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.

Stacey Gardner

Starting a small business for anyone is a risk. It takes a strong individual to take that risk and put themselves out there to start a small business. Once you take that leap, it is a grueling process to take the idea and passion and turn it into a successful, thriving business. It was a huge financial risk for me to quit my job and start my Bookkeeping and Payroll Business. Like most, I was living paycheck to paycheck and couldn’t afford to take a pay cut. When I looked at the “big picture,” it was overwhelming. There was too much to do, and my goals seemed out of reach. Read more>>

Rektok Ross

Leaving my lucrative law career was one of the biggest risks I’ve ever taken. I had been with the same firm since law school, starting as an intern and building a rewarding career alongside coworkers and clients I truly loved. But as much as I enjoyed the stability and success, I knew deep down that my passion lay in storytelling—writing books and creating films. Just before I turned 40, after careful planning with career coaches and lots of soul-searching, I made the leap into a full-time creative career. It was a huge risk, but it’s led me to become a bestselling author, screenwriter, and producer, and I’ve never looked back Read more>>

Susan Ramirez

In 2015, I took one of the biggest risks of my life – I quit my successful, eight-year career in Corporate America to pursue Austin Angels, the nonprofit organization I founded, full time. This was a huge leap out of my comfort zone, but it was a risk I knew I had to take. When I founded Austin Angels in 2010, I couldn’t have imagined how the organization would grow. In fact, I would have laughed if you told me that almost 15 years later I’d be running a national nonprofit. But, here we are – and I wouldn’t have it any other way. What was one of the biggest risks of my life has turned into one of my greatest honors. Read more>>

Emily Golden

Brandon & Emily purchased Print to Suit in 2018 from a family friend. Print to Suit offers custom Screen-printing, Embroidery, and Promotional Products. Working with schools, sports teams, organizations, and businesses is where the joy of customer service is found. When you do business with Print-to-Suit, you are supporting a small family-owned and operated business that values relationships and service. The Goldens are known for providing excellent customer service and delivering high-quality products that serve their customers well. They prioritize time with family and friends and teaching their daughters everything there is to know about entrepreneurship, customer service, and business. Read more>>

Diego Hinojosa Farrera

One of the biggest risks I’ve taken was when I moved from Toronto to Mexico City. Apart from the huge life changing decision that is moving back home after living 7 years abroad, the decision implied the closing of many important personal and career-related cycles. After studying a music career for 4 years in Toronto, the Canadian government facilitated a work permit for 3 years, so I decided to take advantage of that and started my professional musician life abroad. It was all very exciting, but the way the immigration laws worked in Canada, I was somewhat restricted as to which jobs I could do in order to apply to a permanent residency once my work permit expired. I basically had to have a job in which I had a formal contract and I was in a payroll etc. Being a jazz musician, there are not many “formal” jobs like that, but I was able to find a teaching job and made a decent living, even in an expensive city like Toronto. I was very happy and grateful to be financially stable in an exciting metropolis after a couple of years being out of college, but as time passed by, I was teaching more, and playing music a lot less. My dream until this point in my life was to be a jazz guitarist and composer, that is why I had chosen to study in Toronto, because it had a vibrant jazz scene, and was fairly close to New York, the jazz capital of the world. But I was not being able to do that, and I was worried that if I stayed longer in Toronto, I would feel more and more rooted to the life I was building there, and I would be more afraid of taking the risk of pursuing my dream. Read more>>

Bridget Pritchard

I will never forget August 6, 2019 everything that I had once knew I left it all behind to start new with my husband and family. Who actually would up and relocate 6 months pregnant to move to a different state where you have no family and I mean NOOOOO family or friends. This girl did!! I navigated finding new doctors to ensure that my pregnancy was healthy. I believe in my ability to walk away from everything and everyone I once knew to explore the unknown it was then I begin to live a limitless life of unlimited possibilities. Since this move I took a risk in the middle of the pandemic and became a Licensed Realtor. I was navigating having a newborn baby one in middle school and one in high school, but I accomplished my goal I put to the side for years and have become a Top Producing agent at ReMax Homes & Properties South Florida. Risk’s involve rewards. To the man or woman that maybe reading this article ask yourself, “Am I ready for the reward on the other side of the risk I have failed to take’?. Take the risk and WIN! Read more>>

