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.

Sara E. Johnson

During 2020, while the world was shut down I had just given birth to my second baby. I struggled with severe postpartum depression and anxiety. I felt completely alone. I didn’t know how to ask for help. I couldn’t verbalize what was I experiencing, but I knew something was wrong. Family members started noticing how “off” I became. I typically was a social butterfly, but my personality started to shift rapidly. Read more>>

Lizzy Moffett

Switching careers is kind of like walking through a dark forest at night. It is often lonely, intimidating, and you frequently can only see a few steps ahead of you. For me, that journey was leaving my beloved elementary teaching career to become a proud web designer and business owner. It all started back in 2004, quite by accident. Read more>>

Catherine Gray

Starting any business or endeavor is taking a risk. When I decided to raise funding for my movie Show Her The Money – it was a risk. But if you have a vision and feel it’s a calling or your purpose on the planet – then you have to go for it. I thought, no one is telling this story in a film industry about the underfunding of women in venture capital and someone has to create an engaging yet educational film about this topic. I do believe it is film and television that changes culture. I know I had to find like minded people who agreed with this idea. Read more>>

Becka Rahn

As artists, we are risk takers by nature. It’s not the same kind of thrill-seeking risk as jumping out of an airplane or wrestling alligators, but it’s a series of little risks every day putting your art out there into the world. I feel like every day you make a new gamble: Will this piece get juried in or rejected from the exhibition? Will someone buy this from my Etsy shop so I get paid today? Will anyone like this post on Instagram so the algorithm thinks it’s worth showing to a new audience? I don’t know ahead of time what the result of any of these everyday tasks will be in my art practice, but I have to keep showing up and putting things out there and taking the risk. Read more>>

Celia Lopez

Eight years ago, I decided to begin my journey as an entrepreneur with my first business as an independent personal trainer. During this process, I saw a missing gap within the industry for people like me who wanted to create their own fitness businesses. There was no place for us independent fitness professionals to operate freely, and so the concept of wanting to be the change and create PlaceMade was born. Read more>>

Bryan Gomillion

Taking a risk was on of the hardest things I had to endure when pursuing my career path. There are many obstacles that will constantly arise. You have to be able to put every single aspect of your life to the side at one point and truly make it become your entire life. Your friends won’t understand, but realizing that the reward is always worth the risk will show you a new part of life that most people are afraid to enter. Read more>>

Blake Cortes

Everything in life is a risk. Some people take more risk than others and I’ve always been a people who was willing to take a big risk. Did they always work out, heck no. But at least I know when my life is done I won’t feel any regrets of something I was scared to try. Read more>>

Mark Ulriksen

As a kid I was always one of the best artists in school but the thought of pursuing a career as an artist seemed foolhardy. I was afraid I’d end up doing caricatures at Disneyland or some such. Eventually I ended up studying graphic design and for 13 years after college I was a graphic designer and then a magazine art director. But I still had this gift of being able to draw. I had also learned that I was a good creative problem solver, the essence of being in the applied arts. Read more>>

Valerie Magin

Conventional wisdom suggests that when one desires to learn, one seeks out those with knowledge of the subject or skill. But what does one do when there are few if any experts and finding them isn’t as easy as a Google search? Rewind 50+ years…before the internet, before social media, to a time when seeking information required a trip to the library in hopes of finding what you needed. While there were veterinarians available to treat dogs and cats and a few in large animal practices, finding one that treated exotics (as domestic rabbits are classified) was an exercise in futility. And that’s where Caroline Gilbert found herself. Read more>>

Kerri Oberer

My husband actually pushed me to start this business. I had been designing small boards for us at home, and for family events. Then it grew to creating grazing spreads at my son’s birthday party and a friend’s baby shower. He said- why not?! I had been toying with the idea of starting a charcuterie business for years, but just felt the pull at the beginning of 2023. Thankful I took the leap! Read more>>

