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.

Brooke Emory

There are three turning points in my career and they are all a product of taking a risk. I believe that if you really want to make a difference, you must have the courage to dive in headfirst and have the confidence in yourself that you will land on your feet. Your drive must be greater than your fear, the only person that can make that decision is you. Read more>>

Andrew Montpetit

The risk I took was getting into the creative industry in the first place. Ever since I was a child, I was drawn to creativity and art. However, I never even considered getting into a creative industry. The common understanding when I was growing up was that you would never make any money as an artist / professional creative and my main focus was to be a good provider and, hopefully, husband and father for a family someday. Read more>>

Mikem Nahmir

The biggest risk I’ve taken has definitely been separating myself from family and friends in order to be who I wanna be and live the life I wanna live. I got really tired of people telling “what to do” and “how” to do it. I hate when other people make decisions for me. It’s annoying and that’s why I took the risk I took and I don’t regret it in any way, shape or form. It worked out better for me being away from everyone that was trying to control me. Read more>>

Cydnee Mame

I would say starting a new business is a risk in its own. I started my social media management company during the peak of the pandemic with very little direction. In the beginning, I spent most of my time creating the foundation of my business– branding, my website, pricing, offerings, etc. I also spent a lot of time educating myself on common industry practices by watching videos, reading articles, and taking online courses. Read more>>

Paloma Machiavelli

Honestly I’ve taken lots of big risks. The one of a few risks I’ve taken that came to mind is the one when I ran away from my foster home to find my mom in Tijuana. I actually found her within eight hours of searching for her that same day I ran away. I was gone for over a month and I was also reported missing here in the US. The reasons I ran away to find my mom is because I really wanted to see her and I had told social workers and the judge that I was going to run away and find her. Read more>>

scott bryant

Prior to starting our ventures in the cannabis industry, I was working a career where I was challenged, but living comfortably and without much worry. The company was growing, I was successful in my position and things were good! On the other hand, I still felt like something was missing. I had always wanted to venture out and start a business where I could build something where I wasn’t limited by the confines of being an employee. Read more>>

Stephanie Santana

I’m a US Air Force veteran with two degrees in the medical field. I was working with the government until November of 2020. I wasn’t feeling whole and faced a lot of discrimination and sexual harassment. I decided to take a risk and find something that will allow me to feel complete and be accepted. I had absolutely no desire to be a model but people kept telling me I had the looks for it. I ended up auditioning for an agency where they decided to sign me as a model and actress. Read more>>

Indiah Jackson

Being a chef full time hasn’t always been the dream. I started off by working full time at a hospital locally in my city and was working there from the typical 9-5. In that period of time was looking to find myself and my passion. I recently just graduated high school a year early in 2018 so that summer going in to fall I completely dedicated my time and energy into that job to find out that it was breaking me in to a depression. I knew something had to change and something bigger had a calling for me. Read more>>

Ed Hennings

I spent 20 years in prison, and I realized I was in a dark place because I had stopped DREAMING. As a young 20 something year old man, those dreams I had as a kid were gone. When I identified the fact that I wasn’t even living at all, because with no dreams, are any of us truly living. So I started a quest to purposely get my dreams back., to dream so big that it would scare me. For the last 26 years I’ve been dreaming like a 10 year old child, and it has been my source of life. Read more>>

Abigail Anderson

My first exhibition, Transitionary Voices in Nature, is the biggest risk I’ve taken as an artist and marked the beginning of my professional career in this industry. It started as a challenge to myself to share a few pieces of my soul and display the paintings I’ve created from 2020 to 2022. Eventually, it evolved into a full fledged exhibit at the Blue Star Arts Complex. Read more>>

Melanie Christopher

Starting in 2012, after graduating from college with a Bachelor’s of Arts degree in Illustration, I spent the better part of a decade bouncing between jobs that I was not passionate about, jobs that while creative adjacent did not allow me to be truly creative. I was a good worker, a responsible employee. I performed to the best of my ability and would have retired comfortably in thirty or so years. Then I drew a cute ghost with a little speech balloon saying, “Yup, Still Dead…” He made me laugh. Read more>>

