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.
Andrea-liis Mustkikkas
I’m a professional dancer and choreographer from Estonia. It’s a very small country in Europe and most people have never even heard about this country before. I started my professional dance career when I was in high school. I was working with different artists in Estonia and I got many amazing opportunities to perform on stages and be a part of music videos/commercials. During my last high school years I started travelling to attend dance camps and train with world-known choreographers in Amsterdam, Greece, Berlin, London, New York etc. Training outside of Estonia made me realise that there are so many more opportunities for me to pursue dance professionally than my home country has to offer. Read more>>
Randy Rheinschild
It was back in 2001 when 911 happened. I was working someplace in retail as an assistant manager making the equivalency to $150K and my two daughters were young. Both are under 10 at the time. The company filed bankruptcy after the investors pulled out to shore up their own debt. I was totally out of work and unemployment was a whopping 300$ a week. My father-in-law was looking into franchises for us to get into and work together, as he had just retired from the airlines as a pilot. We found a computer software help model to get involved with and we did that for a few years. We were supposed to help with the office suite basically….but our clients wanted us to work on the machines. Like hard drive errors, and operating system issues such as viruses. We dumped the franchise and set off on our own, each of us. I started Rhino Computer Services and he handled the clients at the “old folks home” as he liked to call it. Read more>>
Krista Hedins
Moving from Iceland to LA was the biggest risk I’ve ever taken, and it truly changed my life. Growing up in a small town in Iceland, I always felt a strong pull toward the arts, especially acting. But pursuing a career in Hollywood felt like stepping into the unknown. Read more>>
Tier’a Berry
My voyage has been profoundly shaped by my family’s experiences with my youngest son’s health challenges. I share my story not just as a testament to resilience, but as a source of encouragement for others facing their own struggles. Such random occurrences can put you in a position to take risks. In 2022, we discovered that Amyn has Rasmussen’s Encephalitis, a rare neurological condition that affects 1 in every 10,000 children up to the age of 10. This condition was causing weakness on the right side of his body. The only solution to this condition was brain surgery. On April 27, 2022, Amyn underwent a hemispherectomy, during which the front left part of his brain was separated from the rest. The surgery was successful, and we are now celebrating 2 years of being seizure-free. Read more>>
Anna Thatsanaphonh
I’ve always had a deep passion for cooking, but health challenges have shaped my journey in ways I never expected. After being diagnosed with cancer, I found myself navigating through treatments while juggling regular jobs just to afford health insurance and pay for my medical care. During this time, I worked in several restaurants, always holding onto my love for cooking but unable to fully pursue it due to my health. Read more>>
Anne Rice
I had been a dental hygienist for 30 years or so, educating myself about oral health and systemic health. Simultaneously dementia had hit our family and I was deep diving into the research clearly understanding that there wasn’t a whole lot to do for my family members but realized quickly there was a lot to be done in prevention. So, I’m digging in everywhere and fell on a paper that spoke about oral health status and cognitive decline. It was a little like “you had me at hello” from Jerry Maguire. I went face first and knew I was on to something and dental providers were in a good position to help. Read more>>
Sydney Stephan
I was lucky enough to spend a few years traveling with Holland America Line. I was the female piano vocalist that was entrusted with opening their new flagship, and traveled to over 50 countries with them. This gig became very comfortable and I knew what I was doing! I was saving money, traveling, and got to meet a lot of amazing people. But, we all know that growth doesn’t come from staying where you are comfortable. Read more>>
Kelsey Moyer
When we started Boggy’s Buddies, we were taking a leap of faith into the unknown. It all began with a single hedgehog—one little life that needed saving—and the realization that there was no safety net for small, exotic pets like her in our area. Shelters were focused on cats and dogs, but animals like hedgehogs, guinea pigs, rabbits, and other pocket pets often slipped through the cracks. These animals are just as deserving of care and compassion, yet they’re rarely seen in the same light as cats and dogs. That realization sparked something in us: someone had to step up. Why not us? Read more>>
Ally Christine
