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.
Kennette Pen
Taking a Risk: The Story Behind Arella
Some risks change your life forever. Starting Arella was one of them. It wasn’t a decision made lightly, but rather one that emerged from deep personal loss, frustration with broken systems, and a relentless desire to create something meaningful for survivors of sexual assault. Read more>>
Julie Cantrell
After earning my Master’s Degree in Communication Sciences & Disorders, I became a certified speech-language pathologist and enjoyed working in a hospital with clients of all ages. However, after becoming a mother, I shifted my focus to a school-based practice to better accommodate my children’s schedules and to spend as much time with them as possible. Read more>>
Ashleigh- Jade Searles
The biggest risk I have taken so far with my business is writing the book Start Up 2 Success: 7 Tax Savvy Tips for the Novice Business Owner. I wanted to write the book to help newer business owners with practical and actionable advice or tips to ensure their business is setup for Internal Revenue Service (IRS) compliance. My initial thought was the book would be written in 3 months. What was I thinking! Writing the book took me 2 years. I am a mom of three awesome kids ages 12, 6, and 3 as well as my husband owns his own business and works full time. We are always short on time. Managing having the time to dedicate to writing the book outside of social events and between careers was very challenging. Read more>>
Martha Fletcher
The biggest risk I have ever taken was opening an art gallery.
It started with a vision in the Summer of 2022: a storefront in Arvada, artwork by local artists on the walls, live music, a crowd of people enjoying wine and chocolate. I loved the idea of bringing the community together in a fun way to support local artists. I couldn’t paint or draw, so curating art exhibits was my creative outlet. Read more>>
Tadeusz Gauer
My dream has always been to move to the United States and work with people from the music, film, fashion, and business industries in Hollywood — individuals who are recognizable, respected, and serve as an inspiration to others worldwide. At the same time, being surrounded by the best trainers in the world, learning, exchanging experiences, and discovering new training methods, all while constantly striving to improve myself. Read more>>
Dionna Mcdowell
The biggest risk I’ve ever taken was deciding to take astrology seriously and share it with others through teaching how to use the New and Full Moon cycles to live a more authentic life.
I grew up in a Christian household, where astrology was barely acknowledged. My only exposure was discovering I was a Capricorn, but I never thought much of it. After my second divorce and rounds of therapy, I found myself feeling like something was still missing. That’s when I got a Natal Chart reading—and it changed everything. For the first time in my life, I felt deeply seen. It was like someone handed me a mirror and said, “This is who you truly are.” Read more>>
Jamie Lee Troyer
I am originally from Germany and was working as an administrative assistant in our town hall. It’s a great job – but I just wasn’t happy at all… I grew up in a smaller town & it seemed like – no one really got out of there.
Little side note: My parent always took me to the US for vacation and they always loved everything about the USA. American Cars, Food, Halloween…they even gave me an American name! Anyways… I just wasn’t happy in my job and decided to apply as an Aupair in America (living-in nanny). I quit in July 2017 – found a hostfamily in New York not even a month later – & left Germany in October 2017! I stayed almost two years and traveled as much as I could! I learned and grew so much! Read more>>
Ileen Villa
The biggest risk I ever took was betting on myself. As a first-generation college student, I worked tirelessly in high school to secure a full-ride scholarship, and when I achieved it, it felt like all my hard work had paid off. But sometimes, life has a way of steering you in unexpected directions. Read more>>
Angeles Otero
In 2009 I decided to leave a comfortable job as a pediatrician in affluent community to start my own private practice. I had become a bit weary of having great ideas shot down and wanted to establish a practice where parents and kids were treated in the same manner that the staff and doctors themselves wanted to be treated. We knew it would take all our money, as well as losing our home in order to pour everything into it. We started with myself, my husband and 1 employee and grew to a practice of 9 pediatric providers and a staff of about 26 in about 10 years. Fast forward to right after Covid things were going well with the practice but I became weary of battling insurance companies as well as tired of practicing within certain rules and mandates which made me feel like I was forced to compromise the care I was providing. Read more>>
Nicholas Newell
I chose an eclectic major in college, Religious Studies. I continued on that academic path after finishing my Bachelors degree to get a Masters. At the time, I made that choice because my life had been centered on religious thinking. I needed to understand how my experience had compared with other people’s perspectives. Read more>>
Gangstead