Jennylyn Pringle

I believe that in order to be an entrepreneur, you have to be able to tolerate risk. Growing up inside a family business, I watched both my parents take chances without a guarantee they would ever pay off. It can be stressful, sure, but I also think risk builds resilience—something I’m proud to say I have a lot of. Read more>>

Nicole Madonna

I have spent the last 20 years of my career in the social work field working for others. I have worked in mobile crisis, interpersonal violence and sexual assault treatment and higher education. I have worked for the state, city and public universities. I have found all of my work to be very rewarding and taxing at the same time. The burnout and compassion fatigue is real! But I always persevered for the love and passion I have for my work. Read more>>

Ali Osborne

Prior to owning & creating a small jewelry business, I was working 4 jobs. spread clear across the board. Deep down I knew my true passion was designing and making jewelry. At the time, I was just creating jewelry as a side hustle, showing up to small local pop ups throughout Santa Cruz County. It’s because of my friends and loyal customers that today I’m where I am with Desert Moon. Their encouragement and validation was what lead me to quit all my jobs and solely pursue jewelry making. Read more>>

Kendra Goheen

There was a moment, ten years ago exactly, when I realized that so many of my life choices had been made based on fear. I have been a life coach for 26 plus years so I am open to guidance freely. It was this particular time in my life when the bottom was falling out in numerous areas that were in transition. I was in pain, my mind was cloudy, I was depressed and my health was starting to show it. Read more>>

Grace Zaras

When I was 23, I moved from West Virginia to New Mexico. I did not know what to expect in New Mexico; all I knew was that I wanted to study the science of disordered communication. I have been practicing as an ASHA Certified Speech-Language Pathologist for over 6 years. The children whom I have helped are unforgettable; the greatest lessons I have learned have been taught by my students. Read more>>

Roxy / Angel Cruz / Flores

We both feel as if the biggest risk we took was the opening of our shop location. There were many risks taken from the day we both decided to simply open up a business. Some of those risks being financially, mentally, life changing and adaptations, to the little knowledge and experience of how a business ran. We both have a full-time job thinking, “We should be good, right?” So without even thinking twice we jumped into the shop hunt. Read more>>

Maria Larsen

Starting my photography business was a huge risk for me and a really scary process. My strive for perfectionism coupled with a nagging fear of failure, always held me back from putting myself out there. It’s not like I’m scared of trying new things, but rather scared of the logistics involved that might hinder my plans. Read more>>

Rian Cult

You never know it’s a risk until you make that leap. I used to be a drummer, I still am, but it’s not my main focus anymore. I started out playing drums and I was really good at it, but I always felt like I needed to do more than that, there was more to music to me than drums, I had to write, i wanted to sing, to say something beyond the rhythm of the drums. Read more>>

Ashley Stone

Moving across the country during a pandemic was no easy decision. Despite everyone’s best efforts to stay safe, it can feel stifling to be uncertain of anything and what could happen next. Taking a risk and going beyond comfortable limitations can often come with many rewards that you can’t find in your comfort zone. That’s why I decided to move from Connecticut to Texas after spending almost 2 decades in the same area building my businesses. Read more>>

TEdra Z Knox

had no intention of opening a coaching practice, even though I was passionate about assisting others in identifying their obstacles, collaborating with them to find solutions that work best for them, and keeping them accountable. I had little knowledge of the coaching field, I knew certain coaches and supported and believed in them, but I didn’t truly think I could succeed in that field. Read more>>

Chanel Grant

I risked it all for myself for my business for my children for my future to have a better life as we all no being a entrepreneur business owner is not easy you have your ups and down good and bad days we make it look easy but it’s not your literally broke all the money you make goes back into your business or family you have to keep going no matter what there’s no looking back because there nothing there you have to put god first because everything that your experiencing is meant to happen you just have to be patient and trust the process so me taking a risk on myself and believing in myself is what changed my life. Read more>>