One of the biggest risks we took was launching our nationwide business with absolutely no money, no loans, and a reliance on word-of-mouth referrals. We started in our small Ohio town, providing essential services to clinicians and patients. The initial risk was immense. We were foregoing any salary, investing all our time and energy into building the business from the ground up. We actively chose to take on pro bono work, knowing it would delay profitability, but believing it was crucial to establish our reputation and build trust within the community. This decision stemmed from our deep-seated belief in the importance of accessible healthcare. We felt a moral obligation to ensure patients received the care they needed, regardless of their financial situation. Our small-town beginnings meant we faced the possibility of complete failure – the potential of investing years of our lives with nothing to show for it was ever-present. Read more>>
Ashley Blankenship
If you would have asked me a few years ago, I would have told you I’m pretty risk averse because I like to feel a certain sense of physical safety. But, as I’ve gotten older, I’ve realized my choices throughout my life have been extremely risky emotionally. While I have zero aspirations to jump out of a plane, I’m often willing to be spontaneous and completely change the trajectory of my life. I think the biggest risk I’ve ever taken is starting Red Rocks Spirits. Owning a business is so incredibly difficult. It’s probably the hardest thing I’ve ever done, it’s also very exciting. I never know what the day will hold. Even when I wake up thinking it’s going to be a simple day, inevitably something happens to change all that. I enjoy having to solve the puzzle of problems I face every day. It definitely keeps me on my toes. Read more>>
Harrisson Ball
Moving from Australia to the United States was the biggest risk I’ve ever taken, and it has completely transformed my life. Eleven months ago, I left behind a stable career as a brass educator with Sydney Catholic Schools, where I had worked for three years. My role offered a comfortable lifestyle, a fantastic salary, and deeply rewarding experiences teaching and inspiring students. However, I felt a strong pull to pursue a dream that had been growing within me: becoming a full-time musician in the vibrant and competitive Los Angeles music scene. Read more>>
Andrew Harrison
Music was an unplanned journey for me initially. My parents immigrated from India in the 80’s and I was born soon after. My whole life I was being groomed to enter the medical profession, specifically, Ophthalmology. When I entered college, I was a pre-med/biochemistry major attempting to do just that. After my first year, I really didnt enjoy what I was doing, and started exploring other options. My friend group at the time was made of fantastic pianists and I spent a lot of time listening to them perform the great works of Beethoven, Scriabin, Mozart, etc. I played saxophone in the school band, but I was drawn to the music they were playing. Read more>>
Tony Fernandez
In early January 2024, I was asked to audition for the leading role in a CBS Super Bowl short film as an iconic football coach / owner – Al Davis. Immediately, I started intense research on the man and his life. Given that I have no specific football background or deep-cuts knowledge of the sport, this seemed like what we would call “A big swing” – and I hadn’t played a character type like this before in a major studio project. It certainly felt like a big risk! The more I researched this real-life sports figure, the more I thought “Crazier things have happened, I could actually do this role.” My ever-supportive wife in particular thought I could embody the role. Actors often need to hear that simple “Why not you?”. Read more>>
Tony Wolf
In early January 2024, I was asked to audition for the leading role in a CBS Super Bowl short film as an iconic football coach / owner – Al Davis. Immediately, I started intense research on the man and his life. Given that I have no specific football background or deep-cuts knowledge of the sport, this seemed like what we would call “A big swing” – and I hadn’t played a character type like this before in a major studio project. It certainly felt like a big risk! The more I researched this real-life sports figure, the more I thought “Crazier things have happened, I could actually do this role.” My ever-supportive wife in particular thought I could embody the role. Actors often need to hear that simple “Why not you?” Read more>>
Kati Howard
I finished graduate school in 2004, and started a wonderful job as a Nurse Practitioner in a large Women’s Health practice. I loved my job, and really was passionate about taking care of women. The doctor’s that I worked for, were wanting to open a medical spa within the building that we were located. A collaboration of OB/GYNs, family practice, plastic surgeons, and myself developed and opened Awaken Med Spa in April of 2008. The business barely made it financially for the first few years. And as many businesses encounter, we had difference of goals, and ideas within the partnership, and therefore, rearrangement and buyouts of shares of Awaken occurred. Read more>>
