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.

Sarah Silverman

At the end of 2021, after working on the front lines of the Covid pandemic for 1.5 years, I—like many other health care providers—was feeling extremely burned out. My role as a mental health provider in a major hospital center ended up being one of the most challenging times of my career. While helping others navigate the impact of the pandemic on things like mental health, sleep, and social relationships, I wore burnout like a badge of honor, but I knew I had to take a step back from conventional health care after feeling overwhelmed for months. For the first time in a long time, I took some time off and was able to prioritize my own health and happiness. During this break, I felt the nudge to start my own health consulting business and took a leap of faith. Read more>>

Jenni Hecht

In 2013, I was working a full-time job in a factory and working part-time as a photographer. I despised the factory job as it was hot, dirty, and hard on my body. When I received my tax return that year, I realized it would be enough to pay my bills for three months, so I approached my fiancé (now husband) and told him I wanted to quit my job and dive into my photography business full time. He was adamant that I keep my job and worried that we would be put into a situation that would hurt us financially, but I reassured him that if it didn’t work out I would get another job. Read more>>

Mish Fultz

I went from working at a local salon to renting a suite at Sola quickly. I realized I couldn’t grow anymore at the salon I was in. So then to escalate to a full on salon with other people a year and 9 months after opening up my studio was just so crazy. It honestly still feels like a dream sometimes. Learning who’s really there for me throughout this journey was also an emotional awakening. You lose a lot of people you out grow; but you also meet so many more people who choose to grow with you. Im working endlessly to make myself and my family proud of my salon and my choices! Saying all of that, I love every minute of it. Having such an incredible team has made this chapter all that more empowering! Read more>>

Mia Drewniak

Pursuing music is a rick. Pursuing any dream is a risk. But the outcome might be something truly amazing. When I started writing my songs I was so excited. I loved the feeling of having something to show the world. Something that I’ve created. I was so excited to put it out there, I would put everything, good bad – doesn’t matter. I was always so happy to see my peers work, so I thought – there’s nothing to be worry about – more than that – it didn’t occur to me someone could say anything bad. Read more>>

Deborah Newmark

When I was 17 1/2 my fiancé was diagnosed with a terminal cancer. I decided to move out of my parents house to live together with my fiancé so I could care for him. As you could imagine, this was a life altering experience. I thought I was just taking care of him but what happened was I learned about love and the fragility of life that changed me forever. I could never not be grateful for the precious gift of life after that. It also opened my eyes to appreciate when you think you are doing something for someone else you are also doing it for yourself in very profound ways. Maintaining my positivity, even in adversarial situations, was something I have embraced throughout my life which helped me get through the loss. Read more>>

JENNIFER MANGAN

Taking a risk can seem particularly scary, like diving off a high-dive for the first time. Heart pounding, you question whether you should even do it. The answer: of course you should! Seize the moment, and wonderful things will happen. I took a huge risk when I asked my now-partner Michael Fisk to join me in forming The Business of Creating Institute. BofC grew out of a completely different project, you’ll be intrigued to know, and now we are over 5 years and 32 panels in. Read more>>

Jeff Curry

II have a long history of embracing risks in my life. As a former professional skier, I endured numerous bone-breaking injuries without even recalling their exact count. During one unfortunate injury that confined me to the couch for months, I chose to utilize my spare time constructively by working towards establishing my own company. Amid the darkness of that period, I made a conscious effort to focus on the positive aspects, leading me to conceive the idea of the lantern logo. This symbol served as a reminder to always seek the light, even during challenging times. Subsequently, I embarked on one of the most significant risks of my life: leaving my job to fully pursue a career in leather crafting. The prospect of supporting myself solely through the sale of leather goods was undeniably daunting. Read more>>

Kimberly Henriquez

Taking a risk on opening Obra of Love just by following my intuition was both exhilarating and terrifying. On the one hand, it was amazing to feel so connected to my purpose and to know that I was following my heart. On the other hand, it was scary to put everything on the line for something that was so uncertain. There were many times when I doubted myself and wondered if I was making the right decision. But I always kept coming back to my intuition, which told me that this was the right path for me. And I’m so glad that I listened to it. Read more>>

Daniel Booter

One of the biggest risks I’ve ever taken was leaving my high paying tech job and starting my company, FCI Group. As a visionary leader I took the approach of solving a problem in a very niche market in the Hospitality Industry, by providing our Investors access to high quality, high, barrier to entry market Investments and providing high returns to our Investors. I knew that my job in tech could only take me so far and I wanted more. I thought about ways to do something more fulfilling for myself and was able to use my connections and think of the idea to create a real estate syndication firm. Read more>>

