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.

Alyssa Pfennig

In 2021, I moved from Indianapolis to Mexico with my 2-year old daughter. Now, we’ve lived in San Miguel de Allende for nearly three years and life is more beautiful than I could have ever imagined. My heart always longed to live in another country. I had traveled the world and always thought I would move somewhere with a partner, but that never happened. After I had my daughter, moving abroad still called to me. I had my little partner. It was time. So, in January 2020, I put my yoga studio and wellness center that I owned for over five years on the market and had a buyer lined up. I knew that our lease was up for renewal in April, so I was either going to sell it or close it, one way or another. Read more>>

Lexia Perea

Last summer I chose to live life in fulfillment & let go of temporary satisfactions. In the peak of July 2023 it had been officially over one year surviving day to day ‘life” in La La Land, California. Though Los Angeles is full of bright lights, getting past the gates to make strides in the real Hollywood was harder than I thought. School was one thing but actually stepping out as a creative on your own definitely takes guts & constancy, which I hadn’t mastered yet. Within that year & some post grad. I’d been through a world wind of jobs that were so miscellaneous no skill that I gained could correlate or translate to the next. Forgetting about my own divine talents, I was caught in a fog, just trying to survive. I was lost. Read more>>

Silly Genius

It’s summer of 2019. I had collaborated with my crew on 3 murals back to back that was starting to raise my profile outside of our immediate circle of artist friends and peers. My email was slowly filling with inquiries about murals and potential creative gigs. But I had a full-time job. A full-time manual labor job where I worked between 60-80 hours a week, often not knowing what time we’d go home after clocking in. It was a warehouse that primarily filled orders for contractors building homes and apartment buildings. One order would be a toilet, a bathtub, and some pipe fittings. The next order might be for 10 showers and 300 ft of copper pipe.  Read more>>

Jason Coontz

After years of working in the oilfield industry and making a comfortable salary of roughly 100k a year, I made the bold decision to leave it all behind in pursuit of a passion that only promised a fraction of that income. The passion I was chasing was to open my own gym. I had always been deeply passionate about fitness and helping others achieve their health and wellness goals, and I knew that running my own gym was where my heart truly belonged. So, despite the financial risks and uncertainty that lay ahead, I made the leap and left my high-paying job to make my dream a reality. Read more>>

Martha Gaffney

I decided to go back to full time residential real estate brokerage a little over a year ago for a couple of main reasons. The number one main reason would be, we had an 8 month old baby at the time and we had just bought a house in the Hudson Valley. Therefore we needed the flexibility between our move and baby and we also had no close by relatives we could use for child care. That forced us to take the plunge and go at our real estate business brokerage full time. Read more>>

Shannon Spilker

Taking a leap of faith can sometimes be the scariest crossroads we will ever face. If you would have told me 5 years ago that I was going to leave the Accounting industry to become and teacher and a photographer I would have laughed. It took a leap of faith to change that fantasy to a reality. Growing up, I always had a love for photography, and I was gifted my first real camera (besides a cheap little digital camera) when I was in the 7th grade. Throughout high school and college, I was taking photos whenever I could, but after graduation I just stopped. I had gone to school to be an accountant, and for the first four and a half years of my professional career, all I cared about was work.  Read more>>

Alexa May

One risk that I have taken was moving across the country from Nevada to Virginia. I was following my ex-husband as he is in the military and we have a son. At the time I knew we had issues and that it was probably going to be hard or a mistake. It was, unfortunatley. I struggled with loneliness and wanted to find friends and have genuine connections with people. All I knew that I liked was live music and the beach so I decided to start going to EDM events held in local bars. I was able to meet new people who became some of my best friends to this day. I also got the opportunity to start Djing locally at the venues I would go and see my favorite artists play. Read more>>

Brynn Allison

Taking risks is part of the creative process. If I’m not constantly scaring the shit out of myself, I’m not pushing myself hard enough in either life, writing, performing, or creating. When I graduated from theatre school last May, I felt directionless; it was both thrilling and terrifying simultaneously. I’ve never felt so alive. This year I moved to LA from Michigan, and I started writing about this incredibly transitional period of my life and redefining what “home” means to a 22-year-old newborn adult. Shortly after the move, I was connected with a studio in Boston whose mission was crowdfunding and music all in one.  Read more>>

