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.
Brittany Woodham
I guess you can say my whole business was a risk. In the past 2 years, I’ve learned so much about myself and my motivation. When I first started working as a Therapist no one told me all of the possibilities and the ways I could grow to make a bigger impact in other people’s lives. They also didn’t tell me how I could be a counselor but, still have a level of authenticity that was different than that of the counselors that work for big agencies. When you’re in school for counseling they straight up tell you “don’t go into this field if you want to be rich” it always stuck out to me and confused me like why would they tell us that. Read more>>
Shelly Leal
In Brazil, we are always told, ever since we were little, that we should get a job in the government if we want stability for the rest of our lives. I grew up with this idea and with my passion for building and creating, I became a Business Intelligence engineer in the Air Force right when I was 22 years old. In the beginning, I enjoyed feeling safe – but I did not fit in. I was a kind and gentle person, in need of having those values in my routine. In the military, I felt fulfilled when I collaborated for a bigger purpose, but empty and limited when I was obligated to follow rules and be perfect at all times – the example for the subordinates. I did not want that. Read more>>
Ivan Caraulan
Learning a new profession is always a stress. Like dive in the unknown waters. You see the water surface, but you don’t know how deep is it. I was working as an engineer most of the time. And when starting to learn 3d art, it was a deep dive. More I learn, more questions I got on the way. All was new and unknown to me. Basic thing was very complicated for me, like the person with no artistic skills. But need to just walk, and you will come. Read more>>
Alex Mouneu
Establishing myself as an idependent hairstylist was the biggest risk I’ve taken so far. It was a decision that required careful thought and planning, as I knew I would be leaving behind the stability and security of a commissioned salon. However, I also knew that in order to truly fulfill my passion and reach my full potential as a hairstylist, I needed the freedom and creative control that owning my own business would provide. Read more>>
Shannon Hill
Taking a risk for me might look different than others. I’m an introvert/extrovert but leading with the latter. I love in-person interaction and building relationships that way. Having a business in this era, a lot of connections and engagement happens on social media. I don’t say this often, but social media scares me. That’s the introvert private side of me. Read more>>
Alexandra Schrecengost
As the head of communications and digital at a wine importer and distributor, I found myself struggling to balance the demands of a male-dominated wine world with the responsibilities of motherhood, family and a global pandemic. There was and is very little flexibility. Faced with the loss of friends and family jobs, I made the bold decision to start a virtual experiences and tasting box business, despite skepticism from colleagues, friends, and investors. Read more>>
Jennifer Benson, RD
I have been a Registered Dietitian for 26 years, so I am definitely well seasoned in my field. I started my career working in hospitals, and spent most of my career in acute care and long term care facilities. I enjoyed this work, and with all of the experience I gained, I was very comfortable working in this area of my field. Although I thought many times about changing my direction, I was so completely comfortable that re-learning a whole new aspect of dietetics seemed overwhelming, so I stayed comfortable for a while. Read more>>
Juliette Arciuolo
I went to college thinking I was going to come out being a strength and conditioning coach at one of the biggest colleges in the United States. Although I did work as a coach and private trainer for a couple of years after graduating, I never would have thought I would leave everything behind to start a baking business. While I was working as a personal trainer at a small gym in Pennsylvania, I started baking on the side for fun and a little extra cash. As word of mouth started to spread about my baked goods, orders started piling up and I was working 60-80 hour weeks. Read more>>
Daniel Calderone
There have been several moments during my personal and professional life where certain circumstances had demanded me to become more of a risk tolerant individual. While I’ve encountered and endured a litany of small risks throughout the necessary aspects of my creative career, it was this big risk that changed the trajectory of my entire life. Read more>>
Jessica Peterson
In 2021, a year into the COVID-19 pandemic, I felt I was about to lose my mind. With my entire family at home 24/7, my job at the hospital on hold, and two little kids constantly underfoot, I was ready for a fresh chapter. An occupational therapist by trade, I’d spent the last seven years in a position at a local hospital. Over 8 the years my schedule shifted with 2 pregnancies and maternity leaves. By day, I was Mom; on weekends, occasionally, the Occupational Therapist. Keeping a toe in my career while dedicating myself to my family worked well until the pandemic struck. As the world adjusted, we eventually found an incredible school for our children, and I resumed my hospital job. Yet, something inside me had shifted. Read more>>
