In our experience, most folks, including ourselves don’t have enough of an understanding of risk and the role it plays in our lives and careers and so we have made a concerted effort as a team to have conversations about risk with our interviewees. We’ve shared some highlights below.

Joe Vitale Jr | Recording Artist

When it comes to risk, I like to weigh a lot of factors but ultimately, I always pray about it to see which direction God would like me to go in. When it comes to performances I look at it in terms of financial cost to the group or myself if I am solo. I look at the strategic impact in terms of, will this lead to publicity, more or bigger events, management, opportunities, etc. I also like to look at time impact. What I mean by that is this, in life your greatest commodity is time. There is only one of you and will this, whatever it may be, be worth your time and energy or is it a distraction from your goals & aspirations. Sometimes it can be just something fun to do despite the time impact. Read more>>

Jowan Smith | CEO, Publicist, Event Planner, Author, and Commercial Model

I believe that risk can be a requirement of growth. I took a major risk when I left my full-time career in 2018 to focus on building my business. That risk allowed me to focus on growing my professional and personal brand. I wasn’t able to see the full potential of my business idea when I was doing it part time. That risk forced me to make it work, to make it grow. It allowed me to find talent within myself that I didn’t even know existed. Had it not been for me taking a chance on myself there wouldn’t be a 1,000 Ties or any of my children’s books. So, taking a risk changed my life. Read more>>

Joel Cookston | Co-Founder of Trek Pools | USA Shipping Containers

To me, risk is uncharted opportunity. Some may think opportunity means reward, fame and riches, but opportunity tied to risk is often time a much different reward. The reward may come in lessons learned from multiple failures, networking to meet that one person who can take you to the next level or maybe just finding out how much farther you will go than the person next to you. I’ve taken calculated risks throughout my career, preparing the landing well in advance prior to the jump. The landing in most cases was a new business venture using my own skills or talents to build the shell and gauge the viability of the business. My true goal was to create a product I could market and grow a machine to either produce that product or white label it from a manufacturer. Read more>>

Desmond Reid Jr | Executive Chef

I think of risk taking as being a huge motivator in my life. From a young age I’ve always been competitive and liked to live life on the edge. Without risk there’s no fun or anyway to see what all you can truly accomplish when you’re put to the test to excel. In every part of my career I’ve taken risks and it has helped me see my potential and shown me what I can do whether it’s by myself or even leading a team. Taking risks really does challenge you and puts you in a fight or flight mindset that propels you to the next level. Without taking risks you stay stagnate. To be successful and make an impact you’ve got to go against the grain and do things different. That’s what I’m all about. Read more>>

Paige Braley | The Beauty Boost Cincinnati City Lead/ Director of National Partnerships for TBB HQ

Risk can be so scary. Risk seemingly threatens the familiar, the safe, the comfortable. But on the other side of risk, there is often something beautiful, that you could have never dreamed possible. Don’t get me wrong, I am a firm believer in calculated risk. . . if it threatens your overall sense of safety, basic needs, basic financial health, etc- that may not be the time to take “the risk”. But then again, sometimes when there IS something to lose, the risk + the effort creates something golden. After the pandemic hit in 2020, the industry I had spent the last 15 years in professionally, was gone. Entertainers, singers, and dancers found themselves “waiting it out” or pivoting. Read more>>

Jakob Michaels | Video Focused Marketer

Risk-taking has always been an integral part of my journey. It’s the lens through which I’ve viewed opportunities and challenges, and it’s played a pivotal role in shaping my career and life. Before diving into the world of digital marketing, I began my journey as a mentalist and speaker. I had the privilege of gracing stages at corporate events for renowned organizations like Hibu, TEDx Columbus, and Specialized Speech Pathologies. But beneath the surface, there was a burning passion for something more. I had always known that video was the future, the secret sauce to making a mark in the digital world. Read more>>

Mitchell Bienvenue | Content Creator/Photographer

I believe that risk is an essential part of any meaningful journey, both in life and career. It’s a fundamental principle for growth and progress. The saying “the bigger the risk, the bigger the reward” has been a guiding principle for me. However, it’s crucial to acknowledge that the higher you climb, the harder you may fall. This recognition has always kept me grounded and vigilant in my approach to risk. In my view, the biggest risk in life is taking no risk at all. Without embracing the unknown and venturing beyond our comfort zones, we limit our potential and suffocate our personal and professional development. Read more>>

Amber Massey | Owner. Stylist. Officiant. Epic Elopements

Years ago I was standing in a book store and looked over on a shelf and there was a book about women in business. I picked it up and started scanning the book and a page stuck out to me. It said something along the line, Women in business don’t make as much money as men because we are less willing to take risks. Women are evolutionarily dispositioned to play it safe because we are the ‘nurturers’. Therefore we are less willing to ask for a raise or take a risk of any kind for worry that we will be left in a worse position than the one we are currently in. Once I read that, I started thinking about risks differently. I realize that there is no gain without risks. Read more>>

