Tony Robbins says the #1 human need is certainty, but do you know what the second need is? It’s uncertainty. This tug of war between the competing needs of safety and risk are at the heart of so many dilemmas we face in life and for most folks the goal isn’t to eliminate risk – rather it’s to understand this core human need. In our view, the best way to understand or learn is through stories and so we’ve asked some very talented entrepreneurs and creatives to tell us the stories behind some of the risks they’ve taken.
Maxwell Leacock
The biggest risk in my journey so far is not going to school. Originally the goal was to get into a fashion school and the one I ended up having my eyes on was FIDM (Fashion Institute of Design and Marketing). But tuition for college is crazy so I made the decision not to go to school and take the next couple years to teach myself the craft I wanted to learn. It’s taken time to learn everything I know today but it’s built character and I appreciate the choice I made every day! Read more>>
Sam George
My biggest risk was grounded in a delusional (and perhaps more appropriately named, desperate) attempt to keep my first, long-term relationship alive. As devastating as the inevitable breakup felt at the time, it’s that optimism that lead me to a more authentic, creative, & passionate life. But for some context – Read more>>
Katie Welch`
I went to school for education and spent time in Africa during college teaching art. My experience there ignited a passion for teaching kids from tough situations. For 14 years, I worked in Title 1 schools, teaching and taking on leadership roles. During this time, my husband and I got married, had two biological children, endured three miscarriages, and eventually decided to become foster parents. Read more>>
Lisa Chiodo
My whole life as an international creative has been a risk. Moving away from home to another country with no family, studying hard with no guarantee of work after I graduate due to VISA status, not being able to work outside of college while Im studying because it’s against VISA laws. Its putting everything I have ever wanted in not only my hands, but the hands of the American government in the hopes that they see in me what I see in me, and allow me to live out my dream of being a working professional in the music industry as an individual who works so hard. Performing, singing and playing trumpet are things that I cant see myself not doing. I’ll be performing for the rest of my life and having the drive to do this after calculating the risk proves to me that it’s what I am supposed to be doing with my life. Read more>>
Liza van Deventer
I immigrated to the United States from South Africa to pursue a career in acting and yoga. I have left my whole family behind in South Africa. My husband and I moved to Los Angeles in June 2023 amidst the strikes. We started from scratch. I spent 6 years as a series regular on a South African tv show called “Skeem Saam”. Which is the 3rd most watch show in South Africa with a viewership of 9 million. I have left the comfort of a steady tv job and being known by South African casting directors to be a very small fish in the massive ocean of entertainment which is LA. Read more>>
Crystal Holloway
I’m going to be honest, I’m not a risk taker and have never been one. I have always been known to err on the side of caution. I avoided learning how to sew for twenty years, because I broke a needle once and was too nervous to try again. I avoided public speaking in school, because it terrified me. I never wanted to be the center of attention, because when I was younger if the focus was on me, it was usually on all the things I did wrong. Read more>>
Shannon Pruitt
I had just become a mom and was running on a mix of joy, adrenaline, and sheer exhaustion. Despite the chaos, I desperately missed the thrill of entrepreneurship. A few months earlier, I had closed my wedding planning business, leaving me feeling a bit lost as I navigated my full-time job and new role as a mom. Read more>>
Mari Bryant
There was a time when I had to take a risk. I was working at the hospital and not getting any modeling opportunities at the time. I was feeling a bit discouraged and unmotivated because of the lack of work. Many people think that modeling is non-stop, but in my case, it was slow. I was working at a job that paid well, but it was tiring. One day, I received a call from a designer asking me to walk in a show. Excited, I agreed without realizing that I had to work that same day. When I asked my manager about it, they said no. This opportunity was significant for me because it opened many doors. Although I did quit my job to be in that show, it was still a leap for me. It helped me get back in my groove and realize the importance of taking risks. I believe that if I hadn’t taken that opportunity, I would have still been struggling to find more work and feeling unmotivated in the profession I’m trying to establish as my career. So, the lesson here is that sometimes you have to take risks, especially if you have a gut feeling about it. I’m not saying you should quit your job if you can’t make up your mind. BUT the moral of the story is that sometimes, to reach the end of the maze, you have to get pricked by a few thorns. Read more>>
Jessica Tavares
Starting a business in general is such a risk but starting one when you don’t have formal training in the business can be even more difficult. I have had to seek out classes locally and not so locally trying to better my craft so I’m able to provide some of the best quality baked items to my clients. We will be taking a class at King Arthur Bakery here soon and are constantly researching every item we introduce! Also, using organic and striving to stay 80/20 organic in all we do is even more difficult. Sourcing organic produce, dairy items and everything in between has been a challenge, especially while trying to keep our prices reasonable. We thankfully sourced high quality, certified organic flour but we have done so much research and sourcing to ensure we are able to offer the best we can! Our end goal is to open a local bakery in Summerville offering organic or mostly all organic baked goods! Read more>>