Olivia Crawford

I’ve never considered myself a “risk taker.” That title was always reserved for my older brother growing up. Even now, close friends and family members wouldn’t describe me as such, and for good reason. I was, and still am, calculated, cautious, and careful with my decisions. Constantly weighing my options, talking it over, and yes, making pros-and-cons lists (never underestimate the power of a good list!). Recently, however, I took a rather big leap of faith to resign from my stable, comfortable, and secure full-time job and begin my own private practice, Little Sprouts Speech Therapy. Don’t get me wrong, I still weighed all my options, but at the end of the day, I made a heart-led decision and took the risk. I gave up a secure and stable job that wasn’t fulfilling me to pursue a passion that feels less stable, but far more rewarding and purposeful. You know what they say, “no risk, no reward,” and I have found that to be completely true. Read more>>

Heather Sky

As I was completing the third decade of my life, I was also facing a multitude of transitions. I exited a nearly decade-long abusive marriage, leaving me as a single mother, and decided to re-enroll at university in order to complete my education. At the end of my degree program, I also decided to enroll in a simultaneous 200-hr yoga teacher training program. Between YTT, school, and motherhood it’s fair to say I was in the midst of a difficult (but purpose-driven) balancing act. I graduated from both university and my training program within a week of one another. Read more>>

Michelle Reid

In 2013, I moved to Chicago without a job and nothing really planned at all except a determination to leave my home town- Dayton, Ohio. I graduated from The Ohio State University in 2013 obtaining a BFA in Dance. Promptly after graduating I had my sights set on Chicago so I attended Hubbard Street Dance Chicago’s summer Intensive in the hopes of jump starting my dance career and getting a feel for the Chicago area. After the intensive I moved to Chicago with one of my close friends. I danced professionally with numerous companies in the City- Joel Hall Dancers, Aerial Dance Chicago, Lyric Opera, Winifred Haun, and Banks Performance Project. During my time dancing and Performing with Aerial Dance Chicago, I started to shift into doing photography. Read more>>

Allison Price

You are never too old to take a risk and pursue your passion. I did this almost 10 years ago when I took a risk and left my job as an elementary school teacher to become a Traditional Naturopathic Doctor. I knew I always wanted to be a teacher. I loved teaching! However, I felt like there was a piece missing in my career. While I was an elementary teacher I was also teaching yoga after school and on the weekends. Health, nutrition, and fitness have always been my “hobby”. I was always reading books or listening to podcasts about holistic health and the latest health trends. I also became a client at Nutrition & Healing Center as part of my own holistic health journey. Read more>>

Ana Cruz Hollingsworth

As I look back, I realize there were many risks taken throughout my life. Some risks were taken out of necessity and with no other alternative, and others were taken because despite the fear, I knew it was the best decision at the time. The first big risk I took was at the age of 22, when I left my native country, Mexico, and came to the United States in search of my American dream. A very difficult, scary and risky decision, especially since I didn’t know everything that would happen in the next few years before I saw my dreams begin to take shape. Read more>>

Jessica Jefferson

Building my practice has been one of the most daring risks I have taken on in my life. As the first in my family to graduate from college, earn not one but two advance degrees, I am not averse to challenging myself to do better. I believe that challenges allow you to learn more about yourself and those around you. Now while building a practice can be challenging on its own, but at this time in my life it was more than just a risk, it was something I needed to do. Read more>>

Airyen Vay

Probably the biggest risk I have taken so far was to move from Romania to US by myself. I always dreamt of making it big in the music industry so there was one point, when I realized that in order for this to happen I will have to get out of my comfort zone and make some big changes in my life. First two weeks were hilarious, I had no idea of what I was going to do and I didn`t know one single person. I think I was a bit delusional but If there is one thing that I proud of, is that I didn’t give up back then and I decided to stay, despite the circumstances. .I am a firm believer in listening to your heart when making a big decision and despite the challenges, I am convinced that eventually persistency and dedication will pay off. Read more>>

Lisa Hickey

In 2014, after 14 years, I left my job at as Marketing Director for one of the most successful concert promoters in the world. I started when it was just a small office consisting of two people and a dream to produce a music festival in Austin’s Zilker Park. When I left in 2014, there were 150+ people and a portfolio of music, food, and wellness festivals spanning multiple continents – a meteoric rise that was one of the most significant adventures of my life. Read more>>