Jessica Gilliam

No Risk, no reward. Great risk, Great reward. 2020 was a year of chaos and uncertainty. I don’t have to describe the proverbial roller coaster we rode as a nation as covid-centric regulations dictated our way of doing business and life. Personally, I stood at a crossroads. As our city went into shelter-in-place, my then 7 year old son came home to finish his first year via virtual education. The doctor who I was working for at the time shut down his plastic surgery practice in compliance to Dallas county and nation-wide ordinances. We worked remotely, consulting patients over Zoom and trying our best to keep our staff and our sanity. Read more>>

BethAnne Kapansky Wright

There have been so many risks, along the way, in growing my business and creative vision. One of the biggest ones was closing my brick-and-mortar private psychological practice in Anchorage Alaska to move to the island of Kauai in 2017. I knew I wanted to expand into endeavors beyond clinical work and build my voice as an author and speaker, but I had no idea what that would look like and felt like I was taking a leap of faith into an unknown space. Read more>>

Amanda Reichert

I think one of the biggest shifts I’ve made in my pursuit of a dance career that at the time, felt like a huge risk, was when I decided to leave New York. I moved there after I graduated from college and had the fortune of meeting some of my best friends and working with some truly incredible artists out there. New York (or at least the perception of it) offers up the prospect of endless artistic opportunity- there will always be a class, a show, an audition, a performance to be a part of or a platform offering to showcase your work. Read more>>

Sarah Sawall

I’ve taken a lot of risks in life. The funny thing about risks is that the more of them you take, the more comfortable you are taking ‘riskier’ risks. It’s almost as though you build muscle-memory in your head as you go. You know it will be difficult, but you become more confident throughout the process and you increase your tolerance for anxiety and uncertainty. Read more>>

Dana Kramer

As a Creative Director and Wardrobe Stylist based in New Hampshire and New England, I am most comfortable working within my local landscape. However, in 2023, I had the opportunity to travel to North Carolina when photographer Fur and Lace Photography (who has become a dear friend and source of inspiration for me both personally and professionally) booked me for several creative photoshoots in her hometown. Read more>>

Jonathan Gonzalez

I was working in the Distribution Industry Delivering Beer to Markets for years and also was having dj events on the side on weekends and sometimes during the week, working many long hrs, showering at the full time job to head to my dj events after to then repeat the process. Read more>>

Kwon Hosey

Moving to Atlanta for school in 2023 was the most significant risk ever. My circumstances didn’t favor that move; I just had a little faith. Boxes were checked off one at a time, but everything wasn’t figured out even on the road the day I moved, and I had maybe $400 in my bank account. A few of my fraternity brothers offered to pay my rent for the first 2 months, and I arrived and landed 2 jobs to sustain myself while I was in school taking 5 classes. Read more>>

Cameren Jackson

After graduating with a Mechanical Engineering Technology Degree, I decided to take the risk of becoming a full time actor. I was skeptical of pursuing an acting career which lead me to get my plan “c”, an engineering degree. I realized I wasn’t getting younger and this was the best time in my life to pursue my passion in the arts. After making this life changing decision, I am happy to say my career is ongoing and successful . Read more>>

Erica Xavier-Beauvoir

Risk means we dance with our fears. Usually, these fears are embedded in our cultural, familial, and surrounding reality fabric. Famous Black Feminist scholar Bell Hooks stated, “When we drop fear, we can draw nearer to people, we can draw nearer to the earth, we can draw nearer to all the heavenly creatures that surround us.” Deciding to fully embrace my Psychic abilities at a time deeply rooted in stability, community, and purpose placed me in a position of choice. Read more>>

Brittney R & Jules G

Individually, and together, we took the risk of following the threads of our passions. There is a lot here to try to condense. The essential pieces are that we wanted to breathe hope into the dream of divesting from jobs that were draining our life forces. The big risks here for Britt were leaning into advocating for herself, and taking care of herself in terms of pain management, and saying no to jobs that did not show care for her wellbeing. She also took the brave step of reaching out to her community and loved-ones for help. Read more>>