Maria Fernanda Rico

Stepping out of your comfort zone is like standing on the edge of a diving board, heart racing, looking down into the unknown. It’s that moment where the familiar fades away and the thrill of possibility beckons you to take a leap. While it can be daunting, embracing risks often leads to the most profound growth and discovery. Growing up I was not very confident and I usually struggled to get out of my comfort zone. Taking risks would often scare me, but that did not change the fact that I wanted to be an artist. I always loved the art of acting and visual storytelling. However, sometimes my fear of risks would often lead me to hide away from taking part in this art. As I grew older though, I started recognizing that life is too short to sit around waiting for things to fall onto your lap without you doing anything to get them. This is when I decided to put some of my fears aside and started taking part in several high school plays/musicals both as an actor and artist. Read more>>

Jason Jackson

In 2020, I was enlisted in the US Navy and had decided that I was going to transition back to civilian life after my current contract ended in 2021. The only problem was, what was I going to do for a living? I decided to try and fulfill a lifelong dream of mine and release an album of original music. I reached out to an amazing producer by the name of Adam Hawley and sent him a demo. After listening to the demo he agreed that we would be a good fit to work together and we started writing and recording the record that week! Fast forward to Spring of 2021… I just got out of the Navy and released the record (titled, “Movin’ On”). It took less than 6 weeks for my fist single to make it onto the Billboard top 30 chart. From then on, I’ve been pursuing my career as a solo artist full force, releasing another record, “All In” in 2022 and my third release, “Looking Up” is releasing this month! Also, I was signed to Hawley’s growing record label for this latest release. I never in my wildest dreams expected to go from a sailor in the Navy to a Billboard charting saxophonist on the span of a few months. Read more>>

Zarrette Rogers

The biggest risk I’ve taken would be leaving the corporate world to pursue my passion for music, modeling and acting. After graduating college, I began working with a finance consulting firm where I rose through the ranks to become a Principal Contractor, overseeing and managing trade processes and operations for financial institutions. Through the years though, I found this high-stress and corporate structure wasn’t fulfilling. To feed my creative passions, I began a self-proclaimed “hustle” era, working finance by day and music by night. Taking that risk paid off, as one of my modeling jobs ultimately led me to my current role as the Advocacy and Key Accounts Manager for Martingale Cognac in New York. Read more>>

Shannon Wiles Jessica Bowland

In the midst of the pandemic, when uncertainty loomed and many salons and others businesses were struggling to survive, Shannon and I (Jessica) took a leap of faith and opened up Moxie Huntington Beach. Fueled by our passion for hair and a vision for a welcoming community, we transformed an old dilapidated supercuts into our dream salon. It was a super spontaneous decision (when Jessica was giving Shannon a haircut) that blossomed into a vibrant space for creativity and connection. From the very beginning, our mission was to create an inclusive space where hairstylists could thrive and feel supported. Once the lease was signed and we got to work. The whole place was gutted within a week ,it was so fun to see the space so blank and really envision our plan. Read more>>

Floraina Three Hawk

As a young girl I knew I wanted to be a part of the medical world, my grandmother was in nursing and care giving and I looked up to her and my mom, as she also did care for the elderly. My hopes were in the surgical world. I dreamed of being a part of drastic healing in another humans life. On the other side I was very different from other people, I was born to see and feel other peoples pain and sickness in their bodies or emotional body. This helped me be more aware. I was taught at a young age to work with plants and energy to help heal sickness within myself and also create positive energy in my body. I went to school and chose to do surgical technology, the fastest way into an operation room. I loved being a part of saving lives and helping people heal, but something was always missing, and my natural gifts were itching to be used. Growing up I had to deal with several healing moments in my own body with cancer or pre cancer. Read more>>

