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.

Jenny Doyle

I feel like life should be a risk. God gives us all gifts to use for the good of one another and humanity. I know that when people are at the end of their lives, they always have the regret of wishing that they took the chance and did whatever passion they had or thing in their heart. Read more>>

Lauren Clark

I started my photography business when I was 17 and a senior in high school. I had a mentor who guided me through the process to get a tax ID and a DBA at the county courthouse and I was on my way with big dreams to take my friend’s senior photos to pay off my new camera before I graduated high school a month later. Read more>>

Daniel Tanasa

Engaging in any aspect of life entails a certain level of risk, and it is our responsibility to assess and determine which risk-reward balance justifies taking a leap of faith. Any pencil will look sharp before it was ever used, the fear of making mistakes should not immobilize us from taking action. Read more>>

Gary Stuart

I was successful with Day jobs to support my inquiry into a European healing modality no one ever heard of… I took a leap of faith to give up a day job to lead workshops and events nationally with great success. Read more>>

Lisa Apple

I quit a nice, comfy, well-paying job at 26 years-old to pursue the unknown and unstable career of music, writing, and teaching. I had grown up in the creative world – performing, singing, dancing, writing. I started out in college as a voice major at Belmont University, but after a rough bout with vocal nodules, I ended up getting my degree in music business. Read more>>

Lee Harrington

In 2004, I had a car accident that left me unable to consistently show up at my day job. Between doctors appointments, inability to sit at a desk for a long time, and challenges negotiation with a supervisor that didn’t understand, it left me in a tough situation. Read more>>

Avery Norris

It’s a funny thing being an artist for a living. I’m not out there curing diseases or flighting crimes, or putting out fires. 9.9 times out of 10 I’m very rarely physically putting myself at risk. You can argue that being an artist is a selfish career. Do we do it for the acclaim of our work? Read more>>

Lana Elco

Taking a risk is my life theme. Choosing to be an entrepreneur is a path full of different risks. I feel deeply grateful for my mother role-modeling taking risks and bold entrepreneurship for me since my early years. I grew up in post-Soviet Ukraine, a chaotic and free environment full of opportunities and risks. Read more>>

Barbara Schubert

Embarking on a modeling and acting career at 53 years old was a bit of a risk. Not a big life changing one; if it hadn’t worked out, I would still have my day job, family, and friends, but putting oneself so literally out there on display is not without risk at least to the ego. Read more>>

Lindsey Ganzer

Open the hospital was the biggest risk I have ever taken in my life. I have been an emergency veterinarian for 12 years, and worked as an associate at several practices in Georgia, Colorado, and various other states. For two of those hospitals, I was promoted to the ER director position. When one of those hospitals sold corporate, I saw a dramatic shift in the culture and focus within the hospital, lead by the new ownership. Read more>>

Tammy Lovin

In the dynamic realm of Extended Reality (XR), comprising Augmented Reality (AR) and Virtual Reality (VR), the role of a digital artist transcends traditional boundaries. As an Emerging Tech Specialist, navigating this fast-paced, ever-evolving environment is not merely a job; it is an exhilarating adventure. Read more>>

Joe Dinardo

I was in my software consulting job for about 5 years. I had started my mindfulness coaching business about 2 years prior and was working on both of my jobs for that time – weekdays (and some nights) were spent in the consulting job and weekends (also some nights) were working with clients 1-on-1, doing what I loved. Read more>>

Breakfield And Burkey

Breakfield and Burkey were writing technical white papers and technical manuals for Auerbach press some 20 years ago and they did the publishing and marketing. We tired of having to update the materials on a regular basis so we thought about doing fiction with technology baked into the story. Read more>>

Julie Blouin

Life has a way of pushing us to make bold moves either because of obstacles, pain, or simply the lack of joy in our every day life. Life is destined to be lived to the fullest, not confined by the fear of the unknown, limited by societal expectations or dulled by routine and monotony. Read more>>

Camille Cintrón Devlin

I have been working as a public and media relations specialist in the performing arts for over 15 years—basically the entirety of my career. But it wasn’t until about four years ago, in 2019, that I began my journey as a independent consultant. Up until then, I had dabbled on side projects while holding a full-time position within an arts venue or institution. Read more>>

Terrice Thomas

One of the reasons Mentoring is so important to me is because I experienced it firsthand from my boss during my first professional job. She took an interest in me that went beyond just my career and helped me to grow personally as well. She also worked with me on those weaknesses she noticed, giving me tools and advise on how to improve and become a leader. Young professionals really need that guidance. Read more>>