Vincent Delaney
After spending almost 20 years as a playwright, I was challenged by an actor to try writing for film and TV. I spent a year avoiding the entire idea because I felt like I already knew who I was a writer. And to be honest I was scared of becoming a beginner again. I’ve always been someone who fixates on challenges–I remember auditioning for my first play at 15, not because I wanted to act but more because the audition seemed so terrifying, That decision ended up launching me as a theatre artist. Read more>>
Kathleen Garito
After a successful 21-year career in retail, I decided to leave my demanding job and pursue my passion for interior design. The decision was inspired by my desire to adopt my daughter internationally and build a life that allowed me to be the mom I wanted to be. In 2005, I enrolled in a 12-week interior design course and launched my design firm simultaneously. Driven to learn more, I pursued an AA degree in Interior Design while managing my growing business and waiting for my adoption referral, which took three years. Just two quarters from graduation, I traveled to China to bring home my daughter, Isabella Rose Xi Garito. I later completed my degree and I was asked to be a professor at one of the top Interior design schools in Newport Beach. Then I fully committed to my thriving design and staging business. Read more>>
Nate B
Taking up photography was by far one of the biggest risks I took in my life haha. As we all know, photography can get very expensive. Whether it be camera body and lenses, protective and/or maintenance pieces, flights/hotels/rental cars, the expenses absolutely start to stack up as you attend more and more conventions . However, as with anything else in life, you have to weigh the risk with the reward. If I didnt invest my money and time so much when I first started, I would have surely missed out on many of the opportunities I was afforded. Read more>>
Logan Miller
About five years ago, I decided to take the biggest risk of my life and start a record company out of St. Louis, MO with a good friend of mine. We had no money (or really anything that would’ve made this a good idea), but we each had some small industry connections, believed we made great music, and had a desire to see creatives in our city have a better way forward in music. We signed our first artist in early 2020 (Lloyd Nicks) and got to work on his music. We sent his first single to radio in August 2020 and were stoked to see it chart on Billboard Top 50 CCM for 21 weeks, peaking around #31. We kept grinding for the past few years, trying to raise money to compete with major labels throwing 6 figures at marketing and promotion. In 2022, my partner and I went separate ways and I was left running the label – bringing in another friend to help manage the finances. At the same time, running the label had really birthed an interest in entertainment law, so I began dreaming about potentially going to law school. I believed in what we were doing, so I kept grinding – even after investing thousands of my own money to see this dream happen. Read more>>
Sarah Vorva
Like most photographers, I knew I wanted to pursue photography, but life ended up taking me down a different path first. Throughout my entire life, I’ve had a camera in my hand, or a camera in front of my face. See, it was my mom who had a love for it. She captured everything growing up. Not only for our family, but for others too. When I was in the 8th grade, I was tasked with setting up my small school’s yearbook. Mom and I did everything ourselves and produced a great little yearbook for them. Throughout high school, I burned through so many disposable cameras. I love capturing my family and friends. These moments are now little treasures to look back upon. Read more>>
Aleah Farb
Starting Sugar + Bubbles Co. has been the biggest risk I’ve taken in life so far, and I can guarantee that it’s not the last. It is a scary thought to think about leaving the arms of comfortability and job security with a normal 9-5 career, but eventually I got to a point where the idea of staying stagnant and not doing something creative was an even greater fear. The funny thing is, as soon as you accept your fears and no longer let them rule you, you discover that it doesn’t break you and instead your world opens up. You just have to learn to dance a different way. Read more>>
Nico Parducho
Working as a freelancer in the theatre industry is full of the unexpected. Many practical people with regular 9-5’s tell you it’s a risk to go for your dreams, especially if it’s in entertainment. I was fortunate enough to have my family and friends support me when I told them that I wanted to become a Stage Manager. However, no matter how much support I had, I had to face the reality that this career is a risk. I remember the moment I knew I wanted this. I was stage managing my first show in high school, and my dad passed away. Tech week had just started, and I couldn’t bring myself to think of anything else besides the show. Read more>>
