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.
Samora Smallwood
The biggest risk I’ve taken was pretty recently, when I made a massive pivot in my career. As an actor you play characters in the service of an overall story. And I was a natural born storyteller (there are years worth of old camera footage my grandfather made of me doing accents, practicing comedy, and telling tales. So it made sense to everyone when I decided to go to theater school then became a professional actor. In the past couple of years though, I’ve felt called to start telling my own stories. As a child I’d written plays, cast them, held rehearsals and put on shows. My siblings and I even had the gall to charge our neighbors money to come watch! As a school kid, I’d written stories and even placed in the “Young Authors” program. And one of my best memories is when, in highschool, I’d written a fictional piece about Marilyn Monroe. Read more>>
Brooklyn-raye Conley
I made one of the biggest, most life-changing decisions of my life when I dropped out of school to pursue a new-found career in film. Picture this: it’s March 2023, and I’m on spring break, feeling the usual relief and anticipation of a brief break from classes. Suddenly, my friends/business partners approached me with a proposition that would turn my world upside down. “We’re going on a screening tour to showcase our film *When I Wake*!” (*When I Wake* was our first project under Lucid Village Productions, and it was taking off—we had over eight festival selections and were planning an east coast college screening tour). At the time, I was a co-founder of Lucid Village but only part-time. Balancing our business with school was tricky, and now I’ve found myself pulled in two directions. Read more>>
Jennifer Boileau
The biggest risk I’ve taken is on myself. In my life, I’ve had to learn to trust myself and recognize the gentle nudges (that can be really easy to ignore when we are tied up in the busy-ness our lives) are really what is steering us in the direction we are meant to go in. In my own practices to support my anxiety and wellbeing, I recognized that the strategies I was learning to support myself would be beneficial for others as well – but in a very non-traditional way. From being in a law enforcement family, I knew the kinds of stressors officers were facing as well as the stressors on the family, I knew that to bring the practices into law enforcement/first responder world, I would possibly be stonewalled and perhaps wouldn’t work out the way I wanted them to, but I got to a point where I recognized there wasn’t an option NOT to keep going. I truly felt like the work I was doing, the training to be culturally competent, and the drive I had to bring it all to life was something I couldn’t walk away from. I believed in it too much. Read more>>
Barbara Gonzales
One of the most significant risks I’ve taken was transitioning my business from a general focus on organizing to honing in on creating a digital organizing planner. For years, I’d been helping people organize their lives, offering guidance, and tips. But as I worked, I realized that creating a digital planner, something that could serve as a daily tool and provide consistent value, would not only help people in a tangible way but also give my business a clear and distinctive focus. The shift was daunting. It meant redirecting time, energy, and resources to develop the Wonderfully Made Home Organizing Planner and hoping it would resonate. I was used to interacting with clients one-on-one, which had a predictable rhythm, but creating a digital product felt like entering unknown territory. There were moments when I questioned if narrowing my focus like this was the right choice. Would people see the value? Would they be interested in a digital tool for home organization? Read more>>
Karla Pineda
The biggest risk I took was leaving a stable, steady-flowing practice to start Layers Counseling Specialists. I had a solid position with a reliable client base, so the thought of stepping away to build something from scratch was daunting. I worried about not having clients, facing potential income gaps, and whether I could handle the challenges of marketing and management. But underneath those fears was a drive for something more: I craved the freedom to create a different kind of practice—one where clinicians could grow, focus on their niches, avoid burnout, and provide truly specialized care to clients who needed it most. I wanted to build a system that supports both clients and clinicians, giving clinicians the opportunity to invest in their skills and create a positive impact in their specialty areas. Read more>>
Decker Rush
