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.
Craig Avera
I think risk takers have a genetic screw loose to make them that way, myself included among the category. For better or for worse (honestly, both), I’ve never been afraid to take a risk if I know there’s a high reward that can be grabbed as a result. Read more>>
Ilana Held
Risk taking has always been a big part of my life. I remember the first thing I learned in high school, in period one art class: art is all about taking risks. That lesson has stuck with me through all my decisions. It’s part of what led me to move to Wales and build my career as a musician, as well as what got me through being deported and stuck in lockdown. When I was living back in Boston in 2020 with no hope for the future, I started roller skating at the skate park and I had a friend who taught me how to drop in. The words she told herself when she wanted to try something new were “do it scared” because if you don’t do it while you’re scared you never will. Those words have really impacted my life and led me to rebuild a world for myself that I actually enjoy. I now have them tattooed on my arm. Read more>>
Michelle Collins
Being an entrepreneur is inherently risky. There are so many unknown quantities. It takes courage to venture out into the unknown. It is very high risk, high reward. I learnt about “intuitive hits.” This is when a thought comes into your head and you are compelled to act on it. There something bigger than you that propels you forward. You have to have faith to trust that voice. Read more>>
Mykel “MeekFro” Trent
I’ve always been a risk taker without even thinking too hard about it. Always have been. When everyone said “no, that’s probably not a good idea” I of course still would follow my way of thinking. The degree I chose to take up, the men I chose to date, the friends I chose to have, my career…all of the picks are quite risky. Read more>>
Caroline Hagerty
A key ingredient for great communication is EMPATHY. Emotional intelligence is essential. As the great Maya Angelou once said “At the end of the day people won’t remember what you said or did, they will remember how you made them feel.” I intentionally take time to notice the person I am speaking too. Read more>>
Scott Hudson
I’ve always enjoyed taking risks. I think many people who enjoy competitive sports are the same way. Growing up, I played lots of sports and was an avid sports fan. There is a binomial result to competition: you either win or you lose. I like to be confident in a winning result, but also be prepared to lose. As I’ve grown older, business is my primary outlet for competition. The results may land in more of a gray area, and it’s hard to tell on a day-to-day basis whether you’ve won or lost. Risk mitigation has increasingly become a part of our business strategy. But, at its core, a lot of business still boils down to taking calculated risks and being prepared to do the hard work to increase the chances of success. Read more>>
Emerson Geter
Risk taking is a major aspect of building confidence and discipline. In my opinion, once a person takes risks, they must be discipline in order to not allow their risk to overcome them. Having known this beforehand helps me take risks when the time presents itself. Read more>>
Pamela Abbott-Mouchou and Lauren Bragg
First, “rolling the dice” should be a thoughtful process. We recommend embarking on a solid “information gathering” quest so you can understand the full picture of your endeavor. Weighing all pros and cons and enrolling only positive figures/friends for support will help you understand all possible outcomes. Read more>>
Chris Rorrer
I talked about this in an interview a couple of years back, but the daily reality of risk-taking is ever-evolving in my life and career. The practice of taking daring chances (which is often against my nature) and walking in faith is what has enabled me to have a fulfilling career, with just the right people and circumstances coming into my life along the way. A friend of mine recently commented that Los Angeles is one of those places where you can “choose your own adventure.” There are limitless opportunities, but after living in the area for almost six years, I have learned to first be grounded in my purpose and value system, and have a community of friends to support me during the frequent challenges and frustrations of being a musician-entrepreneur. This keeps me motivated during the inevitable setbacks. Making a living in this field, at least in my case, requires an open mind to tackle projects that may vary incredibly in scope from one another, and the readiness to learn and expand upon a myriad of technical skills in order to help make the art come to life in a genuine, but also efficient, way. It is my modus operandi to exceed the client’s vision, even if I am being stretched by the project (I am currently scoring my first film as the composer). Read more>>
Keilana Ellison
I developed my ability to take risks by putting myself out there and taking the good with the bad! Ever since I was a kid, I have enjoyed taking risks, risks that are thrilling, exciting, challenging, yet ultimately, innerly rewarding. My mom has always taught me to go after what I want very early on, which became apart of who I am today. I feel like having confidence and being bold has helped me take risks. The funny part about taking risks is that you never really know of the outcome until you take them and you have to have an optimistic mindset, but at least you are plunging forward, past your comfortability zone. Read more>>
Hope Limyansky-Smith
I developed my ability to take risks by restructuring the way I view failure. As an artist, you will have pieces that do not work out. I have tried to view my failures not as some sad loss, but as an opportunity to grow in my knowledge of my craft. If you can break down why the piece didn’t work out, then you can gain a new understanding of your medium. This information can help better the next piece that you make. When you take the negative stigma away from failure, taking risks seems far less scary. I am excited to push materials to their limit. What is the worst that could happen? The piece could break, and although that can make you feel sad at times, it gives me an opportunity to learn and grow. I often tell my students that if they are not failing every once and a while, then you are playing it safe. Take the risk. Learn from the successes and the failures. Push yourself to grow past the fear. Read more>>