Elizabeth Lyons

Being a creative person almost always involves taking risks. The biggest challenge with this stems from the fact that creative people are often risk averse. Because taking risks allows for “failure” (please note the quotes). I’ve taken many risks as a creative, some that felt as risky as jumping from a plane without a parachute, even though they were the kinds of risks others took daily, without wincing. Read more>>

Victoria Nielsen

The biggest risk I’ve ever taken was being willing to go on a journey of self-healing and discovery. It can feel scary to expose all the things you’ve kept buried inside, but once you begin to uncover the layers of yourself, you can finally come home to who you really are. Read more>>

Amanda Moran

I have taken many risks in my career and, especially, in my adult life. I think taking a risk feels scary because of the desire of a successful choice or possible consequences of failure. It was risky to chose a school and path no one in my family or community had taken before. Read more>>

Kaylyn Marie

The biggest risk I’ve taken was actually starting my business! A little back story – I had a very rough pregnancy with my son and was forced to take medical leave from my job early on. After having my son in 2018, I had used up all of my medical leave and vacation, and was left with no maternity leave, ultimately leading to me quitting my job to take care of my son while surviving off my husband’s income. Read more>>

Shannel Wheeler

I’ve taken quite a few small and big risks in my life, but the most recent and impactful one was my decision to leave my job in 2020 to become a full-time creative entrepreneur. Before you assume that I rode the wave of “The Great Resignation”, I can boldly say that I did not. Read more>>

Queso Tone

A risk I took was switching fully to the Pop genre. I started doing my music solely rapping and was always scared of what people would think if I started singing. However, around the time I started working on my album “Raw Ambition” I came up with the theme of breaking through chains. Read more>>

Kristi Angevine

After 10 years of delivering babies, doing surgery and working in a busy private practice as an Ob/Gyn, I stopped full-time clinical work to start my own business as a life coach. Quitting my work as a doctor took a crazy amount of courage. To be an ObGyn meant I’d spent 4 y in college, 4y in medical school and 4 years in residency training before my decade of private practice. Read more>>

Sam Led

In 2017 my life fell apart. My marriage fell apart. My community experienced two life changing natural disasters ( deadly mud slide and one of the worst wildfires in California state history) in one month, To say it was a stressful was an understatement. Read more>>

Emily Knauer

I took a major risk when I decided to walk away from financial stability and bet on myself 100%. I left a toxic relationship that felt safe to run my business full time and depend 100% on myself and my earnings. It was scary, but four years later I would never go back and don’t have a single regret. I’m proud of myself for leaving and taking that risk. Read more>>

Katt Rardi

Quotes about regret always found their way to me. Every time I doubted myself, a little spark of inspiration would remind me that anything is possible. I have always feared a life of regret more than not doing something out of fear. From an early age I knew it wasn’t going to be an option for me to have a back up plan. It was either all of nothing. Read more>>

Maria Coyne

A risk I am proud to have taken is releasing the song “Something Good” out into the world. It is the latest single from my band Maria and the Coins and marks a shift for us musically and artistically. It is more rock-driven and the subject matter and lyrics are the most intimate and vulnerable of anything we’ve released thus far. Read more>>

Stephen Holding

In 2019 I was invited to paint a 2-story mural in Greensboro, North Carolina. At the time of leaving for the trip, I was two weeks out of surgery for an infected gall bladder that needed to be removed. I had been unemployed at the time, had very little money to spare, and given my modest status as. a muralist I wasn’t offered much in terms of compensation. Read more>>

Eric Haines

Any creative endeavor involves an element of risk. To create something that didn’t exist before means by default that the act is not anchored by copying or plagiarizing something that has already been proven. Of course, there are frameworks that a creative works within; there isn’t a painter who remains completely uninfluenced by the other paintings they’ve seen, or a musician who remains uninfluenced by other music they’ve heard. Read more>>

Sonya Philip

There been many times when I was worried or reluctant to do something. I started designing and selling patterns about 10 years ago. I sold them through an Etsy store and was strictly online retail. A local business reached out to ask whether they could carry my patterns wholesale, It didn’t make sense to me, getting half the amount of money for my product, so I said no The buyer of that store was very understanding and we stayed in touch. Read more>>

