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.
Nicole Saunderson
The biggest risk that we have taken so far is deciding to leave our secure full time jobs and pursue our passion full time. My husband and I have both been open to risk and change in our lives, as both of us prior to knowing each other, on a whim decided to move halfway across the country (Me from Chicago, and Mike from New Jersey) to start a life in Florida (And that totally worked out for us b/c now we are happily married with our amazing son Colin!) Fast forward a few years, we both have secure government jobs and our photography company. Read more>>
Carly Thurman
Saying yes is the ultimate risk. In this business, everything you do is risky. It’s not finding organs to save lives but none the less it’s a high pressure, high stakes job that shuts wimpy behavior or your personal needs down at the door. If you say yes to any of it, yes to another added client on a full roster, yes to something you’ve never done before and logistically have no ground to stand on, yes to large yet fragile installations you’ll need two Marvel Superheros to suspend for you but you don’t so you check your life insurance instead. Yes to throwing money at any situation to make it all work because it’s all on the line to get it right every single time and it’s your meal ticket. Read more>>
Marisa Plotnick Yibirin
I have always loved taking photographs and the feelings that it has given me. Being able to capture a moment in time and know that it will last forever is a feeling that is hard to put into words. Growing up my father loved to photograph all of our childhood moments and I feel that is also one of the ways I feel connected to him and the past. When my dad passed away, one of the ways that I coped with the grief was by photographing. It was my way of channeling my pain and sadness. I was able to capture the beauty that is all around us. Read more>>
Michelle Doyle
Starting Hott Tarts was a huge risk. I didn’t know it at the time, but looking back, I knew nothing about the food industry. I just loved baking and making people happy. When I started Hott Tarts, only friends and family had ordered them to support my new venture. Then, one day I received my first order from someone I didn’t know. I was beyond excited! Word soon got out in Cleveland thanks to some friendly local food businesses and early customers promoting Hott Tarts. I began to get so busy that I had to figure out ways to make Hott Tarts faster and faster. Read more>>
Daniel Dang
We first opened our small business in 2016 under a trademarked name. After 5 years of being in the boba industry, we gained a better understanding on the operational standpoint and established great relationships with our distributors. In the beginning of 2021, we decided to take the risk in becoming independent – be our own brand. Read more>>
Josey Omokheyeke
Being a creative and having this dream of being a pop star, I feel my whole life has been about risk. From studying music in college to moving to new cities by myself to pursue my dreams. I think the biggest risk I’ve taken was moving to Nashville, with no car, no set place to live yet and a part time job that paid $10 an hour. Keep in mind when I moved I had no friends in the city either. However I had faith and determination I would figure it out and I did. Nashville taught me alot about myself and the music industry. Read more>>
Amy Fitch
For me, it really was shooting weddings and focusing on creative/artistic photos on my own, hoping that my vision was good enough to translate through my work and represent such an important day in people’s life. The pressure, the no do-overs, the challenges that arise sometimes with no time to spare, the sudden complete and total change of plans. Keeping people calm, remaining confident and getting the job done. Wedding photography is certainly not for everyone. Read more>>
Steff Barton
Raised in a Baptist church in the heart of the Midwest, I learned from an early age to cleave to the tried and true and to stick with the straight and narrow. Following this path and fulfilling my heart’s desire to help others led me to a successful career as a nurse. Life seemed safe and easy enough, and I felt I largely had control. In an instant, though, my world radically changed when my mother died. Read more>>
Don Pedigo
I’ve taken the ultimate risk in life, in my opinion of course, and that’s staying with the music. It’s truly a challenge to stay on an adventure like this while maintaining the picture moments most of us envision through the years. More generally speaking I’ve chosen so far, to stay with the horse that brought me to town if you will. The risk of being a songwriter and musician is like any choice really, time value. Sometimes it’s not what things mean but what they are worth to you. That leads me to say there’s meaning in worthiness. Read more>>
Shaundrel Smith
