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.
Kate Tipton
The biggest risk I’ve taken so far is betting on myself! About two years ago, I decided it was time to finally leave my comfort zone. I left my hometown, quit my stable job that I actually enjoyed, moved to my dream city, started a new job, quickly realized that job caused too much stress & anxiety, which is what led to the decision of starting this business, Purpose Under Palms. Read more>>
Katie Lee
Deciding to open a business was a big risk for me! I never really saw myself as a big risk taker in my 20’s. I always played it safe and stayed inside the lines. While owning a business was something I dreamed about, it wasn’t anything I thought I would ever truly execute. I remember graduating college with a fresh degree and no idea what was next. I was in a season of trying to figure out what my career path would look like and ultimately what I wanted to be doing. Read more>>
July Bailey
I feel like this right now has been the biggest risk I’ve ever taken. When I think about the amount of people I personally know that have failed MISERABLY even though they’re top tier talent, it kinda scares me. I’m talking bout people who I’m nowhere near when it comes to writing, singing or performing. They are just that good. So when I see that, it’s almost like “dang. If they failed, I’m DEFINITELY not gonna make it.” Then I remind myself that they’re not July… and July is THAT girl. Read more>>
Nathan Delva
I took the biggest risk of my life packing up all my belongings and moving to Los Angeles California in February of 2022. This by far has been the hardest thing I’ve ever done but the experience has been like no other. My month there I had no car or job yet so I went through some up-and-down struggles. Throughout that time I book my first casting video in the second week of living in LA. Read more>>
Trena Wilson
As a Central Florida Native, I’ve always been a big dreamer. I inherited my entrepreneur spirit from both of my parents. If anyone would have ever told me that I would own 1 business I would have probably believed them, however I would have never imagined me having the pleasure of being a Serial Business Owner. I began my Entrepreneur journey while I was in middle school, and it continued on while I attended the University of South Florida in Tampa, Florida. I enjoyed helping others, whether it was by providing personal care, or business consulting services. Read more>>
Kenyon Johnson
I began graphic designing at the early age of 15 years old while in school and continued working part-time for (8+) years. After those short years, I realized my passion for entrepreneurship and was ready to take the leap of becoming a business owner. This fuels my passion for small-business and economic growth and progression in my community. Read more>>
Kaz Langness
It is always a risk telling opening your mouth, because once you do..you tell the world who you are. A risk that can lead to criticism from others, having judgment being handed your way, & even being misunderstood by others of this world..the list can go on. Without taking a risk, that means we are not trusting God, the one who has placed us here on this earth for specific reasons. We fail to remember that without risk, there is no story. Read more>>
Sharla Edmondson
The risk I took was opening my spa during the pandemic. I knew that with Covid-19 still having an affect on people I still chose to take the big jump and start business on my own. It was definitely scary but I took all the proper precautions to make sure my clients had a safe environment to come and get the wellness services that they needed. Since the pandemic was stressful I felt an urge to get out there so I can help people relax, destress, and take care of their needs. Genesis beauty company has been thriving since opening day June 1, 2021. Read more>>
Alister Kruizenga
Believe it or not as I’m writing this I’m only 23. I quit my job at a place called tech defenders when I wanted to try to risk being a photographer full time by myself. It was definitely scary. Being so young and trying to figure out taxes (or just the general sense of financial literacy) is terrifying for someone so young. But I’m also the happiest I’ve ever been. I guess I wanted to introduce a little chaos into my life. But I think you should only do those risks when you know you’ll be alright financially. Never go without a plan Read more>>
Sara Pizzi
The career as an artist is risk taking at the same level of any other career- the only difference from any other job is that the pathway is not linear as others. For most of the job titles there is a direct course of study, directly connected with an internship or to organizations which may help you to find a position or will directly hire you. Being an artist may mean that each of us has a different degree, title and level, complete different experience and background. Both are following the exception of tasks, projects, deadlines and workload. The network is fundamental in both. Read more>>
alexys pelissier
Since the moment I decided makeup is what I was doing I knew I wanted to experience being a makeup artist in LA. You would think that over the years I would’ve built up a network of people out there, but I didn’t. I always looked at it as something that would just happen in the future or I’d go when I got booked. Something in me changed at the beginning of the year around February 2022. I had this urge to just follow my heart, and experience new things that I’d been putting off. Read more>>
