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.

Marlina Devery

This past winter I submitted a self tape for the open call of a Broadway play. I looked up the casting director on Instagram and saw that one of my professors from college followed them. I decided “what the hell, why not?” so I reached out to my professor and asked if she could put in a good word for me. I was incredibly nervous after I sent the email, telling myself it was a mistake and that I burned a bridge professionally. Read more>>

Charlotte Lea

Taking the leap to move countries, start anew, and establish my own business in the U.S. was a significant risk that has shaped my journey. Several years ago, I made the courageous choice to leave the UK. Leaving behind familiarity, family, and a well-established career, I set my sights on California. Starting from scratch was not without its challenges. Looking back, I can confidently say that taking the risk to start again was a transformative experience. Read more>>

Christine Anderson

Taking a risk for me was leaving behind a career in 2013 that seemed set in stone. I went to college to become an art educator in Chicago. I spent 5 years at a prestigious program to quickly realize this was not the path for me. Within the first year of teaching art at a high school my stress skyrocketed, I was unfulfilled and knew I wasn’t walking in my alignment. That year I left mainstream academia and pursued my passion for yoga. Read more>>

John-David Swiger

The biggest risk I took in life was leaving my job in 2017 to become a full time Artist. Myself and my brother, Michael Swiger, had recently graduated from separate art schools with degrees in Graphic Design. After a few years of corporate America, we decided to open our own Art studio/gallery in our hometown of Gulf Shores, AL. We only had a handful of clients to start with… Some weeks were good and others we scraped by, but we were proud to be working for ourselves – calling our own shots. Read more>>

Dr. Ciara Lumaj

Veering away from conventional medicine, I decided to pursue a Naturopathic Doctorate (ND) instead of Medical Doctorate (MD), meaning I would take sacrifice recognition/licensing in all states to only on a state-by-state basis causing massive limitations on my scope of practice. Why would I do this? Because naturopathic medicine prompts creativity, innovation, and recognizing that the standard approach of “one-size-fits-all” is not what heals one from disease, rather, it can momentarily stop a process. Read more>>

Krissy de Groot

After a decade working in Theatre Administration, I became a Stay-at-home parent to my two little boys, both under 3 years old at the time. Being a SAHP was the hardest job I ever held. I found myself questioning whether or not I could do it every day. I needed something creative, and had always been fascinated by floral design, so I started taking Floral Design night classes an hour away from my home twice a week. Read more>>

Taylor Tote

The biggest risk I’ve taken was on my most recent project due to be released this summer called “Middle Name.” In late 2022, I received an offer for a full-time position that was too good to be true. It was in the entertainment industry, had an incredible salary, was bicoastal, and my employer was very similar to myself and seemed very supportive of me both in and out of the job. Read more>>

Natalie Milligan

One of the biggest risks that I have taken as a business owner was when I decided to take an internship in Paris for two months during my busiest season. In addition to owning a Simply Millie Studio, a small jewelry business, I am pursuing a Marketing degree at The Ohio State University. To stand out in my program, it’s important to gain internship experience. Read more>>

Lauryn Eaddy

Taking a risk includes going beyond your comfort zone. Risk does not always involve taking a risk for a job. Taking a risk does not always involve moving to a new place or a new environment. Taking a risk does not always include taking in a new relationship or connection. Read more>>

Brittany Hiser

I took a huge risk opening Java Jackets. I never owned a brick and mortar business and the only coffee shop experiences were from previous jobs. A couple of things I knew for sure: If ” they” could do it so could I and I knew our community was missing a neighborhood coffee shop so why not me? I dabbled in the idea of opening the shop for a couple of years but I dabbled with self doubt which really kept me from taking the leap. Read more>>

Grace Jung

I don’t think risk-taking is a singular task that happens just once in a person’s life. I see risk-taking as a daily challenge to be overcome. Being a stand-up comedian forces me to risk my ego, dignity, face and reputation every single night when I get up on stage. It’s an excellent way for me to put this challenge into practice and remind myself of how high the reward is when I take these risks while also appreciating how cataclysmically awful I can feel when that risk does not lead to reward. Read more>>

Derrick Mayo

So I am my father’s son (we literally have the same first name) but unlike him I am a risk taker. If you know yourself and you have an energy flowing within you beyond explanation for something you want, take the risk. There is no reason to waste time and contemplate on something you think about everyday. Yes there may be things like information or access that you lack as key tools to start but if there is a will there is always a way. Read more>>

Ryan Essick

I took the risk of becoming an artist in the first place. My trajectory from when I was little was to excel in school, get a good job and live my life down a straight and narrow path. But something inside me wanted to go after something worthwhile. From where I’m from, the hopes and aspirations of becoming a professional music artist were unheard of simply because no one where I came from had done it before. Read more>>