Kara Maguire
About six years ago I walked out on what I thought was my dream job. It was the first real opportunity after college where I was able to apply my degree, and at the time I felt that I needed to do whatever it took to prove I was there to stay. Unfortunately I was very wrong about the opportunity itself. I was convinced in the wake of my resignation that I had made a massive mistake; one that could affect the rest of my life. I was right, but not about it being a mistake. Everything in our lives, every decision before us, has a risk associated. Maybe it’s simply stepping out your front door, or trying a new restaurant for lunch. Maybe it’s accepting a promotion at work or quitting your job altogether. Of all the big decisions presented before me, the main force behind them has been a gut reaction, saying “I need to do this”. I needed to quit my dream job; I was being manipulated, I was being overworked, and my future would have had a completely different outlook that was not the one I dreamed of. This wasn’t so different from my decision to study art and science at a local university instead of going to a more prestigious art school, or my choice to finish high school online instead of completing my last two years in public school. All of these decisions ended up providing different paths when I chose not to follow another. Read more>>
Theodore Ramirez
A good friend of mine always tells me, “Life is short!” It’s a phrase you might hear a lot and not think twice about it but it always resonated with me. I want to experience so much out of life and whether we want to admit it or not, nearly everything in life involves risk. Relationships are risky because the other person can abandon or betray you. Leaving a day job to pursue your true passion is risky because you’re leaving the security and comfort of a stable income. I believe taking risks always worth it, even if that risk leads to disappointment. At least you tried and learned new things in the process. Read more>>
Will Craig
I have always been the type of person who took risks and marched at the beat of his own drum and made no apologies for that. I’ll be honest it sometimes hasn’t been received well. But, when I am passionate about something I become laser focused. And until I achieve the goal I don’t stop trying. Every position I held, when I was in the corporate world I started at the bottom. I eventually moved up and became an Executive and it didn’t take me long either. I am solutions driven so naturally my mind goes into finding a solution not focusing on the problem. In finding solutions most times you have to go against the grain. I wasn’t afraid to step outside the box and I for sure understood my value and I wasn’t afraid to ask for a promotion or more money. Most people are afraid to walk into there bosses office and ask for a new role or more money. Read more>>
Aaron Sharp
I’d love to give you a prolific response here, but it’s pretty simple. I realized that not taking the risk would leave me in the same place as taking the risk and not getting the desired outcome. Therefore I have nothing to lose. I think it’s important to understand that I don’t just take random risks. I take calculated risks. There’s certainly a difference. My advice is to always research an opportunity, but don’t research or analyze it so much that you’re paralyzed and don’t act on it. Please don’t be afraid to fail. Most people are so afraid to be bad at something, that they can’t be bad at something long enough to get good at it. Read more>>
Tequilla Nicole
Since I was a child I’ve always been one to dance to the beat of my own drum. I never wanted to do what everyone else was doing which enabled me to take risks and fulfill my curiosity. I love to learn and explore new things and without taking risks I never would have started a business. Risk is usually viewed as a bad thing but to me it is trying something new and if it doesn’t work out that means try another way or try something else. Read more>>
Amy Scruggs
As the saying goes, “The Greater the risk the greater the reward”. I have found that to be true throughout my life and career. I am more afraid of regret than failure. That mindset has allowed me to take the big risks. I believe in the daily pursuit of my passion and potential. If I don’t succeed at something, it is an indicator that steers me in the right direction. No is a powerful word to accept. The power of “no” or something “failing” means that I am being protected or promoted for the right direction of where I am supposed to be. Read more>>
Bethany Rose
I guess you could say that I have always been a risk taker. It really started with my goal to play Division 1 basketball in college. I grew up in a small city in Iowa, and was a late bloomer but I always had a vision, I just had to figure out how to make it happen. When I got the opportunity to play at a junior college in Iowa, I took the risk so I could be one step closer to playing at the D1 level. My risk paid off, as I ended up transferring to a D1 school – California State University, Fullerton. This helped me see that risk taking can pay off, but I had to work hard to achieve the desired results. I also learned along the way that I didn’t want to live in regret. I would rather take a risk and try to achieve my goals/desires rather than never know. Read more>>
Jay Edwards
One of the biggest decisions of my life was to change my major in college. I say “decision” because at the time I thought it was an actual “risk”, meaning that if I deviated from my original Music Production degree & got a General Studies degree with a focus in music, that I would be doing my career a disservice. It was January of my junior year & I had come to realize I had earned 120 credit-hours. So, after a couple weeks of asking people what their advice was, I made the decision to switch over to a different major so I could graduate early. The three big takeaways I got from this decision were that I was totally in control over this aspect of my life, that a degree doesn’t define your value or potential for success, & that peoples’ advice totally depends on their life experiences & world view. Later that year I moved to Houston, TX in my car, where I would meet some really kind people who supported me in my dream to do van-life in LA. Every risk I’ve taken has always been well-thought-out & worthwhile. I would encourage others to really think about what they want their life to be & take action to make that happen. Read more>>
Idara Bassey, Esq.
