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.

Noontides

Music had always been a major part of each of our lives, and when we met back in 2009 in Kansas City, in a lot of ways, it became something that really brought us together. When we got married in 2012, we continued to play, write, and perform a lot together, and though it was something we were super passionate about, it was always kind of something we did on the side. Read more>>

Diana Ossa and Josh Dobken

Like for most people, 2020 was a year of change and challenges. Working from home and in complete isolation from sick family members, the uncertainty of the future started to create a lot of questions for us. At the time, we were living in a 700 square foot apartment in Seattle, Washington and working our W2 jobs as architects – a demanding profession that doesn’t have high compensation and often requires working 100+ hours a week. Our careers were cutting down on time to have any life outside of work, be present for our families, or to even think of starting a family of our own – we started to question our path. Read more>>

Robert Griffiths

If it’s one thing that the recent pandemic taught me, is to take the opportunities or risks if you will, when they arise. I got wind that the French Air Force were due to train at a local beach to me back home in Wales, UK. I knew the area well, having witnessed and photographed the Royal Air Force training there several times before. The beach is used for natural surface training for pilots and crew so that they can use what they learn in real world scenarios. Read more>>

Courtney Hammonds

I consider myself to be a courageous leader who is not afraid to take risks. Such a character trait is evident in the fearless achievements I managed in my former role as the academic fashion director. Such developments included the expansion of new academic programs including The Bachelor of Fine Arts in Fashion Design (BFA). This signaled a pivotal direction for the institution as the fashion design program was at the forefront of recent programs and technologies in the southern region. Read more>>

Tanya Rose

I went to school for the culinary arts and graduated college with an associates degree in Baking & Pastry. I love cooking and being able to work with my hands. After graduation, my career as a chef grew and I started working full time as a pastry chef for several restaurants in and around Seattle. Read more>>

Tennah Watters

At the age of 48 I found myself living in my car after my 19 year marriage ended and in major pain from fibromyalgia and withdrawals of 17 prescribed medications. I had been on these medications for many years and I knew that I had to find a better way to live. I went back to the one thing that always made me feel better and took almost all my physical and mental anguish away. Cannabis. Read more>>

Rashadah Jordan

The biggest risk I have ever taken was moving to Texas alone. I had no one here. Of course, it has been a few years and now I am established but at the time, I knew I had to be here. I just did not know what I was getting myself into. I overall felt like Texas was home. It was strange but I tried getting here for 2 years. When I finally thought I was leaving, the pandemic hit. I tried during, but of course, no one was moving during that time. At the time I was a new graduate starting my career. Read more>>

Brittney Sutton

The most impactful risk I’ve taken was leaving my job as a middle school teacher, during the pandemic to pursue entrepreneurship. As a licensed natural hair stylist, it was always just something I did on the side. The Pandemic gave me time to think about life outside of my 9-5. Although it was my side hustle, it was close to what I made as a teacher, which we know in this country is not much. Read more>>

Mary Tyler

My husband has always wanted a CNC plasma cutter, and we decided 2022 might just be the year to get one… He had wanted one, since he was in high school, and with his experience in metalwork, welding , and just over all ultimate handyman, and my love for decorating and crafting/creating, we decided to blend those things and buy our machine and open an Etsy shop with home decor we designed and made with our plasma cutter. Read more>>

Rhyan Geiger

Since I became a dietitian I have always had an interest in recipe creation, blogging, media, and other unconventional routes that a dietitian can play a role in. After passing my credentialing exam I was very interested in pursuing my passion for helping others eat more plant-based foods. But, as most college graduates do I felt I needed to get a job in corporate America to become successful. Read more>>

LaMonica Cartier

At the beginning of 2021 after having several conversations with my support system, I decided to quit my 9-5 to give all of myself to building my brand 444DESIGNSTUDIO. I debated whether or not it would a good idea to quit my job and risk it all. Eventually I decided if I took a calculated risk it would be worth it. Read more>>

Aisha Johnson

I discovered massage 6 years ago while getting a chair massage at my daughters new school. I knew that I was destined to be a massage therapist in that moment, it was like an Epiphany. I didn’t start right away I set some goals to accomplish before hand. One was to get my drivers license to that me and my daughter could get around easier. I started school in 2017 at the Holistic Massage Institute while working full time as a dental assistant and finished January 2019. Read more>>

