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.

Evan and Stacey Smith

Evan: I didn’t fall in love with art until I was in my early 20s, but this has been the only thing that has stuck with me. The pursuit of art is inherently a risk in a society that does not value art or artists, so we all have to be creative in how we pursue it. For me, that meant starting college in my mid-20s and taking one step at a time. It’s meant slowly building up my own shop and studio at home over the last ten years, and pursuing a variety of learning opportunities, relationships, and commissions. Read more>>

Meg Elam

Making the transition from holistic hairstyling to loctician was exciting and rewarding, but it is important to be aware of the risks involved. It takes a lot of courage to go out of your comfort zone and focus on a particular technique, especially one that is not “normalized” in the hair industry, and requires a big commitment from your clients. A definitive risk I took was making the decision to dedicate myself to mastering the technique of dreadlocks and shifting my entire business to service dreadlocks. Read more>>

Amy Crews

So funny you should ask me to “paint the picture” for you when asking me to share a story about a time I took a risk. When I was a fine art major in college it was an entirely different time for creatives. I was literally by professors and advisors that the only fields I could go into were to be an art teacher in schools or find a different field that would use my creative talents. That would be medical illustration or graphic design if I was lucky. Read more>>

Nichole and Rick Frazer

I knew my husband, Rick, wasn’t super happy at his job before COVID. Then having to go back after having 7 months off made it all the more obvious to him. While his job as the Executive Chef at The Saint Paul Grill was a prestigious one, it wasn’t fulfilling to him. His duties required more time on a computer than it did in a kitchen. A few weeks back to work was all it took for him to tell me how miserable he was. Read more>>

Melissa Farrell Ortiz

I am someone who until more recently lived most of my life in a very calculated and predictable way, always looking for a sense of control and stability that I often didn’t find in my childhood. Growing up, like so many others, I had a home that was often influenced by the effects of problematic mental health issues and substance use. In the first 3 years of my life, Read more>>

Maria Hall

I am Maria Hall and the story on how I founded Made in Michigan with love is A very interesting and lengthy story, so I willl try to shorten it down A bit for you. As someone who has worked in the medical field in A wide range of positions for 7 years prior to the pandemic. I thought my career would be in the medical field, however God had another plan for me and my life. Read more>>

Kimberly Patota

I am a highly creative person who thrives in small goal-oriented groups. I earned my Bachelors degree from Marist College in Poughkeepsie, New York in 2016, as a Media Studies & Production major accompanied by a minor in Studio Art. Upon graduating, it was time to step into the real world and find work. This was when I had to really sit and think about the types of jobs I am qualified for. With all my internships and experiences within my classes, Read more>>

Phil Rice

I never imagined I would leave my hometown of Detroit, but the dream of becoming an actor was too strong to ignore. So, at the beginning of 2018, even though I only had a few hundred dollars to my name, I took the biggest risk of my life and made the move to Hollywood. Read more>>

Teresa MiZZ Entertainment” Edwards”

Becoming an entrepreneur is one of the biggest but most rewarding risks you can ever take. My husband and I are both passionate about music. We are what you may call…eclectic when it comes to music. We love different types of music. But the one thing we totally agreed upon was that our mission was to create good music one beat at a time. Read more>> 

Chelsey Sellona

One of the biggest risks I have ever taken was leaving my Civil Engineering job to pursue Music Production and Audio Engineering as a career. Read more>>

Isabelle Nanin

Title: From France to England to Ecuador: The power to create my life.
As a child, I would always help the other kids to be seen and to be heard. It was so natural to me. I would ensure that they were included in games and could shine. Read more>>

Allison Schmitz

In February of 2021, I had the idea of opening a studio space. Our idea for this studio space would be that it could be rented for photography and small parties by the hour. I came home one day and pitched the idea to my husband. At the time, I envisioned this could be a project that we could work on and maybe open in five years or so. My husband being who he is asked, “why not now?” and we began touring commercial spaces that week. We signed the commercial lease and it was one of the most nerve-wrecking things I have ever done. Read more>>

