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.

Kathleen Jones

The biggest risk I have taken is a blind leap of faith into full time art before I had any representation or presence in the art world. I was teaching high school and painting in the evenings and posting on Instagram, but that was the extent of my art career. I sold a few pieces through social media here and there, but I was very much a novice. I applied to Anne Irwin Fine Art’s Emerging Artist show, but I wasn’t sure if I would be accepted. I had to make a decision whether or not to renew my teaching contract for the following year before I knew if I had even been accepted. I took a risk and did not renew my teaching contract, and just had faith that this was my path and things would work out. At the end of the school year I found out I had been accepted into the show. I submitted four paintings, and they all sold before the opening, which prompted Anne Irwin to keep me as a represented artist. The rest is history! Read more>>

Sarthak Sahoo

Upon entering college, I wanted to enter the art and design space. I was already invested in drawing, painting, and playing piano, and I wanted to enter my foot into as many doors as possible. Earning a BFA was a big risk, taking into account the economic situation of the world and how hard it is to find work. After getting into my major after being a premajor for a year, I started to explore different avenues for my creative vision. Pre pandemic, i was creating works of art that reflected political circumstances in south asian countries, as well as reflecting on cultural identity. I explored video, sculpture, digital illustration and collage, and even founded a local streetwear company that screenprints on top of secondhand clothing.  Read more>>

Gabrielle Briggs

One cold winter day, I decided I was going to take a walk around my neighborhood to clear my head. It was a warmer than usual day and the stay started off weird in general. For one, I never think to walk around, and I wouldn’t dream of doing it in the winter. 10 minutes in, something told me to speak out loud all the things that have been bothering me. Per usual, I started reflecting on my business. Thinking about the things I shouldn’t have done, things I could have done better and of course what I could be doing now in the present moment. The minute that I started being hard on myself, it made me get very emotional but this was different than my usual spirals. I was warm, almost like a warming sensation but it was like 20 something degrees outside. Then I felt comfort, almost like someone wrapped their arms around my inner child and guided me through all of the emotions I was experiencing. This day birthed a series that, after months, is currently coming to fruition. That walk was about growth, letting go of dead weight and truly seeing myself for who I actually am and being comfortable with not fitting into the box I felt I was placed in. Read more>>

Lucrezia Mapelli

One of the biggest risks I’ve taken was deciding to leave Italy and move to the U.S. to marry the love of my life, Johnnie Ray. While it was a deeply personal and exciting reason for the move, I was still faced with significant challenges, especially when it came to starting my makeup business in a new country. At the time, I was living in Milan, working alongside some amazing makeup artists and building a career in the fashion and beauty industry. Although I had found a level of success there, I knew I wanted to build something more—something of my own. The decision to move was life-changing. On one hand, I was about to begin a new chapter with Johnnie Ray, which gave me a sense of support and love that made the transition easier. But professionally, it felt like I was starting from scratch. I had to leave behind the network I had built in Milan and navigate the makeup industry in the U.S., where I had no established connections. It was a daunting challenge, especially in the beginning when nothing seemed to happen as quickly as I had hoped. Read more>>

Cristina Esteban

When I graduated University, I was one of the lucky few who actually managed to score a job right away. It wasn’t in the Industry I saw myself in longterm, but it was a great job nonetheless, although I wasn’t truly happy. I had interned at a record label when I was 18 years old (my first ever internship) and in the back of my mind I kept going back to that. I kept thinking about how important music had been in my life, and that what I truly wanted was to work in the music industry. It was important to me that the job I had was something I truly enjoyed and was passionate about. And for me that was music. So when I was 25 years old, I decided to leave my job, and my hometown in Spain, and move to Los Angeles. I had never been to LA before, but I figured, if I wanted to make it in the music industry, that would be the best place to start. Read more>>

Vi Duong

As I’ve grown older, I’ve realized that I truly thrive on challenges and discomfort. Whenever I feel stuck or stagnant, I start questioning my purpose because I know I’m capable of more. I credit my mom for instilling a strong work ethic in me. Coming from an immigrant single-parent household, my siblings and I had to learn to take care of ourselves, as my mom was always working. That experience shaped me into a grinder. One of the biggest risks I’ve taken recently was quitting my stable full-time job. That position provided financial security, but over time, I felt unfulfilled and constrained by the 10-6 office routine. I had been freelancing on the side, essentially working seven days a week, trying to balance both worlds. Even though I enjoyed the work and the skills I gained, I wasn’t satisfied knowing I was only earning a portion of what my efforts could produce. I knew I had the drive and potential to do more, but I needed to challenge myself and take control of my own path. Read more>>

