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.

Jesse McCarthy

When I first thought of starting a podcast connected with my work in early education, I had some doubts, including self-doubt. -I don’t know anything about recording, so what will I do with that? -I don’t know if this thing will be successful, so what if I just make a mess of things? -Do I even have the time for this?? But I had a lot I wanted to say about early education and parenting, especially in Montessori, so I thought, ‘Let’s just hop in and see if people find value in this..’ They did, and I enjoyed doing it. Read more>>

Caity Eng

As a teen, there are limited opportunities for social media/content creation internships and work. I am extremely passionate about social media and content creation, and I am dedicated to applying for opportunities, no matter how small of a chance I have of getting it. A risk I took was becoming a teen social media manager and influencer/content creator. I first got into social media work by applying to be a social media team member at Aid2Day, a startup non-profit, when I was 14. Read more>>

Josh Rhett Noble

“The greatest risk is the one not taken.” The entertainment industry is an incredibly volatile, unstable career to embark on. Your entire livelihood relies on those in charge believing in what you bring to the table as an artist. There’s great risk in following the path as it is. However, making the decision to uproot your life and move back home after years of garnering connections in another city was an enormous risk…and one I now know I would do again in a heartbeat. Read more>>

MARIA ANDERSON-MOTON

The pandemic brought the best out of me! Originally, I worked multiple job and was extremely unhappy. Being away from my husband and kids caused me to mess so much time. This time I am unable to get back and to think it was from companies that gain while I lost. In the past I wanted to be an entrepreneur but was afraid of failure. In 2020, I decided to take that risk and never looked back. Some family and friends questioned my actions and made several attempts to point out the negative aspects. Read more>>

Bri Wenke

I recently packed up several large paintings and flew to London to exhibit my work for the first time internationally. Traveling with large original work was terrifying on its own, not to mention that our checked bags were lost (and since recovered) on the returning flight. The cost was high to make it all happen, but I knew that I needed to take a bigger step, to expand my network. and experience a taste of a different market. I am now in conversation with several galleries in the UK, and feel incredibly inspired upon returning to my Charleston studio having met so many new people and artists. Read more>>

Joseph Sullivan

I moved out of my home permanently at 20, across the country to Los Angeles, CA. I didn’t have a position lined up or a network at the time and had never been there prior. My one local friend then was in an entirely different industry. Despite the culture shock of a different coast and lacking resources, I pushed forward and always ventured into new spaces. Within two-weeks I was conducting an internship with the Grammy-awarded studio behind RnB icon, Frank Ocean. Read more>>

Alex Svoboda

For years, I was a closet musician. I played guitar alone and I made sure to only sing behind closed doors. I always dreamed though, of sharing my music with the world. My biggest goal was to someday play for an audience and to perform the songs that I secretly wrote. After college I took a job and moved to Big Rapids, Michigan. This small, rural, farming town was lonely at first. This led me to spend hours with my guitar in my little apartment. I so desperately wanted to share my talents with the world but I didn’t know where to begin. Read more>>

Crystal Porter

Starting a brand-new business with no real prior experience in the “World of Weddings” was a big risk! Looking back, naiveté kept me blissfully brave! The other factors that have kept me afloat are the support of my husband, family, and fellow wedding pros; the fact that I have the personality of “glass half-full” (and its probably wine! So… woohoo!!); that officiating a wedding ceremony is such an honor; hearing the joy in couples’ voices as they describe how grateful they are for a ceremony that is warm, sweet, romantic, fun and unforgettable… Read more>>

Jesica Yap

I am a proud second-generation Indonesian of Chinese descent. For the first 17 years of my life, from kindergarten until I graduated high school, I lived in a small town in North Sumatra, Indonesia. My family never moved around. I only knew one home until I left for college. After high school, I moved to Kuala Lumpur, Malaysia, a vast cosmopolitan city that is worlds different from my hometown. I did my college transfer program there before relocating to Boston. Read more>>

Mandi Sabourin

For years I had a dream of being my own boss. Starting a business either on my own or with a partner. I didn’t have a clear vision of what I wanted to do, I just knew that one day I would be an entrepreneur. I started working when I was 15 and was a loyal and reliable employee. Never having gone even a month without a job. Read more>>

Jaida Whitfield

It was the top of September 2021. I received a direct message from “a stranger at the time” about attending a summit that was a just a couple weeks away from happening in Columbia, SC. The scheduled dates were September 18th to 20th. Totally skeptical, I didn’t know who the woman was that jumped in my DM nor did I know anything about the summit she was promoting. Oh course, several questions were asked and she quickly responded without hesitation and with great detail. She sent over all the information I needed to make a decision. I contemplated what to do for days. To say it was indecisiveness was an understatement. I even prayed about it. Read more>>