Greta Ertl

In 2023 I took the risk of hosting my first out of state retreat in Sedona, Arizona. My friend Rosie and I had been attending yoga retreats around the world for years and decided we wanted to create our own. Though I had experience hosting workshops and local retreats in Minneapolis, this was a much bigger financial risk. Read more>>

Telsys Tarallo

After having an amazing career working for experiential marketing agencies and then having two kids (12 months apart). I quickly realized that agency life was no longer a fit for my new mom lifestyle and responsibilities and working for someone as a single mom wouldn’t be natural. Read more>>

Zoel

From my earliest days, I sensed that the world was more than just a place to exist; it was a canvas awaiting my creative strokes. Every decision felt guided, as if the universe conspired to provide the steps and people for my journey. Moving from my hometown in Argentina to settle in New York never struck me as a risk back then. It felt like the natural flow of life. Read more>>

Ashley Lasseigne

While creating art for some is easy, selling is HARD. Hello there, I am Ashley Lasseigne, owner of Ashley Lasseigne Textiles. From a young age my parents new I had a niche for art. Growing up I attended art lessons and really focused hard with fine arts in college. I started with my first business in interior design and decorative faux painting (which was a huge thing in the early 2000’s). Read more>>

Cecilia Caparas Apelin

“Embracing our vulnerabilities is risky but not nearly as dangerous as giving up on love and belonging and joy—the experiences that make us the most vulnerable. Only when we are brave enough to explore the darkness will we discover the infinite power of our light.” – Brene Brown Read more>>

Kristine Schomaker

Almost 10 years ago now, I quit my stable job in an Emergency Room to take my business of being an artist/mentor/manager full time. Things were changing for me in the medical field and I wasn’t happy. I knew it was now or never. I always feel that life is too short and we have to do whatever it takes to make us happy. Read more>>

Aziz Cem

Embarking on the journey of my martial arts career was a significant risk that shaped my life in unexpected ways. Back in 2010, fueled by a burning passion for karate, I aspired to join the Turkish Karate National Team. The dream, however, was met with skepticism and even mockery from the national team coach. Determined, I persisted in my training and self-improvement. Read more>>

Belkis Clarke-Mitcham

My story isn’t a fairytale; it’s more like a gritty novel with a twist of triumph. Picture a young girl, grappling with the shadows of childhood sexual abuse. That girl was me, groomed and betrayed, learning early that my value seemed tethered to pleasing others. Read more>>

Heather Hope

One of the biggest risks I have taken is joining the Peace Corps to serve in Mali, West Africa from 2001-2003. I hadn’t even heard of Mali when I learned I was being sent there. What I found out before going was that it was one of the five poorest countries in the world that was facing desertification due to people collecting the trees for fires to cook their meals. Read more>>

Domonique Revere

Leaving a stable, well-paying job to start a business was a decision that unfolded against the backdrop of a desire to create something meaningful and aligned with my values. The story begins with a deep sense of discontentment in my corporate job, where financial stability coexisted with a growing feeling of emptiness. Read more>>

Zen Ase

In 2017, stressed out and contemplating early retirement from teaching ( which could have been financially disastrous), I began performing as Zen at the Sugar Hill Lounge on Poetry Lounge Sundays. It was supposed to be a hobby. But at a different open mic, the owner approached me asking if I would curate an actual poetry show with a flyer and an itinerary. Read more>>

Brad Rushing

I have spent my entire life “jumping out of planes.” Not literally. I am not fan of heights. But I have never been risk averse when it comes to following my heart, my muse, my intuition. Part of that is thanks to my very loving and supportive parents who saw potential in me before I even could understand the concept. Read more>>

Eva Valentine

I certainly wouldn’t categorise myself as a “risk taker”…I prefer my comfort zone, familiarity and routine. Though life sometimes has other plans and you realise that something needs to change. For me, and perhaps like most, COVID was a time of personal reflection, and a time of losing your job. I was living in Los Angeles, for the past 10 years, as an event management professional and finding myself furloughed until further notice. Read more>>

Brian Levy

The journey into starting my own business wasn’t a meticulously crafted plan from the outset. It all began when my brilliant wife nudged me about doing something in the field I was already in. Read more>>

Bennie Brimage

Taking a risk and stepping into the unknown can lead to remarkable outcomes. Here’s the story of my journey with Rivalry Edition: Twenty years ago, I conceptualized an idea that lingered in the back of my mind. It was a vision for a project that had the potential to redefine how sports news is delivered and consumed. At the time, I shared this idea with an advisor who saw its promise and believed in its potential. Read more>>