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.
Rich The Mack
A big risk I had to take during my adolescence was dropping everything to pursue music. Back in 2017 I was fresh off of playing sports at my school and fresh off of an injury- two things that don’t combine well at all. I spent most of my time training or practicing to get better at football, track, etc however things didn’t play out the way I expected them to. While my love for sports was at an all time high- so was my brand new love for writing & listening music. Read more>>
Jasmine Newton
A risk that stands out in my journey is when I made the decision to transition from offering low-priced photo sessions to implementing sustainable pricing for my portrait photography business. It was a crucial turning point that required careful consideration and the courage to step outside my comfort zone. Read more>>
Kori Hennessey
Over 6 years ago now, I took a risk by first stepping in the doors of the LGBT Center of Raleigh. I was still internally exploring my identity and really struggling to fit in and find purpose. I was a different person back then, but I wanted to put myself into an uncomfortable situation to get out of the feeling of being stuck. This risk wasn’t just about discomfort though, it was also about safety. Read more>>
Erin Blackwell
Pretty much every decision I have made in my business has been a risk. Deciding to start a photography business when I had no experience at all, deciding to move states after building a successful clientele, and most recently deciding to move into my dream studio. Read more>>
Hanna Olivas
We took a risk and entrusted our business to our first employee. This was a defining moment in our journey. Adriana and I, had poured our hearts and souls into building She Rises Studios from the ground up. As the demands of our expanding venture became overwhelming, we realized it was time to seek help. The decision to hire our first employee was not one we took lightly. We knew that finding the right person who shared our passion, drive, and dedication was crucial. Read more>>
LaToya Drish
I believe the biggest risk was doubting myself. Before I started Simplicity, I had daily anxiety due to overthinking situations that hadn’t even happen. I would literally, talk myself out of the idea of starting a company within 30 minutes for over a month! I kept fighting with the ideal of losing. That was until I realized why I was doing this, who I was doing this for, and how I was doing it. We are our biggest enemy sometimes. Read more>>
Tasha Jay
I’ve been singing all my life however, when I moved out to Dallas, I got exposed to a lot of musical resources. I started working at a music school, Createvation in Frisco teaching kid’s voice lessons in 2018. There I was able to explore recording and the ins and outs of that. At that time I then decided to explore what I like to call the start of my music career. I started off with a cover album outlining a few of my favorite artists and songs. Read more>>
Lisa Engle
My coaching business model was more a “command” than an idea. I felt clear direction to start supporting mothers in a professional capacity (I had done so for decades in a volunteer role) and to use my experience working with so many to be a benefit to myself, my family, as well as the moms i would serve. Read more>>
Kate Cook
I believe continuously taking calculated risks is part of my daily task list as a successful, creative entrepreneur. This goes against everything in my type A personality, as I yearn for some days with a more rigid and guaranteed schedule. However, the minute I feel comfortable, I also know that my business and the artwork I make is in jeopardy of becoming stagnant. Read more>>
Don Michael Mendoza
When I connect with younger people, (I am still a young-ish person!), in my industry, I always tell them not to fear asking for what you want and to push past anyone who tells you “no” because to me, “no” means you just knocked on the wrong door. Read more>>
Daniel Paddack
All my life I’ve taken risks. From an early age I knew I wouldn’t find fulfillment from taking the easy and safe route. I always had trouble in school, I got my first job delivering news papers, later getting a job through a family friend at an amusement company, and moving from Illinois to Northern California as soon as I turned 18. I started farming and did that for three years until I decided to move back to Illinois and get my associates degree in applied science. Read more>>
Laura Green
Have you ever quit your very stable, yet tragically repetitive, job to do something completely different with zero safety net? Great, me too. I’ve been a physical therapist for the last 13 years and a few months ago I stopped working at the hospital so I could pursue comedy content creation (specifically in the running space) full time. Sounds absolutely bonkers when I write it out like that. Read more>>
Andrea Cora
I grew up in a small town in eastern Venezuela, and my entire life I attended a Catholic school where the school principal was a priest, so religion played a very essential role in my daily life. Anything that was “different” was criticized, and because of these upbringing issues, I found it very difficult to make decisions as a child. Read more>>
Tessa Montgomery
I started my photography journey very organically. My now husband and I got our dog, Ash, while I was still in college and I decided to buy my first camera to help me document our days with her. When I first picked up my camera, I had that “ah-ha” moment and instantly knew that photography would play a huge role in my life. I’m naturally the type of person who tends to play things pretty safe and up until starting my business, I had gone a more traditional path through life. Read more>>
Natalie France