Kevin Jackson | Singer, Model, Podcaster, RN & Creative

I think taking risks, not just in business but also in life, is extremely important. It’s a bit of a cliche, but I truly operate by the adage: “You’ll never know until you try.” I absolutely believe in taking chances, because who knows; that one chance that you were bold enough to take might create the moment that you’ve been waiting for, that could end up changing your whole entire life. How will you know, if you don’t at least try? Taking risks is how I’ve gotten to the point that I’m at in my life today, and what allowed me to start my business in the first place. If I didn’t take a chance and believe in myself, my brand and none of my business ventures would even exist. Read more>>

Anthony Church | Music Producer & Podcaster

I view risk as a necessary part of growth for anyone especially when you’re in any creative field. For me it’s just been about having faith to keep going each and every day even though nothing is promised. When you pursue something like music there’s no clear path to success and the road is full of risks that need to be taken to keep seeing results. Read more>>

Joseph Dulin- Didonato | Gallery and Commission Artist

Risk is one of the most important parts of our lives and careers. Shaking things up can be intimating but I don’t want to wake up in 30 years or even tomorrow and wish I had taken that chance. Opportunity will only knock, its up to us to run out of that door. We can always stay home and fall into routines and have excuses why its better to do something later “I’ll do it when I have x amount of money” or “ill wait for the next offer”. The tough realization is that the window of opportunity is only open for a short period of time. We all have fears and insecurities but we also have passion and desire, which will outweigh the other is up to you. Read more>>

Bill Schuller | DJ Entrepreneur Business Owner

When first starting this business we were paycheck to paycheck so starting this business was a big leap of faith. This was the epitome of standing on the cliff and jumping either you fly or fall. We took our income tax check and used it to buy the equipment to start the business. Read more>>

David Bullivant | CEO and Professional Underdog

Risk is a part of all of our lives and I think for some it is more daunting than others. A healthy respect for risk I feel is necessary to achieve any sort of long term success, though a flash in the pan is certainly possible for those who believe they are impervious to risk too. My own risk tolerance is relatively high by most people’s standards, and this is something that I think has played a large role in my life. I wasn’t generally someone that I think would be described as impulsive or unpredictable growing up, but I do think i had many instances where taking a risk was positively reinforced, and through these experiences I learned to be more confident in myself, and confident that things do work out in the end. Read more>>

Dre Wien | Founder, sustainable clothing boutique LADDER

I think I have a different relationship with risk than most people in that I’m a pretty big risk taker. My philosophy is that I always know what I’m leaping FROM and I can usually return to where I was before if things don’t work out. For example, my thought process when starting LADDER was that if it didn’t work, I could return to my career as a writer or nutrition coach. There’s always more money to be made somewhere, so I take the risk. I’m more scared of not doing something and regretting it than doing it and failing. The other thing that has helped me to assess risk was getting very clear on my values. Read more>>

Chris Bianchi | CEO of CB Entertainment + Legend Recordings

I think risk can be a quite intimidating feeling or thought for anyone. In my opinion, as long as you’re confident in your approach, and make a quality plan, taking risks are crucial to continued growth. For myself, taking risks on many occasions and quite often has paid off. It does not mean it was random or unthought but as the saying goes, sometimes with “no risk. no reward” Read more>>

Mike Khukuri | Digital Magician

I am most certainly a risk taker. Throughout life’s journey, we evolve, acquiring new skills and strategies. Our desires and priorities change and we naturally outgrow aspects of our past. I have helped build several companies, both for others and for my own ventures. Whenever I reached a point where I felt I wasn’t realizing my full potential, I took what I learned and went to seek out fresh opportunities. Every contract or job I took served as a valuable lesson, not only shedding light on my own aspirations, but also guiding me in laying the foundation for achieving them. Read more>>

Ahshia Cavin | Bridal Hair and Makeup Artist & Educator

“As someone who has taken many risks over the course of my career, I’ve learned that having faith is so important when stepping out into the unknown. When I first made the huge leap to leave my stable corporate job and start my own business as a new mother, it was extremely scary not knowing if I would succeed or how I would provide for my family. In those uncertain times, leaning on my faith in God gave me the courage and strength to take that risk. I believed that if I worked hard with integrity and let Him order my steps, it would all work out as it was meant to. Read more>>

CIDNEY MOORER | CEO + SKINCARE SPECIALIST

Risk over regret. I think, taking a risk in life is very important. To step out on faith and go after your passion is an action that everybody should take. I took a risk by quitting my job and betting on myself, putting my all into my business, has made me a very successful woman. If I did not take the risk that I took, I would still be working at a job that made me feel less then. My whole life has changed since then am I risk became rewarded! Read more>>

Dr Jesse Sanders | Mental Health Therapist * Speaker * Public Figure * Influencer * Conversationalist * Best Selling Author

Risk-taking is an integral part of personal and professional growth. The way we perceive and approach risks can shape the trajectory of our lives and careers. When it comes to risk, I believe in a balanced perspective that combines careful analysis with a willingness to step outside of my comfort zone. In my life and career, taking risks has played a pivotal role in opening up new opportunities and pushing me towards success. Whether it was starting my own business or pursuing challenging projects, I have learned that calculated risks can lead to immense rewards. Read more>>