Shay Samuels

I knew at a young age that I wanted to be successful. I wasn’t sure what that looked like, but I was determined to work towards my goals. What some people would have counted me out for, I considered my blessings. I was a young mother at the age of 16 and 17 years old. I used what should have been a “mishap” as my push. I was surrounded by a lot of young mothers who had given up on life due to their circumstance, Read more>>

Erika Reyes

So, we all know about Covid, and how it took a toll on everyone in many different ways. It shut down the world in ways I never knew it could, but we. Never stopped the bills and things continued to pile up and we were both out of work and running out of ideas and things to sell. I have always loved crafting needed to escape in my own way and take care of my mental health. I did a lot of thinking and one day, of course after talking to Kyle, I decided I was going to start my own business, make my own money and become my own boss! Read more>>

Emily Noel

The biggest risk I have taken thus far was moving to Nashville to pursue my dream of music. I came to Nashville for the first time in September 2019 to attend the Josie Music Awards with 4 nominations. My best friend accompanied me on that trip and I don’t think a single hour passed by that I didn’t say “I am going to move here, this is where I need to be.” After returning home to Pennsylvania, the reality of “there is nothing here for me anymore” hit me loud and clear. Read more>>

Molly Lovette

My whole career has been built around taking risks. Growing up, being a “famous singer” was always my dream, but it wasn’t until I went off to college that I truly believed that my dream could become reality. As a senior in high school, I did what most everyone does and applied for college. But during that first year of university I began writing, performing, and building a confidence that I had never seen in myself before. I came to the conclusion that if I truly wanted to be a singer, then I needed to leave school and jump headfirst. Read more>>

Dru Sousan

Taking a risk is a great topic to talk about with Honeytree. As the first Meadery in Nashville as well as the first Meadery in the country to use beer yeast rather than wine yeast to make all of our product it is safe to say we love risk, When we first had the idea for Honeytree it was very difficult to get investors. Everyone gave us the same answer of “where is your proof of concept”, As the first in town there was no proof of concept. Nashville had tons of breweries and a few wineries but no Meadery yet. Enter Honeytree! Read more>>

Dante Heard

Taking risk is something I never been afraid of. In recent years, I’ve learned to better calculate risks and make more informed decisions. In March of 2021 I was presented with an opportunity to purchase the same building that houses the Lancaster City Boxing Academy, where I have boxed since high school. It’s run by my business partner, Coach Will who I co own the building with. The building also houses G&D Visuals LLC ran by myself and my business partner, Gabe Pena. Prior to the purchase, I spoke about buying real estate in 2021, Read more>>

Arikah Nash

I think the biggest risk is believing that others will believe they can be healed and be empowered in the medical field, and that a performing mermaid can be magical, proactive, dedicated, unconventional enough to help along the way. I drive around in a wrapped Subaru that says Heal by 3, in a predominantly allopathic and affluent area, where clout in the medical practice and pharmaceuticals industry is the judge and the people who subscribe to it and finance it, as well as die by it, Read more>>

Ceylin Öztarhan Mullally

One of the biggest risks I have taken in my life was on the path to reinventing myself. I studied law in college to become an attorney-at-law. Several years after being in practice, I realised it did not suit the person I was evolving into. I decided to take a risk to start over. I was magnetically drawn to clay, to the potter’s wheel, so in 2016 I made the step to learn the craft. It was tough at times, I remember doubting myself, but I kept going. Read more>>

Eliasim Orellana

I think to me the biggest risk was starting my mobile-photography business. I was and always will be an artist first. At first i was not sure if people would understand what i do and how things. A regular photographer is there to capture the moments as is, while on the other hand i try to capture the best of what was. The memories that truly stick with you the most out of any situation, i try to capture in photographic or video form. Read more>>

Amanda McLenon

I have taken professional leaps a few times in my life, and took a risk with each one. Early in my undergraduate career, I transferred out of the school of engineering and into biology education. I immediately felt relief and a sense that I was on the correct path. I taught high school biology for about 7 years. In need of a break, I applied for a sabbatical to live on a sailboat and work for the National Ocean Service studying coral. Read more>>

Daryl Bennett

In the early days of my DJ business, I was ready to take my business to the next level. I needed lots of lighting and sound equipment to make my vision become a reality. In my music career, I had accumulated a lot of professional guitars, amplifiers, pedals, etc… I sold nearly everything to fund my DJ business. It was scary and sad at first, but I realized that I was evolving as a person, and my priorities were changing. Read more>>

Mikkel Emery

All my life, I have taken risks in the pursuit of doing something bigger than what most expect. Following your dreams and sticking to them comes at a price, and that price may be losing people along the way. I have moved all over the country and continued Another Mans Trash with many members, and very good close friends who share my vision with me. Read more>>

