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.
Dru Davis
Starting a business and quitting your 9-5 job is always a risk. It’s terrifying. And I had a great job, too. I was a full-time worship pastor at a great place with a great boss. Healthcare was provided! But I left. It’s still scary. At the old job, my day-to-day life wasn’t effected by attendance, you know? If people didn’t show up, I would still get paid. Whereas now, I need clients to have income. It’s an entirely different way of life. Ultimately, I want to make music and help other people make music. So if I have to take a risk to live that life, then I’m okay with that. Read more>>
Richard James
February 28th of 2020 I quit my corporate job to pursue our business, James Family Tax, full time. March of 2020 the world shut down with the Covid lock down. This was undoubtedly on of the scariest moments of our life knowing that we had just left “comfortable” to now “uncertainty” with a family depending on us. However, all of the groundwork that had been laid began to pay dividends. We had tremendously loyal clients who supported us with business and referrals, and we were set up to take care of people virtually. Read more>>
Collin Rowland
Risk has been a common theme in my life. I even wrote a song about it once. It’s all about faith. Why would one take a risk of any kind unless they believe it could have a positive outcome? One example of this in my life has been selling our 100 year old home, our commercial investment properties, and art gallery in Covington, Kentucky and moving to Sarasota, Florida. We were well established in the greater Cincinnati, Ohio / Covington, Kentucky area and very comfortable there; Read more>>
Camden Yacobucci
I take risks every single day of my life. The idea of becoming a globally paid musician as my career is probably the biggest risk I will ever choose to take. I wake up everyday thinking what’s next. What sacrifice must I make today to improve not only my career but also myself. There is always a fire inside pushing me to keep going and to never give up. It’s like I can feel adrenaline constantly making my heart beat faster and faster as I make music and perform. It’s an itch I can’t get rid of. Read more>>
Sarah Hess
I am a marriage and family therapist by trade and decided to branch out into children’s fashion design and e-commerce apparel and accessories in 2018 which was an area I had no training or expertise in. It has always been fascinating to me how the roles and expectations for girls have changed over time and how we are still not showing up for our girls as a society. The idea of a world where being able to authentically be yourself and to be proud of the uniqueness that everyone embodies is such an important concept to me. Read more>>
Michael Norton
High risk high reward is what I believe in or start small and think big. When we started Madison snack no one knew who were and we had fight. Every entrepreneur needs to know how to fight. You have to able to take a hit and give up back. That why today we are successful in what we do. As a owner I took all the money the pain and all suffer because it’s important to be to build generational wealth. I had no problem with laying it all on the line , because failure leads to success. Long days and long nights has got us to this point and we are still growing Read more>>
Lauren Oliver
My biggest risk has definitely been stepping out onto my own and investing myself, time and money into starting a business. Honestly at the beginning of my career I never wanted to own anything. I wanted to be able to come in and love what I do and leave without any other responsibilities besides leaving my clients happy. I realized that my happiness and theirs goes hand in hand. And thus the idea of Fades of Glory LLC was born. I love that I have the control of being able to creative a beautiful, positive environment that people can come and relax and enjoy themselves and their time in my chair! Read more>>
Taylor McKinney
Changing career paths and starting my own business was one of the biggest risks I’ve ever taken. I grew up in a very small town in Wisconsin, where being an artist (particularly a makeup artist) didn’t exactly seem like a realistic career choice. Not only this, but I grew up in a time where YouTube and other social media platforms (e.g. Instagram, TikTok, etc) didn’t exist — So makeup in general wasn’t what it is today. That being said, I turned my back on my dream of being a makeup artist at the age of 18 and decided to pursue a bachelor’s degree in addiction counseling. Read more>>
Jenn Bays
Turn on any business coaching podcast, youtube video, or IG live and one of the key pieces of advice you’ll hear when going full-time is to have a nest egg. That you will want to save 3-6 months of your current income to prepare to leave your steady paycheck. However, I left my “cushy” 9-5 and ventured into the online world of being a virtual assistant. This was a shock to most who knew me. Read more>>
Winley K
Starting my own private practice was one of the biggest risks I’ve taken. When I first began my doctoral journey my goal was to become the director of a university counseling center (preferably at an HBCU). I saw university counseling centers as a space where you encountered a vast array of student needs and mental health challenges at a pivotal point in human development (I.e. emerging adults). As a part of becoming a psychologist we were required to complete a number of practicums to gain real world experience working with clients/patients. Read more>>
Alejandra