Janet Vermillion Moos
In Plano, Texas, nestled in the heart of the one of the original neighborhoods, exists the world’s very first Texas-shaped pool. It opened in 1961 and was a private, exclusive swim club for almost 50 years. Yet, by 2007, The Texas Pool had fallen out of present memory and was in danger of being lost forever. I was among a handful of volunteers determined to save it. For the next several years we barely kept the pool afloat. I began to conceptualize ways of saving The Texas Pool that didn’t involve digging out the deep end each season. Read more>>
Ross Dixon
HGTV was one of the most popular channels in my household for years, watching people master the art of flipping homes, and finding vacation houses was inspirational. I would watch these shows with my wife, and ask myself at least once every episode: Why can’t we own international real estate? The concept of living abroad for most people poses more questions than answers. Many people hate their job, and some even hate the cities where they reside, yet they struggle to come up with a plan of action to develop additional income streams and become a digital nomad. Read more>>
Chase & Ally Photography
In June 2022, we moved from Florida to Colorado to follow Chase’s dream of living near the mountains. We have no family or friends in Colorado, and it was a huge risk for us to try and rebuild a client base in a location where no one knew us! In Florida, we have a client base of over 100 people, and the community in general recognizes us from our social media advertisements and appearances at community events over the years. Read more>>
Sami Skinner
Never in a million years would I imagine speaking in front of a large group of people. I grew up with an extreme fear of public speaking. I remember in 11th grade we had a presentation, AS A GROUP OF 2, and when it was our turn to come up and present I told the teacher I had to take an emergency bathroom break. I would have rather my high school class think I was going to shit my self then talk in front of them. True story. Read more>>
Josh Webber
Initially: Big Red Jelly was formed out of a perceived need in the marketplace. The primary founder, Joshua, had a business that require the services of a big regularly but yet in search for a satisfactory partner, supplier, service provider was dismayed at the offerings in the marketplace. Thus, he began providing those services to his existing
business in-house. Very quickly in 2016 and 2017 it became obvious, based on inquiries from customers for the existing business that they like what was being done in the digital space and could they be referred to the agency Joshua was using? Read more>>
Chohnice Daniels Travis Whiteside
We took a big risk opening our own Chiropractic office towards the tail end of the pandemic. Not only did we step out of faith opening our office we also opened another business called HOTWORX. Three years ago after graduating from Chiropractic school we both chose to take an associate position at different offices in Memphis. While we learned a great bit during our time there, a lot of it was learning what we didn’t want to do if we ever opened our own practice. Read more>>
Joseph Dulin- Didonato
The biggest risk I’ve taken would most certainly be becoming a full time artist. The thing people never tell you about taking that leap of faith is that, it is never just the thing you want to take a chance on, its everyday after that. Becoming a full time artist meant that I would no longer have the safety net of a company pay check. Everyday became a struggle, but a good one. If I’m not searching or manifesting my next project- then I wont get paid. This means I wouldn’t be able to provide for my daughter. Read more>>
Stacey Vanthuyne
I was raised to believe that “its better to be safe than being sorry.” I lived my life, as my parents and those experiencing success around me had been raised to believe….finish with strong grades out of high school, get accepted to university, complete a degree, find a job with a pension, get married, have kids, save for your retirement and if you do all of that, then you will live a happy life! So that’s exactly what I did – achieving success in my corporate role, earning over six figures, getting married, having two beautiful girls and from the outside my life was good – I mean, who was I to complain as I was also led to believe that to want more would be selfish and that as my life was better than many, should be satisfied with the life I was living. Read more>>
Andrea Reid
To grow and learn in life, we must take risks. If we don’t, then we will never know if we will succeed at doing something. Taking a leap of faith, I took a risk when I wrote my first book, “Treasured by God.” As an editor of books, I’m accustomed to editing my clients’ books but never thought I would one day write my own. One of my greatest concerns was what friends and family members would think of the content that I included in the book. It takes courage to tell your story by sharing it in this manner. Read more>>
Chante Pantila
