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.

Brittany Goff | Product Shop Owner, Podcast Host & Business Strategist

Everything worth having requires being uncomfortable. We quit growing the moment we live in complete comfort. Living a life that matters require making educated decisions both in personal life and business ownership that are motivated by our greater “why”. Being an effective risk-taker is part of being a successful business owner. Not every risk is going to play out as a home run BUT it is all worth it for the few that are. Starting a female-owned, small business was a risk. Placing our first large product order was a risk. Hosting our first large event in Dallas was a risk. Starting a podcast was a risk. I can say I do not look back on any of those leaps of faith with regret but instead with great peace that I had the courage at the right time to say “let’s try this”. Read more>>

Katie Waara | Wedding & Events Planner

The story of my life and career has been entirely by “risk taking” in terms of verbiage. In lieu of this interview, I would like to reiterate it as walking by faith. Growing up I had many admirations of what I could become but never knew what I wanted to be. There was loads of pressure for me to go into a field where I could get a job quickly and start living a very domestic lifestyle. When I went to college, I did a degree field I was entirely uninterested in. I hated the course work, hated the tuition and really hated having to work three jobs to pay for the degree. There were many tears in the five and a half years it took for me to finish my Bachelor’s Degree of Finance. It wasn’t until I graduated that my life and career started to pave a path. Read more>>

Kemberley Portis | Owner & Curator

I believe some risk taking is essential. When you take risk, it may challenge you in ways that help you grow. In someways risk helps you discover a strength you never knew you had. I never was the type of person to take a risk. I was that one person in the group saying, “wait let’s research and ask questions”. It wasn’t til I was good and grown, when I decided to just jump out and go for it. My first HUGE risk I took was relocating to Texas. This one risk turned out to be a pivotal point In my life’s journey. I began to follow my heart and dreams and began a journey in entrepreneurship. Read more>>

Myah Brown | CEO/Founder of Myah Symone Boutique & Flight Attendant

Risk taking is the only reason I have a business! I had an idea, and I acted on it. At the time, I had no money saved. I had no business model. I had no idea where to begin. Taking a risk is such a pure form of commitment. I told myself that I was going to do this by any means necessary. That promise is what kept me motivated to work harder and learn new strategies. When I first launched, I ran out of money because I didn’t know what I was doing and had no real plan. All I had was this purpose, so I couldn’t let that setback discourage me. I went back to the drawing board and planned better, saved more, and really focused on what I wanted to put out into the world. I encourage everyone to take that risk; start that business; chase that dream. You will either succeed or learn a lesson. Read more>>

Carolyn Ellis | Abstract Artist

Having been raised by parents who had common sense and the Gospel elevated to the same level of priority, taking risks, that is making decisions based on passion and desire, as opposed to reason and logic, did not come easy for me. Committing time and money to something which could easily end up as a total wash was madness, right? When I started painting I was 62, finished homeschooling 6 children, and for the first time in my life positively passionate about something – making abstract art of all things! My analysis at the time was that if I didn’t grab onto my vision of painting fulltime, I would be missing the adventure of a lifetime. Having the advantage of my husband still.working full time and my beginning to collect Social.Security settled the issue. Read more>>

Angela Henderson | Author, Speaker & Educator

This question takes me back to my perfectionistic personality in childhood all the way to my present “ish” adult mindset. There’s such freedom in being RISK-ish. I am a children’s book author. But I’m also a single mom of three kids, an English Language Arts teacher, and a type 7 in the Enneagram. That’s important. I’ve done art since I was six years old. My bunny rabbits needed to be perfect before I moved on to anything else. I started pottery. I did nothing else for my entire senior year. I went to college and earned scholarships and spent countless hours in the library to maintain that monetary award. Playing it safe? Probably. But then I had kids. I began reading children’s books with them. We dreamed together. Read more>>

Toni Biggerstaff | Massage Therapist, Corrective Exercise Specialist & Owner

As I look back at my life, I realize that the times I have taken a risk, I haven’t regretted it – but that comes with a caveat. I tend to have a fear of failure. There are many times I can think of when I was afraid to set a certain goal for fear of not doing well. I wanted to know I would succeed. I simply wouldn’t start something at all to protect myself from feeling like a failure. This means that by not starting a goal at all, left me with a lot of regrets. I recall making the decision to not pursue becoming a doctor because I was afraid I couldn’t make the grades to succeed. When I think of this now, I know will never find out whether I could have become a doctor because I never tried. Read more>>

Jill Miller & Jamie Harrison | Teacher Wellness Advocates

Risk taking is a part of dreaming. When you have a dream placed on your heart, it usually involves risk and sacrifice to help it flourish. It might be risking income or sacrificing time, but no matter what, to build a dream, you have to take risks. Risks are what set you apart from others chasing after dreams. When people play it safe at every turn, they might get somewhere, but they won’t stand out. We’ve realized that to capture people’s attention, you have to think outside the box and be willing to fail. Along with that, being transparent lets people know you’re real and you’re trying. It’s important not to be overly impulsive when taking risks, though. Knowing the consequences and assessing each situation is responsible. It’s whether or not you choose to take the leap that sets you apart. Read more>>

Dayne Weaver | Pitmaster

Taking a risk is the most important step. I was fortunate enough to have my wife encouraging me to jump off the cliff. I worked full time during the week and spent every weekend working on our business for about 1 1/2 years before I worked up the courage to quit my job. That was one year ago. Until then I was only partly committed to the dream I had for my business. I feel like you really have to fully commit before you yourself and the others in your life take you seriously. Read more>>

Nancy Peham | Certified Professional Organizer & Owner of Helping Hands Personal Services

I think risk taking has been a theme in my life. My first big risk was probably when I left college after about a year and a half. I had no idea what I wanted to “be” and I felt directionless. I met my first real boyfriend at the time and we decided to take a road trip from Minnesota to California and back again camping all the way. We spent 6 weeks traveling from one State park to the next, never staying in a motel or a cabin, just sleeping in a tent. It was an amazing adventure and taught me to live outside my comfort zone. My next leap of faith was to follow my passion for dance. Even though I doubted I could have a career it has always been a love of mine. I had studied ballet and modern dance for several years beforehand. Read more>>