while digging a French drain. That costs me more time and more money. Risk is speculative, just don’t be afraid of it or you literally cant grow. Read more>>

Glenn Franklin | Actor, Massage Therapist.

Because without risk you don’t get anything or anywhere in life. Can you imagine where you’d be if your dad or your mom didn’t risk everything and ask one another out? Risk is a threshold that you must pass through to get what you want in life. Meaning if you don’t take the risk and you play it safe, you will either lead a boring and unfulfilled life or you risk it all and try and succeed in getting what you want. Regret is something that can affect you forever. So I happen to believe in “No More Regrets”, which means that if I believe that I will regret taking a risk by not doing it I am doing it. I have never been shy and if you know me, as long as it is a great thing to do with amazing rewards I will do what needs to be done to get what I want. I know that life is a series of risks so I choose to not play it safe. That is why I chose to step into theatre and film and not be afraid to audition, or act stupid. Read more>>

Elvin Rosa | Student Athlete, Business Owner, Actor

Taking risks has always been a part of my life, whether in baseball or acting, or owning a business. I think one of the most important things I have learned is that, the best chances of success are when you have thought through thinks and your risks are calculated. However, regardless of the outcome, every risk, win or lose, was a learning experience for me. Learning to take risks taught me to get out of comfort zone. I learned that you can never be afraid to fail, 0r you may never know your full potential. Read more>>

Aliyah Houston | Sustainable Skincare Curator

I think risks are very important to take, I actually think they are almost necessary in order to say that you’ve truly lived. There is a quote I like to reference when something threatens to push me out of my comfort zone or I feel inadequate for a task; “You will never reach your true potential living life in comfort and routine. You’ve got to take some risks!” – Kylie Francis In 2017 I was a broke undergrad student and Dunia Organix was just a concept, at the time a business idea for 5 or 10 years down the road when I was “established in my career and could afford to take the risk”. Fast forward to 2019 I made the choice to stop waiting, to embrace taking the risk, and in 2020 Dunia Organix launched! As we speak about risks, ironically enough I sky-dived the day before I launched my business. As we climbed to 13,500 feet I thought about all the things that could go wrong. What if my parachute fails, what if I land wrong, what if… I think what stops us a lot from taking risks are those “What If” questions. Read more>>

Crystal Hines | Artist & Swimsuit Designer

Taking a risk is one thing I wish I did when I first started drawing. I was so scared that no one would like my drawings, I given up art all together. Now, that I am older I’ve came to realize you have to take a leap of faith in everything you do! Take that risk, jump over that hurdle. Who cares if no one likes your artwork but you! Taking many risks has really made me grow as an artist, because now my art designs are on my swimsuits. I’m an artist and a swimsuit designer. Read more>>

Rosie Vann | Entrepreneur

I really don’t identify as being a risk taker because I love routine and stability. I do consider myself very entrepreneurial and I try to never miss an opportunity. That said when I reflect on my professional career I can see that I am indeed one that will jump in feet first when I believe in something or feel inspired and that can manifest itself in all sorts of ways really. In 2012, I made the decision to start my own business with a co-worker of mine. So I left my “cush” managerial position @ a popular corporate retailer in Southlake. We created a ladies mobile fashion boutique called, Couture in a Can. So not only did I risk my regular income, I also spent my savings to contribute to getting us up and going. In addition to changing directions professionally, I got a divorce during this same time. So hindsight, which we all know is 20/20, it was quite a lot of change and risk all @ once but honestly I was so busy hustling that I didn’t really take notice of that until years later. Read more>>

Abby Bagby | Artist, Arts Facilitator, and Stylist

Taking risks feels like standing on the edge of a pool of water, not knowing how deep the water before you is. You can choose to stay on the edge–safe, but wondering what might have been–or you can step forward into the unknown, confident that whatever depths you find yourself swimming in, you can adapt to the challenge. It’s always scarier to take the plunge alone, so I’m a big believer in seeking out community. Throughout my life, I have been fortunate to work alongside wonderful mentors and collaborators to create challenging and evocative art environments. I took a huge risk to launch Odyssey Studios, not knowing if Dallas would welcome what I had to offer, and the onset of the pandemic threw an additional wrench into my plans. What I found after a year of isolation and delayed events was a team who I could not imagine working without–the incomparable Brie Underhill and Colton James White–and a more mature understanding of where the arts in Dallas is moving. Read more>>

Nate Price | Certified Personal Trainer

Going off on a whim to start my fitness business was a huge risk. I knew it wouldn’t be easy to try and develop something from pretty much nothing, but I had/have the drive to continue with my passion to help others achieve a more quality lifestyle. Without taking risk, you always wonder “what if”, and I was always taught to pursue what I believe in. Even though the odds can be against you in some cases, there is always that small probability makes taking a risk well worth it. I believe that everyone should attempt to do something that they are truly passionate about regardless of where you are in your life. Risk taking encompasses the essence of the mindset to “make it happen” by any means necessary. Read more>>

Ellie Skochdopole | Creative Director & Marketing Consultant

Risk is what started SKOCH Strategies. It might give people anxiety to say this (maybe even me, a little bit!), but there was no formal strategy process behind starting my business. It was something that happened pretty organically, as I was between jobs and in a new city. I began taking on freelance work to fill in the gaps, and before I knew it, I was able to keep busy full-time. Even though some would caution against jumping into a business, I do think there is a lot to be said for taking risks and following your gut. I believe we have all the tools that we need to succeed if only we have the confidence in ourselves to do so. I read something about imposter syndrome once: a person can truly do anything if they care about it enough. If I realize I am doubting my abilities before taking a risk, I try to remember this. And, most of the time, I find I am up to the challenge. Read more>>

Ashton Smith | Clothing Company Owner

risk taking is one of the most important aspects of being a business owner, you never know what is around the next corner unless you are willing to take that jump. back when i first started i was always afraid of taking the next step because nothing was ever certain but if you don’t ever bring yourself to overcome self doubt and fears you will never succeed in anything to the extent that you are wanting. if you have something that isn’t guaranteed but it is still an opportunity to progress or get connection and you don’t take it, WHAT ARE YOU DOING? the situations that i have gone to just thinking nothing of it is usually when i found exactly who/what i needed to help me take the next step. but if i was never to walk into rooms that i didn’t know one person and just start talking to people and making connections where would i be? we will never know because i took the step and i urge you to as well. Read more>>