Caleb Gutierrez

I’ve been creating since I was 13/14 years old. When I sold my first art piece (framed) I was 17 years old. Didn’t really know what to make of it, that I could make money off my own art. I have always worked in restaurants and cafes at the same time I was making work. It would frustrate me a lot not being able to create and being stuck at work for 8 hours washing dishes. All sorts of different jobs. Having these great ideas for a painting, song or installations while I was on the clock. Would make me wonder if I was really running out time being here. Read more>>

Anisa Genesis

During preproduction for my first short film, “I Used to Know Her,” I got fired from my job. Fortunately, I had already bought the props, but I knew I would have to figure out everything else that wasn’t taken care of. As I continued working on other projects, I realized that it never got easier. In one way or another, my projects—or the projects I was supposed to be part of—weren’t guaranteed to happen. I constantly had to figure out how to pay for things, how to get to locations, or even how to execute an idea that was more complex and different from anything I’d done before. Read more>>

Emily Kramer Throckmorton

When I was 20 years old I felt lost. I was in and out of different colleges, didn’t know what I wanted to do as a career (I was always into sports so academics came last.) I moved back home and started lifeguarding at our local YMCA. I didn’t feel satisfied with my job so I decided to take a leap and try out for the Virginia Beach Lifesaving service (ocean lifeguard position) that was 2 hrs from my parents home. I didn’t know a single person but took a chance on something that I thought I would be good at, maybe a fresh start. I got the job, rented a room (at the time I found on Craigslist! Read more>>

Adam Joshua

Starting my own business was a challenge from the beginning. It all started with an idea. In 2016, I decided I wanted to own a production company after bouncing back and forth between 9-5 jobs. I began with video production and photography, since that was all I knew how to do at the time. My prices were cheap, cheaper than anyone EVER. Over the past 8 years I worked on projects like feature films, reality shows, documentaries, and short films. Most of these projects were provided by another company and so my company sat dormant while I built my own skills in the industry. Read more>>

Eric Olvera

When starting this band, I was unsure what would come out of it and how much work would need to be put in. I had always wanted to start a band and It’s something that if I didn’t do now, I know I would regret it later. I live a comfortable life being supported by my parents in all avenues, so pursuing something that has no guarantee and is incredibly hard to do full-time was daunting. I decided to take the jump a little over a year ago and although members have come and gone, I still have plenty of great memories and am still working towards my dream of having a full-time career in music. Read more>>

Shawna Corkins

I’ve had my small business with my Husband as more of a hobby since 2017, We made cosplay weapons and i started to do some Baby sensory blankets for friends who was having kids. Baby sensory blankets have different texture material to stimulate the brain during tummy time with a soft side for relaxing if parents wanted to cuddle/ play with them on the ground. I also started making No Sew Fleece Blankets for Cancer patients i knew close to me. Fighting Cancer is a rough thing to go about and hearing the story from my aunt how people always said that the Chemo medicine was always cold and patients were cold and bringing blankets with them to keep themselves warm.. Read more>>

Reece Palamar

Quitting my first brand was a big risk for me but I had to do it after my first week with my second one. I created a separate gaming and film brand around the OG’s of youtube and their style of content. I used that to grow my first brand. But after the success of my ReeceIsRandom brand in its first week. I decided it was time to make a change, especially after achieving 100k followers in just 10 days. Read more>>

Caryssa Sornia

Almost 12 months ago, I, along with my partner Jake Cassady, embarked on an exciting journey to enhance education in the Panhandle of Florida. During a brainstorming session, I recognized a need to strengthen the community and expand educational opportunities for professionals in the Pensacola area, particularly those who have graduated from The Cassady Academy, a local trade school. Read more>>

Dina Gusovsky

I had a pretty comfortable and stable career as an Investigative Reporter/Journalist. I’d broken big stories and had received accolades, but there was always something drawing me to comedy. After years of hustling, I got an opportunity to join the Writing team at Late Night with Seth Meyers. It felt thrilling but also terrifying. I wasn’t a spring chicken anymore and I had no idea what to expect in this new position — but I’m so thankful I took the risk. Sure there were bumps in the road — there always are — but I also knew this wasn’t a road too many people get to travel (apologies for all the cliches, feeling sentimental!) and so I tried to approach each challenge with a healthy amount of gratitude and fear. But mostly fear. Read more>>

Koji Ono

Actually I was majoring in the Law at my university but I wanted to pursue my dream so I decided to go to performing arts industry after graduating from university in Japan. This was my first time to take a risk. I had no guarantee to make a living with this industry but had a firm decision. Fortunately after a few years later I could make a living with my performance jobs. And I kept working in Japan over 12 years as a musical actor. But I can’t stop my own dream that not only a performer but also an organizer or a producer I want share the Japanese musicals with all over the world.