To begin, we’re Hunter and Carson and we began Gangstead. With any band from any genre it’s a huge step taking your ideas and molding them into a reality, especially when that idea involves the coordination of other people. There’s a specific day in mind actually, we were sitting in the attic of an old friend and started playing around on the instruments. This wasn’t the first time we’ve done this, but it was definitely different. That’s when the conversation came back up about starting a group, and then Hunter ordered the first drum kit right there in the middle of the jam. Once we started practicing in the garage, it escalated very quickly. Within two weeks we practiced together many times, and in one day we wrote our first song Velvet Jones. It moved very fast after that and came to a point where this was becoming something more than just us jamming with each other, this was becoming something real. Read more>>
Crystal Castorena
Two years ago on January, Friday the 13th, with tears in my eyes and peace in my heart, I took a risk on myself and my future by stepping away from my career as an educator and stepping into my role as an intuitive facilitator. It was a decision that I went back and forth with for at least a couple of years but one that I never thought would have been possible. I always envisioned myself retiring after my lifetime career as an educator. I always believed that all my hard work and degrees had to be used at its full capacity and stick with this career path that I had chosen for myself. Although I loved teaching adults with disabilities, and seeing them blossom into independent and productive members of their communities, there was still something missing in my life. Read more>>
Dragana Sreckov
As someone who began their journey studying literature, I never imagined I’d one day hold the role of CFO in a thriving IT company with over 200 employees. It’s been an incredible path filled with unexpected turns, challenges, and growth.
Early in my career, I worked briefly as a substitute teacher, the natural extension of my education. But when life nudged me into office administration—a position I thought would be temporary—I found myself at a crossroads. It wasn’t long before I was offered an opportunity to move into financial administration, a field where I had no prior experience. Despite the fear of failure, that decision to step into the unknown set the stage for the next seven years, during which I grew into the role of financial director. Read more>>
Lisa Garrett
I grew up in a small town with limited opportunities for artists, but I was determined to make a living through creativity. Throughout my life, I found ways to support myself as an artist in many different mediums. Academics didn’t come easily to me, but creating and expressing myself always felt natural. My passion for art was so strong that it attracted opportunities and work my way. At a young age, I learned to take risks, rely on faith, and manifest my dreams into reality. I believe that when you live and breathe your passion with gratitude, it will eventually become part of your life—remembering that what you put out into the universe always comes back to you, which is why it’s good to move with kindness and patience. Read more>>
Ashley Herrera
After starting the journey in real estate by rehabbing and reselling homes, my husband and I decided to take a bold step into homebuilding. This was a move that wasn’t even on our radar at first. The idea came from one of our sub-contractors, who casually asked why we weren’t building homes. Little did he know, we were still relatively new to rehabbing homes, but his question planted a seed: Why not? Read more>>
Emma Brinkman
I’ve taken a lot of risks in my life that have brought me to where I am now, personally and professionally. I’ll begin with a bit of background. In my twenties, I lived a more “conventional” life. Although my life has never really been conventional, to be honest. So, I married young, bought a home, and started an organic farm business with my ex-husband. We worked extremely hard building the farm from scratch, and after 5 years we had a thriving farm and homestead. However, at this time I had an awakening, thanks in large part to reconnecting with my body, when I realized I was absolutely miserable in my relationship and had been suffering emotional abuse for the past decade. Read more>>
Sierra Turner
I found myself at a crossroads in my career. After years of working in a stable job I enjoyed but found I missing being creative. I had a none stop desire to start a podcast. I wanted to do a project with my husband. The idea was to share cases from one of my favorite shows growing up. Unsolved Mysteries. I thought it would be interesting to see what had been solved since the show started and what other cases we could shine a new light on. However, the thought of putting out my own work out into the world to be judged was daunting. Read more>>
Leyla Elkhishin
Taking the leap to start posting my content was one of the scariest yet most rewarding risks I’ve ever taken. I used to be incredibly insecure, constantly worrying about what people might think or say about me. The fear of judgment and failure felt overwhelming, and for a long time, it held me back from pursuing my goals. Read more>>
Cortney Rose
I took a risk and bet on myself. For ten years, I had been teaching 3rd grade and had just begun my 11th year in the classroom. During my tenth year, I applied for a computer teacher position at another school—a job that felt like the fresh start I needed. When I got the offer, I accepted it. However, before the school year ended, my current principal approached me, expressing her desire to keep me on staff. She promised to create a similar computer position at my current school, and feeling a mix of loyalty and hope, I accepted her offer. I even called the other principal to let her know I wouldn’t be joining her team after all. Read more>>
Diego Soto
Taking risks is a necessary part of life, but let’s be honest—it’s scary. It’s terrifying to think about changing everything: your life, your identity, your comfort zone. Growing and expanding sounds great in theory, but in practice, it can feel overwhelming.