The biggest risk I ever took was trading a stable, well-paying job for the uncertain life of a musician. Before I made that leap, I worked in experiential marketing for a major brewery. It was a solid career—I got to work with big brands, create memorable experiences, and it provided a steady paycheck. But despite the stability, something was missing. House music had always been a huge part of my life. I was that person who never missed a show, a festival, or an after-hours event. I would stand there and look at these DJ’s and go “I could do that. I know I can”. I used the first stimulus check to buy my first DJ controller and never looked back. At first, DJing was just a hobby, something I did to bring back some joy in those isolating days. But the more I practiced, the more I felt like I’d tapped into something real—a part of myself that I’d never fully explored. It ignited a fire in me I hadn’t felt before, a deep passion I couldn’t ignore. This wasn’t just a side gig; it felt like what I was meant to do. Read more>>
Stephen Collins
While it seems so long ago now, our family entered the food industry in 2015 & in the meantime, has reinvented the business on five occasions. In each instance we had to assess & mitigate different risks. First, we established a food truck, serving authentic Australian cuisine in the east valley of Phoenix, AZ. Along that journey, as we better understood our new market, we undertook a refit of our food truck to incorporate a gourmet coffee & drink aspects to its operations. Then, COVID descended & we commenced home deliveries via our SUV, to customers who already supported our food & coffee truck. During that period, we were asked to establish a permanent stop inside a residential community in NE Mesa & one day a week became two days & then finally six days a week. Our current operations now include a brick & mortar cafe. Read more>>
Melissa Vanoss
A time I took a significant risk was when I found myself saying “yes” to my book coach, who asked if I would launch my book in just one month. As the reality of my commitment sank in, I realized it was a big risk. Typically, when launching a book, it’s advisable to have a ‘warm market,’ a fan base, or at least a decent social media presence. However, when I said “yes,” I had none of those. Sure, I had contacts in my phone, but my personal network was cold, and my social media footprint was nearly nonexistent. I hadn’t used my own social media accounts for over seven years because I had been managing several small business accounts on the back end. So, I hadn’t seen the need to post on my own. Read more>>
Liliana Epps
Recently I took a risk by reaching out to old friends I hadn’t spoken to in a long time. Now to be completely honest the 3 people I reached out to were all cis-men…that I’ve kissed before….we’ll leave it at that. BUT dear friends of mine to say the least. All three of these boys are people who know me deeply and who I know and care for deeply. However, it was still very scary reaching out because I’d either been ghosted and/or rejected in the past. So you might be thinking “Lily, then why reach out?” Well… I’m crazy. But the good kind of crazy!! Enough time had passed, I let go of my pride, and decided to honor my longing for their friendship and nothing more. Read more>>
Lovlee Tang
I have taken many risks throughout my life. It was early in my motherhood journey that I knew I wanted to be more present and available as a wife and mother. I was not sure how I would make that desire come true, but I knew that the path would be made clear somehow. Learn to expect the unexpected. Experiencing an unexpected miscarriage in our third pregnancy was devastating for me, and it caused me to make a major pivot in my life. The early loss of our third pregnancy made me realize that life is too short! This pivot point led me to take a big risk and create a business that would evolve with the growing needs of my family, allow me to generate an income, while providing a valuable service to my community. Read more>>
Saskia Staeuble
I survived a stroke at the age of 29, leaving me with left-sided paralysis. I was conscious and clear-headed, but I couldn’t move or speak. I ordered my arm to move, but it wouldn’t. I was scared, but most of all I was angry with myself. I immediately realized: “I never pursued my dream of singing!” And: “What if I can never sing again?” I felt like I had completely lost myself in my life. Although my life was “perfect”—I was engaged to a nice man, had a big apartment on the outskirts of the city of Lucerne in Switzerland, my boss even offered me to take over part of the practice where I had worked as a nutrition and motivation coach. But wait, yes, there is this BIG DREAM inside me that I have had since I was a child: to sing and touch the hearts of people all over the world. When I was lying in that hospital bed and the nurse came to wipe my saliva because I had absolutely no control over my face, she looked at me with concern and compassion and asked me: “What is wrong with you, Miss Staeuble” (my last name). Read more>>
Rachael Derossi
Taking the leap to start my own marketing agency, The Marketing Dept., has been my biggest risk yet. Sure, it felt like a daunting plunge from a comfy corporate job as a single mom, but I believed in my process and myself. With a track record of launching two other companies, I knew the drill: spot a need, conduct some serious sleuthing, assemble a rockstar team, and dive in. I like to feel confident that the rewards will outweigh the risks—and have a solid ‘oh, shit!” plan in place too. Entrepreneurship runs in my blood, and I’ve embraced the adventure more than once. Before launching The Marketing Dept., I built and flipped rental properties and started, then sold, a commercial excavation company. My motto? Never take “no” for an answer until every option is exhausted—problem-solving might just be my only real superpower. Read more>>