Asia Joy

The biggest risk I’ve taken in this life was granting myself the permission to unravel without bias or judgment. Releasing myself from the roles and expectations that were placed upon me since youth. And making it a point to protect and honor those discoveries regardless of what or who I would “lose” in the process. The fear and mourning that came with this decision was crippling. In fact it pushed me into a deep depression. I never realized how much I anchored my worthiness to the roles that I actively resented. It’s a conflicting feeling to rest in. Having two parts of yourself pleading at you to let them live. And even though I knew which one I was choosing this time, it didn’t make it easier. Read more>>

Roybert Echeverria

Leaving my country family and friend to come to USA following my dreams even tho I just finished dentist school at the time! Every fight I have is always everything on the line, kill or be killed , every fight is the most important fight of my life, could be 1 step closer to my dreams or 3 steps back, everything has to be calculated, and the risks are even and nothing is guaranteed!! That’s my life DAILY Read more>>

Linn Yong

I left the big cities of Singapore as a Product Designer to join my then fiancé in the small forsaken town in Sandakan Sabah, situated in Borneo Island. Together with zero experience in the hospitality business , We slowly rebuild our run down family hotel that was built in the 1960s & from I kicked off my first of 3 restaurants across 2 cities as a self -taught chef. Even for my husband who grew up in Sandakan , it was a difficult adjustment moving back home , The family hotel property is situated in a seedy part of old town, One day while standing on its flooded water logged rooftop we thought it would make an amazing bar and dining space and if all else fail we would at least made a safe haven for ourselves. Read more>>

Michael Kivland

Starting this business was the biggest risk I have taken. I was working as a salesman for 12 years. In those 12 years, I had a lot of success – I made good money, but it didn’t matter to my psyche. I wasn’t happy. The role I was in for 12 years was toxic. The people I worked with were toxic. It was ripe with every toxic workplace element you could dream up. A CEO born out of nepotism, backstabbing employees, lies from upper management, unqualified promotions, etc. You name it the ailment and it had it. My psychology degree was telling me that I had to leave for my mental health. I was stressed, tired, and worn down. It was time to break the chain. Read more>>

Syeara Dunlap

Taking a risk is synonymous with choosing to work out of passion and purpose, which has to be the biggest risk anyone (including myself) can take. Working out of passion and purpose is my life changing risk, because (in each stage of life) that choice is always accompanied with smaller risks and decisions that could either keep one in alignment or stray them away. Read more>>

Sarah Elhourch

I think it’s important to note before getting into it that every choice we make is an educated guess. We make choices based on a number of factors, and often times a big factor is how secure, safe, or stable this choice is. I believe that is the one factor that could use a little flexibility and here’s why. Read more>>

Destiny Herrera

In the beginning of 2023. I was a stay at home mom to a 1 year old. I was home 24/7. I felt like I was losing myself. I had money saved. Not sure what I wanted to do with the money but it was just sitting there. My partner was fetching ideas on how to get me involved with a hobby or “side hustle” so I can feel better. Nothing caught my eye. I wanted to be something more than “just a mom”. I loved being a mom so much, but I knew that couldn’t have been my only label. So I continued to search for something. We came across the photo-booth world. It intrigued me. Read more>>

Sandy Cowen

I’ve written three books from age 74 to 78; the book before those came ten years prior. All four of those books were triggered by a significant risk I took nearly 40-years ago. Making the choice I did, made it possible for me to become an expert in a field I knew nothing about before. Two of those books are on holistic healing, the first with impressive endorsements. In retrospect, it’s crazy because I never considered myself a writer in my profession, but the impact of what happened after I took that first leap of faith changed my health, my life and compelled me to share that information with others. Now, at 80, I can honestly say that there’s something to the adage—no risk, no reward. Read more>>