That’s exactly what I went through when I decided to start my own business, Tu Nueva Realidad (Your New Reality) It’s now one of the most recognized spiritual platforms in Latin America, but back then, it was just an idea, a dream. Read more>>
Diksha Malhotra
Taking risks is inherently tied to growth, and my story is a testament to that belief. One of the most life-changing risks I’ve taken was leaving behind a thriving career in Bollywood to pursue my dreams in Hollywood—a move that not only tested my resilience but redefined my perspective on life and ambition. Read more>>
Kelley Nazarian
Honestly, the risk I’m taking is right now- I’ve went from working for other doula agencies, to getting my own referrals to now being a full-blown agency that hires both birth/labor and postpartum doulas. During the beginning of the pandemic, I found myself out of work from our local ymca due to covid restrictions and thought it was a good time to reassess what it is that I wanted to do with my life- something I would be both good at and passionate about. That brough me to “hey, what about becoming a doula!?!” It was perfect because I couldn’t have any more children of my own due to my last pregnancy being so high risk and knew I would miss being around babies. So, the next step would be to get certified, but hard times were definitely upon us, so I literally saved five dollars a week until I could afford to take the training and become certified. Read more>>
Sydney Sprenger
I moved to Charleston in April of 2024 for a job opportunity. As time went on I realized that job no longer served me. I ended up walking out of that job, which was my sole way of having an income to live in Charleston, and I picked up a couple social media clients and haven’t looked back sense. Read more>>
Olyveya Mazier
At the age of 14 I took the risk of deciding to choose ballet as my career path, Ballet can be tricky as you are not guaranteed anything – a job, career, earning a living… many people have to give up once they hit the age of 18-22 due to not being able to earn a living, however this poses a problem as many give up their education and are left without a good high school learning experience. Read more>>
Linda Brandt
After a decade of leading the Lean In Together MSP Network and telling others to “lean in,” I took a big leap of faith last spring and resigned my public health job of 17 years.
Support and outside perspective is that made this leap possible. It began when Magali, a Parisian Lean In leader, asked me, “Why don’t you let yourself have a better life?” I could not give her a good answer. Read more>>
Daniel Cusimano
The biggest risk I ever took was leaving college after the first semester to take a semester off and work for the Disney college program. The risk wasn’t the fact that I was leaving school or working for Disney, but it was taking an unconventional approach and timeline to college experience. Why it was a risk is because everybody told me I shouldn’t do it that I should stay on the traditional path, but I’ve always been a firm believer that when an opportunity comes up in front of you you need to take it. The reason this was such a pivotal moment in my career is because if I didn’t do the Disney college program, I would’ve never met the person who got me to apply for Netflix‘s hit reality television show The Circle. Read more>>
Karema Dejesus
I was a stay at home mom/wife. I had always been active in my church and in my community. I’ve always known I was called to help others and then tragedy hit.
