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.

Ariany Cespedes

Playing safe is something that I’ve been told in this industry over and over. To be honest, all it does is hold you back from the life and career you’re capable of creating. I’ve been able to open the door for opportunities by taking risks, especially writing to people I want to work with. One in particular that caught my eye was a production company in LA that I’ve been following for a while. I adored their message, films, content, and their perspective on the acting industry. Read more>>

Cornell Mapp

Taking a risk involves commitment to being an ambitious individual. Taking a risk is only a nervous thought, it’s never an action. The action in itself is you just attempting elevating in life. You can not elevate without “taking a risk”. I took my first big risk when I created the 1891 Hot 10 which now has surpassed where I could have imagined it going. Read more>>

Joe Callari

“You can’t connect the dots looking forward, you can only connect them looking backwards.” – Steve Jobs Any decision in life is risky, 98% of people decide to take the risk of doing what is easy and convenient now, only making their life harder in the end down the road. “The reason most people fail instead of succeed is they trade what they want most for what they want at the moment.” – Napoleon Read more>>

Mya Ferguson

I remember when I moved away from home in 2015 to Saginaw Mi, I went to this salon open house with my uncle. I was fresh out of high school and hair school, I met the owner at open house, we met and spoke briefly. She told me to apply to work there so I did. I still didn’t have my license but I said nothing! I was told how to apply so I stayed up and worked on a resume and made sure I had everything on point! I was so nervous because I wanted this job so bad but wasn’t licensed yet. Read more>>

Amber Hutchings

As the director of a very large event, the Utah Valley Parade of Homes, we were faced with our biggest challenge in 2020 when the pandemic hit. Every event was cancelled left and right, and I was faced with a very big decision on whether or not we needed to cancel our event that summer. Over 35,000 people attend the parade each year, and come from many states outside of Utah. I had to come up with a plan B should we have to cancel. Read more>>

Donisha Brewley

In 2022, I decided to rebrand Irreplicable Brand and begin to market the brand as a company that could deliver custom products and experiences even if done in the masses. We worked really hard to gain a strong following and to build a report with all of the people who would support IB in any way. We implemented new services such as virtual and in-person styling, closet revamping, decluttering assistance, and of course designing new lines to share as well as pushing the Tr22S3lf line. Read more>>

Emanuel Dominguez

The biggest risk I’ve ever taken took place in the month of October 2022. After working in tech sales for 7+ years, I chose to leave the corporate world and go all in on my dream of creating music full-time. Although I started making money as a DJ in college, never did I imagine it becoming my main source of income. What started as a hobby, slowly turned into a side hustle, however it was years before I came to the conclusion it was time to pursue my passion full-time. Read more>>

Maria Dinoia

I feel everyday that you own a retail store is taking a risk! In my position as apparel buyer, I am deciding what I think customers will like and will sell through. It is definitely not an easy decision, as there are countless apparel options to choose from. From style trends to material to price points, all of that factors into the decision of what I THINK will sell well for us. Sometimes the risk pays off and other times, clothes end up going straight to the sale rack. It’s a continual and ongoing guessing game and I’m not sure anyone has apparel completely figured out! Read more>>

Petrona Joseph

The biggest risk I’ve ever taken was on myself. For the last seven years, I have worked as a PR consultant on a part-time basis but since November 2021, I am a full-time Publicist with no safety net. I just did it! I started my agency, and at first – I was afraid of not being able to make payments to my contractors or not being able to pay for my own personal lifestyle. I don’t do much advertising but with word-to-mouth referrals, I am very busy. Read more>>

Arit Emmanuela Etukudo

The biggest risk I’ve taken… so far, was packing up all of my belongings and moving to the UK for 2+ years. I graduated from college a year prior and was having trouble finding a job as an artist, as it goes. One day I decided that I didn’t need to be where I was anymore. Things around me felt stagnant and uneventful, I wasn’t thriving in the ways I knew I could. So on a whim, I applied for an MFA. Read more>>

Breanna Gronli

Taking a risk is something that is very hard for me to do. I enjoy consistency, so when a friend mentioned I should go back to school and get my Masters in Social Work (MSW) I laughed at them. For several years I was told this and then finally one day I took the leap. I am forever grateful I took this giant leap of faith because if I hadn’t I would still be at a job where I felt I was drowning. Read more>>

Manica Walker

When you think of risks in starting a business, you may immediately have anxiety and find a million reasons why you can’t start. That was me and it took years for me to learn my value and see that I was gifted in the things I put my mind too. It was ten years ago when I told myself that I needed to do some type of fun hobby to keep myself busy after retiring from the Marine Corps. I didn’t need to work due to the benefits of the military, but knew I couldn’t become a couch potato. Read more>>

