Legend holds that Cornelius Vanderbilt had built a massive fortune in the steamboat shipping industry, but then realized the railroads were the way of the future and invested almost his entire net worth into railroads. The gamble paid off and made Vanderbilt one of the wealthiest entrepreneurs ever. But risks are inherently…risky. How do you think about risk and how has it affected your life and career? Some of our community favorites share their perspective below.

Cindy Montgenie | International Speaker & Executive Coach

I consider risk taking as part of the journey of pursuing your dreams, unlocking your full potential, and living a purpose driven life. All the major accomplishments in my life have included taking major risks. It started after high school, when I left French Guiana where I am from, to pursue a higher education in France. Then I took the risk to leave France to study abroad in. What was supposed to be a one-year exchange program turned into a 20-year international corporate career, living, and working in Latin America and the USA. Along the way, I have rejected twice a major promotion and once I asked for a demotion to be more focused on personal matters. Those were risky career moves. Then I took the risk of leaving a great executive position in a global company to launch my own business. Read more>>

Rasy Ran | Photographer

The freelance career path I chose is very volatile, so there’s always this small layer of uncertainty that keeps me on my toes. In the push for improvement, I try to constantly explore ideas with new clients and push creatively to see their reaction. That’s when I realize risk isn’t only personal, but a two-way street that needs to be reciprocated and explained through a thought process. Other times it just happens in spur of the moment. In my personal life it’s more mitigated and the choices are safer because the current economic times upended all we knew about security and stability. So it has shifted my workflow to be diligent and to always seek a purpose. Sometimes I do treat risk like a numbers game to feel like I can get ahead of the curve, but also have to force myself to look past that and just stop thinking and just do. Read more>>

Taylor Cottingham

Most of the time when you take risk everything falls in your favor and you wonder why you were even nervous about it. The few times that it doesn’t go exactly as planned its still a learning experience and you gain knowledge from the situation. If you look at the positives its a win-win. My business actually started because I took a risk! I did my very first pop up shop at a big event having absolutely zero knowledge and barely enough products to fill up a table. With the help of google, pinterest, and my Fiance I had such a successful night and learned so much! That was my first time ever really talking to people about crystals and I loved it. Taking that risk gave me the motivation to keep going and start my website. Read more>>

Jenn Barrows | Mentor & Advocate

Today, I risk rejection and judgment by stepping out in faith to share my dysfunctional past and alcoholism, subsequent recovery, and a love for Jesus that set me free. In a culture that celebrates excess and hides pain behind social media smiles, I want others to know there is no shame in seeking help for your alcoholism or other problems. My journey was filled with people who showed God’s love on a daily basis and led me back to my Christian faith. I want to shine that light for others. I established the Refined + Recovered ministry to share my experience of healing and growth in the hope that others would be led to recover from their difficult pasts and current pains. Jesus gave His life for me, I can certainly risk my reputation for Him. “Indeed, I have refined you, but not as silver; I have tested and chosen you in the furnace of affliction.” Isaiah 48:10. Read more>>

Hilaire Baumgartner | Food Photographer and Food Blogger

My views and attitude towards risk taking has dramatically changed since starting Baumassfoods. Before, risk taking (when it comes to career and money), was not something I was comfortable with. I always played it safe and had very little desire to step out of my comfort zone in that way.

 Now, I have a very YOLO mentality when it comes to risk taking with my career. You never know who you’ll meet, connections you’ll make, and what opportunities may arise if you just take that leap. Before, I didn’t fully see the importance in doing so. I know now that in order to advance yourself and career, you have to be willing to do things that scare you a little bit. Even if the risk you take doesn’t end the way envision, you can (and should) still learn and grow from it. Read more>>

Kat Gurley | Seamstress, Photographer, Graphic Designer

I find that when you focus primarily on worry of an unknown outcome, you tend to miss out on some of your greatest opportunities! The last year alone has proven that taking risks builds a greater confidence for myself and business; which in turn gives my consumers trust and loyalty to my brand! When you go outside the box/ dare to be different – you attract an audience that looks to conform to self rather than the masses, a parallel to SévWraps’ idea that we are all our own Queens who deserve to wear special Crowns. Read more>>