Jasheana Hamilton

Well it all started when my father passed away in June 28th, 2020 from cardiac arrest. I got the call while doing regular daily chores, walking my dog. Life had shifted for me an instant, like it couldn’t be real because he had flew to Houston to see me a month prior and we had last talked 2 days before the news of his passing. My reality bubble cracked because it was then that I finally realized life was short, and entirely too unpredictable to live a life that you complain day in and day out, Read more>>

Okeeba Jubalo

My name is Okeeba Jubalo, from birth. I did not leave North Charleston, South Carolina, and go out in the world to find my blackness. I brought it with me to Atlanta as a fresh-faced college student in 1993. Honestly, my life was and is one big risk. I am a black man, and on top of that, I am a black man who is a professional creative who doesn’t work for a corporation. The risks are nonstop. Read more>>

Elias Giannakopoulos

Real estate was the biggest risk my business partner/sister and I decided to take on so early in our lives. I am only 21 and my sister is 20 years old we decided to buy an investment property during COVID-19 while the lockdowns were happening. We thought that was the craziest life decision we have ever made, and now we own a real estate software company. The reason why this is so crazy to both of us is that we had no clue how to code and how to build a company such as this one. Read more>>

Kristin Mosley

In 2019-2020 I went through a bit of a struggle with my career. I was laid of twice in one year and when this happened I had a major doubts when it came to my future. I had no idea what my next move would be or how I was going to survive. It was the start of the pandemic and the world shut down so there was no way I was going to make it, I thought. Luckily, I had a bit of money saved to help keep me a float but at the same time, Read more>>

Lauren Kashuk

When you decide to go for it, truly, it means putting yourself and all that you stand for on the line. I took a huge risk in creating RETROSPEKT, initially as a virtual festival during the pandemic. It was the first time I bet on myself, and my company, and the team I assembled, without a larger client hiring me/us. It was also financially one of the scariest decisions I could have made. I invested every dollar in my savings, on every credit card, and then some. Read more>>

Xavier Robert

Being an artist and defining what that even means is a very tough task. Artistry ranges anywhere from the simplicity of creation to the refinement of providing value to others with it. For myself, that artistry exists in the realm of music creation and spreading my work with the masses. Regardless of all the variables and different interpretations that define what it means to be an artist, I don’t think I’m far off the mark by suggesting the following: one of the key sources of an artist’s success is “opportunity”. Read more>>

DJ Hov

I like to say I have to take risk everyday , not knowing the outcome of my income of a monthly basis all while trying to strive to make my passion my career.. Read more>>

Alyssa Engdahl

I quit my job as an on-air radio morning show host in November of 2022 with ZERO plans for what would come next. I no longer felt comfortable in my role at the company and wanted to grow. I was terrified to take the leap but I had an enormous support system and decided it was the right time for a change. For weeks I felt unsure about what the future would hold for me; but here I am on the greener side of the fence in Feb of 2023. Read more>>

Catie St. Jacques

Quitting my job during the pandemic to become a freelance graphic designer. Covid was an uncertain time for all of us, and during that time my mental health plummeted. The company I worked for decided to ramp up the workload – perhaps in an effort to keep our minds off of what was happening in the world. It was very difficult for me to stay on task and focus, I felt like what I was doing was pointless. I was having panic attacks and the worst anxiety of my life. Read more>>

Maryjo Anderson

Being someone who hates taking risks, my biggest risk in life was quitting my 9-5 daycare job (I was a daycare teacher for almost 5 years) to start my photography journey full time. It was the biggest leap of faith I have ever taken in my life, and it has been one of the most rewarding decisions I have ever made. Read more>>

Jen Roberts

Starting any business is a risk. Read more>>

Greg Orosz

The biggest risk I have ever taken was going to college. Up until Christmas break of my senior year of high school I had every intention of joining the military and then working for my family business upon finishing my service. The week before break, my track coach informed me that he had a handful of colleges looking at me to throw on the track team and because of that, I applied to the two schools that were in Colorado. Read more>>