When it comes to taking risks, it is essential to understand that it involves stepping outside of our comfort zones and embracing uncertainty in pursuit of growth and opportunity. Taking a risk means venturing into the unknown, being willing to face potential challenges or failures, and recognizing that the rewards can be substantial. Read more>>
Stoney-Doom
Stoner groups in general are still highly scrutinized in our country… Now imagine being an obnoxiously bold Stoner Metal band in KANSAS of all places – The state that is often joked about to likely be the last state to legalize Cannabis (if ever)… Cannabis prohibition began almost 100 years ago. Read more>>
Oscar Torre
When I first decided to pursue acting full time, I was working as a therapist at a mental health hospital in Miami. To pursue this dream I felt that I needed to focus on it full time and that meant letting go of my job security and risk it all. I also knew that eventually I would have to move from Florida to Los Angeles. I’ve always loved a quote that says, “Jump and the net will appear,” the net was certainly not there when I jumped. Read more>>
Caitlin Krumm
The risk I took in purchasing a building before the pandemic was significant. Throughout my life, I have had a deep love for art and painting. However, I was always taught that a nine to five job was the responsible path to take. As a result, I could never fully dedicate myself to my passion for art. Read more>>
Eleanor Duelley
When getting my Masters in Nutrition, I needed to work over a thousand clinical hours in order to get my board certification as a Nutritionist. I decided to begin working in a conventional doctors office that specialized in weight loss, as I thought I would gain experience working with helping people with their nutrition in order to lose weight. Read more>>
Henry Chappell
In life, it’s all about choices. You get to choose to either stay in the box or decide to step outside of the box. It’s all up to you. More specifically to me, I am not afraid to take risks and make sacrifices when it comes to my dream. My dream is to turn my Dreams To Reality. When it comes to my dream to become a professional music artist I will do whatever it takes to make sure I make it happen. Read more>>
Sunshine RA
When it comes to life, one thing I suggest is that you take a risk on yourself. We are all given gifts, certain advantages, or things that just light our souls. There will come a time in life where opportunity will knock on the door, and most likely it will challenge you to change, think bigger, and even Ames some sacrifices. Read more>>
Amy Anthony
Risks. I think we take risks every day! But to answer the question, I will focus on the risk I took stepping away from the seeming security of a corporate job to what was, at the time, unknown. The backstory, the thread, is that I love being outside with plants. Being alone with plants, observing what is around me. I grew up gardening, weeding, tending to plants, the landscape as well as camping with my family, hiking and overall exploring the wetlands and wooded areas around our house. Read more>>
Rachel Bearbower
Being burned out is nothing new to nonprofit sector and seven years into founding my nonprofit, I found myself exhausted. While I wasn’t ready to leave, I knew something needed to change. I decided to take a leave of absence from my role leading the nonprofit organization that I loved, nurtured and poured everything into over the last almost decade of my life. Read more>>
Aisha Harrison
In early 2019 I decided to quit my long time adjunct teaching job and work in my studio full time. The risk was not only in reducing our household to one income (at least for a while) but also because teaching was part of my identity. My whole life I knew I was going to teach. I taught little kids to read when I was in middle school. Read more>>
Cara McNamee
I decided to start my practice as a side gig at the end of 2019, thinking of it as a supplement to my income. I had one or two patients when COVID hit, and had to pivot and figure out how to see patients in their homes while also re-evaluating what to do with my general practice job. In the end, I cut back on my regular job and leaned into my own practice more, primarily because of the financial freedom allowed by the student loan pause due to COVID. It allowed me to develop a client base and expand my offerings despite the public health emergency, while keeping my clients safe. Read more>>
Antwon Harris
Leaving the familiar and secure path of teaching and coaching to venture into the realm of entrepreneurship in education was a risk that I embarked upon with both excitement and trepidation. It was a decision that required careful consideration, as it had the potential to significantly impact my career and future. Read more>>
Brenda Carsey
Simply put, music is my life. It’s something I choose to do every day that I’m lucky enough to wake up. It persists because of my choice to recommit everyday to the path I am on and to do my best to stay as open as I can to the ever unfolding nature of total unknownness that is being an artist and musician in a society and a profession filled with gatekeepers whose sole purpose is to limit access. Read more>>
Brittany Burton
Currently, I am taking the biggest risk of my life. My grandfather got sick in 2022 forcing me to drop everything and move back home. Sadly, he passed away leaving me and my family devastated and heartbroken. As a result I had to stop working in order to take care of my mental health and help my family gain our sense of what our “new normal” would look like without the matriarch of our family. Read more>>
Velisa Woods
My life has been all about risks being taken. Most of the things that I have done throughout my life came with sacrifice and leaps of faith. I earned 3 degrees with two children and always had a side hustle. I’ll give you one story of a big risk that was taken in 2019. After leaving the South and living in Las Vegas for over a year with my teenage son, I got to a point where I no longer had a teaching job, my unemployment was running out, and I had 2 months left on my lease. Read more>>