Dhruvi Darji

DROOVYY embarked on her journey as an independent artist in 2023, after spending five years DJ’ing across India. While she initially never envisioned herself as a singer, songwriter, lyricist, or producer, her passion for standing out creatively pushed her beyond the DJ booth. Originally, her plan was to break into real estate while growing her DJ career internationally under the moniker “Pumpcue.” However, life had different plans when she made the bold move to Los Angeles, aiming to expand her DJ brand. DROOVYY has always been driven by a desire to be different—to be recognized for her originality and work ethic. She sees creativity as her true “net worth,” and with that mindset, she took the biggest leap of her life: evolving from a local DJ to an international, independent music artist. Read more>>

Slava Bodrov

I saw my first tattoo on a sailor back in Ukraine when I was 6 years old and I thought it was so cool and wanted tattoos at a young age. Then when I was 12 I learned how to build a tattoo machine and how to tattoo from a neighborhood guy who had learned serving time in prison. At 14 I asked my mother for a real tattoo machine and she was very supportive so I started just practicing on myself and friends.My official career began at 19 when I started working in an actual shop in Kiev. -I went to school for architecture and studied sculpture. Although I wasn’t very passionate about it at the time, I now value and take what I learned from University and implement it in how I design tattoos. Read more>>

Ceslie Carlotta

Being from Central California, I had the opportunity to travel to the Bay Area, Los Angeles and San Diego often. I loved being on the coast and taking trips to the beach, the weather was always beautiful and the food options were limitless. I felt like the opportunities were endless in the city and i knew from a young age that i wanted to move to LA or San Diego and work in the fashion industry. Continuing this further, when i graduated high school i went to a Junior College and planned to transfer to either University of Southern California or San Diego State University. Furthermore, while i was at Junior college i had all of my transfer units completed except my transferable math course. Math was such a challenge for me and i really had to persevere to complete the units. Nevertheless, I completed this course and thought i was ready to graduate but thats when i was told i was still missing units and needed another semester. Read more>>

E’toyare Mcdonald-williams

It has been a long and challenging journey for my family and me. For the past four years, I have tried to find my place in education through several school districts in the DFW area, and each district’s continued inequalities in education, employment, and representation in leadership positions are rooted in our country’s shameful history of racial discrimination and systemic racism. This demeaning treatment motivated me to step out on faith, leave public education after 23 years, and pursue entrepreneurship for the 2023-2024 school year. I started as an educational consultant bringing educational awareness to understand Adverse Childhood Experiences, (ACEs). To spread more awareness, I also became a host of Be Victorieus podcast, a weekly podcast created in April 2022 that shares stories of real people who have intentionally chosen to delve into the impact of Adverse Childhood Experiences (ACEs) on mental health and explores effective strategies for healing and resilience. The podcast streams on YouTube and all podcast platforms! Read more>>

Mikki Paradis

I was 22 when I started my business. A business in a industry where women were not common and not really welcome. I’ve heard it all. People asking me if the business was my fathers or husbands, people telling me I am so pretty I could be selling makeup at the belk counter. I went to a meeting once where the potential client refused to meet with me because he was convinced Mikki was a man. Truly ridiculous stories I could fill a book with. I won’t tell you that there weren’t days, many days, where I questioned what I was thinking for choosing this path. But even in my doubt I knew this risk was worth it because this industry needed me! It needed someone young, that looked at life, people, and construction differently. I didn’t take it all in stride. I used many opportunities to teach men what was and was not appropriate, I was intentional to build a better dynamic in construction for women with the hopes that if some little girl grew up and wanted to work in this industry it would be a better, and safer place for her. There is still much room for improvement, but I see little signs every day that the industry is becoming more inclusive! Read more>>