Dylan Wheeler

I’ve put a lot of effort and focus into risk-taking recently, and I have found tremendous success with it. By success, I mean mostly personally. I’ve really been able to prove to myself that I am capable and worth it. This has ranged from making costly purchases that have then paid off in dividends to auditioning for theater productions and on-camera roles (both of which I’ve done for the first time in the last year). Risks don’t always work out, but you never know until you try. Read more>>

Jess Obert

Back in the summer of 2018, our six-year-old daughter, Payton, told us that she wanted to host a lemonade stand in our driveway. After adding it to her summer bucket list, we knew we had to make sure it happened. She made a trip with her dad up to the local hardware store to get some lumber to build her stand. She knew just what she wanted it to look like. We challenged her to donate the proceeds and think about where she wanted them to go. Read more>>

Dawn Levian

To create a business one of a kind in your area or not to!? That was my question posed 4 years ago to myself. I had found a business idea that I connected with, believed in to my core and could see the vision of. However it was also going to be the only one in the area. And yes everyone needs to be a 1st for there to be more I get that. However would the idea catch on, would it survive, would others believe in it also or was there already not one because it wasn’t a good idea? Read more>>

Anthony Sleiman

Against skepticism and doubts, I made the daring choice to pursue a career in night photography, with a focus on capturing the ethereal beauty of the Milky Way. Despite the prevailing notion that such a niche specialization would have limited appeal, I was determined to follow my passion. Through countless hours of practice, study, and experimentation, I honed my skills and developed a unique style that resonated with fellow night sky enthusiasts. Read more>>

Kaylee Meyers

I was born and raised in a semi-small city in the Midwest and always had a dream for moving far away where the weather is always nice. Most of my family stayed within driving distance of my hometown and for me, I felt like that was settling. I’m anything but a settler. After college, I took a risk and moved to Florida to do an internship for strength and conditioning. Read more>>

Tiffani Neal

In 2018 I was in a successful career as an Account Executive with a fortune 500 Healthcare company. Loved my career but I wanted something different. I knew that I could be successful at what I was doing because I had been great at it. As a top performer and best selling sales representative something was missing, I wanted more. Read more>>

Douglas Smith

Any time in life that you take a risk, many thoughts would rush to my head, such as, “ what will people say about me?”, “ what if I fail?” But on the flip-side of the coin, I also ask myself, “ what if I’m really good at this?”, “ what benefits will happen if this works out?” Read more>>

Roscoe Robinson

Certainly! Allow me to share a story about a risk I took in the realm of motivational speaking—a passion of mine that I had been nurturing for quite some time. The backstory begins with my early fascination for public speaking and the power of words to inspire and uplift others. I had always been drawn to stories of personal transformation and believed in the potential for individuals to overcome challenges and achieve greatness. Read more>>

RACHEL MIFFLIN & KAREN VICK

4 months ago the ladies of MKT found out that the retail store front they had been renting was being sold. At the time Karen and Rachel were extremely worried about the future of their company and what path their business should take. After a lot of deliberation and prayer the ladies decided to completely shift gears. In April 2023, MKT Clothing Co moved to a new warehouse location and closed their retail store front. Read more>>

Colin Page McGinnis

Since 1922, SproutFive has been at the forefront of providing holistic, high-quality early education to children from six weeks to five years old. Embedded within affordable housing, education institutions, workplaces, and nonprofit hubs, SproutFive’s unique approach integrates child care with social work, empowering families and promoting women’s participation in the workforce. However, even with a robust history, SproutFive faced challenges in an industry plagued by outdated practices and regulations. Read more>>

Milo Estevez

I’m not a risk taker at all, at least that’s not who I was. I tend to be more analytical to calculate to the best of my ability my next move…big or small. With that being said, I’ve always tried to “play it safe” in my professional career. Following the idea of having a stable job with a decent salary and benefits all while doing something I enjoy to climb the corporate ladder, you know? Read more>>

Naphatia Edwards

I started my acting career over a decade ago in musical theatre. I was working on it every single day. Come 2018 and I became pregnant. I was still pursuing my career, but things seemed to be slowing down. After I had my daughter, Covid started soon after, things came to halt and I decided to take a break and focus on mother hood. Read more>>

Sydney Wilson

If you are from Atlanta you often wonder why people are “outside” while you are at work. It is what everyone at work says they “wish’ they could do. My name is Sydney Lashon since the age of 16, I have worked. I have had so many jobs it is not even funny. I enjoyed being independent but did not enjoy staying at a job for too long. I thought something was wrong with me. As I got older it hit me that it is not the work it is who I am working for. Read more>>

Michael Wall

The past few years have not gone quite the way I would have liked them to go. I had many concerts and performances canceled and not rescheduled. Many of my musician colleagues became hesitant to perform in public together. My own creativity stalled as a result–my second album should have come out last year but I’m still working on it–and I really hit a creative rut. I needed something to shake the rust off of me and get me back to action. Read more>>