Elizabeth Sanchez
Leaving a secure business partnership to embark on a solo entrepreneur with an opportunity to explore my capabilities, face challenges head-on, and develop a deeper understanding of my own strengths and weaknesses. Through this journey, I have come to appreciate the importance of self-reliance and the power of a dedicated team in achieving success. Self-Discovery: By stepping away from the security of a business partnership, I was forced to confront my fears and insecurities. This process of self-discovery allowed me to identify my true passions, values, and aspirations. I realized that I possessed untapped potential and a burning desire to create something unique. Read more>>
Lori Kinsey
My Tsunami of Change There I was, sitting in a domestic violence shelter, with a clipboard in my lap. I was filling out a form asking me to “Check off all that is applicable to yourself or your children within the last 48 hours.” I was shocked to resonate with the list of traumas as I began to check off EVERY box except surviving an attempted homicide. Read more>>
Shelley Herman
This is an exercpt from my memoir titled “My Peacock Tale: Secrets Of An NBC Page.” “Once I had my Page uniform and access to all the buildings on the lot, I set my sights on meeting Dick Ebersol. Dick had been named Vice President of Late Night Programming at NBC. I tried to do things by the book and get an appointment to meet Dick when he was in town, but I could never get past his gatekeepers. I wrote letters and even waved to him if I saw him in the hallway. But nothing, no luck. The shortest distance for me hasn’t always been a straight line. Read more>>
Shabnam Ghazizadeh
After completing extensive surgical training at the top programs in the country to become a double-board certified facial plastic surgeon, I chose to build my boutique cosmetic surgery practice in Newport Beach, CA. Establishing myself in the competitive landscape of cosmetic surgery in this saturated market is risky. Newport Beach is a hub for plastic surgeons and patients seeking cosmetic enhancements. While there are many cosmetic surgeons in this area, I am one of the only female plastic surgeons and offer a unique expertise and experience for my patients. Read more>>
Shania Stowers
I started my business when I was 15 years old, I was working at McDonald’s making $7.25/ hour. I always felt like that wasn’t enough for me even as a little girl and I hated doing the work even though I was very grateful that I had a job so young. I talked to my uncle who is a business owner at Northshore Teez how I would be able to start a clothing line/ boutique. He hooked me up with all the information & even gave me items he didn’t sell and told me to try & sell them. But taking the risk and spending my small McDonald’s checks to start my line was a risk for me.. almost every single penny. I always wanted to save but knew I wanted to try something new & ever since I figured out that I wanted to be a business owner. Read more>>
Tim Peakman
One of the biggest risks that I have taken in the past was to leave a secure career in pursuit of building my own online business. Having served 16 years in the Royal Air Force, some of the countries in which I served were not without risk, but the thought of ‘going it alone’ and leaving the safety of being an employee filled me with equal levels of fear and doubt. Read more>>
Jorge Perez
Business is all about taking risk, I started my business at 24 and I was very daring at that age, I felt I had nothing to loose and it has paid off since we celebrated 12 years since my first launch.. Now that I’m older it’s definitely scarier to take big risk because there is so much more at stake but in business you have to always take risk but first make sure you do your homework and make sure to always stay consistent. We expanded to men’s apparel this year and the response has been great and I finally get to wear the samples so that’s fun! Read more>>
Michelle Boback
In 2017 my family and I took a huge risk, and moved countries to our dream location. Moving countries alone is huge, and we were already in our early 40’s, with two young kids. My husband and I leapt from our comfortable homeownership life in a country we knew, to a new life of financial insecurity and the rental market and of course, this all occurred in a country that was new. This was a huge risk and six years later we’re finally starting to feel like we’re making some headway. This is not the risk I want to share though it is just the context of what was happening when I took a leap of faith. The risk that I feel was much greater it was the decision to switch careers a year after we moved to LA. I decided to leave my lucrative and, at one time – my dream job, for a career I had dipped my toe into 30 years prior. Read more>>
Monnyca Gammel
In my life, I grew up knowing to not take risks and stay on the safe side. Life can be so unpredictable and when you take a risk, you normally don’t always know the outcome. Growing up, I knew that working a 9-5 job would be the best way to go when it came down to my career. I gave this a lot of thought in 2017 when I graduated high school and soon came to realize that a 9-5 just wasn’t for me. I felt that there had to be more I could do with my career. I thought to myself many times that there is someway I could turn a passion of mine into my full-time career. I always took pictures on my phone, but I wanted to do more with photography than pursing it as a hobby. Read more>>