Gretchen Crilly McKay
I had been teaching elementary school for 30 years but was at least 10 years away from retirement. I loved teaching for the first 25 years but the last 5 I had felt burned out. I had begun studying shamanism in 1994 with the Foundation for Shamanic Studies and was seeking spiritual guidance about what was next for me. Upon encouragement from several friends, I went to see a visiting African healer (Sangoma). Read more>>
Erin Harrell
I feel like the best thing anyone can do is take a risk. I took a risk from moving from my small hometown in Southern Illinois to the big city of Memphis to pursue a career in music. It started from an early age of knowing the only thing I wanted to do in life was be surrounded by music. Music from the beginning to end. I moved to Memphis in 2021 to study music business and recording technology at The University of Memphis. I still study there, but the first two years here I was not doing what I wanted to and I felt like nothing was truly happening for me. Then I went to an event in Atlanta where I met some amazing people who took me under their wings. I worked with them a couple times for free before they truly gave me the opportunity to go stay in Florida over a summer and work as much as I could. During this time I met different production companies in Orlando and I got to travel to Ohio for a two week show run of a music festival. It felt like I was on top of the world. Then it was coming time for me to go back to Memphis for the fall for school. I did not know what I was going to do once I got back, but I knew I had a starting point. Right before getting back I received an email, and I got the opportunity to be the Memphis Chapter Intern for the Recording Academy. That was huge for me! I knew I had something to look forward to upon arrival to Memphis. That is not the only risk I took or even still take. I have a motto that I will work for everyone for free at least once. That probably seems weird, especially with rising costs today, but that alone got me two different jobs with production companies. With those production companies I get to work at cool places such as The Peabody, Minglewood Hall, Loretta Lynn’s Ranch, and so many more. While I am on those jobs I have been able to branch out and work as an A2 at The Overton Park Shell, work smaller music festivals, and gigs at Lafayettes Music Room. With my internship at the Recording Academy I was able to get in contact with an amazing engineer at Sam Phillips recording where I currently intern and work on amazing projects with. I was also able to go to the 2024 Grammy Awards week in Los Angeles which was surreal. This last year and a half has been a complete whirlwind of experiences and meeting different amazing people, and I would not have that if it wasn’t for the fact that I took a risk. Not only did I take a risk though, some amazing and kind people have taken an even bigger risk on me and I am forever grateful for that. Read more>>
Micah Rustichelli
In 2022 I was feeling tired of my studio work and exhausted by a demanding day job. Over the previous years I’d gradually fallen into a rut of painting for sales and content creation. My days in the studio felt like a treadmill exponentially getting faster as I tried to keep up with the endless sprint of the race that I thought I was a part of. When I did feel success the payoff was short lived until the imaginary impending doom would return. It was at this time that I made a crucial decision to pull my practice apart and reassemble it. I was nervous to make this change; The insecurities that had led me to this unhappy place also had me believing that to change my work would cost me my audience and stability. Read more>>
Marie Valencia
The last year,I have had many personal ups and downs..Living in rural Southern New Mexico created many hardships in my career as an Artist and long time Performer.If it wasn’t for the Farmers Market in Socorro,I would have really lost my confidence.The ladies, over there were nothing but welcoming. Read more>>
Kaylee Smiley
I was 24 years old, working for a corporate company in a cubical office Monday – Friday. It was mundane. I was uninspired, and quite frankly, bored. I remember thinking, “Nobody actually enjoys their job, so this will be fine for the rest of my life.” What a sad thought to have! Read more>>
Cassandra Solmonsen
Trigger Warning: Assault
Florals by Cassandra was a risk, most if not all businesses are. But Florals was special (I know all parents say that about their baby) it wasn’t a risk because it was a business or because it was a different direction than my degrees. Florals by Cassandra was a risk because it was the first thing in five years that I had done for myself that was not for my safety. You see, from 2016-2022 I was wrapped up in a court case against my rapist, a case that honestly wasn’t even mine. I was just a piece of evidence for the state to show a pattern of behavior and I had lost myself in that fight. Florals by Cassandra has helped bring me back to life and reconnect with the person I was before the assault. Read more>>
Kathryne Imabayashi
Embracing Passion Over Comfort: My Journey into Entrepreneurship
After retiring from a long career in education, specializing in early education and the inner world of boys, I found myself at a crossroads. The conventional and safer path would have been to supplement my retirement income through familiar means—teaching English, tutoring, or part-time teaching. Instead, I decided to put all of my time and energy into continuing to follow the passion that has been a driving force in my life for almost thirty years. I wanted to support the world of boys and those people that are in it in a much deeper, focused way. I was going to start a business and help parents understand the world their sons are living in and guide them to have deeper connections and better communication with them. Read more>>
Melinda Fouts, Ph. D.