Katie Sharp

One year after my husband and I got married we had the opportunity to move to Japan with his work. Neither of us had ever been to Japan or had even considered vacationing there before the opportunity to move was in front of us. So we boarded the plane with our one-way tickets to Nagoya to begin life in a country and culture that was vastly different than where we were currently living in Cincinnati, Ohio. Japan was so different – from driving on the other side of the road, to having six separate trash/recycling cans required in our small high-rise apartment, to learning how to not eat or drink while walking – the Japanese truly appreciate slowing down and sitting still to enjoy a hot cup of tea or coffee! Read more>>

Alaya Lee

From my earliest memories, music was my native tongue. Melodies were interwoven into the very fabric of my being. I exchanged ordinary childhood moments for piano lessons, adolescent gatherings for rehearsals, and countless nights of sleep for the pulsing rhythms of improvisation. A cycle, repeated for 18 tireless years. Three months post-graduation, a degree in Jazz Piano in hand, I found myself back in Taiwan. Seated before the worn piano of my childhood, the familiar notes flowed from my fingers, my hands moving with machine-like precision. But, amidst the perfect chords, something vital was missing. Read more>>

Kimberly Cowan

“Taking a Risk”…this resonated with me the most. So allow me start from the beginning. As an artist and painter, it is engrained in me to always keep my creative eye sharp, but as Capricorn, that creativity MUST come with a steady paycheck. I had never questioned my journey in the industry as much, until I moved to California with friends on a whim (1st risk). After that, I made it a point to stay in the fashion space, whether retail or as I thought, doing fashion sketching for magazines. But I soon realized, that was not my path. Read more>>

Nicole Campbell

After the loss of our babies, we took a leap of faith and started our non profit, the Hayden & Crue Project. We weren’t really sure exactly where this road would lead us but we knew exactly what our mission was going to be, to give back to the unspoken hero’s who took care of us in our darkest of days and help the families who may face unimaginable loss like ours. Quickly, we decided to take a massive risk and give families exactly what we wished we would have had while losing our babies, access to valuable time that we so badly wished we would have. That’s how the Angel Suite came to be. Read more>>

Rory Alvarez

Coming from Chile a place with different social standards and structures it was hard to be a free thinker or to have a voice that was not going to be shot down. Sometimes where we come from might make it difficult for us to thrive and live out of your own passions and that’s where taking risks is the best thing you can do. If they say up ,go down,Right? Go left. Let nothing define you but you. Not belonging sometimes is the best fuel to find your voice as an artist. Read more>>

Marlin Darrah

It’s always worth taking a risk, to pursue your dreams. Many advised when I was young to not follow a path into the creative arts. They said it there was never a guarantee of income. What will you do for retirement security? But I’ve learned that through a life of traveling and meeting people around the world – there are certainly no guarantees, at all, in life. Fortune favors the bold. I’m so glad that I did ignore the practical advice of certain family members, and instead I followed my heart and dreams. Read more>>

Claudia Castillo

I have taken risks throughout my life as I believe that is the only way for us to learn, make an impact and move forward. A major risk that I took was to leave my home country of Colombia where I had studied social communication and was a radio and television producer. Since my love was always in the arts and design, I chose to come Fort Lauderdale to study at the Art Institute and to transition my career. The opportunity to live in an area that had more cultural diversity and an LGBTQ community was a motivator for me. Read more>>

Danielle MORRIS

I never really thought of myself as possessing an entrepreneurial spirit until I stumbled upon my passion with Ardor. I have always been creative but just never found what I was actually good at. I have learned that the world is filled with risk and uncertainty, which these days, that feels truer than ever. However, it’s important not to give in to fear. Fear clouds your judgment and can take away your view of the big picture. While struggling to pay student loan debt, I had been following the Dave Ramsey plan, working overtime; doing everything I could to stay afloat. During this time my mental health was also suffering, just doing what I could to survive and get through each day. Read more>>

Miguel Crandell

Being in the game as young as I was, when it came down to thinking about college I knew that I would have to make a huge decision. I was blessed to have extremely supportive parents. No matter what happened in their day to day lives, they still managed to always provide as best they could for my sister Melody and I. Part of me never thought I’d ever see the day I would live in another state, my whole life I saw the same cold streets. I dropped everything I had in Denver to pursue my career as an entertainer in LA. Working as a Pro Assistant at Hollywood Vibe Dance Convention, it opened many doors for me prior to my move. It had also played a huge influence on wanting to take my career to the next level in Hollywood. Read more>>