Kellee Halford

Honestly, I wouldn’t know where to begin, so I’ll start with when. 2020 in the middle of the COVID pandemic, I officially became an entrepreneur and started my consulting business. By 2020 my creative community and their various connections often asked for my input, advice, knowledge and skillset to help them perform various tasks, from stage play production to taping television pilots and everything in between. Read more>>

eva f

I never intended to be an artist since I quit art before I was even a teenager. I was upset that I was told I didn’t try on a school self portrait when I had put my heart into it, and after all, art was not a practical way to support myself I knew even at a young age, being raised by a single mother. Four decades later, I now lived in NYC, a childhood dream I had growing up in Oklahoma, when the pandemic hit. Read more>>

Anthony Gibson

From a professional set income, to a faith based lifestyle I was a successful educator and coach for seven years In our public school district system. I made $250 a day no matter what, even during the summer and holidays when I did not have to work. Being from the bay area of California, I grew up in the hood and never seen money like that. I loved it, I could spend money on whatever I want to every day because of what I knew I had come in no matter how hard I work. Read more>>

Sharlyne Carla Rogers

On December 31, 2014, I officially resigned from my three-year role as an administrative assistant for a small commercial appraisal company. I actually had the letter typed months before, so I was very excited when I was finally able to leave it on the owner’s desk. This was the biggest risk I had ever taken, but I wanted to walk into 2015 as a free woman. Although I was a single mother with mortgage, credit card, and student loan payments, I knew that it was time to step out on faith and pursue my passion. Read more>>

Anna Nuby

Believing I could start a business war the biggest risk I’ve ever taken in my life. Six years ago I was in a very toxic and clueless part of my life journey and everything that could go wrong, did! My father was ordered by my grandfather, I had fallen out with my mother months prior because of a domestic relationship I wouldn’t get out of. Read more>>

Ciara Monroe

In 2018I decided to go back to school and get my Masters in sports management. I had never worked a job in sports and I never played a sport, but I knew I loved basketball. I knew that I wanted to talk basketball and have my own show on ESPN. The dream was big and I did not know how to actually make that happen. I continued with school but I was not focused. I felt like my life was falling apart, I felt alone. Read more>>

Christian Google

Growing up I never had entrepreneurship in my mind. I was raised by a single mother who I watched work 2 jobs most of the time. Always made sure I had any and everything I ever needed to succeed in life. As I got older I got wiser and experience became my best teacher. When I went to college I met individuals whom helped me change my perspective on how life could be verse how it actually was. Read more>>

Janet Baltzersen

I’ve taken a lot of risks in my life, and looking back I don’t regret any of them. I believe that truly great things are on the other side of risk. As you get older you are able to discern when a situation no longer serves you. But taking risks was never easy for me. Fear is a powerful emotion, that can really prevent us from being our best selves. For me, leaving a salaried, safe job, with benefits and retirement, and going out and branding my own business was a huge risk. And scary. Read more>>

Jackson Wooten

Every day I’m taking a risk. Trying to do something creative as your career is financially stupid – there’s no guarantee of success. There’s no safety net. I struggle to pay my rent. The “check engine” light is my nemesis. I don’t have a savings account. But I’m fulfilled every day because I spend my time doing what I love. I think that’s pretty cool. Read more>>

Melissa Polanco

I have never been one to take a lot of risks but I decided to pursue an entrepreneur journey when I founded my beauty brand. Entrepreneurship was never something that I thought about and certainly not my with introvert personality. When I started this journey, I really didn’t know much about running and business and learned as I go. I have always been a firm believer that as long as you have passion for something, you can learn anything. Read more>>

Sharena Loggins

The risk I’d like to share is investing marketing dollars into your business. When I started The Regal Phoenix, my business took off faster than I could keep up. The problem was never keeping up with the orders, but it was rather creating a foundation and brand message that sustained the business when the market changed. Read more>>

Tracey Hague

I left a twenty year career as an English teacher in Rhode Island to pursue a film-making career in Nashville. I directed the theatre company for my high school for years and taught film studies, so everything in my life was pointing me in this direction before I even realized it. I had also been writing for a long time and knew I didn’t want to wait til I was retirement aged to begin! Read more>>

Auriel Gallimore

Not too long ago, I was your typical millennial—obsessively thinking about the future and striving for “success.” I completely bought into hustle culture and the work hard-play hard, sleep when you die mentality. I went from a rigorous high school program to graduating from an Ivy League University, to working for Teach for America, and was on my way to law school. Read more>>

Tori Herring

I am typically not much of a risk taker, but I did take a big risk when I started my business. I was in college, majoring in accounting when I decided to open my online boutique. I had no idea what the future would hold for my business, but it was a flexible job while I was in school. When I graduated with my degree, I had to choose to pursue my business full time or start a career in accounting. Obviously, full time business owner is a much greater risk than a secure job in accounting, but that was the choice I made. Read more>>