After having a successful private practice as a Jungian-based Psychotherapist, a global CIO suggested I become an executive coach because she had had several executive coaches throughout her career, and in her words, no had helped her and I did.
After taking an executive course for 8 months, I launched myself as an executive coach. I learned I could still use the tools and techniques I had crafted over time but in a different way, like I did with the Global CIO. Read more>>
Byron Carvil Cecil Napier
Biggest Risk I call it Leap Of Faith Street Journey Pokémon Master Quest I decided to pack my things and move to LA and made a decision to live in my car i have gym membership, i rent storage unit for my clothes and make sure to protect myself, dreams and passion its all i need to survive in LA. i finally arrive in LA and i didn’t waste know time i used internet by the library and build profile using Actors Access, LA Casting, Casting Frontier, and Backstage and since there is extras Company i can apply to maybe i can get my sag card credits. I just used my navigation to get from places needed to go. I found an awesome parking space near the beach and gym i just use that parking space to eat and sleep plus & eleven have microwaves and i found another security job to work at production studio. I booked my first job from Central Casting, the show called This IS Us and i meet Sterling K Brown and he gave some advice and while everybody was eating make sure to pack the leftovers in my bag for the rest of the week for food. I was living in my car for 9 months and Covid happen i was still living in my car praying it was airborne i made sure i wore my mask and everything etc i was bike security guy i meet Jaleel White and he game me some advice too i said why stop there. some times every Friday. i want to feel the bed I book a room hotel room for just every other weekend because one my favorite shows the owl house comes on that show help me feel happy and i love the voice cast especially Mela Lee and i was curious i listen to her interviews im interested to do voice overs since IG best place to communicate i sent her message and she replys back she’s very nice and amazing i wrote on my vision board to meet or take a class with her soon. then i message other people on there like Daniel Curtis Lee aka Cookie from Ned’s Declassified School Survival Guide and he replies too with amazing motivation and finally i wanted to look more into video games mocap so i message Nick Apostolides from Resident evil 2 remake and told me about The Mocap Vault studio Richard Dorton and thanks to Mekel Kasanova podcast interview with John Eric Bentley I message John Eric Bentley who voice Barret Wallace final fantasy 7 remake and gave me more helpful advice. I just continued listening and reading these amazing people interviews and helpful advice and made me the person of who i am today. i finally took acting class in LA Anthony Meindl’s Actor Workshop and meet so much amazing people along the way. I had few months left until I move to my place I discover other amazing actors live in their car during the times in there early career too so I watch their interviews to feel inspired towards the journey and just to keep my mind from spiraling to negative place while listening and watching actors and actress like Jonathan Majors, Kelly Clarkson, Sam Worthington, Tyler Perry, Hillary Swank, Lil’ Kim, Steve Harvey, and Micheal B Jordan. i finally on may 2020 i moved into my first studio apartment. Read more>>
Jonny Violet
I wanna first say that I’m incredibly grateful to be here. I have a song I’m working on after taking a lot hiatus. It’s a rap song and it’s very powerful and strong. I wanna put it out soon. It’s a major risk that I plan on taking because I’m known for singing. I’m not known as a rapper. But I hope when the song comes out it will make history and make an impact Read more>>
Elma Panagaki
Moving from Greece to Los Angeles was undoubtedly the biggest risk I’ve ever taken. I arrived with no plan, no job, and no experience of the US, but from the moment I set foot in LA, I felt an inexplicable sense of belonging, especially when I first saw the vastness of the ocean. Read more>>
Maura Allard
At the end of 2020 I sensed I was in burn out. I always felt I lived my life in some state of low level anxiety but this felt larger and it was. Since 2014 I had been climbing the ladder in real estate and by 2020 I was licensed in 2 states, obtained my broker license, specialized in working with Senior Citizens and had assembled a team of 3 agents, 1 assistant and 1 social media whiz. From the outside it looked like I had it all and for a long time it worked until it didn’t. Read more>>
Jess Tiel