Amber Kwong

The American Dream. To open up your own business. Taking a huge risk. To leave that steady paycheck and go all in on the dream you envisioned. The one that when you told others, they just couldn’t see it. This is exactly what I did Christmas Eve 2010 and I’ve never looked back. Read more>>

Carrie Bower

For years I worked as a wedding photographer. After 200 weddings, I was burnt out. You’ve heard it said again and again that artists are “starving.” I desperately wanted to get into a new type of art, and of course to earn enough to keep it from being a financial loss. I wasn’t sure if I could make it in an artistic field other than photography. Read more>>

Rebecca Kussmann

Being a business owner involves a lot of risks – from inception aka actually deciding to start your own business to everyday decisions that can result in a big win or a huge loss. My first risk was deciding to leave the first PR agency I ever worked at when I was 25 years old after only two years experience and branching off on my own. It was definitely a risk and a lot of people told me I was too young to make the leap, but I knew in my mind that it was the right decision. Read more>>

Juliana Lievano

I come from a family of entrepreneurs. All my life I’ve been surrounded with people that own their business. Coming to this country as an immigrant was a big change. I had other ideas for my life; I wanted to be a tv reporter. But there was no way I was able to accomplish that here not knowing the language. Read more>>

Cristina Victor

I strongly feel being willing to take risks is a huge and essential part of being a creative. When I started my art career as a full on practicing and exhibiting artist, I was deeply committed to a performance project that consumed my life and work for 4 years. I started to feel somewhat trapped by it even though it was all anyone wanted me to deliver for shows or events. Acknowledging that I longed to explore my work through other mediums and that the project had likely run its course I decided to bring it to a close despite the demand. Read more>>

Brittney Espiritu

Opening my store Storm Kalmerz in a religious town was definitely a risk. I had been running it online for 5 years, but decided that now would be the best time to open up a physical location. I knew there would be some backlash, but I went ahead with it anyway. Luckily, over time more and more people have been receptive of my store being in their town. Read more>>

Gheri Thomas

The act of starting a business, in itself, is the risk. I am very open and honest about the fact that I have been learning everything as I go and terrified every step of the way. From the moment I came up with the concept for ID’vour in 2017, I had no idea how I would execute it. Not only due to the financial resources being nonexistent, but that it was unheard of for manufacturers to produce for “made-to-order” slow fashion brands. Read more>>

Christopher McCoy

The biggest risk I’ve taken was leaving a promising nightclub DJ career to pursue weddings full time. When I made this decision I was spinning in several of Charleston’s most popular venues, had a loyal following of fans that showed up at all my events. Read more>>

Joshua Starr

The biggest risk I’ve taken as an independent artist was spending thousands of dollars on studio time and publishing platforms without a legitimate fan base. At first I saw a good turn around because I have a good support system , but after a month or two it declined dramatically. It felt like I was wasting money and time trying to do things on a larger scale without putting in the groundwork first. Read more>>

Cody Cook

Pursuing my small business full time was a huge risk in itself; we’ve all heard sad stories about those who create a company and fail shortly after due to a number of very real and unpredictable circumstances. Back in 2016/2017, I was unemployed, low on cash/savings but determined to bring my vision to life. I invested whatever savings I had into my business. I wanted it to be its very best. I spent time educating myself on the products I would be selling, so I could give my customers a knowledgeable purchase every time. Read more>>

Raheim Fender

In the year 2020 my group and I were getting ready to embark on a promotional tour along with releasing our brand new single and music video “Rawcuss”. Unbeknownst to us, Covid 19 would strike, shutting down the entire world, literally putting our music career at a halt. I was devastated, I had invested all my money into the venture and it seemed as though it would all go down the drain. Read more>>

Esperanza Camara

Back in 2020, my retail management role was eliminated. I was offered a different role, but it didn’t feel right, because if I accepted, that meant someone else would lose their job. I cried to my husband, telling him I felt displaced and I didn’t want to go back. We were driving home from the beach, I was in the backseat with my almost 1 year old, and he looked at me through the rear view mirror and so matter of factly said ” So don’t. Read more>>