Eden Chinn

About two years ago, I co-founded an art gallery and multimedia creative space called All Street Gallery, which has storefront locations in the East Village and Chinatown in New York City. Physical space in New York City is challenging to maintain and, during the height of the pandemic, people developed new ways to stay connected and conduct businesses online. However, during this time period, I felt incredibly impacted by the communities I was able to connect with in person. Read more>>

Vera Lotus Onatah

The biggest risk I have ever taken was 2 years ago. I left a career that it took me 25 years to cultivate in order to pursue my passion as an Elemental Fitness Oracle. I was working on my craft as a barre instructor and Soul Shift Practitioner part time wile working full time. My journey of self exploration and inner child healing let me know I was meant for more than working a unfulfilling job for 40+ hours a week. Read more>>

Tyler Rudd

Taking a risk is one of the most important things we as human beings are meant to do. Yet, it is the most terrifying thought. I grew up in a Baptist Church. The entire Bible talks about people being tested by God as he puts them on a journey, thus testing their faith in him. Now, as an adult, I realize not many Christians are willing to walk with God on their journeys. People these days always say to never “Get Comfortable” and stay at a certain level that is not our full potential. Read more>>

Jordan Lacenski

Entrepreneurship is always a risk. There isn’t a checklist or a map to show you how to get from point A to point B. There’s no perfect model, perfect team or advisor. You learn by falling and failing and getting up again. You update your contracts based on experiences where you’ve been wronged or unprotected. You hire the wrong people and learn how to fire those people. You charge too much or not enough. Read more>>

Michelle Castelloe

This is a story about the risk of leaving a well-paying job with health benefits, while being married to a creative, self-employed husband and a mother of four daughters, to become my own boss and run a small business. There is no guarantee of salary, no health benefits, no guaranteed success, only hopes, dreams and strategy. Read more>>

Che Chinn

Embarking on the journey of establishing Wellness Abound was a significant and transformative risk in my professional life. Prior to this endeavor, I had established myself in the world of luxury spas, having dedicated substantial time and effort to cultivating a promising career. Simultaneously, I played a pivotal role as a program director for a Massage program I had initiated, further solidifying my presence in the industry. Read more>>

Austin Greene

December 31st, 2023 is my last day of work before I get laid off from my day job. My natural inclination is to immediately rebound and get another day job to support my family. Instead, I’ve decided to try and go full time as an actor. I’ve worked on enough projects last year that I began to realize it may be possible to survive off of my dream. But a lot remains uncertain, and I have my fears. It seems that this might be the push that I’ve needed all along. Read more>>

Norissa Williams

In many ways 2020 was a catalyst year. Many of us entered the year the same as we would any other. We’d heard of Coronavirus and how it had begun to wreak havoc in China. Yet, for those of us continents away, it seemed to be an unfortunate problem, there (not here, but there). We moved about our lives perhaps with increased awareness, but it would not yet shape our existence the way it would come to. Read more>>

Emily Vann

The US has an ongoing issue with sexually transmitted diseases. According to World Health Organization: More than 1 million sexually transmitted infections (STIs) are acquired every day worldwide, the majority of which are asymptomatic. Each year there are an estimated 374 million new infections with 1 of 4 curable STIs: chlamydia, gonorrhoea, syphilis and trichomoniasis. More than 500 million people 15–49 years are estimated to have a genital infection with herpes simplex virus (HSV or herpes).