Matthew Zaremba

To be creative, is to take risks. Pushing past the fear of failing and embracing the reality that you’ll likely fail again and again. It’s picking up lessons in the frustration or shortcomings and learning from them. It’s problem-solving. Trying again until whatever you’re working on starts to inch closer to the vision you had, or starts moving in an unexpected but promising direction that surprises you and keeps those creative gears turning. Read more>>

Sergio Arce

Back in April 2020, the Corona Virus had cause a big change to everyone daily life. For me, it meant hospitalizations were rising, both me and my spouse worked in healthcare now with bigger workload with higher risk. My two daughters were not able attend school in person and the need for home schooling. Before things started to reopen and life started to normalize again, I had decided to become a stay at home dad and focus on my family and also my passion as an artist. Read more>>

Rachel Jackson

It’s crazy how one day you’re hanging out in someone else’s Twitch stream, talking with everyone in chat, and then a few months later you’re taking that risk and pushing the ‘Start Streaming’ button yourself. I started off as a viewer. I signed up for Twitch and started watching one of my now good friends sometime in early 2017. Read more>>

Lina Camboulin

Not too long ago, I was a Software Sales Account Exec, climbing the corporate ladder and helping big time clients like Walmart, Target and Walgreens with their IT transformations. I had done everything that society said was the key to success – graduated from college, fancy 6 fig job, owning a car, living in an apartment by myself, Read more>>

Jon Meyer

The list of true risks I’ve taken in my life is pretty short, in fact, list is the wrong word because that word implies multiple risks could be listed. In the eternal nature vs nurture debate of what shapes a person’s personality, I’ve had a lifetime of both sides of the debate working to entrench a staunch risk aversion into my ethos. The idea of starting a small business might as well have been as laughably improbable as visiting the Moon. Read more>>

Suneel Kulkarni

For me, personally, the very first-step of even embarking upon a creative endeavor like Turn Sound On involved taking on a sizeable amount risk. “What will people think?” and “Can this really be a career?” were the two questions often found bouncing around in my head. Read more>>

Shenita Sanders

One of the biggest and best risks I have taken so far is opening a spiritual and energy healing practice during a global pandemic. I walked away from earning a secure income to risking it all for wanting to be of service to others in my own unique way. I knew in my heart that what I have to offer is beautiful, needed, and impactful. Read more>>

Emma Sledge

It’s no secret that wild Florida is an unforgiving place. Between swampy terrain, reptiles that could easily kill you, and innumerable biting insects, getting out to the best fishing spots can be risky. Sure, you can catch fish from the safety of a dock or while boating down well-maintained waterways, but my experience is that the best fishing is done in the deep woods or far in the shoal grass where many boats can’t go. Read more>>

Ashley Kates

I opened StrongHER, as Mom+me Strong, March 14, 2020. Two days later Covid shut down all fitness facilities. To say that was a devastating event and year is minimizing it but I am thrilled to say I am still here and thriving thanks to an expensive, scary, but rewarding decision! But it was not and is not easy. Both 2020 and 2021 taught me a lot about who I did not want to be, Read more>>

 Kayla lofaro

The biggest risk I have taken is opening discotheque! It was the height of the pandemic. Salons were not even allowed to be open and the salon that I was working out had closed and I figured “is this my time?” my dream has always been to be a salon owner. I wasn’t ready mentally or financially but I figured, am I ever going to be? I just jumped in, and I am so glad I did. It’s the best decision I’ve ever made in my life. Read more>>

 Aja Campbell

As a business owner it’s always scary to go out and leave your regular life behind and when I say regular i men your safety net having something to Fall back on like a regular job. It was always scary to take a risk especially living in Los Angeles. I always thought to myself if I don’t take the risk I’ll be stuck in a spot and depressed but if I take the risk it can go either way. You could win or you could fail, Read more>>

Alexandra Gerros

Yes, I agree we tend to overlook risks and sometimes to get yourself out of a pattern, you have to undertake a risk so big that it forces you to figure out how to get through it and adapt. My life as a business owner began in Brooklyn, New York in 2014. I was 35 years old and purchased an existing consignment shop close to where I lived in the beautiful neighborhood of South Brooklyn. An area that never experienced rapid change like the trendy areas of Brooklyn had over the years. It is steady and holds its exterior of large homes on a hill by the bay. Read more>>

Stacy Mohs

Small business ownership and the idea of starting with nothing with a dream to grow and become something is always a risk! Can the business thrive, how do we drive customers and sales, what is the best way to promote a unique business that includes adventure and getting people out of their normal box? Read more>>

