Risk-taking is at the heart of making a difference, but often we’ve been conditioned to avoid risk as much as possible. So, we asked some successful risk-takers to talk to us about how they developed their comfort with taking risk.

Jitesh (JP) And Jay Patel

We learned about taking risks by watching our parents. They came here from India in the mid-70s with basically nothing and built a life from scratch. When you grow up watching people leave everything behind to chase something better, taking business risks doesn’t feel that scary anymore.

The real lesson came when Jay moved to Pittsburgh, and we kept saying we’d stay in touch and build something together. We talked about it for years, but never did anything. Finally, we realized we were doing what kills most good ideas – talking instead of building. Read More>> 

Jodie Bishop

Well, when it comes to risk, this is how I see the world and the people in it. There’s 8.2 billion people on this earth. Out of those billions, there’s millions of people with an idea. Out of those millions, there’s thousands of people that draw out a plan to that idea. Out those thousands, there’s hundreds of people who attempt to execute that plan, but fall short because they failed and they don’t try again. Out of those hundreds, there’s only a few who keeps trying..adjusting..fine tuning their approach so that they can make their dream and idea come to life.  Read More>> 

Josh And Lindsey Mullins

Growing up, both of us (Josh and Lindsey) were rule followers, we wanted to do things correctly – to a fault. Before Lindsey met Josh, she went through some tough times emotionally and she started to trust God more and take risks of her own.

After Josh met Lindsey, she was a catalyst in helping him be more open to taking risks – quitting his 9-5 and starting his own photography business, which is now best known as Josh and Lindsey Photo. Taking this leap together into a small business wasn’t easy. In fact, some of the risks were tough—like eventually restructuring our packages or raising prices to reflect the value we bring. But growth usually lives outside our comfort zone. Read More>> 

Don Nguyen

I’ve made a lot of mistakes in my life—some of them turned out surprisingly well, and others… not so much. But I’ve learned that even when I fall flat on my face, I can still get up, dust myself off, and most importantly, learn something. That’s what gave me the confidence to start taking risks.

Now, to be clear—risk-taking is still hard. And terrifying. I’m a serial self-evaluator. I’m always asking myself: What worked? What didn’t? Could that have gone any worse? What can I do better next time? It’s a blessing and a curse. That kind of self-reflection helps me push through the fear, but too much of it can kill spontaneity. Read More>> 

Jake Peluso-Harper

Most of my childhood was a loss of control. I would always be grabbing at straws, hoping that I can prepare emotionally, mentally, physically- whatever it may be for the task at hand. And when doing so I often went in with the wrong assumptions and came out hurting more. That’s when I looked inward and needed to grow, so I started developing a more experimental and risk taking mindset. Instead of weighing the pros and cons so heavily, or talking myself out of things, I just went with it. Read More>> 

Kazy

First and foremost, I want to state that living life is a risk. Walking down the street is a risk. Driving a car, taking the subway, being a corporate litigation attorney, being a performing arts major, working at UPS – all carry their own risks and rewards. When I decided to make the creative arts my career path, I knew some of its inherent risks, but not all. Looking back, even if I had known all the risks, I would’ve still moved forward. No regrets. I’ve always thought that one should live their life as it was for their last few moments on earth. If you are blessed enough to hit your mid 80’s, do you want to look back with regret or will you smile with the comfort that you did all you could? Read More>> 

Kim Pheiffer Ebert

I would say I’m a “calculated” risk taker. I do think about and develop a plan in my head and I don’t rush in but have definitely taken some risk that have paid off. The ability to take more grows as you see some success (along with failures) but the success has outweighed the failures so you decide to take more. the biggest risk I took in my career was going from a single designer to hiring a small team of designers. 15 years later I’m glad I took the risk Read More>>

Subduer Dre

I come from a family of risk takers. Overtime as a youth growing I watched my loved ones take risks on what he or she wanted to accomplish and also receive the outcome.
Despite if the outcome was good or bad I developed the ability to understand that anything you want comes with taking risk and applying action. Read More>> 

Krisi Olivero

I am uniquely highly logical and highly imaginative. This is great, until it comes time to take a big risk. As soon as a risk is presented, my brain not only immediately imagines all of the best possible outcomes, but also all of the WORST possible outcomes, then I promptly start working out how I would address every scenario, good or bad, until my brain turns into goop and falls out my ear. Cool right? I know, very effective.  Read More>> 

Derek Lott

I developed this ability by rebuilding my confidence in high school after My Dad (Ralph Sanders) Kept trying to put my confidence down physically & verbally…It started to give me the push to take risks because “I wanted to get away from the hurt.” In Life if Your not willing to take risks because of Your situation/Dreams & Goals You won’t ever Thrive in Life. Read More>> 

Tyshera W.

I developed my ability to take risks during a time when life wasn’t aligning with the expectations I had set for myself. There’s often this idea that once you graduate from college, or even pursue a graduate degree, opportunities will fall into place. But after completing my master’s program, I quickly realized that wasn’t always the case. Despite my education, I kept getting turned away from jobs because I didn’t have the three or more years of experience they were looking for. It was frustrating, and for a while, it felt like I was stuck at the starting line all over again. Read More>> 

Quince Dais

I developed my ability to take risk once I realized that’s the only way I’ll be successful. If you want to be a successful entrepreneur you have to take risk. I learned how to take risk from starting my clothing brand. My very first drop for my clothing brand did terrible, but since I took that risk I learned from it and improved ever since. In the moment I took a loss but in the long run it turned into a win real fast. You also have to be open to failure. Failure is not always bad, it’s only bad if you don’t get up and try again! Read More>> 

Jamie Perez

I read successful people’s stories. All of them took insurmountable risks, faced a ton of rejection and kept getting up every time they fell flat on their faces.

Your biggest dreams happen on the other side of the risk you’re scared to take. I don’t want to settle for mediocrity or going with the status quo. I’ve always had big goals and dreams and none of those things are achieved by being comfortable and safe. Read More>> 

Megan D’Andrea

I developed my ability to take risks when I decided to launch my social media brand, NurseMeggyD, while still in my undergraduate nursing program. At the time, I was balancing a full course load, clinical rotations, and work, yet I chose to step into a very public space where my personality, ideas, and expertise would be on display—and open to both support and criticism. It was a leap of faith because it meant investing time, energy, and resources into something without any guarantee of success. Read More>> 

Asia Boyd

When I look at risk I view it as opportunity. Being successful on purpose is one of my newer motto’s. Essentially, it just highlights how imperative it is to be intentional about your process. Also, never viewing things as failure. In my mind , I don’t fail, I learn.

Some say pressure bust pipes, but pressure always makes diamonds! Take the risk. Read More>> 

Brittnee Patterson

I think my ability to take risks was woven into who I am from the start. Even as a child, I was never one to follow the rules just because they were there…I’ve always been curious about what might happen if I did things differently. I naturally gravitated toward going against the grain, questioning norms, and testing boundaries. As a teenager, that instinct definitely didn’t always serve me well, but it taught me resilience and self-reliance. Over time, I learned how to channel that same boldness in more constructive ways. Now, taking calculated risks has become one of my greatest strengths, and it’s played a huge role in shaping my success as an adult. Read More>> 

Andrea Stephania

My relationship with risk has evolved through three key phases. Early in my career, I was naturally risk-averse, which limited my growth. I realized I was missing opportunities by always choosing the safe path. The turning point came when I started reframing risk from “what could go wrong” to “what could I learn.” I began taking calculated risks in low-stakes situations first – volunteering for stretch assignments, proposing new ideas in meetings, or learning skills outside my comfort zone. Each small success built my confidence. Read More>>