Nick Brooks

In 2016, at at just 25, I had a what most people would consider ‘it all’. I was living in Dallas, TX making almost 6 figures a year, owned my own home as well as two other rental properties, and was living with the girl of my dreams. I was working in Education and positioned to move up rapidly at my company, but with all that I still felt unfulfilled. In my heart I was a creative, always had been. I had come up rapping but that career didn’t pan out the way I thought it would. Read more>>

Chelsea J

Risk taking is always measured in any business. The idea is that with being an artist, everything is a risk. There are no sure fire guarantees in this business. The only guarantee is that you will be taking leaps. You have to trust your own judgment and use discernment but sometimes you will be pulling that parachute chord midair. That’s the beauty of making music. You never know when a song or lyric might come to you. Read more>>

Ryanna Hammond

Since my early twenties (I am now twenty-six), I have known that I wanted to own my own business. I always came up with business ideas in multiple fields but nothing ever seemed right so I continued on the path of working 9-5s. This past summer, I was teaching reading online, and I genuinely enjoyed the job. I woke up for what I thought would be another day at work but about thirty minutes in a strong sense came over me that the job was no longer right, that I was meant for something much more aligned. Read more>>

Amina Harper

It started back in February of 2023. I was working in fine art as a painter, and there wasn’t a single area of my life where I wasn’t struggling. I had just helped a local gallery put on a group show and I was standing outside of the venue wondering what I was doing here and why I was continuing to try so hard for something that amounted to boredom and mediocrity at best. I went home and decided that I was done with my fine art career; fifteen years of chasing completely down the drain. Read more>>

Fp3 The Legend

It’s never easy to truly take criticism, especially nowadays with social media giving pretty much everyone a platform to voice their opinions, whether they’re wanted or not. But one thing I learned growing up was to take leaps of faith sometimes because you never know what your outcome could be, I started putting out my music on SoundCloud back in 2017 and I would’ve never saw myself doing this full time and actually sharing my story with the world. Read more>>

Wendy Graf

Being a playwright and having your work viewed, read or produced is always a risk – you subject yourself and leave yourself wide open to anyone with an opinion, good or bad, smart or stupid! Every time you submit your material it’s a risk – you must develop a thick skin and learn to take rejection, as it isn’t always about the material it could be about a myriad of reasons. Every time one’s play is produced there’s always a risk: will it go well? Will it get good reviews? Read more>>

Julia McGuire

Anyone producing an agricultural crop is taking a risk. Urban and suburban beekeepers especially take risks because most of our bee yards, also called apiaries, are someone else’s residential back yard and we can’t control where the bees go to get their food, called foraging. Even if we could corral the bees and limit them to one residential property, it’s best for them to visit other sites as a way to have a diverse diet. Just like humans getting all the food groups, diverse forage is healthier for bees according to an overwhelming number of academic studies. Read more>>

Coloma Muro

At the age of 25, I was running the Spanish office of an international European company. I had 110 employees that I personally trained. Beyond my office manager duties, I dedicated my energy into developing skill-specific training programs to promote employee development, and into measuring and reporting on marketing campaign performance, among others. Read more>>

Vasily Klyukin

One day I started to do everything I put off until later: reading and writing books, travelling and taking adventures. I went to Venezuela and Notrh Pole, did an ice driving and Olympic bob run, reached Everest base camp by helicopter through invisible clouds, crossed Atlantic Ocean meeting storm But I didn’t feel scary trusting my guides, professional pilots etc Read more>>]

Kristin Revere

I don’t steer away from risk-taking in business. As a visionary leader, I often have twenty new ideas floating around in my head. I only act on the ideas that make sense for the core values of Gold Coast after my team has input. We created The Becoming A Mother course during the early stages of the pandemic when in-person services were halted as a way to connect our doula clients and offer support outside of West Michigan. Read more>>

Daniel Komforti

The decision to leave the security of a regular 9-5 job at a general outpatient physical therapy clinic and dive into entrepreneurship was not made lightly. The journey leading up to this pivotal moment was a blend of self-discovery, professional growth, and a desire to make a more significant impact on the community. The story begins with a growing sense of dissatisfaction in the routine of the traditional work setting. Read more>>