I think one of the biggest risks I’ve ever taken was hiring my best friend. She’s my soul-sister, and I love her with ever fiber of my being. But going into business with a friend can more often than not be the kiss of death to the friendship. We discussed that risk, and set very clear and realistic expectations. We created a special contract that had clear terms of how to dissolve the business relationship if one or both parties decided they wanted out. We negotiated those terms from a loving place, and really talked it out about what it would actually look like to walk away. Read more>>
Kylie Vennefron
I think publishing a book in and of itself is a risk. You never know how readers are going to react to something that you’ve poured your heart and soul into. But you write books for yourself and publish them for the readers. Finishing a book is a huge accomplishment, and you can decide to either take the risk of publishing it and earning inevitable negative feedback, or you can keep it for yourself. I have no regrets about writing and publishing, and each release is a risk that I am happy to dive into. Read more>>
Kiara Davis
What many perceive as taking a risk, I consider a leap of faith. One of the most significant and gratifying steps in my journey as an entrepreneur was entrusting my gifts and talents to the Lord, Jesus Christ. In doing so, I committed to bringing glory to His name through every gift/talent he has blessed me with . This decision required a profound act of faith—surrendering every dream and goal to His will, relinquishing my own control, etc . It taught me to rely on His guidance and the wisdom found in Proverbs 3:5-6, which instructs us to trust in the Lord wholeheartedly, acknowledge Him in all our endeavors, and lean not on our own understanding. Read more>>
Clothilde Ewing
Hands down, saying out loud that I planned to write children’s books. I have been blessed with a good and varied career. I have worked in television news, for The Oprah Winfrey Show, in politics and now at The Chicago Community Trust, Chicago’s community foundation. While I have worked in high profile jobs; but one of the consistencies is that I have been able to stay comfortably behind the scenes. Pursuing a career as an author meant I had to put myself out there in a way that I hadn’t needed to before. Read more>>
Trey Sanders
One of the most significant risks I’ve taken was stepping out of my comfort zone to save Texas Southern University’s Homecoming Concert. In 2023, the concert was unexpectedly canceled, leaving the students disappointed and the university scrambling for alternatives. As an alumnus of TSU and someone deeply passionate about the music industry, I felt a strong responsibility to intervene and find a solution. Read more>>
Marisa Skolky
The biggest risk I’ve taken is quitting my corporate job and starting my own business. This switch demanded that I level up, show up fully, and be committed to living in integrity. I was committed to sharing my divine gifts, owning my authentic power, and honoring my true purpose as a healer and transformation doula. Read more>>
JAMES MOORER
The first business I ever created was a mobile disc jockey company, Jamesong Entertainment. I had worked for another company for a few years and left for something more stable in banking. But I kept getting calls from people who wanted to hire me. I worked part-time as a deejay but didn’t think there was enough business to sustain a family. Read more>>
Lisa Grisolia
I previously worked in finance, specifically processing and underwriting mortgages. At the time, makeup was a side job that I was doing for people I knew. One day I was having a terrible day at work, it was a high pressure atmosphere and yelling was considered normal at the time from superiors and I had an epiphany. This was when I decided I really wanted to try to do makeup for a living, so I signed up for makeup classes. Some people did not understand why I would leave a stable job to try to do this. To me it was as easy as it is now, I love what I do. I love the emotion that comes along with making people feel good about the way they look. I have also done horror and love that I am able to get a different type of emotion, maybe the shock factor, it is fun, it has always really been fun. Read more>>
Dr. Nicolya Grigsby Williams
Launching my own coaching business as a single mom was a significant risk that I took, but it was a decision that was driven by my passion for helping others and my desire to create a better future for my family.
The backstory to this risk begins when I found myself in a job that no longer fulfilled me, and I felt a pull towards pursuing my dream of becoming a coach. As a single mom, the idea of leaving a stable job to start a business came with uncertainties and fears about financial stability. However, the thought of not pursuing my passion was even scarier, as I knew I wouldn’t be happy settling for a job that didn’t align with my purpose. Read more>>