Jennifer Accristo

One of the overarching defining moments in establishing myself is when I was studying in the Shamanic Academy under Rose Cole and we were doing a module on boundaries. One might think what do boundaries have to do with spiritual work!? Yet it was a honing of the ability to center and direct one’s energy, to shield oneself, to fully examine tendencies of codependence, to be clear with one’s intentions, to master one’s response to life, to practice direct communication, and be fully authentic without fear. Read more>>

Blake Kennedy Kimberly Rumfelt

Kimberly and Blake met in San Antonio Texas in 2015. It is here that Good Hope Studios was born and they merged their creative practices. In Fall of 2022 Blake was offered and accepted a position at NC State University’s Craft Center as the Clay Studio Manager. For seven years they had built a community in San Antonio and now it was time to take a risk, to move 1300 miles away and expand their community. Since the move, Good Hope Studios is growing new roots, building a new studio and forming new connections. Read more>>

Kreg Weiss

Back in 2004, I had been active in the yoga and wellness industry for some time, and I noticed this new trend of “streaming” platforms emerging. I also noticed a problem with people’s retention and commitment to yoga practices outside of the studio. I connected with two other wellness professionals who had experience in film production and we set up a video production company along with one of the first online yoga video subscription services. Consider back then, few people had laptops (and tablets were non-existent), so many people doubted that our venture would succeed. Read more>>

Kay Thomas

This story is more so of the crazy way I went full time in my business. My senior year of college I was working my business part time. I graduated college in May 2018. I already had job interviews lined up. By mid June I had already started and quit about 4 to 5 jobs. The last job i got hired at was a door to door job selling cable and internet. Read more>>

Sherri Sherock

A risk I took that made a huge impact on my life was deciding to leave my full-time job in a profession I spent over 20 years in. I took that leap and started my own business in a different field and in my mid 40’s to live the life I always wanted. My dream was to work from home with the flexibility to make my own schedule, do what I love and be there for my kids. Read more>>

Carly Yost

I’ve always been fascinated with fashion & modeling, and I wanted to pursue it at a higher degree, and in a city that is fashion forward, so I took the risk and moved across the country to Los Angeles. This is my first time living alone & moving away from family in hopes that i can pursue fashion as my full time career. Whether its me continuing to model, personal style, & creative direct on sets. So far everything has been paying off & im continuing to network in the city & im manifesting that the rest of 2023 is great! Read more>>

Aaron Shaw

Risk is not merely the avoidance of failure; rather, it entails embracing failure. Contrary to common belief, this aspect is not inherently negative. Without the possibility of failure, there can be no chance of achieving success. I firmly believe that there are individuals today that are inherently inclined to embrace more risks, be it in their personal or professional lives. There’s also individuals that only take calculated risks to minimize the likelihood of failure, I do not perceive myself as belonging to that category though. Read more>>

Aaron Evins

I recently took the risk of leaving my 14 year career in the Air Force in order to be able to be a full time musician! 2 years ago, I was making the most money I ever had, but was also the most unhappy i’ve ever been. When it got to the point where I was in tears driving to work, I knew i needed to chase my dreams or my adult job was going to kill the artist in me by molding me to conform just to survive. Read more>>

Stephanie Daily

I spent 13 years in the insurance industry. In my last job as a Territory Manager for a large insurance company, I had great success. In 2007 when the mortgage and insurance industry tanked I was let go from my position. Seven days after I got married. After that happened I decided insurance was no longer for me. Fortunately, I have a very understanding husband. He suggested that instead of going to another insurance company, I do something I really wanted to do. Read more>>

Christopher Schumacher

I don’t really have a specific example of taking a risk other than just pursuing creative endeavors in general. There’s a Hunter Thompson letter that says it better than I can, but the idea of taking a risk to achieve something you feel called to do rather than just swimming with the current is something that takes courage. Read more>>

Edgar Everyone

Recently I was invited to join a group of 15 people and travel deep in the Brazilian rainforest, to spend time with an indigenous tribe called the Yawanawás. The trip would include learning about their culture, and 3 ceremonies with ayahuasca (the plant medicine that has been revered by many for centuries). At first I was a bit scared to hop on that adventure, but there was a little voice inside of me that keep telling me to go, so I finally booked my tickets and embarked on the journey. Read more>>

Nicole Holland

Leaving a very comfortable landscaping career in the low desert and investing in Cactus Mart on the heels of a long recession. I had many important people tell me they didn’t think “now was the time” considering the real estate bubble bursting and nobody knew where Morongo Valley was. This was still pre social media frenzy. Not much was happening in the high desert in those days. But I really loved this place and grew up shopping here and always loved the originality it brought. I trusted my gut and heart that I belonged here. Read more>>