Dior The Chocolate Doll

The biggest lesson I have learned from what I have been through is ..If it’s in your heart ,don’t be afraid to take chances and risk. If you believe in your self and God, your dreams can, and WILL be fulfilled. Never allow anyone to make u think otherwise. I had to really learn that because there were times when I didn’t have support. Times I was in a relationship and being told my vision would never happen. Or I would never become the person I am today. Negative vibes like that makes you doubt your self at times. You just have to look past it and put your trust in yourself and be your own team. Look at yourself in mirror , adjust that crown and make them eat those words right up with your success. Anything is possible when u believe and have faith. And having someone that pushes your greatness is always a plus too. Read more>>

Moriah Mcnutt

I was born and raised in small town Indiana. I shot my first wedding in 2017 and quickly grew my business. By 2021 I was shooting 25 weddings a year. In November of 2021 we picked up and moved to Jacksonville. At the time, I had started an online boutique with a business partner and took a risk of moving to Jax to open a store front. We were open for about a year and a half. Being a storefront owner took almost all of my time and my photography business took the back-burner. Read more>>

Lisa Elsis Amy Scotti

Both Chef Amy and I (Chef Lisa Elsis) dreamed of being pastry chefs as small children. Our parents dissuaded us, telling us that only men were chefs and women could not earn a living baking professionally. I became a Stockbroker and Amy became a Speech Therapist. We both continued to bake and cook for friends and family, but had to put the dream of doing it professionally aside. During 2020 and the advent of COVID-19, Chef Amy and I actually met virtually for the very first time on a food blog. We discovered we shared the same childhood dreams. Once the restrictions of Covid eased up a bit, we actually met for lunch in a parking lot under a tent and in that one moment became friends for life. We spoke of our lifelong dream of becoming chefs and decided that it was time to stop being afraid, to act in spite of the fear. Read more>>

Jarieka Potts

The first risk I took was betting on myself. I started when I was 10 years old and I wanted to make some money for myself. I started in lawn maintenance with equipment from the house. Having only a lawnmower, I borrowed, an electric weed eater, electric hedge trimmer, electric blower, and drop cord from my God Father. With all of those items including a gas can, either in my hand or Tetrised on the push lawnmower I was pushing around the neighborhood to see who yards needed cut. I lived in a codasack, my first yard/client was my next door neighbor. From one, grew to four within a few days of consistently going out. I gave my number to my clients so that they could contact me if I was needed in between or scheduling of every 2 weeks. Read more>>

Susie Castellion

Starting a Cattery with importing from Europe the finest cats to start was a huge process. Making sure they get the best care along the way. Health testing the kittens to make sure health is top notch to breed. It is a gamble but I was lucky to start with healthy parents. Read more>>

Leah Severson

Twenty years ago, I made what some might call a “bold move”—others might call it “pure insanity.” I quit my full-time gig as a television news producer to dive headfirst into the world of portrait photography. Why? Well, let’s just say the idea of capturing smiles seemed a lot more appealing than chasing breaking news stories. Just a year later, my husband looked around, decided he wanted in on the fun, and quit his full-time job too! So there we were, two slightly sleep-deprived parents with two kids under the age of three, trying to run a business. It was like herding cats—if the cats were toddlers and the business was a juggling act of epic proportions. Read more>>

Daniel Lamb

It’s hard to have a simple relationship to “risk.” But Read more>>

Natalia Martinez-kalinina

I learned how to ride a bike at 21 years old. That same year, I found myself riding around West Lake in Hangzhou. Escaping, dodging, I had half-circled the lake when the lightning first heralded the oncoming downpour. Soon, the rain began to fall in fast diagonals, racing down from the darkened clouds. My contacts shifted, my vision blurred, and my clothes were edging dangerously close to transparency, but with my feet firmly planted on the pedals, water streaming down my face, and the bike skidding, I smiled broadly through the fat drops. Read more>>

Ec Michaels

From a career perspective, the biggest risk I’ve taken was leaving an organization that had given me my first “adult” job, supported my education in animal welfare, gave me a career path/promotions and generally offered a plethora of additional opportunities. It was comfortable and I was quite content. I knew that while I had experienced exponential growth in my career, that there was potentially more learning elsewhere. Read more>>