Danielle Metcalfe-chenail

When I was 25 years old, I took what felt like a huge risk: I quit the academic path I was on between my Master’s and PhD and launched myself into the unknown. I’d always loved school and research and was generally good at it. I had a clear vision of getting a doctorate in History and then become a professor myself, spending the rest of my career in university settings where I could geek out about ideas and facts, teach others, and write books and articles. Except I was generally miserable in my Master’s program. I still loved getting lost in the library stacks and spending hours in the archives, but there were a lot of things I hadn’t bargained on: toxic instructors, grants that weren’t renewed, and a lot of departmental politics. Oh, and real life crashing down on me from all directions. Read more>>

Rachel Caesar

I made the decision to leave my executive role because I could no longer ignore the toxic culture and the horrendous incidents I witnessed regarding employee wellness. It was truly heartbreaking to see how an organization, whose mission was to help others, could be so damaging to its own employees. I couldn’t wrap my brain around how something that was supposed to foster growth and well-being could be the very thing tearing people down. I watched as employees were mistreated, undervalued, and overworked. They were expected to give everything they had to the mission, yet they received nothing but stress, exhaustion, and burnout in return. Read more>>

Mike Ponder

My story begins as a young military member that was injured in combat and several injuries after returning to the states. I was medical retired out of the Navy and my career was destroyed. I travel many places after this raising my children and trying to make it as an artist. I averaged 300 shows a year up and down the east coast. I took and chance and was able to enroll in Camp Southern Ground and it changed my life! I took a chance and moved to Nashville and returned to school at 51 years old for sound engineering and music production. I graduated in December 2023. It was hard considering I am clinically deaf and blind in one eye. But I did it and now I play 6 days a week on Broadway and have produced several artist! Read more>>

karla carranza

I think this is an excellent topic for creative entrepreneurs. What creative doesn’t take a risk while embarking on a profession that doesn’t always provide the financial returns necessary to be a full time artist? Personally, for many years I could not be a full time artist and worked a corporate job by day. I worked as a Sales Executive in technology, then publishing while living in Boston and New York City. It provided stable salary, commissions, and health benefits. On paper it looked alright, and I actually loved working but often times I felt I was living the wrong life. I would come home and be someone different, someone with hidden tattoos (this was back when tattoos were not really acceptable in a corporate environment) residing in a loft full of art, fashion and music. At my core, it was a dual life. Read more>>

Jose Zaragoza

Art is all about risks. It’s about whether you’re willing to share a certain aspect of yourself or not. Every time I take a photo, I take a risk. It’s always between two questions, “Will the audience like it, or do I like it?” But I always stick to the second option. I think it’s crucial to stick to who you are as an artist. I do what I do because I love the craft, I love doing what I do and I’m not doing it for gain. My art is not about doing it to attract people, it’s to make genuine art, and people like it because it’s authentic. I think genuinely liking your craft and doing it for yourself is such an important risk to take as an artist, making art that’s true to you and who you are shines through in the final outcome. Read more>>

Christine Sopa

Before I started my business in 2003, I worked for a publishing company and had a very stressful job. During this time in my life I was a young professional, was married with two young children, working 50-60 hours per week, and was studying for my masters degree. If someone were to ask me at that time if I felt stressed, I honestly would have said no. I truly did not feel stressed because my definition of stress was a wigged out person who did not have control of their life. I over-controlled my life…which was part of the problem. After several months of severe stomach issues, I finally went to the doctor (who has time to go to the doctor when we are “busy?”) and I was diagnosed with chronic ulcerative colitis. I was admitted to the hospital for 5 days and the doctor wanted to do surgery and remove half of my colon. I refused, mainly due to fear and a gut feeling it would lead to more issues. Read more>>