As we move through this life, oftentimes we carry our experiences with the world with us. However, far too many of us are not vigilant enough in assessing the risks that this can pose on our personal development and overall wellbeing. As humans, we tend to fixate more on the negative circumstances we have encountered than our positive. It’s easy to justify this growing pain over time, and I found that we are often rewarded for our self neglect. Read more>>
Tonia Herrero
Throughout my career as an art therapist, I’ve constantly had to take risks in order to reach the success I have today. Before becoming an art therapist I was a public high school art teacher for ten years in Oakland, CA. I absolutely loved my job, but I reached a point where I truly realized it wasn’t the best fit for me. My favorite aspect of being an art teacher was the relationships I built with my students and how I experience the therapeutic benefits that my art curriculum provided my students who almost all came from challenging backgrounds. Read more>>
Paul Krauss
My partner and I moved across the United States in 2017 to start the Trauma-Informed Counseling Center of Grand Rapids, MI. At the time, there were not too many therapists in West Michigan area that were practicing trauma-specific therapies such as EMDR Therapy or Somatic Experiencing Therapy. It was very scary to rent a building and begin to offer trauma-informed Clinical Supervision in a new state, with a different culture then I was used to. Not only that, but I soon found out that a lot of consumers didn’t even now what “Trauma-Therapy” or EMDR therapy was at all. Read more>>
Matt Sesow
I had been working as a software engineer since graduating college in 1988. In 2001, after layoffs at the “dot com” business I was working at, I decided to live off the sale of my paintings as a full-time artist. I had been selling my paintings as a hobby when I began painting for the first time as an adult in 1994. Since 2001 I have worked hard to live entirely off the sales of my paintings. Read more>>
Andrea + Brooke Herbert
In 2020 the world was hurting and so were we. In the midst of the pandemic, we decided to take a risk and broadcast our hearts and struggles for the world to see and hear. December 7th, 2020, we launched Gold Ivy Health Co. and the Ivy Unleashed podcast. As health coaches who didn’t grow up with a lot of guidance, we are obsessed with stories and personal development. For years, we shared inspiring podcasts, books, and resources with each other. We knew that if what we were sharing was helping us, it would probably help others too. Read more>>
Brandy Kimble
I did the most terrifying and exciting thing this year. I left my secure corporate job of a decade, to be a full-time photographer! I had been doing my fun photography “hobby” thing on the side for 4 years but never really considered what it would look like as my career. Really I was just scared to trust myself that much. But then a few things happened… Read more>>
Danielle Burton-Haselrig
I started my real estate career at the beginning of the COVID pandemic. We were all so unsure about what life was going to be like at that point but after working in veterinary medicine over 15 years, I was burnt out and knew I needed a change. The hours were so long and it left little time for me to show up for all the important things for my kids. So, with my partner’s blessing, I left my long career as a practice manager, took the first stimulus check and enrolled in real estate school. Read more>>
Jenny Fassino
Moving over ten times in twenty years, I had to continuously emerge as a new female artist in every city. Wanting my art to stand out, I needed to take more risks within my own work. I was told repeatedly by others that if I wanted to succeed I had to follow the rules of art with color, technique and composition. Going against this advice, I continued to add and remove layers of paint, developed my own textures and techniques to create pieces that spoke to me emotionally and represented the stories I wanted to tell. Read more>>
Da Inphamus Amadeuz
Deciding to become a dj was a huge risk for myself and career. I was at the height of my music video directorial career and was transitioning into filming content for radio. An opportunity presented itself for me to get on air, as a personality but I would need to learn how to dj. I literally purchased a laptop and went to work. Dj’n night in and out at venues etc without knowing how to actually dj. I was learning on the spot. But on the other side of fear is a reward. I stood with it, perfected the craft and here I am today Read more>>
Alyssa-Monet Young
Surprisingly, the most considerable risk I’ve taken has been within the past year. In February 2022, I was laid off from a job that I truly enjoyed and was ideal for how I saw life going for myself. I was devastated because this was my first layoff, and I didn’t have a plan. So the following day, if not within a few hours of finding out, I had to figure out something all while trying to complete my master’s degree in performance psychology. I decided to create a budget and cut back on a lot of things I didn’t need. Read more>>
Kristina Ward
“I am free”. These are the last words ringing out in the chorus of one of Kristina Ward’s chart topping single “Be free” and they perfectly describe an artist who’s ready to liberate others. In Ward’s debut album, #UNFILTERED, she vulnerably explores the darkest places of her heart allowing listeners to journey with her to the light. Read more>>
Claire Obryan