Alexsandra Dattilo

The biggest risk that was taken was when my fiance had brought me home full time to become an artist. We weren’t sure if Open Idea’s Acrylic would actually take off or not due to me not having a very big networ, so there was always the risk of having to go back to working for someone else, to another company. Which his goal was to not let that happen after I had taken so many years of work related abuse. He could see what was hidden beneath my talents that I was noy quite sure of yet. With his help and encouragement, I took the leap to try a pet portrait of our personal dog Sitka, thankfully it was a niche that I never thought was a capability of mine! I had so much fun and loved how I felt after seeing the finished product! Best risk I’ve ever taken Read more>> 

Melina Chadbourne

We are not professional podcasters. We are three Millennial Bostonians with a particular sense of humor that wanted to spend more time with each other. And that took the form of a podcast. When work moved us away from each other, it became so easy to lose touch, but this podcast is a way for us to connect over something that brings us joy. Our differing education, careers, and experiences allow each of us to speak to different things. Sometimes we agree, sometimes we disagree, and sometimes it’s a mixed bag. Either way, we always bust each other’s chops. It’s a fun cocktail of movies, culture, and our own family dysfunction. Read more>>

Melissa Watson Erickson

Taking the leap to open The Funding Studio was one of the most significant risks I’ve ever taken, both personally and professionally. Before launching The Funding Studio, I had a successful career as an in-house fundraiser. But there was always a part of me that felt something was missing—a desire to do more, to serve a broader community, and to have a more direct impact on the creative landscape across the United States. The backstory to this risk lies in my passion for regional storytelling and my frustration with the limitations that traditional funding models often impose on artists and innovators. I saw firsthand how many talented creators struggled to bring their visions to life simply because they lacked access to the right funding opportunities. Across various regions, despite their rich cultural tapestries, many areas were underserved in terms of professional support for artists and innovators, especially those with projects that had social impact. Read more>>

Hannah Morse

One of the biggest risks I’ve taken was making a dramatic shift from a career in women’s health to the world of aesthetics. I was deeply passionate about working in the Postpartum/Nursery and had always dreamed of a long-term career there. But over time, the intense physical and emotional demands of the role began to feel unsustainable for me. I remember asking myself, “Can I keep doing this forever?” I knew I needed a change—something equally rewarding but with better work-life balance and more control over my professional life, while still allowing me to connect with patients. Read more>>

Dariel E. Vega Seda

Being a dancer at least for me it’s always about taking risks because i have to deside on whether I go the “normal” or “standard” way or follow my dream. It’s always been like that because when you’re starting in this business you still have to have a normal job to pay your bills. The wish of every professional dancer is to live dancing and being able to make enough to just dance plus other things that comes with it. So in my case I am still thriving to make this goal happen in the meantime all it takes is risk, if you fail you learn from it if you don’t also learn from it to make you succeed. Read more>>

Naiqian Chen

Looking back at the pivotal moments in my life, I realize how often I’ve taken life-changing risks. At age 13, I left my home country and family behind to live as a boarder, marking the first of many bold decisions. A few years later, I made an even more dramatic shift: three months before the application deadline, I abandoned my liberal arts path and enrolled in an art school. That spontaneous leap set me on a new course, one that I hadn’t anticipated. Originally, I envisioned a future as a freelance editorial illustrator. Yet, somehow, I found myself standing in front of a classroom, facing a role I never imagined—teaching high school students. It’s hard to picture where I’ll be in the coming years or what I’ll be doing. Uncertainty seems to follow me at every turn.  Read more>>

Maria Martinez

One of the biggest risks I’ve ever taken was leaving my well-paying, stable job as a program manager at a hospital to pursue a mental health private practice, eventually expanding it into a group practice. Growing up as an immigrant, arriving in the U.S. at 8 years old with my mom and baby sister, survival was our main focus. As a child of immigrants, we’re often taught to be grateful just for having a job—security is everything. Leaving something stable to start my own business felt terrifying because it defied what was ingrained in me, both as a person of color and as a woman. But taking risks is a leap of faith—a faith in ourselves. I asked myself, “Do I believe in myself enough to know that no matter how I land, I’ll figure it out?” And the answer was yes. Read more>>

Despina Scandalis

Owning a business involves takings risks especially in the beginning! Once I graduated from Esthetician school and got licensed I was fortunate enough to dive into a paid internship at a privately owned skin studio here in Los Angeles. There I really learned how to create and retain a clientele and learned about advanced skincare treatments and products different from what I learned in school. After 2 years working there I felt ready to go solo. The owner was very supportive of me building my clientele as well as assisting with hers while she was unavailable. The opportunity showed me the financial dedication and commitment you need to make to build your own treatment room. Read more>>