My mom was diagnosed with acute scleroderma and things were looking bad. Eventually the disease took her life and I was stuck with the trauma of losing one of the greatest influences in my life. Thankful for my faith in God, I asked Him “Whats Next”? I believe God used the loss of my mother to inspire me to help bridge the gap of physical and spiritual health, a disconnection that has taken place with people of faith. Read more>>
Chris Jones
I’ve now worked there for 15 years. One of the largest challenges I’ve seen for us is that we create a large slate of amazing, first-class offerings and then quickly have to do it all over again. Each of those class offerings acts like a single glass that we need to fill with water, and if any does not receive enough water, we have to remove it. This hurts in a number of ways: disappointed teachers and students and lost revenue for the organization. Read more>>
Valentine Brkich
Ten years ago, I left my secure, good-paying, full-time job as Senior Marketing Writer for Robert Morris University to take a stab at freelance writing. My kids were in the 1st and 3rd grades at the time, and I wanted to be able to spend more time with them. It was a big risk. Although I’d built up a large list of contacts, there was no guarantee that I’d be able to find enough work. But I was fed up with the rat race, and I wanted to at least take a shot at working for myself. Luckily, my wife’s company was doing well, and she fully supported me in my decision. Ten years later, I’m still freelancing, and we didn’t lose our house, which is nice. It’s still an ongoing struggle finding new work, and at times I’ve thought about getting a “real” job again. Read more>>
Scott Stafford
I believe that any individual who’s crazy enough to want to live a freelance lifestyle understands the risk(s) they’re constantly taking – the never ending uncertainty.
12 years ago, I was working for a large entertainment theme park here in Southern California as a Sound Engineer when one day I just decided I was done with the rat race of the politics, scheduling and everything else I was no longer enjoying about the job. It was around that time that I was considering going full time freelance. I’d had other friends successfully doing it, and I admit I was a bit jealous. Read more>>
Transit Nomad
Don’t be afraid to take risks when it’s necessary. The biggest risk I’ve taken was moving my businesses from Ukraine to the United States. I had no idea if it was going to work as I would have to start my marketing from scratch. Even though I had the experience and I knew what to do, it took me several months to start getting clients. In the meantime, I had to work other jobs to support myself. Once my marketing efforts started to pay off, my income went up substantially and I used that profit to start new businesses. At this time I own and operate 13 small businesses and I’m very happy I made the move. We have a saying in Ukraine: “Those who don’t take the risk don’t get to drink champagne.” Read more>>
Kimberly Charest
Being a creative is synonymous with taking risks. I learned this with the first decision I made when pursing a creative career: changing my college major.
Growing up, I was encouraged to have creative hobbies but pursue economical options for a career. As such, I often pushed writing aside in favor of “getting ahead” in high-school. I figured if my goal was to get a college degree as efficiently as possible, I might as well take multiple summer courses through community college to graduate faster and make myself as academically favorable as possible to obtain a scholarship. Writing, as much as it meant to me, could never be relied upon for more than a hobby. Read more>>
Jacquelyn Vasquez
I have always worked. It was as if work was ingrained in the way I live my life, but I was never satisfied. So even though I always worked I stayed with a side hustle. Almost as if I was always looking for a way out. I even started a business with my, husband at the time wasband now, and that business failed terribly. So a big risk was to start yet another business and invest yet again even though I had lost terribly in the past. Then the risks kept coming. I left my husband and became a single mother yet again, but then the risks kept getting better. I took a risk at dating again met the greatest love I ever experienced in life. Read more>>
Madi Balman
Taking risks was never in my wheelhouse until I became an entrepreneur.