During the end of 2020, for fun my sister and I started formulating our own skincare products. Making simple versions of body butters, scrubs, and lip balms. During this process I realized that I had developed a true passion for skincare and the formulation of healthy skincare products with pure ingredients. Recognizing this passion of mine, I was left with one decision. To either take a risk, a leap of faith and start my own business or to let my fears get in the way. I think all business owners go through this mind battle, the initial fear of starting a business. Read more>>
Jay-P Gallo
Way back when, I was living paycheck to paycheck. I went from one job to the next to be able to pay my living and still have some time to do something that seemed give me a little more purpose. Music and art deserved all my time but I just didn’t seem to be able to find any time for stuff like that. Reality isn’t for the artist, hence the artist designs new worlds where they can expand in a better existence. Reality teaches the creative that art and music are free and that to be able to make money out of this and live to be creative, the creative doesn’t just have to breathe the lifestyle, but to get out of their comfort zone. On 2017, after an unexplainable malfunction in my body, Read more>>
Kody and Soudabah
Towards the end of 2020 the team behind St Pete is Super Cool were stuck at a crossroads, stay at their jobs or take the leap and start our business. In the beginning of 2021 we decided it was enough talking and to take a chance! Your only young once you know! It was scary leaving our jobs that made sure our bills were paid and start a venture that wouldn’t see income right away. We had the full support of our families though and throughout that year we pushed ourselves hard to show the community of St. Pete that St Pete is Super Cool was a media company that stood for the little guys! Read more>>
She Keene
My name is She (short for Sheila) and I am the creative force behind “Redefining She.” For more than 20+ years, I was a Robotics & Software Engineer for the Dept of Defense. I always knew I wanted to retire early so I could create a “Chapter 2” and fortunately, I was able to do just that when I was 50! Little did I know my “Chapter 2” would be in a field that I have ZERO experience or knowledge of. Talk about risk, right?! Read more>>
Victoria Fonseca
Deciding to Pursue my passion was a culmination of risks that completely changed the trajectory of my life. Starting with leaving the security of a corporate carer for a part-time position as a group trainer a year after graduating college with massive debt from school loans, no certification or experience in personal training yet. I felt so separated from myself it became unbearable, I knew I couldn’t continue living that way. Read more>>
Carissa Espey
My Bread and butter has always been cosmetology and things for me at the salon were a little slow a couple months prior to Covid19. When COVID19 hit I was completely out of work, I was low on cash and needed to figure out something to do. I had more time to dive back into old hobbies, such as painting. I have always loved painting and thought “let’s do something related to that.” I had a small amount of paint and brushes lying around, took the cash that I had and invested in coffee mugs and wine glasses. Then with the small following I had on social media I started promoting custom mugs and glasses for sale, slowly orders were coming in and it kept me busy for a short amount of time. Read more>>
Wren Vadasz
I’ve been lucky enough to do what I love for a living- I know that is rare. I decided at 32 (along with some beautiful people that advised) that if I didn’t decide to pursue things full time then, when would I? It’s been scary at times, lots of ramen and mental health boundaries I’ve had to overcome… in the end it’s all been worth it. I wake up to do what I love every day that I want to. I travel, I get to experience things I never though I would, and most of the time I even get to experience them with my partner, Mark, and that’s pretty incredible. Read more>>
Yarelis Rojas
At the beginning of the year, I took a big risk and a leap of faith by leaving my job of 15years. I had been trying fo many years to come up with a good plan for my business and at the beginning of this year I started fresh with a new name and new understanding of how to run it. Back in may I made the decision to leave my regular job and focus on my business full time. The outcome has been incredible! Read more>>
Naya F. Powell
In 2019, I left the security of corporate America to pursue Spa Utopia. Having experienced a level of corporate burnout personally and understanding the importance of workplace wellness, I felt called to use my experience to help others navigate the same thing. Little did I know the following year, we’d be hit with a global pandemic that would put workplace wellness at center stage. Receiving a contract to provide spa services for the NFL Superbowl, positioned me to have an intense level of focus which resulted in winning a SXSW pitch competition, becoming a best-selling author, launching a sold-out luxury wellness retreat, and successfully pivoting to a digital wellness platform. Read more>>