Tony Luu
Growing up I knew working a normal 9-5 was not my true calling in life. My mother side of the family are all mainly entrepreneurs with a lot of us owning nail salons. I vividly remember spending weekends at the salon and talking to so many customers that have been going there for years. Something about watching my mother run her business always peeked my interested whether it came to buying supplies or even building genuine connections. Being first-generation Asian American. There is a lot of added pressure to be successful and live up to high expectations. During college, I got a job as a quality inspector checking various parts for BMW’s vehicles. I worked my way up to quality supervisor and managing 15-30 night shift inspectors. I credit that job in making me understand what true hard work really was since I was working 50-60 hour weeks on top of being a full-time college student. Read more>>
Simone Knego
One of the biggest risks I’ve taken in my life was deciding to climb Mount Kilimanjaro. This wasn’t just about climbing one of the world’s highest mountains; for me, it was a chance to confront years of self-doubt that had held me back in so many ways. As a mother of six, constantly juggling responsibilities at home and at work, I’d often felt unsure of my own worth, frequently questioning if I was “enough” in all the different roles I played. When the opportunity to climb Kilimanjaro came up, I knew it wasn’t just about reaching a physical summit. This was my chance to tackle a mountain that was both literal and metaphorical. I didn’t fully grasp what I was signing up for, but I understood that if I could overcome the challenges of this climb, I might finally quiet the self-doubt that had lingered for years. I needed to realize what I was capable of. Read more>>
Brandy Alexander
Moving to Arizona was a significant risk for me. I was born and raised in Cleveland, Ohio, where I raised my three children and where most of my family still lives. At the time, I was in graduate school, working toward my Master’s in Nursing, and working as a travel nurse in NICUs across various states. As I started envisioning my long-term goals, I knew they included opening my own medical practice. Two key requirements shaped my decision on where to relocate: first, I wanted to work in a state that was NP-friendly, where I could operate independently; second, I hoped for a warmer, more temperate climate after years in Cleveland’s less-than-ideal weather. Arizona fit both needs perfectly, so—without knowing a soul there—I packed up and moved nearly 2,000 miles away, alone. Read more>>
Constance West
I must be honest in saying that the biggest risk that I have ever taken is becoming a business owner. I do not have a background in business, therefore, my dreams of becoming an entrepreneur were built on a dream. Lord knows, I did not know the first thing about where to start, but there is one thing that I have always had no matter the circumstance or season of life that I was in, and that is my faith. I was raised to know that no matter what I am going through, I can always go to God in prayer. This has been exactly what I have done and I am blessed to say that I have had my practice for 8 years. These past 8 years have not always been roses and rainbows. I have had seasons of uncertainty and self doubt. I faced days when I questioned whether I was strong enough or even worthy or capable to help others in the capacity of a therapist. I struggled with confidence, financial literacy, and my biggest hurdle was fear. I allowed fear to dictate my direction which spiraled into seasons of self deprecating thoughts. Read more>>
Melissa Nadeau
On September 20, 2023, I was significantly suffering from burnout without realizing it. Exhausted from the moment I woke up; I collapsed into a pile of tears, going back to bed after getting my kids off to school. I knew something was wrong, I knew that I did not feel like myself. I felt like I was coming apart at the seams; unraveling. Unable to take care of myself for an entire week, I was diagnosed with dissociating, and severe depression. I was convinced that leaving this world permanently was the only solution. My family deserved better than I could provide. My time on earth was finished. Read more>>
Kim Nguyen
At the beginning of this year, I found myself at a crossroads. I had a stable job with great benefits and a pension—something many people dream of. Photography had always been my passion, but it was just a hobby. It wasn’t until I started taking it more seriously and honing my skills that I began to imagine a life where photography wasn’t just something I did on the side. Still, the thought of stepping away from the security of my 9-5 job was daunting. I had a family to consider, and stability meant a lot to me. But my husband, Khoa, has always been my biggest supporter. He encouraged me to follow my heart and pursue my dream. With his unwavering support, I made the decision to reduce my hours at my job and give more of my energy to photography. Read more>>