Lee Phillips

In March of 2021, I took a risk by opening my own psychotherapy and s*x therapy practice. Before starting my own practice, I was part of a group psychotherapy practice that accepted health insurance. I do not accept health insurance at my private practice, and I was fortunate enough that most of my clients followed because there was not a certified s*x therapist at the group practice. My clients went from using their insurance to pay out of pocket to see me. Read more>>

Dilcia Giron

It would be, leaving everything behind! My home, family, friends, culture and moving to the USA, without having nothing. It was very difficult and painful, but I kept pushing through. It never gets easy for an immigrant, specially for a female immigrant like me. Resilience is not something we’re born with, but built over time through our experiences. Read more>>

Donny J

One may think they know of the greatest risk to take. Then, they would simplify it by defining “risks” such as skydiving, water-sports, gambling, or even flying in a plane. The biggest risk I’ve identified is taking a risk on YOURSELF. The greatest risk I’ve ever taken was betting on myself. Risking my free time, sleep, public image, energy, blood, sweat, and tears; All to exemplify my character whilst possessing confidence, poise, bravery, versatility, courage, and being audacious. Read more>>

Miguel Tarin Torres

The single biggest risk I have taken has been moving to Ohio from Mexico in 2017. I was born and raised in San Luis Potosi, Mexico.I had just finished high school and the stars aligned so I could spend some time with my uncle in Stow, Ohio. The original plan was for me to get my Green card and then go back to Mexico to study music. Luckily, I brought my bass along and got in touch with Jack Schantz, who was the director of the Jazz Studies program at the University of Akron. Read more>>

Arianna Hume & Cassidy Gephart

We both agree that choosing an untraditional path, like starting a business together, is one of the biggest risks of them all! When we chose to create Liberty Music Academy together back in 2019 , we both had to had to make some sacrifices to transition from working more “normal” (and secure) jobs to starting from scratch and building a business from the ground up, knowing that there’s always the chance of it never taking off. Read more>>

Word smith

I worked as a government contractor for 13 years while I was building my music career. I knew it would be impossible for me to become a full time musician without having a foundation and being realistic about my chances. Similar to sports; everybody doesn’t make it to the pros and in musical terms that would be a major record deal. I had security, a regular paycheck and even a 401K so leaving the cushion of a government job wouldn’t make sense to most. In my mind I wasn’t living out my passion as a government contractor; I was just doing what’s needed to support my family. Read more>>

Ashley Owens

The majority of my sales come from in person shows and those can be scary for some artists to think about doing. There’s so much unknown. Will people like my things? Will they buy them? Will people even show up? The answer to all of those questions is, we don’t know. But you always have to take that chance. My first big craft market was terrifying but the amount of love I got back from everyone filled me up so much that I couldn’t wait to do another one. Sure, some markets can be great and others not great at all. Trust me on that. Read more>>

Saundra Golden

As a little girl growing up with a father who only had a elementary education and a mother who gave up college to become a housewife, life wasn’t easy and money was scarce. However, my father was a hard worker and my sisters and I were always provided for. While we didn’t always have what we wanted we always had what we needed. As a young girl around the age of 6-8, I wanted to play the piano, but little did my parents know that by making arrangements with a well known church pianist to teach me and my sister how to play piano I would end up being sexually assaulted by him and never able to tell my parents. Read more>>

Morgan Myers

Taking a risk, I would say that is my specialty considering I’m all about the famous quote “YOLO”. Have you ever been at a job of 14 years and said “ I’m ready to work for myself”? Well, two short years ago that was me and guess what? I did just that! Going out on my own was scary, exciting, and the best risk I have ever taken. I can now support my family with no worries, travel, save, and give my son the life i always dream i would be able to give him. Read more>>

Josh Caudle

When planting our church it was a huge risk and a big leap of faith. Anytime you do anything that requires any level of faith that is a risk, but if you are consistent and focused things can transpire. I started Fulfillment Church because of a vision and a passion to help others. We started during Covid, and we have been growing and building via social media and online. Taking the risk was worth it, because we collectively have done some really cool and awesome things. Read more>>

Casey Mallon

Life is always about making choices and sacrifices. Like leaving a job to try and create something you love to do and are passionate about. While foregoing financial security can be scary, you will never regret going for it. It may sound cliche, but it’s very true that you will regret the things you didn’t do more than risks that you did take. Read more>>

Justin “Drop boi” Brooks

Being from a very violent city of st.Louis Missouri I’d have to say the biggest risk I took was “on myself “ The reason I say myself is because when nobody else believed in me I kept striving to be a better version of myself from the previous day . I currently still live by that moral . The late great nipsy hussle said “the marathon continues “, life’s not a race it’s a marathon it’s not bout winning first place all the it’s about finishing ! And that’s exactly what I intend to do ..finish my marathon Read more>>