Dion Leonard
In 2017 I was about to release my first book ‘Finding Gobi’. I was however still working full time for a company that I loved but I felt that this was also going to hold me back if I stayed with them. I wanted to give the book my full attention and see where it could go. After speaking to my wife about my belief that the book was going to be a success we made the decision for me to quit my job and take a chance on it all. My book is now in 24 languages and being made into a Hollywood movie. Read more>>
Jazmin Moreno
A month after my high school graduation, I moved back to Denver, CO. One day, in early winter, the last week of January 2017, my sister and I went to an annual Fossil Gem and Mineral show. We stopped at a booth that sold mineral beads. We talked with the owner for some time, which led to him asking if we would be interested in helping with the gem show that weekend. At the time, my sister Jessica was already working with a phone company, and I was waiting to hear a call back from them, so I decided to help for that weekend. By the show’s end, the team offered me to work with them in the following gem show in Philadelphia. Read more>>
Khallil Stewart
Taking risks is what life is all about. When you get too comfortable it is impossible to grow. I recently took a big risk when it came to my day job. I was working out of a warehouse that my dad manages and had a feeling that it was time for me to go. I began feeling anxious and knew that if I stayed there longer I’d get complacent or just wouldn’t be happy. I am very thankful for the job because during covid I was able to work there while the world was shutdown, but I am a person that has to constantly challenge myself in order to get the best out of me. Read more>>
Jon Evans
Growing up I always heard people say pursuing a creative career was a waste of time. I was told there wasn’t any guaranteed success or financial security in a creative field. I feel as though these type of comments come from people who project their fears and failures onto the other person. Growing up I was never around anyone who pursued a creative career, they kind of just let their creative side die down and never turned to it again. I took that risk. I chose to pursue these things instead and I am more than happy that I did because now it makes me more than happy to be in a job that I love and a role that allows me to be creative and create freely. Read more>>
Robyn Fossen
Taking a risk on starting this business during a global pandemic wasn’t easy it was very hard it’s still continues to be hard there are days where things go right there days where things don’t go right but at the end of the day I would not change anything about what my husband and I have started with this business and the smiles that we continue to put on peoples faces Knowing that you are the reason for making someone’s day that you are that ear to listen to someone when they just want to vent being there for our customers is the best feeling when we think that we are not making a impact we are when they tell us that they love our products when they tell us that our place is always clean when they tell us that we remind them of their childhood Read more>>
Melissa Boylan
I’m not a risk taker. I like to follow the rules and believe that rules are put in place for a reason. Yet, here I am, having left a well-paying stable job as a family physician in a large hospital system, and having taken a huge risk in opening my own Direct Primary Care (DPC) office. An increasing number of medical practices are being bought by large hospitals systems, but I decided to do the opposite and open my own private practice. Many doctors are having to join together in order for their practices to financially survive, but I opened a family medicine office with only one doctor – myself. And while the world was shutting down around me at the end of March 2020 due to COVID, Read more>>
Marie Pickett
Hello. Thank you for having me share a little of my story. The question I chose to answer was about taking a risk. I have had many times in my life where I have had the opportunity to take a risk. I took some and declined others. One of the risks that I have been the most blessed by was when I left the mental health practice where I was employed for almost 10 years. I really had a good job, and I worked with great people. I had many great learning experiences while I was there. Read more>>
Paula Keehfus
I would say I am an average risk taker, not too little, not too much. Twenty-two years ago, I came to the realization that working in retail for the rest of my life was not going to bring great joy or fulfillment to my life. From a rather young age, a painful health challenge inspired me to seek alternative healing for myself as I approached my third decade of life. As I began to find relief from those modalities, I took a passionate interest studying and training in them myself. In 2000, I opened a small online shop and began to not only offer crystal healing tools, but Reiki healing and training to clients both far and near. Read more>>