Emi Matsushita

One of the biggest risks that I took in my life has been jumping all in on starting my business. I’ve had this notion that I was destined to be an entrepreneur, realizing that I didn’t fit the mold of working for someone else’s dreams or doing the 9-5 hustle. It was not for me. Even as a small child, despite growing up in a traumatic household that told me to play small to be safe, I had a gut feeling that I was meant for BIGGER things. Read more>>

Laurie Roberts

My story consists of two risks…The first was starting my own business with the emotional support of my late husband and his willingness to do whatever job he needed to do in order to help me succeed. He was an artist, with unsteady income. I was the main supporter, but I had to try, the worst thing that could happen would be getting a job working for someone else. It was terrifying. My Dad had instilled a strong work ethic in me and I knew I could do it, but it would not happen overnight. Read more>>

Kaneesha Willer

Since middle school, I knew I wanted to help others – to serve and make a difference in people’s lives. My mom sold insurance to people and was a foster parent. My dad ran a tow company. I grew up in the country – the boondocks of Oregon, in a town not even incorporated until 2006. Read more>>

Femi Adebanjo

I took a risk to buy my first home in 2002 cause I was tired of paying someone else’s mortgage & boom a week later get laid off from work. The risk I took just stretched my tolerance cause everyone told me to sell it before the 1st Payment was due. I don’t really subscribe to that theory. Had to buckle down & figure it out that life is all about risks. You don’t take them, you will never know how far you can actually take something. Stayed in that house 4.5 years & then scaled up to a bigger place Read more>>

Paul Giret

The biggest risk I have taken thus far is when I gave up a secure career path to pursue my passion. At one point in San Diego circa 2013 I was the Director of two Film Festivals, the President of the San Diego City College Film Society, and one of the two active founding members of the San Diego Film Consortium. My life was filled with constant deadlines. From organizing the judging of hundreds of film submissions to booking venues and hosing live events, my schedule was constantly full yet somehow, I managed to be involved in the production of many independent films as well which was truly where my heart was at. Read more>>

Diego Roq

There’s always a risk of failure when you decide to fully commit to your own artistry. I decided to commit fully to my filmmaking with the desire to solely live off of the projects I work on and things I create. Before starting to venture down the road of my own company I worked for another visual company in a small way and I wasn’t happy. I felt like I had more to offer but I didn’t want to give away all of my creativity and energy to someone else; I wanted to be apart of my own movement. I wished to change my circumstances but always struggled with the how. Read more>>

Sarah Morey

Lucky Money Entertainment is all risk-taking, hence the name. I started writing songs when I was seven years old because I wanted to have a song on the radio and I haven’t stopped betting on songs since then. I have always known that music is my passion and what I will spend my life doing, so I decided that I wanted to move to Nashville, TN to pursue music when I was ten years old. Being born and raised in Tampa, FL, though, it took me eight years after that to finally get to Nashville. Read more>>

Amanda Greer

It’s always a risk putting your life out there for the world to see and critique. There will always be strangers there to judge your every move or think they know what’s best for you. It can get daunting at times and make you question yourself, your choices, or your purpose on a social media platform. However, I’m a true believer in the saying “with great risk, comes great reward.” Sharing my motherhood journey as a stay-at-home mom has allowed me to connect with so many different women who share a similar lifestyle or family structure. Read more>>

Kaylynn Young

My biggest risk is putting myself out there … daily. I am a total doof in real life, but to catch that on camera and then share it with the world? It’s an entirely different level of crazy. Some of my craziest ideas have gone viral – and I haven’t done much more than put myself out there and be 100% myself. Take the risk. It pays off – even if you feel like a complete idiot. Read more>>

Caroline Dorick

I took a huge risk once; I rolled the dice and placed a bet on myself. When the world was telling me I couldn’t…I did! I suppose the best way to explain would be to start at the beginning. At the age of 26 years old I found myself a single mother of a four month old baby girl. I had a full-time job in which I was told there were no possibilities for advancement, so I needed to decide how to make more money for our little family on the side. That’s when my grandmother came to me and said, “I’ll help, if you tell me what you want to do that you will enjoy.” and I said, “I think I would like to look into becoming an Esthetician.” Read more>>