Jill Soukup

In a recent class I was teaching, I ran out of time during a follow-along exercise, where the students and I were essentially painting a painting together. So, for their homework, they were to complete it on their own, in what I believed would be a perfect opportunity for them to make unique discoveries. Read more>>

Semline Singleton

Sharing anything about yourself publically is scary. What are people going to think? Am I putting myself out there too much? Is what I’m sharing relevant? All these questions raced through my mind as I worked on my 21-day celibacy guide for women. For almost four years, I rededicated myself to God and wanted to write about the journey and create a guide that would help other women. Writing my story required so much vulnerability and transparency. Read more>>

Chris McPhie

The risk I’m going to tell you about, is how I changed my career path from a stable, well paying job, to a much less stable, burgeoning health field, independent practice. Read more>>

Leah Alfonsin

Starting my current business was a big risk for me. At the time, I was working for a company that I loved and supported me in my personal and professional growth. Over 12 years, I built relationships with co-workers and got to meet a lot of really great people that are still in my life today. But something was missing. I knew I was comfortable where I was and the only way I was going to continue to grow as a person was to build something of my own. Read more>>

Jenniffer Baez

I have always been a person who loves to take risks, for me taking risks is an adventure. I usually evaluate the risks I take ahead of time. I carefully evaluate what will be the necessary steps to achieve it and then I focus on it. Many times we seek opinions from people who have taken similar risks to find out if we are on the right path, Read more>>

Eli Perez

I would say as an immigrant growing up in this country, I have always doubted myself or had impostor syndrome, therefore, taking even the smallest risks or just believing in myself has always been a huge deal to me. I began advocating for undocumented and immigrant communities ever since I landed a job at an immigration law firm (which even applying for the job was so “unreachable for me”, or so I thought). Read more>>

Jasmeet Nanda

From my early childhood, I can remember music always being a huge part of my life. Listening to music, creating music and being around music is what has always brought me happiness. I was born in India and moved to the USA at a very early age. My parents come from a well educated background; a good education and a solid career that follows has always been a strong emphasis in our family. Read more>>

Jen Hershey

Taking risks has always been a part of who I am. As a licensed therapist with a successful virtual private practice, I found myself constantly wondering what was next for me. I had already tried the usual ways of refreshing my practice by getting new office space, but that wasn’t enough this time. I had a feeling that I needed to do something more. As an Aries rising with a Sagittarius sun, I like to think of myself as unique and different. Read more>>

Derek Dames Ohl

I think being in the music industry you take risks left and right. Whether if its thinking outside of the box with a song idea or jumping in your car to drive thousands of miles just to play to an empty bar. It’s easy not to take the risk, stay in your hometown, maybe play a brewery on the weekend and remain in your comfort zone. There’s nothing wrong with that if that’s what you set out for, but if you’re really trying to “make it” then I personally think you have to take every risk presented. Read more>>

Eunice Elliott

Although I’m not someone who enjoys being scared for entertainment because I don’t like roller coasters, scary movies or dating…but I’m always down for a new life adventure which can also be scary, but in a different way. Read more>>

Jessica Davis

As a small business owner, it takes certain level of nerve to go out on your own without a safety net. It’s terrifying and exhausting but some people are meant to write their own story… make their own path. Read more>>

Reem Khashou

All action begins with a thought. Read more>>

Jim Dessicino

I did not take the COVID vaccination. At the time that was controversial, now it seems providential. I made the choice that aligned with my health and morality and was punished for it. I lost my teaching position at Stockton University and almost lost my ability to travel. I run a residency program in Italy called Rome Art Residencies. The travel restrictions brought about by bad governmental policies nearly cost me my livelihood. Read more>>

Lemwhir Valette

One of the biggest risk I have taken was during the pandemic, I was always 9-5 driven or some form of structure. When the pandemic hit most of my jobs closed down. Accounting slowed down a bit and I was dong event planning in times square and all that shut down immediately. I met two of my mentors around that time and both of them in their own respective way; were entrepreneurs. One of them Luis “Lou” Castillo is a body builder / personal trainer and the other Dlyan “Hawaii Mike” Salman is a Chef. Read more>>