Matthew Schlosshauer
I worked with Mercedes-Benz for 10 years before opening my own European garage, this was my first taste of the business life, I had no clue how to run a business or have a mentor to relate to! This was a huge risk because I had a comfortable job with Mercedes-Benz as a technician. The reason why I ventured into the small business life is “regret” I chose not to live with it! Fast forward to the present and I now own a mobile detailing business and I am playing around with short term rental real estate. Read more>>
Donna Tomain
I launched my nutrition business, Good Mood Food in 2020. In addition to being a Nutritional Therapy Practitioner (NTP), I also had a full-time job in sales. It was a constant struggle trying to find the time to dedicate to my business after being mentally drained from exhausting work weeks. I always felt like I was only able to give 50% of myself to my business and trying to get it to grow. Read more>>
Brandon Bally
I took a risk by going to the studio to make music, knowing that in my heart it was something I genuinely wanted to pursue. At the time of my first recording session as an artist, the City of Pittsburgh was in the midst of a lock-down due to the unexpected spread of COVID-19. Luckily the legendary production studio called “ID Labs” was still open, albeit with heavy restrictions to comply with the social distancing mandate. As a matter of fact, I had to wear a mask to even get into the studio that day. Fear racked me prior to the day that I had booked the session held in the same studio that artists such as Mac Miller & Wiz Khalifa had once made smash records in. Read more>>
Kyesha Williams
I have not been a W2 employee in over 2 years. I was kinda forced out of that position and into this one as a self employed independent contractor. My last employer would not cover maternity pay or even short term disability after I gave birth to my daughter. So I made the decision to study for my Real Estate License and haven’t looked back. Doing this is not new to me however. Since I was a kid I knew that I had to take a risk in life to get where I wanted to be. With that being said Ive had multiple businesses and quit my job many times to work full time for myself. Read more>>
Jess Gill
As a child of two educators, I grew up understanding jobs came from defined entities, with structures, benefits, and pensions in place to support their employees. It never occurred to me that entrepreneurship would be an option — and a desirable one — at that. All of that changed at the start of the pandemic. I had recently left my job (by choice) due to its toxic workplace and was looking forward to figuring out next steps. I fully intended to go back to a 9-5, provided it was the right culture, and had several conversations lined up about possible options. Read more>>
Kelly Ryan
For me, taking a risk is synonymous with a leap of faith. Jumping into the unknown is exhilarating and energizing. A fun personal risk I took was when I went sky diving/tandem jumping to celebrate my 50th birthday: what a rush and memorable experience. I’ve taken many professional risks, and I’m going to share with you one that didn’t work out so well, which left me abandoned and unemployed after 90 days on the job. I had a national business development position representing mental health and substance abuse programs and had been employed by a company for 13 years. Read more>>
Anna Vasquez
When March of 2020 happened I lost all my scheduled clients, with the exception of 4. A lot of my staff moved out of the area or they were no longer available to pet sit. I was forced into a situation where my 7 years of hard work and sacrifice may no longer pay off. The future was completely open, should I continue with my current path or strike elsewhere? Would I retain proper staff again? Read more>>
Shardae Walker-Simpkins
I can remember working in the beauty industry and feeling torn between staying in the career that was comfortable and trying something new and totally out of my comfort zone, which was becoming a birth doula. I had already signed up for birth doula training and paid a deposit but worried about the total cost of the program because at that time, my husband and I had just started our lives together and weren’t in the best place financially so I began second guessing whether I should go with it or not. Read more>>
Taylor Warren
Starting my business was one of the biggest risks I took. I decided to take a break from college and simply find me, who I was, what I liked and what I wanted to do in life. In October of 2017 I launched my brand, Taylor Nycole. I didn’t know what I wanted to do exactly but I knew I wanted to do something that had a positive impact on others, I wanted to be voice for those who really didn’t have one. I launched my business with so much fear, I didn’t know if people would actually support me, what if I turned into a joke, Read more>>
Rev. Jenna Sullivan