Terricha Phillips
Ever since my childhood of moving around in various Cleveland neighborhoods and summer travels visiting relatives in Maryland, Washington, D.C., and Florida, I was accustomed to picking up and moving from place to place. Moving to a new home and street was like an adventure, Read more>>
Brooke Ferreira
I had always dreamed of opening up my own group practice. I knew I could figure out the logistics of running a practice because I enjoyed organization and problem solving. When it came to betting on myself, I was scared. Thoughts consumed me of the risk it would be. Would anyone really want to be a part of my team? Would clients see the value of my work and want to entrust me? What about the financial risk for my family? What if I just can’t do it? Read more>>
Valerie Espino
I’m originally from a small town and always had dreams of moving to a bigger city where there would be more opportunities. Being self employed with young children kind of complicated those dreams untill 2021 we came to Florida on vacation and fell in love ! We decided taking a chance on ourselves was well worth the risk ! We went back home began selling all of our belongings including our home and moved our family and businesses to florida(tampa) . Read more>>
Nicholas G. Ashton
Misunderstood in life on a personal level led me to taking personal risks to find out who I truly am, between struggling with alcohol addiction and mental health, changing jobs over and over, then starting my own businesses, to moving and living with different family members and . then eventually finding myself living in a 1967 12′ trailer in an orchard learning about myself and how to cope with my addiction, and eventually understanding my mental health and how important it is to take care of. I found painting as a vise. Read more>>
HETAL DESAI
23 years of my life I had created back home in India that included family, friends, culture, education, career, tremendous amount of memories and lot more, all of that was left behind, 23 years of my life was left behind because I blindly trusted a man and decided to marry him within just a day of meeting him. Read more>>
Liz Anderson
First of all, just want to say how honored I feel to chat with you today! Thank you again for the opportunity to tell you a bit about my myself. When you first start creating fashion editorials, you are forced into various unpaid positions (wherein you must essentially sacrifice your time & creative energy on your own dime). You know with great conviction that the “high you feel” Read more>>
Salisha Thomas
I’m from California, born and raised! I went to school there and worked at Disneyland. It has always been my dream to live in New York City, but whenever I asked anyone for advice, they would tell me that I had everything I needed right there in California. Everyone discouraged me from leaving. So I stayed. And became a sad chicken tender. Then one day, after moving less than 5 miles for 2 hours in traffic on the 405 in Los Angeles, I lost it. I yelled at the top of my lungs: WHAT AM I DOING HERE?! Read more>>
Shivashish Ahuja
Pursuing a career in filmmaking in Hollywood as an immigrant from India is undoubtedly one of the most significant risks I have taken in my life. It was a leap into the unknown, a journey filled with uncertainty, challenges, and a relentless pursuit of my dreams. Read more>>
Cheldin Barlatt Rumer
I am an immigrant (Sierra Leone, West Africa), I am a mother (Sydney Rachel, age 12, and Chase Rogers, age 5), I am a former Division I Athlete (Field Hockey and Track and Field – La Salle University, Philadelphia), I am an Adjunct Professor (Temple University, Philadelphia – Personal Branding). I am a relentless entrepreneur passionate about connecting remarkable women to inspiring stories. Read more>>
Lucinda Smith
Hey Everyone My Name Is Lucinda Smith And I Simply Believe That My Entire Life Has been About Taking A Risk. I Grew Up In Foster Care Until The Age Of 9 When My Siblings And I Were Adopted By My Parents Darrell And Benita Short. Being A Product Of Foster Care Where I Found My Self Moving To 10 Different Homes Before I Was Adopted The Biggest Risk Was Loving And Opening My Heart To People Over And Over Again Hoping For A Different Result. Read more>>
SalsaQueen Zapata
After my 2nd divorce, I found myself needing to provide for my 7 children. With no education (not even a high school diploma) or work experience, my options were very limited. I received half of a tax refund, roughly $3000, and had a choice to make. I could either spend the money on clothes, travel, etc. or risk it in a new business. Read more>>
David Fhima
The restaurant business is a risky business. The only chance for survival is your passion for the business. Not just the food. The daily fires (literal and figurative). Every restaurant I’ve ever opened was a risk. Many restaurants, if not most, close within the first year of business. I’m proud to say that, yes, I’ve opened and closed restaurants, but they’ve been open for many years before I’v had to close them. Read more>>
Sophia Franzone
Upon graduating college in 2013, I always worked a corporate job with a stable paycheck and did the same tasks every single day, but I had a bigger dream. When I had my son, I knew it was now or never. Even though I was a single mom at the time, I quit my job, used everything I had in savings for what I thought was going to be used for a down payment on a house, and started on an entrepreneurial journey as a Financial Advisor. Read more>>
Petar Arsić
Without risk, there is no growth in life. Everyone of us is faced with some decision making in our every day life, and almost every decision is a risk in some way. Every little decision can influence your life in a grand manner let alone the huge ones. Like any other, my life also was filled with some important decisions that I had to make. Read more>>