I knew that I wanted to do something with people, but I didn’t know how I could turn my socialization skills into a career. I was the child who would get their name on the board for talking and now I communicate for a living. I’m grateful for my experiences, the injuries and the triumphs have shaped me into who I am today; an educated, Black and Filipino female doctor, and I have the honor of helping people heal everyday. I get to use my relationship building skills and my history to help people change their lives through the gift of therapy. Read more>>
Arielle Burnette
The Fall of 2014 I decided to look for freelance work while still working a full-time job. I remember going on a site similar to UpWork to post about my social media and public relations skills. Within a few days, I received a call and had a conversation around what I might be able to offer. To be honest, I had no real model for how much I would charge or even a real plan on how I was going to get clients. Read more>>
Noah Moses
To be honest, I’m in the middle of taking a risk. One that I’ve been struggling with for a few years now: releasing my own music. I feel like it’s a big risk, putting this very personal piece of art you’ve made out there hoping someone will like it, and coming to terms with the fact that potentially no one will. Regardless of that though, I feel that we all should have to be true to ourselves and our convictions, to release the song, to open the business, to write the book, and not let fear dictate our decisions. a motto I try to live by is, “A life lived in fear is a life half live”. Read more>>
Tanya Rice-Berry
I never would have thought I would be in the career I am in now. I always knew I wanted to help people. I wanted to be a labor and delivery RN. This was years ago and then I felt I didn’t have the stomach or nerves to be a nurse so I went to school for medical billing and insurance coding which was right up my ally. I enjoyed this career and working behind a desk , headsets on talking with different insurance companies. Read more>>
Shawn Stuart
After retiring from the US Air Force with 20 years of service and 5000+ days of deployments I thought my risk taking days were over but then came the idea of opening a gym. Which I considered to be a considerable risk. Only to be in finalizing my building lease stage and a global pandemic arises. Not only making my process of building out extremely hard but it also shut down the entire active gym industry. One year after retiring from the Air Force I’m now embarking on the largest risk to date outside of my previous combat and tactical career in the military, seemed odd something not life threatening being such a huge risk it was and after considering all things the risk was worth taking and I did. Read more>>
Brittany Williams
Growing up, I always questioned myself while boosting others. I really didn’t know if I had what it took. I’ve always been good with my hands, styling clothes & etc. but I just didn’t feel like it was good enough or I was. I used to sit and watch YouTube videos thinking I could be that girl too but was to afraid until one day I didn’t want to be afraid anymore. I decided to post the videos & pictures. Now I’m here. 
Read more>>
Karen Starns
Risk-taking is a superpower. I left Microsoft after 13 years in search of professional growth and new horizons at Amazon. I left that great job at Amazon to tackle a global transformation at Pearson. And then I boomeranged back to Amazon for more growth. I left Amazon again to jump into my first CMO role at OJO, a real estate tech startup that offered huge impact, incredible personal growth, and exciting potential upside. Read more>>
Jacci Jackson
Entering into the fashion world can be risky for anyone whether you’re in marketing or PR, a fashion designer, or a stylist ; getting your foot in the door can be very difficult. A decade ago when I begin my fashion journey there were limited mentors and resources to help guide my career. I lived in Houston, Tx and most people making any waves in the fashion industry lived in New York or Los Angeles. Read more>>
Tambra Cherie
Radio and television is all about taking risks. I initially went to college for Business Management and Marketing. I graduated and earned my MBA degree just to go back to school because I knew I wanted more. I was always unsure if I wanted to be in corporate America. I disliked dressing up for business classes. I didn’t like having to wear business suits and business attire. I remember interning while in college at a very professional corporate organization in Omaha, Nebraska. Read more>>
JaLena Findley
I started Childish Choreography in 2020 and the main focus was teaching classes in Baltimore, especially because training for dancers was very scarce. However, during my senior year in college, I took a break from teaching to focus on graduating. With that break, I realized that I was drained with solely teaching. Ever since I was a young child, I wanted to be a professional dancer and choreographer. I dreamed of being apart of live performances, award show, music videos and ultimately seeing my choreography hit a big stage. Read more>>
Michai Ashley
Taking a risk, is scary. Not only is it scary but it also brings on anxiety. Taking a risk was going into business for myself. I was fired from my last job as someone’s employee and didn’t look for a replacement. Instead I dove straight into my “part-time” and grew it into the business I have now. BLCK Label wasn’t birthed overnight however its the biggest risk I’ve taken in life besides becoming a mother. Read more>>