In 2021, I decided to publicly come out as a queer person. The pandemic in some ways was an invitation to be with myself. After months of therapy and processing on my own, I decided that it was important to me and my ministry to be fully aligned in my evolving truth. This felt incredibly risky. I mean, what increasingly gay Baptist woman pastor beginning a career in church-work thinks, let’s tell the whole world who we are! Read more>>
kimberly chase
The biggest risk that I have taken is becoming a unknown gospel singer in Brimingham, Al. Being someone who is not really popular and kind of shy. I had doubts about being a singer in Brimingham. I believe that if a lot of people didn’t know who you were they would not support you. Which is kind of a true story if you always speak negative on yourself. Although surprisingly I have been getting a lot of support from my family and friends. People have been showing my EP a lot of love. Two of my songs on my EP have both reach 100 plays on itunes. Read more>>
Mylo Kidd
What’s felt like the biggest risk I have taken in my life thus far is not necessarily one major instance or happening, but more rather an ongoing process that I find myself in the unsteady waters of currently, especially having never felt comfortable enough to do so, as if it was something I was even capable of doing, or if it was the right thing to do. Simply put, it is the risk of fully trusting yourself & your path, even while there are outside (and inner) forces & energies that work solely to sway you away from yourself and what you know & believe. Read more>>
Christian Hanna
Taking risks is extremely important. There is a saying, “there is nothing more dangerous than a man with nothing to loose”. If you live in Fear, it may lead you to living a life if regret. One of the biggest risks i take with my everyday life is skateboarding. There is chance of injury, chance of arrest and chance of success in the sport. It involves the “streets” and as people know the “streets” are unforgiving. Also wanting a career out of a sport that has such an non promised path, leads to difficulty. Read more>>
Bria McCollum
When it comes to music, I feel as if I’ve always taken small risks. Since I started out playing classical and gospel piano, I felt many people always tried to put me into a box because of my looks. In reality, I always had a different sound in mind for myself. My first real introduction to music outside of classical and gospel was metalcore. I always liked how melodic yet intense it was and since then, that is always what I strived for my music to be (despite none of my released songs being metalcore). Read more>>
Coco Crowder
I would say the biggest risk I have taken is diving into Entrepreneurship full-time. It was scary at first, honestly it still makes me nervous. Trends are always changing and evolving and the will to keep up with them takes a lot out of you. The reward is knowing you made a difference and that you will play a role in some part of history. Read more>>
Ann LoParo
The biggest risk that I have ever taken was when I decided at the age of 29 to quit my job as a Social Worker for Cuyahoga County Department of Children & Family Services after 6 years and start over by going back to school and pursuing my passion for baking and pastry. I sold my house and moved to Charlotte, North Carolina to pursue an Associates degree from Johnson & Wales University in Charlotte, NC in Baking and Pastry Arts. I have always had a love for baking and any chance I could be in the kitchen making dessert, it not only gave me a purpose, it allowed me to express my creativity, focus on something that I enjoyed doing and I got a sweet reward at the end that was pure happiness. Read more>>
Dsto Moore
Well on September 13,2018,I took a leap of Faith to go after my Dreams of being a Full-time Freelance Photographer,it was one of the scariest days of my life but I knew it would be worth it in the long run,4 years later I’m glad that I took that risk,im still learning alot about photography and about who I am as a person Read more>>
Wendy Doyle
I appreciate this question. It’s not asked frequently, yet leaders are taking risks every day to better themselves, their teams, their organization and their communities. When I was approached to lead United WE, I was very happy in my current position. I was not looking to leave or to pursue a new opportunity. At that time, United WE had a different name and significantly different approach to supporting women. As a traditional Women’s Foundation, Read more>>
Melanie Bell
After Covid-19 shutdowns began in March of 2020, my entire world was turned on its ear. Now, many of us had this same experience so I do not think that my story is unique. Rather, I feel like its one worth telling because so many of us are still trying to find our way into a new beginning. I had a thriving personal training and yoga instruction business that was reaching hundreds of students per week in a gym setting, at home settings, and also in retirement communities. Once we knew that the spread was serious, we had to shut it all down so that everyone was able to navigate to the best of our knowledge. Read more>>