 Darla Nelson

This topic of “Taking a risk” immediately reminded me of the journey I have been on in my coaching practice. I had been a financial advisor for over 10 years and due to life experiences, losing my dad to heart disease, and the economy crashing in 2009/2010, I knew that I wanted a change. I had worked so hard to become a financial advisor. I had passed all the state exams, some of which took me multiple times of taking, so giving them up was “taking a risk”. Read more>>

Keith & Sherri McDowell

Taking a Risk! That can look very different to everyone, but usually not easy for most. Deciding to start a YouTube channel made me a little nervous, because I didnt know how the public would react or accept what we published. Motorcyclists are our main viewing audience and most of them are extremely nice and supportive people. Read more>>

Angelica Bongiorno & Gianluca Masella

Before the inception of Studio Nola, we, as individuals, had already established thriving companies within our respective industries. However, it was in 2021 when our paths aligned, and we decided to combine forces to tackle ambitious, large-scale projects together. The outcome was beyond our expectations—successful presentations, productive meetings, and a drive that fueled our creativity. Read more>>

Ademola Oyewole-Davis

I moved across the country, all because I knew I could make it. I’m from Brooklyn, NYC, New York, where I’ve been told, “If you can make it there, you can make it anywhere” I always believed that New York would be where I would thrive as an artist. When the pandemic shut the world down, I started to expand my thinking, letting go of my past expectations. Read more>>

Stevie Vanderheiden

I believe the first risk I have ever taken regarding selling my art was at an event called The Joe Expo. I was fairly new to the local art scene and had no experience in trying to sell my pieces. I had been encouraged by friends and family to try to expand locally. This opened a door for me in my community and is ultimately the what got my name out there as a serious artist. I sold a few pieces but the exposure was the most beneficial aspect of that event. Read more>>

Elise Sandidge

Art is risky. Every single day, every single post, every single stroke of a pencil or brush is a risk. As an artist and creative person looking to earn money for my work, the vulnerability of putting my soul out there in the world for consideration by complete strangers is immensely risky. Emotionally, mentally, spiritually. Read more>>

FO$$

The biggest risk I have taken was when I made the choice to change careers and move from Massachusetts to Miami. After a 13-year career as a high school Spanish teacher I decided to resign from my position and move to Miami to pursue my art professionally. It was definitely a risk, leaving behind a stable career with great benefits and a retirement plan to pursue art. Art is probably the least stable career there is, but it’s what I love to do and truly have a passion for. Like one of my closest friends always tells me, no risk, no reward! Read more>>

Peter Roesler

One of the biggest risks I took was at the beginning of covid. Everyone else was shutting down and cutting back. I decided to charge into the fire head on. I aggressively increased our advertising budget while customers were cancelling like crazy because they were cutting back like everyone else. At the beginning, nothing came in, it seemed like a wasted effort, however, Read more>>

Tatiana Abraham Siqueff

Being an international student in the USA, most of the time, means you really took a risk by moving countries for your education. But for art? People back in Mexico told me all the time “Wouldn’t you be happier to just stay here and take a normal career that can give you some basic skills?” or “Are you really willing to leave your family behind in that way?” Read more>>

Grace Wittmann

Summer 2022, I had to take a risk. A risk to work and make money to help myself financially during the school year, or take an internship to gain experience in the field I hope to work in one day. I originally decided to take the financial security and applied for a job back home. A few weeks after I applied, the Wisconsin AHEC CHIP Program was brought to my attention. After a few days of thinking, Read more>>

Inger D. Kenobi

About ten years ago I did the very thing that Elizabeth Gilbert warns us against in BIG MAGIC; don’t quit your day job for your art. The year was 2013 and I was working at the Norwegian Embassy in London. I truly wanted to write and publish a book, but between working five days a week, commuting two hours a day, and not having any meaningful time to write, I didn’t exactly live the life of a true artist. So I decided to jump in on the deep end. I handed in my notice and gave myself a year to finish my book. Read more>>

Joanna Rogers

I took a risk starting my own private practice in a new city in Colorado. I was successfully able to market my work and connect with others in the community to continue to provide therapy services. Read more>>

Altin Sencalar

My senior year of high school I decided to pursue jazz studies as my major in college. This came as a shock to my family as I was very committed to classical music. When I was 16 I was already passionate about music but I wasn’t huge into playing jazz for the social part of high school band. I was concentrating on the euphonium which is my first instrument and was wanting to do the classical performance route after attending the Boston University Tanglewood Institute in Lenox, Read more>>