Carly Church

Let me tell you about one of the biggest risks I’ve ever taken—buying a FIT4MOM franchise just a few months into the pandemic. You can imagine, I’m sure, how everything felt completely uncertain at the time. We were in the midst of lockdowns, people weren’t gathering, and businesses everywhere were struggling. But there I was, a mother of three little ones at home, looking at this opportunity to take on a franchise that thrives on in-person community and fitness. Everyone told me it was crazy to buy a business then, and honestly, part of me agreed. But I believed in the mission of FIT4MOM—connecting and empowering mothers. I couldn’t let the uncertainty hold me back. I knew it was a risk, especially with the kids at home and the world essentially shut down, but I took it on. And let me tell you, it was not easy. There were moments when I thought I’d made a huge mistake. With three young children demanding my attention and a business that had lost 75% of its clientele due to the pandemic, it felt like everything was on the verge of collapse. But I’m not someone who gives up. Read more>>

Cristina Tinoco

My fascination with the beauty industry has been a constant interest throughout my life. At the age of twelve, I took the initiative to shape my aunts’ eyebrows, helped my family prepare for various events, and even launched a small makeup venture while in high school. As a recent college graduate, I found myself reflecting on my long-standing dream of attending beauty school and ultimately concluded that it was a risk worth taking. The process unfolded rapidly; I made the decision to embark on a beauty career and began exploring schools the very next week. Within a month, I was enrolled in my program. Attending beauty school was a remarkable journey. Balancing a full-time job as a receptionist while pursuing my esthetician studies kept me incredibly busy. Then the COVID-19 pandemic struck, creating uncertainty for everyone. The challenges of school intensified, making the experience more difficult than anticipated. Despite these obstacles, I successfully graduated and shortly thereafter passed my state board exams, all during a global pandemic. Read more>>

Jose Manuel Torres

Let me take you back to the beginning of 2020, when the world felt like it was turning upside down. The COVID-19 pandemic was just starting to spread, and people were locking down, shutting their doors, and staying home. The future felt uncertain for everyone, including me. At that time, I was working out of my garage, experimenting with different herbal formulas and starting to see the power these indigenous remedies could have on people. My family and friends had already experienced incredible results, and I knew I was onto something special—something bigger than me. But there was a problem: I was comfortable in my garage. I didn’t have much overhead, I was safe, and I wasn’t taking too many chances. Yet deep down, I knew I had something that could help more people. My heart kept telling me that I needed to step out of my comfort zone if I wanted to truly fulfill my calling. I couldn’t stay small forever. Read more>>

Ar Ink Bmnrs

It was a big risk! I was working as an automotive technician in 2005-2010 Then the recession hit and they were letting people go. I had already started tattooing around 2006 and started my journey. I realized that the dealership was not gonna give me a raise and put me on my own. So I decided to quit. It all started with me, tattooing, and building clientele texting people that I knew for Tattoo work. And when I quit the dealership, there was no more safety net and I was on my own. The most scariest thing I’ve ever done in my life. I do not regret it, because I learned more about myself as an artist and grown my skill to a higher level because of it. And now 21 years later, I get to create art for a living and travel the world. Read more>>

Alicia S. Castillo

Opening my business was a risk in itself. I started with zero clients, besides a few family members. I opened using no loans, no huge savings, or fancy equipment. I didn’t even have a towel warmer or steamer while working on my first client. I knew that I wanted to work towards my own dreams, rather than spending my life working for someone else. In May of 2021, I decided to pursue my passion and opened Aesthetics by Alicia. As I worked on building my clientele, I focused on continuing my education. I currently hold over 15 Advanced Esthetic Certificates, and have built a full book of clients. Read more>>

Dianne Poinski

After many years of creating and selling hand-colored black-and-white photographs, I wanted to try something else, so I signed up for a five-day photo encaustic workshop in Portland, Oregon. Shortly after taking that class, a gallery approached me about having a solo show the following year. I said yes and told them I would exhibit original photo encaustic pieces. I knew this would either be a good idea or a bad one. As it turned out, it was both. The learning curve for this process is steep. While preparing for the show, I had many failures and created pieces I knew I could not show. There were tears and doubts, and many times, I was ready to give up and tell the gallery I would just be showing framed photographs. But I kept going, and after redoing some pieces a week before the show was to be installed, I was able to deliver on my promise. That was ten years ago, and if I had not scheduled that gallery show, I probably would have given up trying to learn how to make photo encaustics. Instead, it has become my primary art form and is what I show in galleries and my studio. Read more>>

Jeff Lopo

First and foremost I’m the pastor of small church in Chula Vista called South Bay Christian Alliance. We belong to an evangelical denomination called the Christian and Missionary Alliance (The Alliance for short). The Alliance was birthed in 1881 when Pastor A. B. Simpson organized a small group of believers devoted to experiencing Jesus in His fullness and making Him known to New York City’s marginalized dock workers. Simpson took a risk when he quite his prestige appointment at his church to start something new in his desire to follow God’s call, to bring His hope to the nations, and to carry out our vision of All of Jesus for All the World. I try to carry that same mindset and spirit into my business. Read more>>