Sean Kohler
To say that I was risk-averse as a child feels like an understatement. Throughout my adolescence, I was very cautious. I took very few risks, generally not embarking on something (no matter how small) unless I was sure beyond a doubt of its success. While this led to a lot of accomplishments, it also created a lack of trust within myself. While it seems like my experiences with success would have created an abundance of trust within myself, it actually left me with very little resilience. Lack of action had caused me to become uncomfortable with uncertainty and overly dependent on external structure. Read more>>
Ryan Laroche
Other than moving from Venezuela to Miami at the age of 20, the biggest risk I’ve taken was leaving my previous workplace to become a business owner. I was working at a lash studio, and while I was content and earning good money, I felt torn—I was happy but not fully satisfied. Over time, I began to feel that the company I worked for wasn’t meeting the promises they had made. I constantly had to advocate for myself, and there was little effort on their part to provide the support I needed to grow. Read more>>
Meliza Carrion
Here’s a streamlined version, focusing on the highlights and removing extraneous details: It all began during my recovery from back surgery, lying on my couch, unable to move. The stillness forced me to confront my thoughts and rethink my life. Always an overachiever, I found the inability to work or work out incredibly challenging. But in that moment, I decided to use the time to quit drinking and focus on healing. Read more>>
Meghan Lamontagne
When you are a creative and choose to make a living that way there is always risk but I remember one particular risk that I never imagined I’d have to take. It was 2021 and I had a steady remote creative job and was in, what I thought, a steady relationship, and in a twenty-four hour period my world turned upside down when my relationship suddenly ended and my remote company (based in North Carolina) asked me to relocate from Los Angeles. Read more>>
Emily Greer
Oh my! So many stories to share about all the hits and misses resulting from my risk calculation training! As a young person, I was unsure of where the boundaries were. Boundaries always seemed to shift to benefit whatever polarity my father was presently feeling. Those situations were okay in that moment for him because he was the head of the household and if he said no it meant no. Read more>>
Angela Sulai Kaeser
Two things have been a guiding force throughout my life, the fear of regret and my intuition. They are still the main drive for my decisions in my personal life and in business. I’m usually not the one that immediately jumps, but I’ll let it simmer and marinate and then I jump. Without taking risks, I would most probably never have became a Make-up Artist, moved abroad multiple times or just simply become who I am and living the life I am today. Read more>>
Curtis L. Harnagel
When we think of “risk” we think big and usually financial, but that first step you take toward something you want is a risk. For me, I have had several career transitions that required risk. For instance, transitioning from a career as a Designer and Editor to Creative / Show Director and Producer has taken many steps to get here with some amazing opportunities along the way. I think my first true win illustrates this point well. Read more>>
Joseph-michael Schulz
Sometimes, the most transformative ideas come from the simplest observations. For me, inspiration struck during an ordinary day working for my father’s door installation company at an assisted living facility. As I watched a woman in a wheelchair struggle to pull open the heavy entry door towards her, I felt compelled to help. She appreciated the gesture but was clearly frustrated by her dependence on others for such a basic task. Read more>>
Julia Brandt
Being so far away from my family in Sweden I have since marrying an american and moving to New York always dreamed of starting my own business and being my own boss so I can travel to see them as often as possible and to be there for all special occasions. I have also dreamed about creating a business that would let me sort of have one foot in Sweden my home country and one foot here in The Us where I am creating my life living with my husband. Read more>>
Carris Bennett Christianson
One of the biggest risks I’ve taken was returning home to Los Angeles after four years away. This is where I knew I could freely express myself creatively and pursue my dreams. I decided to make a complete fresh start, moving to a part of town I never spent time in, where I didn’t know anyone. It marked the beginning of an exciting and uncertain adventure, a chance to rebuild, rediscover myself, and give back to others in a creative way that felt meaningful. Read more>>