Natalie Robinson

When covid first hit everything became a risk. It seemed as though time was stagnant. Being a a 20 year old student(at the time) was hard. Pursuing a creative career and not having access to “hands on” learning was even harder. That’s when I decided to take my first risk. I took a sabbatical for a whole semester. This semester took me away from the traditional learning and led me into developing “real world” skills. It is this period of time that made me the person/artist I am today. From networking with other creatives to creating projects for the community to enjoy. It was my passion to try and pave the way to inspire others. Read more>>

adrienne pratt

I am very happy and satisfied with my career as an artist. It satisfies my creative expressions, and it “feels” like it what I should be doing. The word Risk is defined as “a situation involving exposure to danger”. Does that mean risks are dangerous? I think of the definition for myself as more as a leap of faith, or taking a chance, as well as being true to myself. Maybe risk taking seems dangerous, a possibility for an unknown failure. My dear friend says “if it’s not a hell yes, it’s a no”, and I really try to consider this when options for risk taking are in front of me. Read more>>

AARON ROBEY

Building a business and/or brand is a risk in itself. My entire life has been a risk. I have always wanted to do things that were far out of my reach. Pushing towards these goals took sacrifice of certain things in life. I have put everything on the line several times chasing goals and failing the success I was chasing. I regret nothing. It taught me everything. Failing hurts, but what you gain in return is the ability to handle any situation life or individuals give you. Never quitting is the cheat code. Read more>>

Mary Hastings

I have dreamed of living in CO since I was 16. I was traveling with family and saw the mountains and red rocks of Garden of the Gods and I was hooked-I felt I was home. It took 20 years and lots to trials to get here, but I finally did and have never looked back. I had a place to live for a few months and a potential job, so I hit the road. I changed my career, learned to ski and met wonderful friends that are now family. You need to believe it or you won’t see it-DREAMS DO COME TRUE!! Read more>>

QUEEN ANGELA

I took a risk in 2016 to step out on faith and start an afterschool and summer program to educate, empower and encourage youth to walk in their purpose. Me stepping out on faith has led to me now being a published author of over 50 books, journals, planners and the creation of Aspiring Authors Magazine. I launched AAALAC-African American Authors Literacy Awareness Campaign to bring awareness to black authors around the world while focusing on literacy and topics that affect our black communities others don’t like to talk about. Read more>>

Brandon Sanders

You may have a vision for your life, that everyone can’t see. That’s okay, just know that you have to lean into your vision more than anybody else. No one will believe in your dream like you. I have always trusted my intuition. Specifically, I could share a moment when I had to take a risk to apply for the University of Houston. Initially, the school denied my application. I was devastated, but I did not let that stop me. I took the necessary actions to write an appeal letter to the university. Read more>>

WaviLevato

I have most definitely taken a lot of risk when it comes to me being a artist. Whether it’s financial, time, etc. I’ve had some good outcomes and some bad outcomes out of some of the risk I’ve taken hell, sometimes I don’t get nothing at all but it’s just something about knowing your willing to put it all on the line to succeed at something you love. I’ve quit jobs to pursue my dream and sometimes even put up my last dollar just to buy studio equipment to be able to record myself and learn different softwares. My senior year of high school, I decided to do online classes instead of in person classes so I could focus and lock in on what I wanted to do music wise. Read more>>

Shanice Morales

I took a life changing risk July of 2021. I decided to take a leap in faith and leave the job that I loved. I was so nervous and anxiety was at an all time high. I kept thinking, what if I was unable to provide for my family? What if I failed? I had so much encouragement from my family and words of support from everyone around me. Life is so short and deep down inside I had always knew this day would come. Afterall, is this not what I went to school for? To follow my purpose. Read more>>