Ola Akintola | Owner & Executive Chef, O’s Kitchen Catering

You have to take a risk when you’re doing something that’s outside of the box. You have to bet on yourself, and you have to really just go for it. Now, it really sounds simple and sometimes risk-taking sounds very glamorous but it’s far from that. I think sometimes we settle and play safe because it’s easy and we are comfortable. Because I mean who doesn’t like being comfortable? The real reward I feel like comes on the other side of the risk, it’s on the other side of a “yes” or sometimes on the other side of saying no to self-doubt and complacency. Risks have played a significant role in both my life and career because I approach everything without the fear of failure… because I have taken the risks. Now while some ended in losses, but most ended in wins and regards. I learned something new about myself and my capabilities. I also think risk taking can be contagious, when others see you betting on yourself and taking risks, it shows that it can very much be done. My business wouldn’t be alive today if I didn’t take a risk. Read more>>

Monique YeeFoon | Accountant, Financial Planner

The very essence of being human is taking risks. As humans we take risk in education when we select institutions of higher learning hoping they give us the tools we need to succeed in life. We take on risk in love. But in business people tend to think avoiding risks is better. I feel you shouldn’t avoid risks but monitor then make and in some cases minimize them. The best risk I took was starting a business I took the experiences and knowledge I had gain from working in the corporate environment and started a business. I felt depleted in the corporate environment. So I knew once I left was not coming back. It was the best risk I had ever taken. Now taking risks will scare you to death but that is where you grow and that is where you conquer fear. In the end the best risk is when you invest in yourself. Read more>>

Caitlin Doyle | Personal Trainer & Group Fitness Instructor

I see risk as an absolute necessity. I would not be where I am today without taking some risks. Moving states away from my parents at 18 was a risk, taking a different path than most with my career was a risk, deviating from the norm, in general, requires risk-taking! But, I would say that the best things in life require taking some risks and they’re almost always worth it. Read more>>

Kay Ray | Artist & Director of Tilt Vision Art Gallery

Risk has always been part of my life. Beginning with moving out on my own at 17 and trying my hand at many different professions over the years until I finally found Art. Having started several businesses over the years as well as my experiences as an EMT and eye bank technician helped prepare me for this next step In my professional life. I have found that the best things are found outside my comfort zone and that will always involve some risk. If it’s not worth risking something for then don’t do it. Read more>>

Kelsey Shoemaker | Candle Maker & Small Business Owner

There will always be risks in anything new that you try, but it’s more of an expectation than a struggle. When I first started my candle business, I didn’t know anything about candles, running a small business, or brand marketing. It’s only been a couple of weeks but I’ve glad I decided to make that step towards this goal. It was something that I had in the back of my mind and I’ve enjoyed watching it grow. It’s been a trial and error with some things and rewards of gratitude with others. I had a full-time job at the beginning of the year and decided to take a step back and refocus on my true ambition. I wanted to balance my life out with what I love doing which is photography, as well as create something. My hobbies include things that are not tangible materials so not only did I have to build motivation and confidence to launch a candle business, but I had to know everything that came with that. Read more>>

Jada Jay | Pop Singer, Actress, Dancer, Influencer & CEO of Jada Jay Entertainment

As a performer (singer, dancer and actress) taking risks is what sets you apart. Taking risks essentially makes you stand out in this industry, for example, If I am auditioning for a role in a production, I make sure that both before and during my audition I do something bold and unique. This ensures that my audition will be memorable to the casting director; now whether or not the casting director likes the risk is out of my control. However, majority of the time, my choice to take risks have worked in my favor. When I auditioned for my first AD, I took a video clip from my YouTube channel of me and a friend eating tacos and drinking lemonade while giving goofy commentary about the food. Most of the time for my auditions I am very serious and follow instructions perfectly, but that particular audition I decided to stop being so serious and submit that video clip of me because it showed my silly personality and it showed me having real fun. Read more>>