Jennifer Bogg
In 2019, I decided to take a leap of faith within myself and open my own practice, Green Rose Counseling. With the professional experience I had and the knowledge I had learned along the way, I felt that it was finally the right time to use my skills and begin this next chapter. Although I had wanted to do so for a long time beforehand, it took time and careful preparation to be able to make this move. Finding other who were in support of my success that were also willing to help and be a part of the process, was not only important but very helpful in helping me make Green Rose Counseling happen. Read more>>
Tiranda Ward
I’m just a small-town girl with dreams and an even bigger passion for the beauty industry. It all started when I was in middle school. I would visit my great Auntie who was great hairstylist who did my hair and others hair in the community. I would watch her do the local ladies hair in the community and saw how she made them feel beautiful. Just watching how my great Auntie interact with her clients and the relationships she built with the ladies in community inspired me to want to be in the beauty industry. So I started my journey of being a hairstylist in middle school. Read more>>
Gretchen Dunlap
There are always risks to be taken in life, if you’re the kind of person that isn’t scared of NOT playing it safe. There is something to be said about playing it safe, which I have also learned along the way. But there is something really great and exciting about taking a risk as well. The biggest risk my husband and I have taken is in our life on the ranch. It started with deciding to move from our comfortable home in the city to a 5th wheel on the family ranch. We still had our house as a backup if we didn’t like it. But we did like it, a lot. Read more>>
Renee Asteria Penaloza
In 2017 after getting rejected for a second time from a PhD program, I decided to flip the equation and leave my stable job as a research assistant to become self-employed and delve further into the production side of music and support myself with various free lance gigs. I decided to further my skillset by getting trained in commercial music production and made a vow to myself to write as many songs as possible. I am in a perpetual learning process and try and collaborate as much as possible to become a better songwriter and performer. Read more>>
Dana Toy
As we grow up, we tend to learn from our environments, often mimicking the behaviors we observe even if we’ve been advised otherwise. I was taught that the secure path involved going to school, finding a job, and gradually working my way up. I learned that playing it safe, avoiding risks, and sticking to the familiar were the keys to certainty. Fast forward to my adult life, and I followed the path I knew. I attended school, secured a position with a reputable company, and climbed the corporate ladder. Read more>>
LaQuan Wilson
Last year, I was down to my last dollar. Rent and car payment was past due. Took a chance betting on myself since that’s all I had left. Doordashed between two cities in North Carolina: Fayetteville and Raleigh. I loved being a doordasher since it never really felt like work even though it was very time consuming. The time I spent at home was creating content. I would stack up to at least 4 videos almost everyday and post them while out doordashing. This is betting on myself because majority of the people would have called me crazy and told me to get a regular job. Read more>>
Felicia Shanken
The risk I took was leaving a Federal Government stable job with benefits to embark on an unknown journey of entrepreneurship. It was a scary decision to make, but I knew that I had to take a leap of faith in order to achieve my dreams. It wasn’t easy, but I had a supportive family and a great team of volunteers who helped me along the way. Looking back, I’m glad that I took the risk and started my own business. It was a challenging journey, but it was also a rewarding one. I learned a lot about myself, about business, and about the power of community. Read more>>
Chaz Hawkins
So I decided to pursue film all in one week during my senior year of college at Duke University. You see, I studied Public Policy all of undergraduate. For those who don’t know, that’s essentially the study of the art of politics, and I was expected to graduate with my degree in 2017. I always hoped to bring about social change to better the lives of my fellow black Americans through policy. I naively aspired to be like Barack Obama, which just was somewhat ignorant of me. Anyways, to make matters worse, that fall I was profoundly shocked when Donald Trump was elected to serve as our next President. Read more>>
Anna VonRosenstiel
The story of Carter + Rose is multilayered, comes from many places, and has evolved and changed over the years. I grew up in a creative household; my dad is a builder and furniture designer. A lot of my time was spent with my brother in my dad’s shop and he let us have free range over the scrap wood, hammer, nails, and hot glue gun as long as we didn’t complain. We were an adventurous family and very hands-on with camping, skiing, and traveling. Read more>>