Corbin Johnson
The biggest risk I ever took was moving to Los Angeles at 18 years old to pursue my dream of becoming a professional dancer. I had a clear vision—since I was 12, I’d dreamed of dancing for Beyoncé, the biggest artist in the world. Growing up in competition dance, I was versatile, and my training reflected that. I attended a performing arts high school, trained at a classical ballet academy, joined a contemporary and ballet company for three years, and finished high school at a modern/Horton-based facility. I had options—I could’ve studied dance in college or even gone to Alvin Ailey in New York. But that wasn’t my dream. I wanted to be in LA, dancing on television, just like the dancers I grew up watching. Read more>>
Amy Weir
I went from a full time creative design job as a landscape architect to quickly having two babies under the age of two. I was looking for a way to be at home with my children and yet still carve out some time for myself, so I decided to start an Etsy digital print shop. But, after a successful year with Etsy I decided to start a DIY and craft blog where I could really get my hands dirty with making, creating and building while being able to teach others how they could do the same. I knew from the very start that I would run the blog as a creative business. I hoped that someday if I worked really hard I could call it my full time job. Read more>>
Brian Parsons
One of the biggest risks I’ve ever taken was leaving a 15 year service career with financial stability and job security to pursue a creative career in music and writing. I knew it would come with financial hardships, rejection, judgment, and doubt. The alternative, however, was remaining in a career that consistently drained me. I was depressed, I was drinking, I was compromising myself, and I was never able to be fully present with the people who I cared about who depended on me. Read more>>
Dr. Windy Blades
From the day I left the military, I carried a vision close to my heart: creating a Health & Wellness Center specifically designed to serve Military, Veterans, First Responders, and their families. For over 30 years, this dream simmered in the background, but in early 2024, I decided it was time to act. The world was uncertain, and the market was challenging, but something within me felt called to leap. Read more>>
Dawn Fischer
This story of “taking risks” actually starts as just the opposite. As a child I didn’t take risks. I followed the rules to a “T” I had guilt when I didn’t and I worried a LOT. I tried to make sure I did EVERYTHING perfectly. Why? I guess so that nothing bad would happen. As a little girl I remember having a distinct knowing that I was here to do something valuable. I was fascinated with helping in any way I could & healing whatever needed healing. My hero’s besides Wonder Woman was Mother Theresa, Florence Nightingale and that show about Dr. Quinn Medicine Woman. I went from helping my stuffed animals and dragging in every stray kitten, turtle, bird and even to my grandparents horror several snakes and a baby bat, to channeling that drive into action going into a pre med program in college. Read more>>
Josie Lenger
The transition from being a school-taught photographer to a self-taught one was a significant risk. In a structured learning environment, you’re taught to observe—often as an unseen presence in the background, following others’ leads and learning from their successes and failures. Connections are vast but intangible, and budget is rarely a limiting factor. Then, suddenly, the responsibility shifts entirely to you. You must set your own expectations, take charge of your own progress, and pursue new opportunities. You are the only one standing in your way when it comes to taking risks, building connections, and embracing new challenges. The key is to take risks, make mistakes, and remember that you miss 100% of the chances you don’t take. After years spent in the background, I’m now stepping forward to create my own path. Read more>>
Bethany Kennedy
I have taken the same risk twice in my life. I quit my job. The first time it was to focus on my family and the second time was to pursue financial security. Both of these decisions brought me to my knees where I needed to get very honest with myself and make some inward changes. Read more>>
Simone Assboeck
One risk I took that changed my life started with a university program requirement: an internship. This meant spending six weeks of my precious student vacation interning instead of relaxing or traveling. What a bummer! Hahaha! My creative mind, however, immediately began searching for ways to make this situation more enjoyable. Read more>>
Laquita Dian