Helping start The Skin Clique is certainly the biggest risk I’ve ever taken. In 2019 my partner, Dr. Sarah Allen, and I decided to formally brand and turn our small concierge aesthetics practice into something bigger. We had other medical providers who wanted to join, all over the state of South Carolina. We quickly had interest in other states, and before we knew it we were in 7 states. Then it was 14. And now, The SkinClique is actively operating in over 30 states with over 200 injectors. We are the first national, organized practice of our kind. Read more>>
Lindsay Nalley
My whole life I had planned on becoming a teacher. During High School I took a graphic design class and really liked using Photoshop. My major in college was Secondary Social Studies Education. During my college years I ended up purchasing a new computer with Photoshop and I lost a camera at a concert so I took that as an opportunity to purchase a dslr camera. While in college I started doing photography on the side, teaching myself. Over the time my business kept growing. I graduated college with my degree and subbed full time for a couple years while still running my photography business on the side. Read more>>
Kathleen Rietz
I’ve always been a risk taker because I always believed in myself and my abilities, even as a child. Choosing to attend art school instead of college was a risk. After school, choosing to be my own boss and make a career freelancing in commercial art instead of taking a 9-5 job with benefits was another risk. I choose to living life on my own terms. I survived the economic downturn after 9/11 for more than a decade, and eventually decided a good career move would be to take a job as a product development manager when it was offered in 2014. Read more>>
Sheri Thrower
I took the biggest risk of my life when I decided to end my twenty plus years as a public school music teacher, to become a full time vocal coach and music producer.. I had no other choice. I was burning the candle at both ends by teaching school all day, then traveling to produce on weekends. I was traveling at least once a week during the week, as well. This meant I would teach all day, leave right after school, ,travel to another state for another music opportunity, and back home the same night. I would get home at 2 am, sleep about four hours, then go back to school. This was a weekly event for me. Read more>>
Lara Van Slyke
Growing up, I devoured fashion magazines tearing out pages and pasting them to my walls, dreaming of the designs I could create. I realized fashion design, pattern making and graphic arts needed be my educational background to achieve my dream of creating handbags and accessories. I enrolled in design school in Los Angeles and this paved the way to a variety of fashion positions, yet, I still had a passion to create the lara b. brand. Read more>>
Lanna Schwab
I started a career in the traditional western health care path. I was an Radiologic Technologist. I was in my early 20s when I got my first job working in a big hospital in Boulder, CO. I liked the job itself good enough, but after several years working in the hospital, I started to become aware of all the deficiencies in our modern health care system. Simultaneously, I lived down the road from an acupuncture school and started going to the student clinic for treatments, more out of curiosity than anything else. Read more>>
Andrea Claassen
In 2012 I started my own in-home personal training. I was also working a full time job at a soccer academy. I was struggling keeping up with both jobs and the growth of my own business. Every Friday like clockwork I ended up getting sick before doing the final sessions of the night. My body was stressed out and I was overwhelmed. After seeing me like this for a month my boss called me into his office and told me something needed to shift. Read more>>
Jessica Miller
I worked as a corporate graphic designer for several years and usually felt stuck at my job for the paycheck. After having kids I started teaching graphic design part-time at a small college. I did freelance design on the side. I loved teaching and liked the freedom of freelance but it always felt like a hussle and it was kind of hard to ever feel like I could relax and not stress about where the next job was coming from. Read more>>
Mykia Wilson
In December of 2019, I walked across the stage and grabbed my Psychology degree. Less than 24 hours after my graduation, I was on the road to North Carolina from Baton Rouge, Louisiana. I didn’t have any jobs lined up. I didn’t have any financial or emotional support from my parents. All I had were the money in my savings account, my car, and a prayer. Oh and I had bills too! Apartments are so expensive! I moved to a city I’ve never visited. Read more>>
Nicole Santiago
In 2019, I left the Spanish classroom for my husband’s homeland of Puerto Rico. We sold many of our belongings and packed the rest. We took our dog and three young children on an adventure that should’ve ended up in the Caribbean. During the summer of 2019, Puerto Rico’s governor was overthrown, so we changed course. Surprisingly, we settled in San Antonio, TX. We spent my “starting a business” fund on a home downpayment, and I schooled three children (2 with learning disabilities) while building my business through 2020. Read more>>
Peyton Smith
I always wanted to be in a band. Having only experience playing in my high school’s “modern music ensemble” class I spent a lot of time jealously watching friends play in bands all through high school. I made it a mission of mine to start a band when I would eventually go to college in Fort Worth, TX at Texas Christian University. To my surprise it was a lot harder to do than i expected. The extent of the playing that I experienced there would equate to a loose jam, and that is mostly due to the fact that they never involved a drummer. I was still motivated, but was unsure if I was in the right place. Read more>>
