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.

Samantha Zo

Deciding to start my own creative agency was a risky move, but one that I knew I had to take. I couldn’t shake the feeling that there was something more out there for me, and I was determined to follow my passion for entrepreneurship and creativity. Despite the challenges, I knew that the rewards would be worth it. Read more>>

Dwayna and Donna Williams and Morris

Becoming full-time mompreneurs is challenging, mainly because we have little ones and a family to help take care of. Taking risks, having faith, and trusting God is the only way we have been able to maintain the life we desire to live. The word “risk” was not something we always lived by in the beginning stages of our entrepreneurial journey. Throughout our five years in business, we’ve learned to live as 2 Corinthians 5:7 states, “For we live by faith, not by sight.” Living by faith and taking risks has not been easy; however, the rewards of doing so have been overflowing, and we look forward to the fruits it will continuously bring. Read more>>

Dalton Smith

June 2021 – I decided to sell my house and move out to Denver, Colorado. It was just a few weeks prior that I had returned from a long weekend in the city and I couldn’t get it off my mind. The housing market was up and when I found out what my home was worth, I told the relator to slap a sign in the yard as soon as possible. Easily the craziest, most impulsive decision of my life but I had been wanting to leave Michigan for years and this was my opportunity. Read more>>

Elaina Hittle

The biggest risk I have taken in life was for my business. I was 20 years old and was completely over a job that didn’t treat me with respect, give any raises , and was making my mental health plummet … Aka retail. I was fed up and quit on July 20th, of 2021. It was literally the best, but also a scary feeling to leave a life of comfort in a corporate job, and into a life of unknowns and no security in owning your own business. Big risk equals big reward, and boy was it worth it. As J. Cole, YG, and Moneybagg Yo “scared money don’t make no money” Read more>>

Rachel Deeb

The biggest risk I have taken in life is becoming a full-time freelancer. It is also the best risk I have ever taken in my life. I was terrified to make the jump from working a full-time job to praying I could pay my rent using a camera. I can confidently say, the minute I went full-time freelance, I have never had to ask my parents for help. It was hard at time sand extremely tiring… but the fire was under me to prove to myself and my family I could do this. To be honest, I wasn’t even sure I could do it – but I knew I had a goal and a timeframe to see what could happen. I am so thankful that I had people around me who supported me and my work. I know the work has to speak for itself, but I wouldn’t of gotten here without the people who helped me believe in myself. Read more>>

Rathi Varma

I started dancing at the age of 15 at Shiamak Davar’s Institute of Performing Arts in Mumbai. India. From that moment on, I knew I wanted to be a performer. But, my parents weren’t’ fully supportive of me choosing Dance as a profession as it wasn’t a lucrative career back then. I went on to study Fine Arts and Craft and Visual Communication while continuing to dance on the side. After completing my studies, I worked as an illustrator until the age of 29. Little did I know, fate had other plans for me. In Oct 2017, I met with an accident while riding my bike and broke my forearm bones, Ulna and Radius. My first thought, on my seeing broken forearm was, “How am I ever going to dance again?” That’s when I realised what dance meant to me! Read more>>

Kay Hardeman

I had been teaching elementary school for 28 years at the time I decided to open my shop. I knew retirement was an option at year 30, so I was starting to think about what I would want to do differently. I love to sew and embroider so I thought I could do something along those lines. My dad had a commercial building that happened to be empty at the time I was thinking of this, so I thought I could have spaces for vendors to rent to sell their items and I would do my sewing while running the shop for the vendors. Read more>>

Jenny Duncan

I’ve been doing professional hair for about 8.5 years and I love being able to create looks that elevate a persons confidence. For some time though I felt like something was missing in my career and in my personal life that could not figure out for the longest time. I would go to work and people would be overjoyed with their service but I would still feel stagnant. Read more>>

Autumn Zweygardt

Late 2021 I was still figuring out what items to make most for my business. I hadn’t quite figured out what my niche was. Yet when I saw a Facebook ad looking for vendors for Planet Comicon 2022, I jumped at the chance. I had been trying to get in to other conventions since I started my business with little success. August 2021 I apply. By September/October I had been accepted. It was a huge investment for me and my then husband, but I wanted a chance to prove my little side hustle could make a decent amount of money. And it paid off! It was the best show I have ever done, and it even helped me realize what products I both enjoy making most and what sells the best. That 3 day event gave me the courage to put myself out there more and even reach out to local consignment shops. Read more>>

Sydney Darrow

In October of 2022 I decided to quit my stable, full time job to pursue a career as an artist. I have always known I wanted to make art for a living; When I was young I would spend all day in my father’s barbershop, drawing his customers as they got their haircuts, and then selling them the portraits. At 15 years old I started my first day job as a camp counselor for the YMCA and from that point on I was always either in school or working. I made and sold art on the side, getting 2-3 commissions a year and participating in an artisans market every so often. Read more>>

