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.

Ashley Strong

Making the choice to go into entrepreneurship full-time was a risk for me. But, I am happy that I did. If I’m being honest, I’ve had a regular job before I started my beauty business. I see the pros and cons for both, ultimately taking that chance and going into my artistry full-time was the best decision I’ve ever made. It takes determination and consistency to pursue entrepreneurship. Read more>>

Teala Stampley

I dreamed of being an actress since I was a little girl, but at 30 I was working in a comfy job in corporate America finally making “adult” money. I was able to pay off all my debt and get my credit score right. I had a respectable savings and was in the process of buying my first home. I was really “adulting” at its finest! The only draw back was, I was miserable and depressed. Read more>>

Tynarial Jones

My entire journey of starting businesses and an organization in my selected markets was risky. My parents have musical backgrounds that influenced my musical career but neither of them had the guts to pursue it wholeheartedly. So just imagine the struggle of leading a path that all they could do was support to the level of their understanding and slight experience. Read more>>

Jessica Gleim

When I was just 26yr old, I was diagnosed with Trigeminal Neuralgia (TN), also known as “the suicide disease”. TN is basically, unbearable facial pain. My life as a newlywed, new homeowner and a new doggy owner quickly became a living nightmare. And at the same time, I was also working my dream job – as a graphic designer for a new brand under the designer stationery series with Shutterfly.com. Read more>>

Melanie Nyhan

Within the last few years life has taught me the importance of taking risks to achieve goals. No matter how big or small the goal, I’ve learned that playing it safe, small and timid is not going to place me in a position to live a fruitful life. Read more>>

Denis Sindler

In 2017, in my early 20s, I started my first side business with my girlfriend. We sold organic t-shirts online while I was a full-time student abroad in Denmark and a part-time chef. Despite little time, I was determined to make it work. I won’t lie, this period was hard. I felt pressured to prove to my parents and everyone that I was good enough. Read more>>

Mx. Pucks A’Plenty

The biggest risk I ever took was signing up for a multi week intro to burlesque workshop series. I fell in love with burlesque almost 7 years before I got up the courage to sign up for classes. I had just had my son and I had postpartum depression really bad. I was flipping through Netflix to find something to watch and I landed on this documentary called A Wink and a Smile by Deirdre Allen Timmons. Read more>>

cleveland peterson

I’ve always been able to make changes in my life. I’ve never want to settle. When your life starts at what most deem the bottom it’s often looked at as a bad thing to turn away from that. Coming from Gary Indiana, anything positive was considered weak. When I discovered art I found a way to add beauty to a world that can sometimes be ugly. Read more>>

Melanie Druery Allen

The biggest risk that I’ve ever taken was becoming an entrepreneur. Let me take you back to the beginning. I was raised at a family-owned and operated business my entire life. My job was marketing and finding avenues to multiply money. The thing is, I hated the task and dreaded it. The reality is that I learned so much information that I thought everyone knew. Read more>>

Michelle Lambert

I started in music very young, playing the violin at the age of two. By five I was studying classical singing and piano. As soon as I was able to drive I started to gig professionally playing in bands and as a solo artist all over Northern California. That led me to a scholarship at the Berklee School of Music in Boston where I earned a degree in Vocal Performance. Read more>>

Blair (SDOT) Simms

I think the riskiest thing I did was travel alone to South Africa and to Brazil. Both countries are musically rich and diverse and I think they rubbed off on me in a good way. As a club producer I always have loved electronic music but Baile funk and South African House have always had a special place in my heart. Read more>>

daniel sardi

Becoming a professional in the music business involves taking a leap of faith. Nothing is guaranteed, but if your inner voice tells you that’s what you were meant to do, you owe it to yourself to pursue your dream. I’ve been a musician since since the age of 12 years old. I played the drums for tons of bands through my childhood and majored in band in a performing arts high school named Talent Unliited located in NYC. Read more>>

Marissa Ortiz

I come from a challenging background. At a young age, I experienced things that children shouldn’t had seen or mentally felt. I experienced feelings of heartbreak and abandonment. It was tough and I suffered from anxiety for many years! Through it all, I knew I was destined for something greater beyond my current circumstances. I would envision me motivating others and changing the world at a very young age. Read more>>

Paige Gullotti

“Nothing is impossible. The word itself says, “I’M POSSIBLE.” It’s Audrey Hepburn quotes like this that represent the risk I took and how taking that first step with positivity can make all the difference. I am nobody special, but I enjoy looking back to see how far I’ve come and am grateful for the opportunity to share my story. Read more>>

Chris Kelker-Newlan

After a 27-year career at Wells Fargo in IT Services, I wanted to do something different and work toward doing more good in the world. Talking through this career change with my family and having their support and blessings I turned in my resignation and began the search for my new job. Read more>>