Tali Golergant
I recently had to take a risk in my career that I am very proud I took. It was a challenging choice to make but I felt very empowered and strong when doing so. Currently, I am in the audition process for the Eurovision Contest 2024 to represent Luxembourg. Throughout the process, I collaborated with a couple great producers and songwriters and met some great people in the industry. This week, I unexpectedly found out that the three songs I submitted passed the next stage and was additionally asked to sing for one more track; making that four potential winning songs. Read more>>
MAXIM
Being a full-time artist brings inherent uncertainty, doubt, frustration, and discontent. I firmly believe that to tap into one’s 100% potential, one has to invest 100% of the effort. What you put in, you’ll get out. There are no shortcuts or gimmicks. They are short-lived and not sustainable. Only an authentic and entirely believable work can withstand the test of time. In a modern society driven by the $, making a living as a fine art artist is an adventure, and it is not for everyone. It requires talent, enormous hard work, sacrifice, pure luck, the sprinkle of stardust, and magic. Yes, it’s not going to work without it. Read more>>
Travis Doodles
I was working a job making 6 figures as a videographer, but I was miserable. I was working for a guy as his personal videographer, but the content was pointless to me. He was very wealthy and showed me money doesn’t buy happiness. I was having a conversation with a friend, and said “man if I had his money, I would give it all away.” Helping people is what makes me happy. Read more>>
Destiny Nguyen
Leaving my hometown Minnesota was not an easy decision, but the allure of pursuing my dreams was too strong to resist—even in the midst of a global pandemic. The idea of starting my own small business had always been a passion, particularly in the realm of beauty. Read more>>
Dana Michell
My company Salt and Lime Media was a risk waiting to happen! I was a Reality TV & News Producer for 2 decades before I finally turned a regular ol’ daydream into true reality to go out on my own and start my business. As a TV Producer, the hours are insane. 100 hour weeks are the normal during production weeks and long drives or long stints away from home come with the territory. Don’t get me wrong, I love nothing more than packing a suitcase for the next big paid adventure to exotic locales.. but once you have a family, those work trips get harder and harder, so it was time for me to make a change and take a gamble on doing things a different way. Read more>>
Nick Itkin
I fell in love with the sport of fencing at the age of seven years old. One of the problems with fencing in the United States is that once someone gets accepted into a University many athletes quit competing professionally. Unless you are on the national team, which is top 4 in USA rankings, then you have to fund yourself completely for all national and international competitions. The top 4 foil fencers at the time was one of the best teams in the world, breaking every record possible. Read more>>
Meghan Bellamy
I tend to overthink, but sometimes you just need to take a leap of faith. When I quit my previous job before pursuing a fulltime creative career I was only making enough money to survive. However, I knew with the extra time I would gain I would be able to expand my business. Luckily this gamble paid off and I’m in a much better position now. Read more>>
Sebastian Berenguer
One of the most significant risks I’ve ever taken is the decision to leave my home country, family, and friends to pursue my dream in cinema by moving to Los Angeles. My name is Sebastián Berenguer, and I’m a film director, producer, and live event producer. Two years ago, I boldly chose to relocate to Los Angeles to pursue a master’s degree in filmmaking, enabling me to fulfill my dream of directing and producing a feature film. My life was on a steady trajectory. Over the past 15 years, I have built my reputation and career in large-scale live event production. Read more>>
Jennifer Washington
When I moved to Kansas 4 years ago, I had no clientele and didn’t know anyone but my boyfriend here. It was a big risk because I had never had my own business or even rented a chair. I worked for a corporate salon and spa for most of my time as a hair stylist. I just remember praying about it and telling God that I was leaving it in his hands. Fast forward to me moving here, renting a chair at a salon in junction city and building my client base in 6 months in the mist of a pandemic. It was one of the best decisions because it gave me the confidence to go out fully on my own and open my own salon in Manhattan. Read more>>
Dawn Lewis
The biggest risk I’ve taken is betting on myself. All my decisions are RISK!! I am a product of divorce, whose father died at 29 from AIDS in the 90’s. My parents only have high school degrees. My father used drugs and drank. My mother a young abused single mother with 3 kids under 2. My mother remarried when I was 7 to a man who is now a wonderful father to all of us at 19 not so much. He will dealing with his own pain. I was relocated to GA from Oklahoma at 15 and unbeknownst to me yearning for acceptance. I was proper speaking black girl in GA and too skinny. Read more>>