Victoria Egwudobi
When I decided to start my blogsite, it was very much with the intent to give someone else the opportunity to have an avenue to be empowered, enlightened and inspired through my own personal experiences. As the years passed, I began to connect more with likeminded women and be a direct source to their own health, fitness, and lifestyle journey beyond what I considered to be a hobby at the time. Read more>>
Kayla Lynch
Taking risks is something I am known for, whether that be as small as buying a new backdrop, or opening up a gallery in the heart of Savannah, GA with a good friend. My freshman year of college, I received an offer from a close friend to be a part of their new gallery. It was brand new territory for me, as I have never sold my images at a physical location. I knew it was going to cost a lot of time, energy, and of course money, but I took the risk and it has only gone up from there! Since opening Kayla Marie Gallery, I’ve connected with so many amazing photographers and business owners, and I’ve learned so much along the way. Read more>>
Lauxx ViXen
A risk that I have taken in my life was moving to San Antonio, TX from Maryland. I moved here at 19 years old, and it was just me and my mom. I’ve always said that manifestation without work is nothing. So I made room for my manifestation, and I moved 1400 miles away from home. Physically leaving Maryland wasn’t hard, but leaving behind my friends, family, and the culture of the DMV was challenging. I moved with no knowledge about the music industry, and with minor stage experience. Jumping out there and performing really showed me that you literally can do whatever you set your mind to. Read more>>
Yaseen Jones
While working at my last employer , I would hone my photography skills by offering ALOT of free photo sessions to any and everyone that I could convince to take a chance on me and stand in front of my camera on days off and weekends. I figured if I could begin to showcase my skill and talent by building a portfolio, that the financial aspect of building the business would follow in due time, and IT DID! Several friends and family that I photographed would share their images online, and in the world of social media, that was more than a blessing! Read more>>
Jennifer Bonner
I feel like taking a risk has become a theme in my life. I try to live by the old saying “the worst anyone can say is no”. Moving to Florida was a risk. I come from a town of, maybe, 1000 people, and I always knew I had to leave to pursue my dreams. I had a plan, a lead on an apartment, and a temp agency in Chicago. then I saw an audition in Orlando. I went. I booked it. I packed all of my things and moved to Florida. I moved to California for 3 months to open a show, I took a shot at being a teacher, I ran a non-profit, and I’ve lived many lives and taken many leaps. Read more>>
Carol Keesey
My dream growing up was always to become a writer. I was inquisitive and loved learning and sharing stories and experiences with others. So at a young age, I decided I would become a journalist. After college, I landed a stable job at a large company that provided many growth opportunities. In theory, I had “made it.” But, I still had that feeling in my heart that I wasn’t ready to settle down and follow this career. Read more>>
Pat Buchta
For much of my life, taking a risk was just about the last thing on my mind. As a lifelong sufferer of liver disease, I was doing my best for many years to simply hold down a job and maintain a somewhat normal life. After I finally received my gift of life in 2012, a whole world of possibility opened up to me. With the knowledge that somewhat chose to donate their organs when they died so that I may continue to live, I felt a heavy responsibility to pay this grace forward in every way possible. Read more>>
Roshanda King-Moss
Risk taker? That’s me! Since an early age as a child, I have always taken risks, because being challenged is an absolute thrill for me. About 9 months ago I decided that I would take the risk of walking away from a career that I had built in Corporate America being a Systems Analyst to become a full time entrepreneur. At the time this risk was very scary due to me knowing this was a life changing event for myself and my family. I also knew this could be and/or become a very challenging risk if things went south of what I had planned for. I prayed about it and made the step. Read more>>
Cindy Wahler
I come from a long line of entrepreneurs. All bright, accomplished self starters. As a kid listening to balance sheets, profit margins wasn’t such a thrill. In fact it was sometimes pain staking. Little did I know that I absorbed this and later in life I absorbed this invaluable business model to help launch my own businesses. I consider myself a serial entrepreneur who has taken multiple risks. Read more>>
Phillis Lewis
Almost two and a half years ago, I made the decision to make Love Doesn’t Hurt it’s own standalone non-profit and break away from our fiscal sponsor. I took the risk because I wanted to provide more holistic resources for victims of crime in the LGBTQ+ Community that addressed them as an individual. I liquidated my 401k and invested in myself to educate myself about the best practices of creating, building, and maintaining non-profits. Read more>>