When I decided to dabble in freelance graphic design in 2016, I didn’t realize how much I would love being an entrepreneur. Fortunately for me, I had a great support system throughout college, and I was able to learn more about it before I took the plunge into full entrepreneurship in 2018. Read more>>
Lucia Tringali
I became a business overnight quite literally overnight. The owner of the studio I taught at asked me if I wanted to take over a space they were leaving and within 30 seconds I said Yes! – two days later I had an LLC. Then I woke up the next morning feeling squirrely wondering what did I just do, can I even do this, with what money, what is happening etc. I had already comitted before really brainstorm my course of action- talk about risk. Then to pile on the that, I vowed to renovate the space, spin up booking, financials, website, and app and open within 1 month. Obviously, another risk. A month full of blood, sweat, tears, money, and questions later and I did it! I was able to honor my promise and open THE|BAR on May 1 2023. Read more>>
Lynaea Russom
In a post graduation world, art opportunities have been difficult to find. Early Career artists, both inside of school and out, often are not eligible for most opportunities. In my undergrad career, I always was and always have been a pusher. I like to follow the notion that ‘if someone has no job posting, I will tell them I am applying.’ A bit of a hot-headed approach, but it has gotten me so many things. I emailed about fifty galleries in a hundred mile radius of me with my portfolio and my interest in making connections. To my luck, I heard one yes out of all of them. This connection has been extremely beautiful and has allowed me to curate and host my own shows. I encourage young artists to be as brash as you can with your practice. Luck is half of it, if you don’t work hard and really want it, chances are you will not get it. Read more>>
Phoenix Aka “mohawk” Kellye
Harm reduction is a controversial and commonly misunderstood movement fraught with challenges. While the movement has garnered a lot more support over the last seven or eight years (due to fentanyl, xylazine, and other toxic and deadly adulterants running rampant through some of the drug supply), services as basic as syringe exchanges are considered illegal in many places, and mainstream stigma and carceral or other punitive laws around drug use and distribution creates barriers to enacting positive change. This was especially the case when I started this work in 2012 as a person engaging in drug use seeing both the negative and positive impacts drug use has on people in my community and wanted to find ways to enact positive change without creating more stigma or judgement. Read more>>
Jodi Scardino
I worked on Wallstreet for 15 years and decided to leave and reinvent myself. I decided to pursue Pilates as it changed my life in the past. It was a long journey of the unkown. Where will this get me, will I ever learn the method and be effective. Will I ever have my own studio where others can heal and teach.
It took me from 2013 to 2022 to Learn and become an effective teacher and find a space to have the studio. Read more>>
Seanny Georgie
I have a story about taking risk, I remember around 2006 whenever I first started taking the electronic music I made seriously all I had was a computer that my mom bought me at Walmart at the time with all the money we had at that time which was about 160 bucks combined. Many people told me I needed a laptop or to buy CDJs etc. which sadly I couldn’t afford at the time. So I would literally bring a CRT monitor I bought at a thrift store and my whole computer setup to the venue because it was all I had. I got made fun of but they kept asking me to DJ more and more shows of different genres and more because I always kept the crowd moving. Read more>>
Ouathong Selena Veunnasack
In May 2021, I completed my Bachelor of Science degree in Management with a concentration in Human Resources as well as my eyelash certification in February 2021. With both, I was working as a customer service representative for Robinhood while practicing eyelash extensions on only friends and family. just six months in, Robinhood underwent significant layoffs due to the company’s fast-paced expansion. Despite being promoted to the Advanced Security team and being nominated Employee of the Quarter, I was part of the 8% of the company (about 800 people) let go. I was devastated. I had worked hard performing well at my job—but in the end, it didn’t matter. I was reminded that even when things come your way, things can still go sideways. But, as they say, when one door closes, another opens. Read more>>
Danny Coleman
I was a UPS driver for 20 years and suffered a career ending back injury that caused me to re-invent myself in 2009. I’d attended a small broadcasting school in Trenton, NJ in 1982 due to an interest in radio. Upon completion, I couldn’t find a suitable job in radio so, I put it to the side. When my back went by the wayside, proceeded by a horrible divorce and then followed by several years of unemployment, I’d decided to throw all caution to the wind and re-visit my love of radio; this, despite having no job, very little money and no contacts in the radio field. I saw a Craig’s List ad stating “Radio show hosts/ideas wanted” from a terrestrial AM radio station in Burlington County, Read more>>