Tierra Jones
I have often taken risk during my creative journey. I have tussled over being a full-time creative to having part-time jobs/ gigs to help fund my endeavors. However, the most important risk that I have taken was choosing my happiness. The most recent risk I took was to leave my part-time job and pursue my creative career full time. I had to break my mindset and beliefs of what I thought having a tradition job could provide me. Sure, it provided me with financial stability, knowing that i had a paycheck coming every two weeks was comforting. At the end of the day that is all the job provided for me, and with the importance our society places on Money, Read more>>
SARI FRIED-FIORI
As an artist and business owner, I think this is perhaps the most critical skill needed for success. When taking photos, I regularly experiment with different angles, lighting scenarios, content selection and location. Sometimes what I thought would work doesn’t so I have found that it is critical to take the risk to change up my approach and try to take the photo in a way that I had not previously considered. As a business owner, you must be able to pivot and to pivot quickly in response to feedback from your clients and the marketplace. Read more>>
Savaun Young
The Best Way To Learn About Yourself Is Taking Risk, And Making Sacrifices To Put Yourself In Position To Never Have To Look Back. At The Time I Was Following One Of The Biggest Promoters/Marketers In The Music Business, His Name Was Carlos Brown, 1 Of The Biggest In The Game And Brought Us Artists Such As:”Yung Bleu, Rich The Kid, Migos, Lil Baby, & Many More”, I Was Having Consultation With Him At The Time And He Put Me Right On The Spot Like “Give Me Your Hardest Bar Go”……….& I Hesitated & Had To Learn You Have To Be Ready At All Costs, No Matter The Situation You Tap In To What You Love Most (MUSIC). In This Music Business From That Situation And Him Telling Me:”See If That Was Someone Else That Was More Eager & Hungry, Read more>>
Umi Akiyoshi
Leaving my stable job and becoming a freelancer is the biggest risk I’ve taken so far. To be fully transparent, the COVID shutdown took my steady job away from me, but my conviction to pursue a freelance career because of it was a massive risk. The uncertainty you live with day to day, having little control over how much money you will make by the end of the year, the occasional existential crisis, if you’ll ever be “done” or satisfied, if it’s worth the anxiety….all of it is the risk I take being a full time freelancer. Read more>>
Ashraf Valliani
I always believed in the Alchemist moment of universe conspiring for you to achieve something that you are absolutely passionate about. Growing up, I was always intrigued by a well crafted, well fitted garment on women who had the entire world in front of them to conquer. It was the body language, the power that outfit gave to the individual that I could sense. One of the most important inspirations for my brand came when I took my first trip to the Northern Valleys of Pakistan when I was 10 years old. Read more>>
Hannah Powley
In one defining moment, I decided to take the risk of leaving the comfort of my corporate fitness job—a position that offered financial stability and a managerial role with opportunities to keep climbing the ladder. At the time, my savings were limited, just enough to purchase a laptop as my only tool to kickstart a new venture. Having recently moved back to my parents’ house after the end of a long-term relationship, I found myself questioning the trajectory of my life, wondering, “Is this all there is?” Read more>>
Desiray Marie
My name is Desiray Marie and I am a Bay Area Native. I moved to Texas in July 2019 from California and worked incredibly hard to get to where I am today. In my younger adult years I was in a very abusive relationship – Physically, mentally and emotionally. I was previously diagnosed with manic depression and high functioning anxiety which more recently was re-diagnosed as PTSD and dissociative disorder caused by trauma from that abusive relationship and childhood trauma. Read more>>
Brandie Janow
Currently, I find myself at the heart of a significant transition. I am no longer in the cozy 9-to-5 job that I once had. Now, I am pouring my heart into cultivating something really unique, something that has been missing. Each day is like a brand new adventure. One second, I am learning and growing, the next, I am freaking out, then suddenly, I am filled with so much energy and excitement. It feels like I am on a roller coaster that is both exhilarating and intimidating. Read more>>
Natalie Sady
I began modelling when I was a small child. It was always something I had said i wanted to do full time ‘when I grew up’. I was fortunate that I was able to make that a reality in my life. There were small jobs when I was in my teens, but once I turned 21 it became a full time job. I was aware of how lucky I was being able to work in a different place and with a different team every day, and it wasn’t the 9-5 life. These people became my friends and while we worked hard, it didn’t feel like a grind, work was fun. I got to play dress ups every day, be with my friends and fellow creatives, I also met so many incredible people and experience things that not everyone does. While working, Read more>>