Dr Sean J Harris

I have what’s called an internal risk index in the factor. When making a risky decision, I ask myself could I live with the outcome of the worst possible outcome of the situation. If the answer is yes then I’ll pull the trigger and make the decision to take that risk. However, if I can’t live with the outcome of the result of making said decision, then I will not take that risk. Read more>>

Tania Sanchez Lopez

I feel that choosing the path as a creative is a risk all on it’s on but in 2018 I decided to take a hiatus from my regular job as a nurse to focus on my art and home business. I had become restless at my job. I find that the career is not family friendly. Constantly sacrificing time with my children and felt a calling to do the thing I’ve always wanted to do. Read more>>

Ashley Pittman-Fair

Ha, taking a risk! After grad school, I worked in community mental health for three years. Being a therapist and navigating others’ perceptions of therapists was hard, and I didn’t feel like my clients were being served properly. When Covid happened, I initially thought, “I am for sure stuck in this position!” That fear motivated me to leave my full-time job (with benefits) that did not allow upward mobility to join a private practice with no clients and no benefits. This all happened while planning a wedding and navigating Covid anxiety! Read more>>

Natasha Rubinetti-Kul

I’m still taking my biggest risk! I quit my job in the middle of 2022 to pursue painting pet portraits full time! These paintings are considered a luxury item and not something that someone is in absolute dire need of so taking the leap and going from working with a steady job to doing this was very difficult. I have a wonderful support group consisting of my partner, family, friends, and past coworkers. All of these people were rooting for me to get out there with my talent and I wouldn’t have been able to do it without each and every one of them. Read more>>

Nick Rainey

I took a risk by moving across country from Michigan to Dallas Tx. I was born and raised in Michigan, but I have never enjoyed Michigan’s winters and I would always tell myself when I was old enough and ready that I would move somewhere warmer. So around 2015 I started making preparations to move, I began telling all my family and friends that I wanted and was going to move, but no one believed me. Me and my sister even started talking about moving together and made plans to move, but it just did not work out that way. Around 2018 I started dating my now Fiancé and we decided to move together because He wanted to move to Texas as well. Read more>>

Nate Evans Jr

About 2 years ago I was working a corporate job while running my educational consulting business on the side. During the height of the pandemic I was released from my position without cause and instantly unemployed. Within a few days of being unemployed I came across an advertisement on Instagram from a guy named Jeremy Anderson who is the nations leading motivational speaker for schools. I desired to grow my business speak across the nation as well to students of all backgrounds and Jeremy happened to be hosting a webinar to teach speakers how to grow their business. Read more>>

Taylor Wesely

One of the most life-changing and significant risks I have taken is uprooting my life and moving to Denver. Read more>>

Chessine Nugent

Taking Risks is always something that I believe is better taken. Otherwise, I do not think I would have been as fortunate to have the life I have lived. I have always loved traveling for most of my life. But how do you get paid for it? I was eating one day reading the LA Times and looking at the retail want ads. I was looking for a change in my life when I came across a tiny ad that asked if you would like to start up retail operations on a cruise ship; please apply. I applied and forgot all about it. Read more>>

Samiara Mitchell

When I was laid off I took a risk by not going and finding another job. I seen the end to that job coming so when it happened I thought, that was my chance and a sign to go after my dream. So I used everything I had left to buy a camera and some merchandise for my brand. I spent everyday until the end of that year selling tshirts and hoodies to make a living. Even though some days were slow and I didn’t sell anything, that learning experience was exactly the spark I needed to not be afraid to go chase my dream and make it my reality. Read more>>

Kesha Kent

In 2018, I took a huge leap and bet on myself! For so long, I’ve built brands for amazing companies all while feeling the brunt of not loving the people, systems and politics that with the territory! I quit, that same year I created my LLC, started planning my next move and intentionally started speaking publicly more, set my fees and went full speed ahead into consulting! I loved it, many doors opened and it was a reminder to bet on me! I stayed in toxic work environments for too long, yet, I learned so many valuable lessons of what not to do! Today MrsKeshSpeaks, is thriving and I refuse to shrink back! I love coming along side organizations, however, I’ll never stop building our legacy! It’s been almost five years! My book Networking it’s your Superpower was birthed during that time as well! Read more>>

Daria Amato

I moved from a professional life centered around the metropolis of NYC to the Wilmington area of NC in February of 2021. Covid -19 had virtually killed my business. I had always wanted to move closer to the beach and in a warmer climate, so it seemed like writing was on the wall to bust a move. So I and my family did. I hunkered down the first year I was here cold calling ad agencies and magazines, joining a bunch of networking groups and gave away free stories I wrote with accompanying photographs. Basically I became a marketing machine and it paid off. Read more>>

TJ Dumser

For the most part I always made life choices that were slightly off-center, yet somehow things always turn out for the best. Here’s a little story about one in particular that made my stomach drop but now looking back on it was the best decision I ever made. Read more>>