Susan Crossman

I I had been home with my three children for ten years when my husband was diagnosed with terminal stomach cancer and died three months later. My youngest kids were seven and nine and my husband left a “secret debt” of nearly a quarter of million dollars, which was, thankfully, taken care of by life insurance. But I was in a serious pickle and had to recalibrate my life to go back to work. Read more>>

Janna Willoughby-Lohr

On January 19th of 2021, I got a call from a company asking if it would be possible to make half a million of our handmade plantable seed bombs…by March. At the time, I had two part-time assistants who each worked 10 hours a week and two young boys at home, one of whom was doing virtual school. While my assistant’s eyes bugged out as she mouthed “Noooo. That’s insane!” at me, I replied, “Define possible…” Read more>>

KRYSTAL Vasquez

Epoxy resin was introduced to me by a friend. We started learning and wanted to create art together. I invested and purchased many molds, epoxy, pigments, tools; however, we stopped working together. I looked at the collection I had started and decided to keep going on my own. I started making small coasters and phone grips and that later inspired me to grow and go big! Read more>>

EMILY MILLER

When I was in my senior year of high school, I had really began pushing my business, Emily Miller Arts, and wanted to pursue it full time. While all my friends were applying to college, I was at a crossroads. Do I apply to college and go because that’s what everyone, especially my parents, expect me to do? Or do I follow my heart and my dreams and go full throttle on my business? Read more>>

Deanna Holbrook

A risk I’ve taken is beginning to share my knowledge and practices when it comes to spirituality and wellness. I come from a line of indigenous peoples on my fathers side and a line of healers on my mothers side so I have holistic and intuitive knowledge running through my blood. My maternal lineage is of Italian descent where the witch trials were held hundreds of years ago. Knowledge of herbs, flowers and foods as medicine has been passed down through my family. Read more>>

hannah herbold

I have been fired from every single job I have worked in my life, and it has been many. In 2018, I quit my full-time job with no money, no savings, $10’s of 1000’s of dollars in debt and no way to pay my bills in 2 weeks so I could pursue my creative career full time. Read more>>

Kyiamoni Legacy

I think as business owners small or big we have all taken a risk somehow. One of the biggest career changing risk I have taken was taking the leap to create fondant cakes. In the beginning of my career I only worked with buttercream because I was scared of how my fondant work would turn out. As I first began experiment with fondant if was far fro great. Read more>>

Tina Travis

My career in corporate America was all most people could wish. Developing powerful relationships in the clothing and accessory market, international travel, great food. I loved merchandising and developing products lines. It was my college major at North Carolina A&T State University and I was going to work in the merchandising field forever. Read more>>

Jessica Becker

In 2009 I left the design industry where I had been working in high end showrooms for over a decade. I moved out of NYC and out of the industry to open restaurants with my former partner, which I designed and helped brand. Read more>>

J.Marie Shackelford

After living in Virginia for 16 years+, and having a fruitful following and business, spirit came one day in August/September of 2020 and said, “It’s time to move; pick a place.” Well, obviously, like anyone, I laughed and was like, yeah, right. Well, fast forward to pulling up a map and finding the only place that highlighted for me the Navajo Nation outside of Williams, Arizona. In all this, I was like, this can’t be real, yet I have never doubted spirit, and so I think more it was my logical brain that was having the issue with it. Read more>>

Alicia Wilson

The biggest risk of my life was betting on myself. I have never really been the most confident person. Even to this day when I get compliments about myself sometimes I can’t believe it I never was really popular and my ideas have always come off a little crazy. When I decided to dive into the hair industry and make products. Read more>>

Chrissy Mitchell

I’ve always loved to read ever since I was a little girl but as you grow up life gets busy and life gets filled with other things. I was working a job that wasn’t my favorite. I wasn’t feeling challenged or fulfilled and my mental health wasn’t in the best place so I thought about giving reading another shot as an escape and loved it. Read more>>

Zariyah Arredondo

Personally, I feel the biggest risk I’ve ever taken was to just do exactly what I wanted. Has it been financially risky? Of course! But with risk is resilience and I feel like I’ve handled myself incredibly well in trivial situations or even through rejection. Part of the reason I took these risks was to not only push myself out of my comfort zone, but to make an impact on my community by being authentically myself whilst doing what others may think is unfavorable for me to do. Read more>>

Jason Hunt

You must be willing to count the cost of being an entrepreneur. My wife and I gave up everything to launch into a full-time ministry career. We lost our home, cars, and even our furniture. We made the ministry transition and never made enough money to properly support our family or have the impact on people’s lives that we thought we should. Read more>>