Tyra Taylor

The biggest risk that I took other than deciding to go back to school in my thirties; was buying my salon. I knew that I wanted to own my own salon but I just wasn’t sure how it was going to happen. One day while I was working- the owner of the salon approached me and asked was I interested in buying the business. I remember asking if she was serious. Once she convinced me that she was; all the doubts and fears tried to creep in making me doubt that I could really do it and be successful. Read more>>

Nik Jermaine

Thank you for having me! I think creating our podcast series, Mortuus Est, was definitely a risk. Before this series, I had never worked on an audio drama or podcast or done voice-over, ever. Every part of making this show has been a learning experience for me and the Crazy10 team. Read more>>

Rachel Larson

The biggest risk I have taken was opening up a mobile coffee cart “Fika Coffee KC” back in October 2022. I have wanted to own my own coffee shop since I was in High School. In college I had so much excitement and eagerness regarding my dream. However, every year after I graduated college the dream felt more and more impossible. It didn’t feel tangible and I started to question whether my dream would become a reality. Read more>>

Lora Humphrey

I grew up in a small town in Georgia where there was not a lot of open discussion around alternative spiritual practices and behaviors. I was known as the “creative” child and I remember feeling like I stood out, and not always in a good way. My family decided to move to Florida when I was eleven years old and by the time I reached my teens I was introduced to more open and free-thinking concepts and began exploring more spiritual ideas and practices. Read more>>

Erin Call

My biggest risk was when I decided to host my first ever Full 5 day retreat at the very end of 2020. I knew women were hungry for healing, were craving community and wanted to gather. It was a big undertaking (and during a time of uncertainty collectively)- to plan, hire and execute it. I had never hosted a retreat before so everything felt fresh and new and I had to trust that I could figure out each step as I went. It was the first of many retreats and it catalyzed growth in an entirely new area of Soul Naked. I fell in love with creating sacred spaces for women to come together in this way. Read more>>

Joe Outlaw

I understand that taking risks isn’t something that everyone is willing to do, especially when they are at a comfortable stage in life and when there are many unknowns . I’ve always been a risk taker. Ever since I was a little girl . If someone told me that I couldn’t do something, I would prove them wrong by doing it 10x better than they would have ever thought. Risk taking for me, is really the next level of faith . It’s making decisions based on what you want out of life and betting everything against it. This was a key factor when I started my business . Read more>>

Sam Iaconi

I’ve always been very calculated. I like planning and “sticking to it”, so much so, that in almost every aspect of my life I’m makings lists just to “cross off” tasks and goals. It left very little room for risk taking. In fact, for most of my life I’ve avoided risk taking all together. Applying to the Maryland Institute College of Art for undergrad was the first time I treaded in risk taking; Read more>>

Andy Imlay

Back in 2018 I had the chance to perform at the Orlando Improv. I got the chance and within a month and half had to arrange a flight and hotel to stay at. I knew this could be life changing and it was indeed. Also the time I entered into my first comedy contest in Dayton, Ohio. I didn’t believe i was talented enough but i had some friends who pushed me to do it because they believed in my talent. After all was said and done I placed 2nd of of 50 people. Both events helped further my journey as a comedian. Read more>>

Dick Colligan

I was working on Wall Street for nearly a decade but always had the urge to be an actor from the age of five. When Covid happened I moved to Florida (temporarily) because New York City had gone insane with mandates. After about a year I saw that things weren’t really changing and New York so I decided to move to Florida full-time. My job wouldn’t allow me to work remotely so I was forced to leave and go on my own. Read more>>

Ashley Wilson

The last professional job that I had I was fired from and at that time I was doing eyelashes and I brought Michael blading part time. Once I received the news that I was fired I decided to try to make my part time personal business my full time business. And instead of looking for another job I rented a suite started decorating and crossed my fingers. Seven years, and two business locations later my clientele is consistently growing I’m happy I’m glad that I took the risk on myself. Read more>>

Virgil (Tibbs) Galloway

Taking a risk is what most successful people have done. If you don’t believe in yourself, who will? I’m sure there is someone out there that shares a similar story. Let me tell you my version. After graduating from barber school, I planned to take my skills to the next level by working in a barbershop and being the best barber I could be. For me, it was not about making money but making people happy and giving them the best haircut and service possible. Read more>>

Alexa Shea Johns

“One of my favorite quotes of all time is “Life favors the risk taker.” I don’t remember when I first heard it, or who said it, but It’s a touchstone phrase for me that I often come back to when I feel like I’m on a cliff looking over the edge about to attempt another flight into the unknown. I now see clearly that invisible wings are real things. Read more>>

Heather Fraley

It was definitely taking a huge risk as a single mom, diving into the film industry with no prior experience. I decided to trust and bet on myself. I have no regrets about this decision, as it has changed our lives completely. Read more>>