Melodie Provenzano
When I was attending Parsons School of Design in NYC, I had a very cool roommate from Staten Island, whose grandfather gave me the advice to start investing in an IRA as soon as possible. At that time you could contribute $2000 a year. I remember thinking, “Wow, in five years, I will have $10,000!” During my senior year of college, I started working part time painting costumes for The Phantom of the Opera under the mentorship of Bryan Kollman, who also worked doing the windows at Saks 5th Avenue. Read more>>
Soojin kim
I remember myself as introverted, the shy, quiet girl who would open up after I felt safe and more comfortable, maybe… My early twenties I lived in a world where I didn’t quite understand what self-love was and played it safe. I graduated from the University of Michigan and wanted to go to Parson’s and move to New York. After being accepted into the fashion marketing program and sharing the news with my parents, my father immediately objected the idea. Read more>>
Hope Sullivan
Starting from the beginning… In high school I need by tenth grade I wanted to be a teacher. I loved learning, always wanted to help people in some capacity, and was really good at math. I put all three of those things together and decided I wanted to be a math teacher. I went to school for teaching and received my master’s degree in secondary education of mathematics. After graduating, I moved to Charleston, SC where I began my teaching journey. Read more>>
Levelle Davison
In my experience, taking risks has become a yearly quest. I can’t think of a year, since my formative years, where I haven’t had to take a risk whether it was regarding my career or artistry as a whole. I started my artist career professionally once starting college on a full-ride music scholarship. I often would host shows and initiatives to bring awareness to local talent as well as my own. I had the opportunity of competing on NBC’s The Voice, singing for the Walmart Stakeholder’s Event, and headlining Arkansas’s Riverfest Festival. Read more>>
Jessica Waters
Hi! So I have owned my business J. Miles Design for 3 and half years and along side building a business I also worked a corporate job with Effectv for the last 14 years. When I started my business I knew it was just a fun side hustle, but ended up being a big opportunity for me and for me to do what I love for the rest of my life. I knew that leaving mt corporate job would be a big risk, it was a stable, good job, with great benefits. But if I didn’t leave now, I knew I would regret not going all in on my business. I recently left my job and It was such a good business decision for me. Read more>>
Chantelle Martin
Starting a business is a big risk. You ask yourself will it succeed? Can it actually be profitable? Do I even know how to start a business or what I’m doing? These are all questions I’ve even asked myself while going through my entrepreneur journey. With anything we want to accomplish in life that may make us feel uncomfortable, we need to really lean in to “why” we want it. That why will drive you to take the risk if it’s truly worth it. For me, my why was time & financial freedom for me and my family. Read more>>
Heidi Aghajani
The biggest risk I have ever taken was starting my own practice during the worse time in our world’s history. Everyone told me no. Don’t do it. There is this virus outbreak. Just hold on. But my inpatient heart couldn’t. I had trained over a decade in aesthetics. I was ready. I opened Alchemy Med Spa in February of 2020 and closed for a couple of months due to quarantine shortly after. I was scared, I was stressed, and I was not gonna accept failure. I had invested money in my training, in my studio, in my products and insurance and I was not going to fail. Read more>>
Tish Tensley
In life you will take many risks. I think the best risks are the ones that make you change for the better. I married with 3 children, I worked double shifts at a group home. My life wasn’t up side down but it wasn’t exactly smooth sailing. I knew wanted to change from a job to career doing something I loved. I journaled and prayed for direction. My husband had his goals and road blocks just as I did. We were a family of 5 trying to.make it. One day at work, I saw a commercial for massage therapy school. Read more>>
Hans Gilliam
I have always wanted to own my own business but never could figure out what. I completely stumbled into the driving school industry because of a frustration. Then I found a similar frustration with the BMX program. With both the Driving School and the Non-Profit I saw a complete lack of compassion for the students. Starting a business is probably the hardest thing you will ever do or so I thought. Now starting a whole new program in a sport for the local youth is probably harder. Read more>>
Craig Muderlak
Taking risks has been a big part of my life’s trajectory. Not only do I work as an an artist, but I’m also a mountain guide (I take people rock climbing, mountaineering, and backcountry skiing). As a mountain guide, there is a certain amount of inherent risk in my career – these risks are mostly objective (rockfall, avalanches, crevasses, etc). As an artist, the risk is more subjective like creating something you or others don’t like and feeling vulnerable with sharing yourself in this way. Read more>>