David Voorhees

I had recently graduated from college, got married a day later, then headed for the only grad school that would take me. I was a fine arts majoring in painting and poured myself into creating new works on canvas. I butted heads with my instructor and didn’t meld with the other grad students, so I dropped out of the MFA program. Read more>>

Martin Molloy

Just before I turned 30, I found myself looking for work and unsure of my direction. I saw an ad for a position in my industry (market research) in the local alternative newspaper and while it was entry level, it felt like a start up trying to find its way. I took the job (at a huge pay cut) and it was the best thing I’ve ever done. Read more>>

Dr. Rachna Buxani-Mirpuri

When I thought of expanding my practice it was scary. Until then I had a solo practice. Being in a new country where I hardly knew anyone and the ways of doing business, the very thought of growth and hiring a team was intimidating. My husband who is a vey successful business owner encouraged me but the biggest lesson I had to learn was to believe in myself that I would be ok no matter what risks I chose to take. The rest as they say is history. Read more>>

Joshua Loyd Fox

I believe the saying, “Anything worth doing takes risk” is a mantra for life. My life and faith require that if I want to get to the very top, and achieve my utmost potential, I have to take the leap, without knowing where I would come down. Read more>>

Analyn Scott

“Take the first step in faith. You don’t have to see the whole staircase, just take the first step.” This famous quote from Dr. Martin Luther King Jr., has become one of my favorites because I have been living it out since taking a giant leap of faith and leaving my successful, six-figure, 14 year I.T. Sales career in November of 2014. Read more>>

Aaron Washington

I guess I will start with the cliché of “life is about taking risks”…and this becomes ever so true in the realm of investments. Every investment that has the potential of fruitful gains comes with considerable risk. Risk is inevitable when investing into something or someone so it is a reality I have become accustomed to at this point. Read more>>

Kristin LaFine

I left a six figure corporate job to pursue my passion. Sometimes quality over quantity is necessary. After 24 year’s climbing the corporate ladder I made the decision to take a radical sabbatical to focus on growing my clinical herbalist business. I’m a maker and therefore focus on formulating synergistic blends that heal and balance the body. Read more>>

Alex Cruz

I’ve taken many risks to be in the position im in, such as leaving my job for a year to start my business and fully focus on creating and building the structure of it. I had no money, 2 newborn twins and a great support system from my girlfriend. within a few months I was making money off of my services and doing Uber eats on the side making enough to pay the bills. Risk well taken! Now im able to work a job to fund my business and put the business on cruise control while I seep scaling up. Read more>>

DeMargeo White

I want to say the biggest risk I ever took was becoming an entrepreneur and starting a business. I had no clue to what I was doing or the direction I wanted to take but I knew i wanted to try something different. I was 26 years old working at an Italian restaurant cal6l “Nonna’s Cafe in Ada, MI. One day I was cooking on the line and something in me just clicked like I felt like I knew enough to start my own thing and that’s exactly what I did. Read more>>

Jordan Walker

Shortly after college, I landed a job with a fortune 100 company. I didn’t get the job from having a college degree.My aunt Alicia had worked with the company for quite a while, and had built up connections that got me an interview through a temporary Agency. This was a temporary agency, so I had to earn my stay.My job was working in Document Solutions(Grove City, Ohio) where I processed policies. Read more>>

Tony Deien

Ever since I was 10 years old, I wanted to travel from coast to coast. Forty-five years later, the adventure began. Everyone began asking questions of how I would attempt such a feat. Many shared disbeliefs of being able to make it happen. My trek across the United States began to attract many virtual followers. These followers claimed they wish they could do the same but because of constraints in life it was not possible. Read more>>

Pope Adrian Bless

I’ll never forget the formative years of 2017 going into 2021. 3 out of those four years, I struggled with homelessness. In some way, shape or form. Eventually, life took the upswing and decided for my balance to change. And I ended up working for a company I, thoroughly, enjoyed. Even being promoted within the company to advance and go beyond. Not knowing my passion, in full, I became content. Read more>>

Crystal Wood

In 2019 I began working for a roofing company performing sales and inspections. I enjoyed the job and was determined to be the best inspector possible so I took a course that gave me accreditation as a HAAG Certified Residential Roofing Inspector. Read more>>

Cindy Holt

Becoming an Entrepreneur was never a dream of mine. After serving in the military for 24 years, I retired and did full-time Ministry work. While working in the ministry I was asked to do some decorating here and there and purchased my first Cricut machine. What started out as simple table decorations evolved into making a few T-shirts here and there. Read more>>

Dani Tiscareno

Taking a risk. When you first start out on a business or artistic venture it feels like you are playing a game. Sometimes I would sit back with Barbie and just ask her, how is it possible that you and I are running these companies I still feel like this is isn’t “legit” . Read more>>