Ernesto Holguin

The simplest risk I have taken was joining the Army 3 months before graduating High School. My Senior year, there was an Army Recruiter visiting the Band room asking if any of us wanted to continue with the Army Band. I was a good trumpet player and I had planned to make it my career. I took the ASVAB entry exam and did so well that I was offered a variety of high skilled occupation specialties. I did not want the other specialties and tried focusing on the Army Band. Read more>>

Mariela Henriquez

In 2021 I made the riskiest decision of my life: to give up everything, my job, my friends, my family, and move back to Miami to pursue a dream. I had been working as a company manager at a real estate photography company in Houston and it got to the point where I had nothing left to give and felt like there was nowhere for me to grow. I had the urge to go off on my own and discover things about myself that I didn’t believe were possible in Houston. Read more>>

Lori Garcia

When the pandemic hit in 2020, I was living in Orange County, California. During this year, our industry was completely shut down for 6 months because we were not considered an essential business. I had been working in Orange County for almost 20 years and had a full clientele that I cared for. In January of 2021, my husband had a job opportunity in Houston, Texas and we decided to take a huge leap of faith. Read more>>

Grace Steffen

I only started my business this past year, while finishing my undergraduate courses at the University of Alabama. I actually didn’t major in anything art-related, instead I graduated with degrees in Biology and Psychology. However, I’d been creating art the whole time and had work featured in several magazines on campus. This past year in August was when I decided to start pursuing art more seriously and began preparing work from previous years to feature in different spaces in Tuscaloosa. Read more>>

Josh Roth

Lauren and I have known each other for our entire lives. We purchased our first house together in 2017 in North Raleigh and this house was amazing. It needed some TLC and renovations but had everything we wanted at the time. We knew we wanted to take on renovating ourselves and we are so glad we did because it ultimately gave us the courage to start this crazy journey into flower farming. We knew we wanted to start something together that was ours, but nothing ever really stuck out in our minds that made us want to drop everything and go for it (so to speak). Read more>>

Carrie Williams

Starting my business was the biggest risk I’ve ever taken. Having had a successful corporate career for 21 years, I started to feel like I was meant for more. I was ready for a change, and then the pandemic happened. We started working from home and I realized how much I loved having more flexibility to spend time with my kids. I also started to see how people’s finances were being turned upside down by the pandemic which no one had anticipated. Read more>>

Isaiah Mcswain

At the age of 17, I decided to move out and finish my last year of high school. The turmoil in my home had finally boiled over that Summer. My mother at that time was in a serve & abusive marriage that began to shape the way I lived my life. Growing up in an already improvised home left me scrambling daily to keep up with college application fees, school supplies, and other school-associated fees. I was in choir & track at the time, in which both I owed my assumed dues. Read more>>

J O M i

Man, it’s hard to even find a place to began with this topic. Everyday is a risk as a creative to be honest, especially with the way the media is nowadays. As a child, I did a lot of other activities. I have 2 older brothers, with me being the youngest, it gave me the opportunity to explore 2 worlds before I began creating mine. My parents definitely had a vision for us that really wasn’t catered around creativity at all, prior to finding out that my father was actually a retired gospel recording artist. Read more>>

April Hatcher

My business’ entire existence is based on the biggest risk that I have ever taken in my life. In 2020, I had a literal dream that revealed to me that I could bake cheesecake. When I woke up, I went and purchased my first baking pan, went home and made a cheesecake. I was so excited and immediately started planning how I could use my newly revealed gifts to free myself from working for others. About a month after my dream, I quit my job and JUMPED into full-time entrepreneurship. Read more>>

Sky Choice

Colorado has always been my home. I was born and raised in the Denver Metro area, moved to Alamosa, Colorado for college, and then after a year on tour, moved back to the Denver area to be with my grandparents. It was comfortable there. I knew the neighborhood, the street names, the stores, how long it would take to get to and from different parts of town. After my grandparents passed away, I started thinking about if Colorado was where I wanted to live long term. Read more>>

Annika Hinton

Lost. Such a simple, four-letter word, yet it has a meaning deeper than a thousand others. You feel as though nothing you could possibly do or say could ever have the strength to pick you up and pull you out of the dark abyss of total nothingness that you’ve created around yourself. Read more>>