Qwavaise Sneed | Musical Entertainer & Promoter

It’s played a major role honestly. A lot of people doubted me for taking those risks too. My first major tour with a bookie I paid him to make sure it was set in stone. Didn’t even know the guy. Everyday after I prayed that it wasn’t a scam. Once it was time to get the tickets for the show I was nervous too. That as soon as I show up to this stadium I wouldn’t have what I came there for. And boom next thing I know I’m on tour with Wiz Khalifa. It’s made me take more risks… Smart risks but definitely more! Read more>>

Marlaina Pacifico | Photographer

In my life and career as a photographer and skydiver, embracing risk has been a defining factor. Whether it’s leaping out of an airplane or capturing unique moments behind the lens, it all boils down to having the courage to step into the unknown. I’ve learned that taking risks, whether in dealing with the unpredictability of social situations or adapting to the fast-paced photography market, is about expressing oneself authentically and boldly. What I’ve found is that allowing room for experimentation and making occasional mistakes has propelled my creative journey forward. Read more>>

Deryck Richardson | Published Author, Speaker and Serial Entrepreneur

Taking risks has played a fundamental role in my career as an entrepreneur. In fact, it’s hard to imagine entrepreneurship without risk. When I first embarked on my entrepreneurial journey, I had to make significant decisions that carried the potential for both success and failure. Risk-taking has allowed me to seize opportunities that others might have shied away from. It has pushed me to innovate, to explore uncharted territories, and to constantly adapt to changing market conditions. Some of my most significant accomplishments have been the result of calculated risks, whether it was investing in a new product line, entering a new market, or even pivoting my business model entirely. Read more>>

Miriam Hodesh | Business Owner

I feel like taking risks is critical to growing and learning. If you have a strong support network than taking risks can become a part of your own DNA. In my life, taking risks has led to the most important achievements in my life. I’m sure it has also led to some of my failures too…..but I have a “glass is half-full’ kind of perspective so I will always be the person saying go-for-it! I recently worked on learning about my character strengths. Risk is not a specific option…but my core strengths are probably zest for life and perseverance. A value like risk can be underused or overused….the goal is finding the balance for an optimal use! Read more>>

Tabby Holden (Marsden) | Independent Hairstylist

Taking risks are necessary for growth, you never know what you are truly capable of if you never step outside of your comfort zone. If you know anything about my journey you already know at the age of 16 I made the decision to pursue my career in a much bigger city away from my small little hometown. It was at the time the scariest decision I had ever made but I’m so glad that I did. Growing up with anxiety in an unstable home it seemed like it would be impossible for me to follow my dreams. If I ever dared to try and talk about the things I wanted to do I was told that I couldn’t. I wasn’t brave enough, I cried too much, I was too fragile, too eccentric, no one would ever want someone like me. Read more>>

BJ Wingfield | Fashion Designer & Stylist

Looking back to when I started my business journey compared to now, I can honestly say my view on risk taking has changed. I used to be so discouraged when it came to taking risks. Coming from poverty & not seeing many young black fashion designers whom are men that could be the perfect example for me, risk taking was out of question. Mostly from fear. Fear of not knowing the outcome. But as I grew older and understood trusting the process, without taking risk.. I wouldn’t have come this far. Read more>>

Morgan Staten | Artist

Life is all about taking risks in my opinion. If I didn’t believe in myself and take the risk I wouldn’t be aware of my star power and skill level. Read more>>

Mandy Lehman | Master Designer (Graphic Design & Interior Design)

rom my experience, the saying “with great risk comes great reward” has proven true. I’m not afraid to take a big risk if it makes sense. One example, is when I got laid off from an agency that was tanking, instead of looking for another full time agency job, I decided to start my own design business. I didn’t want to waste any of my energy looking for a job and instead put my full efforts into my new venture. This was a risk since I was the main income for my household. I did feel like it was a calculated risk though considering I had already been freelancing on the side of my full-time job for 8 months at that point…so I knew I had clients to lean on right out of the gate. Read more>>

Cae LaShawn | Independent Artist & Songwriter

Taking risks has DEFINITELY played a crucial part in my life and my career. Without risk-taking, you just never know how far you can actually go. Whether it be calculated or by the seat of our pants, we all deserve to allow ourselves various opportunities to take risks. We can’t always “wait” for someone else to be willing to take a chance. Why not take that chance and bet on yourself? Taking risks, also allows us to step into spaces of vulnerability. I think vulnerability is a place we all could benefit from. It entails putting yourself and your capabilities on the forefront and being able to trust yourself along the way. Read more>>

Joey Doherty | Author & Therapist

I used to glorify comfort, trying to make my life as easy as possible. That wasn’t fulfilling, so now I try to take risks as often as my intuition calls for it. It sure isn’t the easy path, but it is exciting. I still value creating a solid foundation to support myself, and it’s from this foundation that I’m able to take big leaps. This impacts my writing a great deal, because getting out of my comfort zone is like watering my creativity. I try to focus on cultivating a life where inspiration naturally bubbles up. A life where a poem is bound to come crashing in. A life with enough risk taking and enough of the mundane and enough devotion connecting the two where naturally, I write. Read more>>