My life has been full of such “jumping off the cliff into the unknown”-type moments- one, in particular, is when I left a high profile job in Washington DC to work for myself and a few years later move across the country to a city where I knew no one. It did not occur to me at all that this was a courageous (or risky) thing to do. I mapped out this course of action from a rational, methodical, intellectual place (or so I thought at the time); reasoning that if I was miserable in D.C. practicing law, there was at least a chance that the misery would abate if I did something about it. In fact, to this day it is still not something I grasp entirely- where I got the guts to do what I did until I spoke to a good girlfriend of mine recently (who witnessed the whole thing) who was recently contemplating a similar 180-degree turn in her life/career some 12 years later and was seeking my advice. So in summary my ability to take risks was born out of a realization that continuing to travel down the same path in any given situation would not produce anything new. If we even do as much as pivot a little in a different direction, there’s a possibility of creating a better situation. Read more>>
Heather Cox
By being afraid of regret. Whenever we start to pursue something that’s outside our comfort zones, there’s a series of questions we ask. “What if it doesn’t work out?” “What if people judge me?” Our brains are wired to process the negatives that may come from that risk. Read more>>
Molly Buffham
In September of 2022, my husband returned from his year long deployment and was horrified by how my business had taken over our home. It was time to take the leap and get into our first dedicated space for Donut Junkie and it was absolutely horrifying. Read more>>
Corey Hustle
Taking a risk Well Ive spent most of my life working 9 to 5 jobs I’ve done retail,warehouse,construction etc.. Because of these jobs I was able to invest in my music career plus pay bills & all that good stuff 1 took the risk of leaving those jobs alone back in 2020 & I haven’t been back since. Read more>>
Taivia Thompson
My ability to take risk came from being pushed outside my comfort zone. I remember the very first time I was pushed into something that felt uncomfortable for me. It wasn’t my norm, it wasn’t my comfort place, it was a life happenstance. I was pushed into after deciding not to take the risk of change on my own. Change involves a risk of potentially being uncomfortable and I hated that. After being pushed into change and risk taking, I realized how much stronger it made my faith and how much more resilient I became because of it. After that, I saw no need to hold back on taking risk anymore. Read more>>
JaLaura Huff
I’ve developed my ability to take risk by understanding that failure will happen more than usual. Once I’ve stopped underestimating myself I became more confident with handling the pressure that comes with running a business. Although taking risk isn’t always a bad thing, a lot of good can come from it. For instance, new skills, business growth, and it can open up new opportunities. Read more>>
Kristen Grunewald
How did I develop an ability to take risks? That is a great question and I have a good story about that very thing. I was introverted and fearful as a child. Partly because I was born an artist and I was quite sensitive. Being sensitive also can make a person afraid and I was very afraid of so many things! I got sick and tired of being afraid of life. I was shy and I was terrified, and I was sick of myself and so I made a conscious decision to do something about each fear. Read more>>
Taryn Shaffer
Anything and everything that you do is a risk. Some more calculated than others, but when you truly think about it there’s always an outcome to each decision made. My ability to take risk came from practice. It sounds silly, but as a trainer the best analogy I can think of would be in correlation to a muscle. Muscles get stronger with reps, therefore the more you practice something the stronger you become at it. That’s exactly what I did this last year, I put in the reps to build what would call my intuition muscle. What started as an experiment to really trust myself in all the choices I made turned into a new found passion for life in all that’s around me. The key though is starting small, it could be one choice even minor that allows you to get 1% better. As I let go of control more, & spent time grounding into my intuition/self I realized that I can take risk. Often too, we hear, “Without risk there is no reward”. We can play small to the world around us wondering what if…or we can be bold enough to go a different route. It was also in doing this I realized that nothing I was doing was too catastrophic to which I’d die lol. Once my logical brain clicked it became a heck of a lot easier (and more fun). Read more>>
Adrianna Zizzo
My parents have always been huge supporters of my career choices and whether they’d like to admit it or not, they are risk takers themselves. I have changed jobs multiple times and even tried to go the corporate route with benefits and all. I knew it wasn’t for me. They opened an Italian restaurant in their 40s, with two young children and it was a success for 15 years! I’ve always admired them for following their dream. Now, 12 years after their business has been closed, I’m trying breathe new life into what it’s like to be a business owner, all while sharing my Italian heritage & my family’s recipes with everyone and anyone that enjoys my product. Read more>>
Ashleigh Dinan
I’ve never been asked this question but I definitely have thought about this many times because it is rare to take risks but I have realized I kind of do it a lot, haha. I don’t take risks in the way of life or death, when you hear the phrase, “risk taker” most people think of someone who risks their life in a physical way. There is another side of risk taking that has a more long term effect and not just the immediate “jump off a cliff” effect. I definitely am more of the long term risk taker, (but I’ve also jumped out of a plane 2 times and zip lined on the longest/highest zip-line in North America so… I guess that statement is arguable.) Read more>>