Hehe

In 2018, I began to offer virtual doula services which included a membership-style online childbirth education and the world told me I was crazy. People said that you couldn’t possibly support someone in labor without being with them & that in-person childbirth education was never going away. I was convinced that they were wrong and if I wanted to positively impact as many births as possible, I was going to have to utilize the power of the internet’s reach. Fast forward less than 24 months later and the whole world shut down. Everyone was forced to offer virtual services if they were going to stay in business, therefore everyone had to pivot to offer online educational content in order to stay relevant. The (calculated) risk I had taken in 2018 had paid off because as everyone else was learning new platforms and delivery methods, our team was already familiar with such concepts. This allowed us to be able to grow during the pandemic and serve thousands of families as they prepared to have their babies in a time that was unprecedented and very uncertain. Taking risks can feel very scary and sometimes like you’re the only one that believes in your mission.. and that may be true at some points along the journey. But, if you have a clear vision and you are committed to making a difference, one little risk may be the difference between sinking or swimming! Read more>>

J. Robert Parker, C.ht

Well, taking a risk is certainly something I can speak to. I moved to Los Angeles with no planning, having never visited before and did so in under 2 weeks; it was the best choice I ever made. To give some context, this isn’t something I would do on a whim, but personal circumstances left me with a decision. I had discovered my partner of 4 years had a fiancé in another country (while they were visiting said Island nation) and suddenly found myself with nowhere to go and zero desire to remain where I was. So, I moved. I was born in Orange County and in a way, this was returning home. I certainly feel home. When you want to talk about risk, moving blind to LA seems like a fairly big risk but here I am! Twin Ravens, my online hypnotherapy practice, has a new home with me and even though it was sudden and high risk, I couldn’t be happier with where I am and how it turned out.  Read more>>

Dayton Moon

I was born and raised in Arkansas and moved to Missouri when I started high school. I always had big aspirations that the small towns I grew up in simply couldn’t fulfill. I knew I needed to make a move and take a risk to get myself out there. I watched an interview of one of my all time favorite music producers, Mr. Carmack, and he suggested to move somewhere that you have no friends or family nearby so you can focus on yourself and absorb the inspiration from your surroundings and harness that creatively. So I did exactly that. When I graduated high school I decided to attend a small technical school in St. Louis that taught music production and recording engineering. I had no friends or family nearby so it seemed like a perfect opportunity to start fresh. This was my first major risk. I updated my socials to my new location and within a week I had somebody (now a great friend) contact me through SoundCloud wanting to meet up and help me get on my feet in the scene there. I very quickly ended up learning how to DJ and started playing my first shows and competing in local beat battles. Read more>>

Hilary Opheim/davita Paul

A Serendipitous Partnership: From Pilates Conference to Podcast It’s amazing how chance encounters and small risks can blossom into incredible partnerships and friendships. That’s exactly what happened to us. We met in 2018 at a Pilates conference, where Hilary was teaching a workshop that Davita attended. Little did we know that this meeting would spark a journey that led us to where we are today. Just over a year later, Hilary moved to Los Angeles and opened her studio, serendipitously within walking distance of Davita’s. Davita, noticing a familiar name on the studio window, reached out to Hilary. Although Davita usually doesn’t make personal connections with local studios, something prompted her to email Hilary, expressing her interest in seeing the new space. Hilary, always welcoming, invited Davita for a visit and a chat. Read more>>

Dani Fiondella

One of the biggest risks I have taken was during the height of the pandemic. In 2020, I was working at a production company full time but when Covid hit, there were so many unknowns in the entertainment industry as well as most industries. I chose to take the time and make myself more competitive for the career I wanted but when the world was unsure of what it was going to look like, this was a risk. I risked money, time and my career by starting my own company and going back to school again. These were massive financial risks but gave me a reset towards the career I wanted and self confidence in my abilities. In such an uncertain time, I really didn’t want to sit and wait. I took action in my own way. Read more>>

Heidi Negron

My journey into starting my business is a blend of organic growth, passion, and perseverance in the face of self-doubt and personal loss. I was working in the corporate world, surrounded by the stability of a consistent paycheck, benefits, and the financial security most people dream of. Yet, amid this comfort, I felt a deeper calling for more—something that aligned with my values, my passion, what I deeply believed was my purpose. I had already been nurturing this passion quietly on the side. In the beginning days, I had been running a side hustle that began so innocently offering workout sessions to women before and after work in a simple apartment gym. At first, it was just a handful of women joining these sessions. Word spread naturally. These workouts weren’t just exercises—they were effective, empowering, and spoke to the needs of women trying to find balance in their hectic lives. It grew to the point where I carved out space in my home, turning it into a small, intimate studio for classes. Read more>>