Fabienne Roc

I’ve been working as a Creative Director in the entertainment industry for the last few years. While I’ve loved it, anyone who is paying attention right now knows it’s not the best time for creatives. There are so many layoffs, strikes, and pivots within the industry — it’s become pretty shaky and uncertain like many other industries who are feeling it too. When COVID hit, the time really pushed people to look beyond their careers, accolades, and surface-level things. Questions like “Who are you outside of your career/job?” were very loud during those three years, and I think a lot of people began looking within to find those answers or at least had a curiosity spark. Read more>>

Kayla Rodriguez

i’m so grateful for every risk I’ve taken. Even if it didn’t go as planned, there was always something I learned to take with me on my journey. The risk that first comes to mind is leaving my full- time job back in 2021 to pursue coaching full time. I was a full time nanny in NYC and had worked every single day of the pandemic with no breaks while working my business part time. It was so stressful and overwhelming. There were times I would get anxiety on my way into work because I was mentally checked out and unhappy. I was unhappy at my day job and super happy with the work I was doing as a coach. Business was doing well and I slowly warmed up to the idea of leaving my job. If I’m being honest the thought of that really scared me. I grew up in a Latino household where all I was taught was stability in jobs and weekly pay checks. Read more>>

Will Hubert

Every day, as an artist in our society, I embrace risks that come with pursuing my passion. It’s no secret that those of us on artistic journeys often encounter skepticism, with people suggesting that our talents may not sustain us financially. These notions are ingrained so early that they can become internalized, shaping our beliefs. Yet, this only highlights the incredible power of creation that resides within us. I’m fully aware of the risks I take each day, investing my time, energy, and heart into a path that might not offer the stability of a conventional life. I acknowledge the uncertainty that accompanies living with debt, lacking insurance, and without a traditional retirement plan. While I could opt for a more conventional career and attain a decent livelihood, I consciously choose not to. Read more>>

Reginald Jones

Often times, the term “Rocc Bottom” is seen as a negative or bad place to be. Over the years, God has shown us that we all need that time at Rocc Bottom. It is at Rocc Bottom that you learn your strengths, your weaknesses, who your true friends are, and most importantly, how to get God’s attention. Rocc Bottom, even though it’s not our final destination, it is a necessary destination in all of our lives. It is what you do at Rocc Bottom that will prepare you for your elevation. ​Read more>>

Kathryn Krasovec

I have to say that I can’t pinpoint one risk, but rather a series of many risks that have defined my career. When I auditioned for the Lamont School of Music at the University of Denver, where I completed my undergraduate degree, I was awarded a full tuition scholarship to study vocal performance. I guess that was my first real risk, because I had no idea what I was about to embark upon! My next big risk came when auditioning for Masters programs. I auditioned for all of the major music programs in the United States and after careful speculation, I ended up at The Indiana University Jacobs School of Music. Read more>>

Bonnie Fitzgerald

“Dare to fail”. I heard those words from my first artist mentor, and I have made countless life choices as those words rang in my ears. Read more>>

Joey Villalobos

My wife and I moved to LA in the middle of Covid with a newborn baby and a preschooler. How’s that for a risk? I got the ball rolling on my musical career and hit an all-time-high in December of 2019 and had already been making moves to follow my wife from Texas to LA to pursue more artistic opportunities before the pandemic. With the slow down of live music, it was a massive risk to leave when we did. I only had my Gibson rep and the band that I had been playing with was based out of San Antonio, Texas. We picked our home from pictures on the internet and arranged a multistate move over the span of a few weeks from my couch in Texas having never been to the area. I literally saw our home in LA for the first time while I was moving boxes into it. Read more>>

Leah Holston

The best risk you can take is on yourself. No one else will ever believe you the way only YOU can. I believed in my ability to become a photographer in 2013 but I also took a risk in 2022 and opened my own flower shop. It’s a risk to put aside the sure thing of having a “regular” job. In 2010 I had my first son, Jackson. I knew I wanted to document him growing up and I wanted to do it the right way. I started studying photography and learning how to shoot in manual mode, proper lighting, and editing. I won a few online classes and 2 years later I started photographing families and weddings. Read more>>

Candice Jarvis

Growing up, I was always different than my peers. I never fit in despite my multiple efforts and I didn’t have any tangible talents or gifts. I have always been able to see beyond the surface of things and people, however, I never saw it as a strength. I’ve always like to write/journal, I wanted to help people (don’t we all) and I wanted to be in the medical field. That dream quickly dwindled after going through one of the darkest times in my life…oh and passing out in the hospital after seeing blood. Read more>>