Skyler Jafferis

I’ve been the owner and an artist at Skyline Tattoo, LLC. since 2017. Since then, I’ve watched my business grow, my clientele inspire me beyond my wildest dreams, and my team ebb and flow with each year that passes. In 2022, I was in awe as I was a front seat passenger seeing my year completely book out. I’m talking as of the end of March 2022, I had barely two weeks left available for appointments for the rest of the year. I knew something needed to change in order to support my growth and business. Read more>>

Will Gladden

Without taking risks, I wouldn’t own a DJ Business today! Let’s talk post-college… After graduating as a Sport Management Major, without a clue of what I wanted to “do with my life”, I took a risk by accepting a position as a Graduate Assistant in the Athletics Department at North Greenville University (my alma mater). While I would work multiple 60-80 hour weeks, I would have the chance of a lifetime to receive a Masters Degree with all expenses covered by the University. Read more>>

Liana Monaco

My senior year of high school I went through the grueling musical theatre college audition process. I auditioned for 18 schools- including any that were listed on the “Top BFA Musical Theatre Programs” list on Playbill.com. As many people know, this process is extremely competitive, stressful, and heartbreaking. I ended up being waitlisted at 2 of my top schools and was eventually rejected.I was heart broken. I was SO close to attending my dream school, and I was not going to take “no” for an answer. Read more>>

Liz Lagarde

When I started doing pottery, I thought it would be 10 years before I would change from a side hustle to a full-time job. After about six months, doing orders for family and friends in one show, I had to quit my job due to some health issues. It was then I had to decide on whether or not I would find a different job that suit. My needs are going all in on my business. My husband was super supportive and really encouraged me to give it a shot. Read more>>

Remy Watters

Taking a step backwards in business can actually be stepping forward. The best advice I have in business is, put your pride aside. Read more>>

Jessica Libor

In 2020, I lost my job as an event planner for a major retailer. Many people in 2020 lost their jobs, and it can be a scary time. However, I took it as the perfect opportunity to go into my art career full time. That year, I took my artistic work seriously and was able to make enough to support myself. Every year, it has gotten better since then. I’m so glad I took the risk to go into art full time! Because I learned so much over the last several years, I wanted to help other artists who were in a similar position–who wanted to make art their living, Read more>>

Jazz Thorpe

Taking a risk is one of the hardest but also one of the most rewarding things that you can do for yourself. As for my story, taking a risk has been life changing to say the least. By now, Ive told my story of how I became the owner of Summer Daze Beauty a thousand times, but I never tell the side of how much of a risk I took starting a business without knowing anything about a business in the middle of figuring out my place in this world. When I started Summer Daze Beauty, I was in the middle of figuring out life after undergrad, working full time at a job that I didn’t like, and becoming a full time graduate student. Read more>>

Trey Ford

My first step into the mode of entrepreneurship that also requires you to be an employer was at 19 years old running a branch office for Vector Marketing, the entity that recruits and trains sales professionals for Cutco Cutlery. One of the major factors that I had to overcome was the drag/friction created by people in my sphere of influence who thought poorly of the company and opportunity. Although there was a per appointment base included in the pay, this sales position was primarily commission based and thus it required performance for it to be worth driving from prospect to prospect to present the product. Read more>>

Vetta Murdock

I took a risk starting my business. I had never started a business before and I was scared I would fail. I realized that I needed to believe in myself and my dream. I took two years planning how I would start my business. I saved money and made a business plan. I felt like I had everything together I just had one problem. The job I had was a traveling job and in order to start physically working on my business I had to quit my job. Read more>>

KARA WARD

Our story started back in April 2020, when my husband lost his job due to COVID. We decided to refinish our own bedroom furniture, even though we had never done anything like that before, and I posted the finish product on Facebook. We had such a positive response that we wondered if we were on to something! We began flipping smaller pieces out of our garage and they would sell with in minutes. Read more>>