Cassandra Martin

When I first started my art business, I had no idea what I was doing. I didn’t have much exposure and had very little experience in networking. I just wanted to create. Shortly after starting, a friend suggested I showcase with her in the Black Girl Art Show in Atlanta, GA. I started to say no because the event seemed too large for me. I wasn’t sure I had enough material, the thought of being social made me anxious, expenses were adding up and I’d never been to Atlanta. I was afraid I’d lose time and money and embarrass myself. I simply wasn’t ready… at least, that’s what I told myself. Read more>>

Latia Rowland

I’ve been doing accounting since I was in high school. I started out volunteering at a non-profit center for seniors, as an assistant to the controller. From there, I knew accounting would be my career path. When I got to college, the dream job for accounting majors were to always work at one of the Big 4 Accounting firms, and that was no different for me. However, I did have some obstacles like getting pregnant in my junior year, and having to move back home and take some time off. When I did go back to college, I was there more to finish and graduate, rather than participate in everything I could, because I was a new mom. Read more>>

Chand Ananda

Embarking on my journey of becoming a 200 hour yoga teacher it felt like the odds were stacked against me. I was in a place in my life where I know I needed to make major changes but I also didn’t want to give up on helping others. Before I had a terrible habit of putting others needs before my own sometimes to the point of becoming sick & exhausted. I knew I wanted to become a teacher. I also knew yoga was the route to go as being on the mat had become a place of solace for me. I prayed to the universe and asked if this be apart of my path please give me a sign. I submitted my application and continued operating my life as before . Read more>>

Jessica Strupp

I’d say the biggest risk I’ve ever taken was going to my alma mater, The Savannah College of Art and Design. When first looking into colleges, it was difficult to fully understand the weight of my decision. I was 17 years old, a junior in high school, and I had no idea what my future might look like. I’d always known I was a creative person, bouncing from one art project to the next my entire high school career, but there was no real pathway into the arts from my Georgia hometown. SCAD provided me with the pathway I had been looking for, showing me that there was another way besides the classic “starving artist,” Read more>>

Germyah Heart

I am a firm believer that in order to become a champion, you have to take a risk! The biggest risk that I have taken was moving 1000 miles away from my hometown, Milwaukee, Wisconsin. After graduating from high school in 2016, I knew I had to leave Milwaukee. I knew that my dreams were bigger than what Milwaukee had to offer. I always wanted to attend an Historically Black Colleges and Universities (HBCU). My middle school, Milwaukee College Prep, introduced us to HBCUs in the seventh grade. We got on a coach bus and hit the road from Milwaukee to Atlanta to visit the AUC. Read more>>

Deon Claiborne

Just as the pandemic started, I saw a post in a DJ group I belong to on Facebook. They were looking for DJs for an internet radio station (now defunct) called Sound Lab Radio UK. Read more>>

Yashashree Samant

I work as a Copywriter, genuinely love my job and cannot see myself in a better profession. But ten years ago, I had no idea of this profession. Growing up in India, arts is always perceived as a hobby. But to be successful, one must pursue a “safe” career like that of a doctor, engineer, or professor or perhaps get MBA. My parents had set the bar pretty high with their academic accomplishments. Since a young age, the importance of grades was instilled in me. Read more>>

Sherman Shelton

I quit my day job to do this full time. Read more>>

Doyle Turner

I’d met a lot of talented performers, and the conversations had always felt awkward and stilted. Lance Benson had just finished an amazing set in a house concert setting in July of 2018. I was mesmerized and was drawn to his songwriting. He was doing something I didn’t even fully realize that I wanted to do. I approached him after the show, and before I knew what was fully happening, I was asking him to help me produce an album of original songs (most of which had not been written yet). Who was I to ask this accomplished performer anything? I laid out the basic outline of a dream I hadn’t even fully formed yet. Lance was kind, open, and held my dream with a care that showed he remembered what it was like to start out. Read more>>

Steve Domahidy

In 2004, as my business partner (at the time) and I surveyed the land of bicycles for opportunity on how to enter the market and where best we could make an impact, a small band of people were beginning to make noise around the 29″ wheel. We each, in turn, went out of our way to find a 29″ wheel bike and give it a spin, and we both knew, right away, that this was it. This was the opportunity we were looking for. In October of 2004, we sat down in a crowded lunch restaurant in the hallway connecting the Venetian Hotel to the Convention Center where Interbike 2004 was taking place, Read more>>

Markita Cumberlander M.Ed., BCBA, COBA

The biggest risk I have taken in life was leaving my reliable, full time job with benefits to begin my own practice. I did not feel comfortable working for the organization and needed a change. I needed a change not only for myself but for those who identify as I did. I needed a change to help my clients who did not see themselves when they walked into their session for the day. I needed a change for my co-workers who did not feel comfortable or appreciated. I needed a change for myself and for my kids to see that they too can make shifts, be comfortable and successful all at the same time. Read more>>