RIcki Weisberg

The biggest risk I have ever taken was to leave the corporate world and start my PR Agency. I spent twenty years building my career in the nonprofit and corporate world and I was the primary breadwinner for our little family. A lot was on my shoulders. But I felt the entrepreneurial spirit deep within me. Read more>>

Micah

A huge risk I took, that I would do again, is leaving school and jumping into the entrepreneurial world. I grew up knowing that I was going to go to college and get a degree but I was sorely mistaken. It was very soon after school started that I realized I wasn’t going to be able to complete college, not because I wasn’t intellectually able but because it felt like I wasn’t in a place I needed to be. With all the open time on my hands I knew I could hit the ground running on the things I know I want to do with my life, and so I did. Read more>>

Brittany Sundquist

Taking a risk can be defined differently be each person. Many of those close to me would define me as a risk taker. I love adventure, I love to try new things, and definitely express my uniqueness and individuality without shame. I however very much shy away from financial or professional risk. I have always put my family first, even when it meant I felt stagnant. I worked many years in restaurant management because it was safe. It allowed me to have a steady paycheck, it worked with my kid’s school hours, and it kept me in my comfort zone. For all those years, I put myself on the backburner, gave up my dreams for my family and let my mental health decline to all time low. Read more>>

Beth Weber

I had been doing yoga for about 20 years when I found out our yoga teacher wanted to sell her studio. Our Pilates teacher wanted to buy it, but couldn’t do so alone so she asked me. We went back and forth and finally, I decided to take the risk and buy it myself. My goal was to keep the studio open. So many people depended on the studio for their classes, their get away, their sanctuary and fellowship. How hard can it be ? Boy was I wrong. I quickly learned I have no business skills at all (my real job is being a pharmacist) and have no idea what I had gotten myself into ! Read more>>

Keegan Rodgers

In 2010 I was working up north in Big Rapids MI in a job that I didn’t like. I had just gotten out of a 7 year relationship and was floundering. I realized I wasn’t happy and I made the decision to do something about it. I’ve always wanted my own pastry shop / bakery and realized now was the time to go for it. I quit my job, moved down state to my parents basement and went to culinary school. Read more>>

Patrice Maynard

In January 2022, with the help of my business coach, I planned my first online conference for occupational therapy entrepreneurs of color. This happened while running my pediatric mobile practice and in school for my post-professional occupational therapy doctorate. Being a person of color and a business owner, I noticed there was no community specific to occupational therapists (OTs) of color who desire to start a business or are business owners to network, learn from each other, and build relationships. Read more>>

Cameron Gonzales

I’d have to say the biggest risk I’ve ever taken was choosing to shift my career path to something completely different than what I went to school for. In high school, I loved math, and solving number problems just made sense. When it came time to send interest letters to colleges as an assignment in 10th grade, I thought schools with good engineering programs would be a good bet. Engineering was never really my choice, it was my dad’s, but my 10th-grade self needed guidance and welcomed the suggestion. Read more>>

HASE Trek

2018- I decided to become an author. After being fired, on unemployment with lots of time on my hand. Stress, idle time and a passion to want to be different was the catalyst. Since 2015 the thought had been there however, 2018 the opportunity presented itself when scrolling on instagram I saw a associate/co-worker of mine post the release of his own book. I reached out. He gave me the info. Read more>>

Gillian Gibree

In 2010 I was competing as a professional SUP athlete, working as an ocean lifeguard, and yoga and fitness instructor. I was passionate about SUP and teaching my friends and family, and I saw the need to create a quality teacher training program to offer to the public. The sport of SUP was really gaining speed. I wanted to share my knowledge and experience. Read more>>

April Hartman

I’ve been a professional actor now for 17 years. It hasn’t been easy and I think I’ve tried to quit at least a hundred times or more. But I still love it. Every part of it. I knew living in Dallas that I had done all I could do there and it was time to make a change for myself and for my career. I think we all have to reassess our situation from time to time and see what we can do different/better to get where we want to go. Read more>>

Tiffany Riley

I took a risk by quitting a secure job that was just okay, to start my own business as a certified personal trainer (my lifelong passion.) I began by studying nightly after my day at work to get my personal training certification. I am a mom to 4 children, so It definitely was a trying time, which came with many sacrifices. I quit my job after the school year was complete and started taking both online and in person clients. Read more>>