Oh my goodness, my entire life has been shaped by my risk-taking. Some risks have been more calculated, and others have been out of my perceived necessity. Taking risks is often seen as taking a reckless step into the unknown, but for me, it’s also one of the most effective ways to grow, achieve, and influence change. Read more>>
Francesca Escoto
My formal education is in engineering, but I consider myself a multi-career professional, since I have been working in different industries simultaneously for more than a decade. Over the last few years, I built a work-from-home routine that allowed me to rise as a successful IT Senior Project Manager and Chief Operations Officer for a non-profit in Miami, FL. In addition, I coached startups and entrepreneurs, while raising my three daughters. Read more>>
Danielle Garcia
During my difficult second pregnancy, I felt a little lost in all of motherhood and growing another baby. I needed something else just for me. And I quickly got over the bullshit imposter syndrome and reminded myself that I love learning so I can learn all I need to be successful as a virtual assistant. Read more>>
Laura Garner Hine
One of the biggest risks I have taken in my life, and I think any human being can take in their life, is to be vulnerable. It’s quite an oxymoron really- because I have found that showing vulnerability is truly a practice of strength. Once we let down those walls, we open ourselves up to a whole new range of experiences, emotions, and connections. Vulnerability fosters empathy, and can garner trust and intimacy with another person, which can bring strength to relationships and a stronger sense of self. It takes such courage, authenticity, and resilience to be vulnerable, but it sure is a huge pay off when one does take that risk. Read more>>
Shirley Zhang
I made a career pivot not long after graduating from my master’s program. For years, becoming a physical production producer was everything I ever wanted. I worked hard, went to school for it, expanded my skill set views, and thought story development would be my backup plan if I ever got too tired with production. Then the world was hit with a devastating pandemic, and physical productions were shut down. No one knew what was going to happen. Read more>>
Katy London And Sam Sitarik
Before we opened our own business, we were both working for a small practice in Colorado. We had always talked about making our own personal mark in the therapy world, but knew doing so would be a massive risk and time investment. As our passion and knowledge of therapy and creative methods grew, so did our desire to operate in a setting that would foster deeper exploration and a place for people to feel fully understood and accepted. As therapists and lifelong therapy clients ourselves, we both understood how important it was to have a space to feel validated and supported without judgement. Read more>>
Jessica Lima
The Art of Taking Risks: A Journey from Brazil to Los Angeles Taking risks is an essential part of the journey to success. As a Brazilian entrepreneur, my story began with what was supposed to be a simple vacation in the United States. Yet, life had other plans for me. I felt a calling to stay longer and pursue the dream of expanding my natural cosmetics brand, LaTerra, in the vibrant city of Los Angeles. Read more>>
Madeline Stewart
I grew up in High Point, North Carolina, the world’s furniture capital, and always dreamed of working in the furniture and design industry. I graduated high school, attended NC State, and studied at the Wilson College of Textiles in Brand Management and Marketing. My dad was a fabric salesman then, and I knew that my knowledge of textiles, marketing, and business management would be instrumental in my career. Once I graduated, I interviewed with Sherrill Furniture and was given the Southeastern Territory for Hickory White and Lillian August. I was so scared but also so excited. Read more>>
Lee Reid
Offering to build out / work in a metalsmith studio at a Portuguese art residency with less than a year of professional jewelry experience under my belt is definitely one of the riskiest moves I’ve ever made. Very long story short, I was working as an apprentice jeweler at a Jared’s repair shop in 2021. Thankful as I was for the opportunity, it wasn’t long before I became restless and began dreaming of traveling again. I wanted to find a way to blend my love of adventure and silversmithing, so I reached out to a handful of art residencies across Europe in hopes they had a metal shop. To my shock, one in particular expressed the desire to build one, so I said, “hey, I know a gal…” and just like that, they invited me for a work/trade arrangement. Read more>>
Kelly Breuer
The biggest risk I’ve ever taken was leaving the security of a full-time job and steady paycheck to start my own business—all while being a single mom raising two small children. It was a leap of faith that, at the time, felt both terrifying and exhilarating. To add to the challenge, I was living an hour away from any family support, so the stakes couldn’t have been higher. Read more>>