Madisen Rose
I call 2023 the radical clearing. My fiancé and I were planning a year long trip around the world, followed by a wedding and starting a family. In preparing to go, I started to close down my life in Colorado. We were leaving the country and didn’t know when or if we would be back permanently. A month before the last day at my job, we broke up. The two year long process of planning, saving, selling everything, training my replacement was now all for not. It felt like my life was a train, charging full steam ahead and someone flipped the track switch. I didn’t see it coming. One version of me wanted to go back to the life I had just left. Instead, I said “Screw it, I’m going”. Everything in my life changed in a few short months – my work, my partner, my home, my routines, all of it. I spent months abroad mostly in Mexico and Peru. A long layover in Portland to see friends turned into five weeks. I was open to whatever came next and held on loosely to potential plans that could change. Read more>>
Gloria Kloter
When I moved to the USA in 2015, I thought I could seamlessly continue my architecture practice, which I had successfully established in the Dominican Republic. However, I quickly discovered that my architect license wasn’t recognized here, and I couldn’t even use the title “Architect,” let alone open my own firm. This unexpected barrier led me to work as an employee at an architecture firm for four years while I went through the rigorous process of getting my U.S. license. I finally achieved that goal in 2019, but by then, I was settled into the stability of a regular paycheck and the structure of traditional employment. Read more>>
Xica Bee
Taking a risk When you have to believe in yourself 110%. You can’t allow nothing or no one to take you off of your Focus and your stride. I was working in the fitness business for a lifetime fitness Bally’s total fitness curves for women, and I noticed that the one thing that these big corporations cared about was the end number whether or not a person showed up to appointment came to work out, really worked on being the best them. It was making sure that that monthly payment hit the account. Remember, I used to get written up at a certain job not to name which one for calling and contacting clients to see if they knew they were still being charged and they haven’t been in in a while and what Have them come back. And that’s what I decided to step on faith and walk away from making $6000 a month with a company with benefits. To starting my own company and not having benefits to have to get and pay for benefits to not making 6000 right away to maybe making $100 but I didn’t step out and take that risk I would not be as successful as I am today. Read more>>
Shantel Collins
The biggest risk I took in life was not looking back. I was raised in a household that pushed for independence and respect. I am sure those qualities gave me more confidence in areas that I thought I was weak in until I was faced with having to conquer them alone. I was seperated from my siblings and alienated because I was so much like my dad. No looking back; Confident, firm, and opinionated, and goofy; I loved my dad so I seen no wrong in his behavior. Until I was forced to leave his house for those same characteristics we shared my entire upbringing. I could not look back, taking the risk, I dedicated my studying and love for education and to beat the odds to be great regardless of the past I had growing up. So when I got pregnant for the first time, I was a full three months and didnt get to carry it to term and look in my babies face. I knew there was one thing I could never do again! Read more>>
Kristopher Gonzalez
I have been a second grade teacher for almost 25 years. As many people know, working in education can be extremely stressful and most educators leave after a few years. After years of working with students with extreme behaviors that were not addressed by administrators I’d begun to start thinking about moving on from education, but I didn’t know what other careers would be a good fit that I’d enjoy. I did enjoy many aspects of being a teacher, and I was very good at it, but that’s not what my story is about. Read more>>
Takiyah Wallace
“One of the biggest risks I’ve taken was stepping away from both my photography business, Some Sweet Photo, and a long career in public education to become a full-time creator. This decision came at the height of the pandemic, an uncertain time when I accepted an opportunity to work with Meta in their flagship *We the Culture* program. While it was an exciting chance to tell stories on a larger scale, it meant leaving behind the stability of teaching and pausing a photography business I’d built over years. My first book, *The Color of Dance*, emerged from this leap, showcasing dancers of color across the U.S. Then came *Brown Girls Do Ballet*, a children’s book that shows young girls of color—and those with disabilities—that they belong in dance spaces, too. Stepping away to pursue these projects was a bold move, one that involved risk and sacrifice, but I was driven by a deep need to amplify representation in the arts. Read more>>
Adam Toksôz
By nature, I’m not someone who shies away from risk. I’ve always believed that true rewards—whether financial or experiential—require taking chances. Reflecting on my journey, I realize I’ve taken several steps that might seem “risky” to others, but each has shaped my path in art and entrepreneurship. One of my first big decisions was leaving behind a safe path in economics. Originally, I thought I’d just get a steady desk job, but I kept feeling drawn to art. My late grandmother, an entrepreneur herself, gave me advice that stuck: “If you focus on something you’re passionate about, you’ll always find a way to make a living.” Her words gave me the confidence to pursue art, and from then on, I was committed to building a creative career. Read more>>
Marco Tornillo
I had a solid job as a commercial mixer in advertising but it wasn’t fulfilling enough financially and creatively. There were certainly moments that sparked creative insights but I knew I wanted to make a change and work on music full time. I was working so many hours at the studio mixing commercials that I was drained to make music on the same program at home in the evenings. My work was taking away my creative thinking and most importantly, time. I had a tough decision of quitting my steady job to pursue music full time, or to at least give myself new opportunities in my music career, but I did so and was so happy with the decision. Read more>>
Avery Caldwell
embracing risk. After four invaluable years under the mentorship of my former boss, Christina Passanise, I was presented with a transformative opportunity: the chance to open my own suite rental business. This decision came with significant risks, as I had just one month to prepare, all while being nearly nine months pregnant with my second child. Although the timing seemed daunting, I recognized it as the perfect moment to take that leap of faith. I am grateful to say that my journey has been rewarding, and everything is unfolding beautifully. Read more>>
Timothy Milner
Making the intentional change from playing guitar for yourself or attending casual jam sessions or even writing some songs to deciding to make a record is a big change, full of risk. You’re risking a lot of money when you become a recording artist, between instruments, recording gear, loads of time, studio time, mixing/mastering, and distribution. And then you quickly learn that many musicians rarely make any money, and then even fewer make enough to pay themselves back for expenses. I suppose it’s unique from purely business ventures because creating music has its own rewards that have nothing to do with money, but this can be a comfort as well as a burden or even a curse. Read more>>
Livwithjess
Liv: The shutdown of 2020 served as a herald, pushing me to take a leap of faith rather than live a life filled with regret. Seoul had intrigued me due to its distinctive and innovative production style, particularly in music videos that echo the grandeur of old Hollywood infused with a Marvel-esque quality, with complete sets, stunning visuals, and crisp lighting. I admired the industry’s commitment to pushing boundaries and fully exploring creative possibilities, qualities I aspired to learn from. I knew I needed to commit to film full-time, as my previous attempts in NYC had left me complacent and with more questions than answers. Determined to fully dive into my dreams, I resigned from my job, packed up my apartment, and left the city I loved. I didn’t want there to be any backup plan; I wanted to dive in without a safety net because I knew if I did, I would not take my time in Seoul seriously. Read more>>
Miwa Mayemura
What began as a faint idea has blossomed into both the foundation and the future of my business. Taking a chance on this single idea became one of the biggest risks and first genuine leaps of faith I’ve ever taken. Every day that I show up for myself and my business, I continue to take that chance. My vision for Serenaire started as a desire to create something from nothing—a parallel to my own life as an Asian American woman and first-generation entrepreneur. In 2021, I was a 20-year-old college student feeling lost and struggling to find my way in the middle of the pandemic. Amidst this, I took my first step into the beauty industry. Although my budget was tight as a semi-broke college student, I discovered the transformative, yet effortless, power of lash extensions. I even spent most of my paychecks on regular upkeep because it helped me feel more confident in my daily routine. However, it wasn’t just the lashes that made me feel my best; getting lashes done was an entire experience, and I have my first lash tech to thank for that. Her artistry, paired with the bond we built over time, kept me returning. Read more>>