Kelsey Garguile

One big risk I’ve taken in my professional life was applying for and attending CRNA school. There are fewer than 130 credentialed CRNA programs within the United States, and acceptance rates for these programs can range anywhere from 15%-20% – and even lower for some of the higher ranked universities. Prerequisites for applying for these programs are grueling, often requiring additional coursework and certifications to simply get your application considered. During the review process, the top candidates are asked to travel to the prospective universities in order to conduct an in-person interview, and final selections are made from there. I was just one year out of nursing school when I began working on filing applications with some of the CRNA programs that I was interested in attending. I worked at a level one trauma center in Seattle, so I was able to accumulate a vast amount of experience at a young age. By working extra shifts I was able to sit for my Critical Care certification earlier than average. After earning this certification I decided that although I was not at the two-year mark of working in the ICU – which is often the minimum requirement to even be considered by a CRNA program – that I was going to begin my application journey. I was not planning on being accepted into the programs that I was applying to. Mainly, I was hoping to be able to experience the interview process, which would have allowed me to be better prepared once I was able to check-off all the “requirements.” To my surprise I was accepted into all three programs that I applied for. My husband and I moved to Wichita, Kansas and began the grueling journey of CRNA school.  Read more>>

Brandon Bye

In November 2023, Amazon laid me off. It was the best day of the year. I booked a one-way flight to Buenos Aires and stayed for a month. I took the next nine months off, photographing and figuring out what’s to come. It felt like a crossroads, but I didn’t know just how sharp a turn I would take. I worked at Amazon as an editor and writer for Alexa for seven years. At first it was cool, writing for a cutting-edge technology at a company writing blank checks. I was insulated from what people talk about when they talk about working at Amazon. My boss was a playwright. My closest co-worker was into fountain pens and high-end paper. I had a band going. Life was simpler then, but as the economy changed, the values of the company changed. Creative people were no longer valued at Amazon — MBAs and SDEs only. My boss got canned, and save for my pen-enthusiast co-worker, I was alone. And then we were both laid off. In August of 2024, I started earnestly looking for editorial work again. I must have submitted 100 applications for jobs I didn’t want. Boring, lifeless job descriptions all written by AI. My cover letters, filtered through ChatGPT, followed the form. This was not the world I wanted to be part of.  Read more>>

Vera Milan Gervais

The biggest risk I’ve ever taken is believing in myself. It sounds mellow-dramatic, considering how many risks I’ve taken in my life: • Ending a 4-year marriage to my teenage sweetheart when I was 23 and everyone was trying to convince me to stay – apparently being unhappy wasn’t a good reason to get divorced! • Quitting my job and dropping out of my degree program at the same time as my marriage ended because I realized I hated that part of my life too. • Signing up for a survival weekend in the mountains when I’d never hiked before. It was physically and emotionally brutal – and it gave me so much confidence in my ability to tackle challenges. • Impulsively going back to school to study Communication Arts because, while I’d always wanted to write, I’d been told I could never make a living doing it. I’m grateful I did – I defied the odds. • Jumping out of a helicopter into the ocean with $5K of camera equipment on my back because I wanted to visit a sacred Haida site. Worth every second of doubt and fear. Read more>>

Jarron Webster

I moved to Atlanta for a year in 2022. It was a significant move and major decision because my sons are in Florida and being away from them is something I would’ve rather not done. It was a situation in which I was following signs that were occurring, and I felt they were leading me to Atlanta. I trusted and had faith with whatever was happening. I was a few years into the film industry at that point, so I thought everything was related to my film career. I thought it was time for me to “blow up”. It turned out to be a much deeper journey. Read more>>

Taiju Nakane

There are two major risks I’ve ever taken. The first was leaving behind my career in Japan and moving to New York to start over. I began acting as a child, mostly in TV series, but during college, I had the opportunity to be part of an NYU grad school film called A Warm Spell, which was shot in Japan. That experience was a turning point for me. The film ended up being nominated and winning awards at various film festivals, and it introduced me to the way films were made in the U.S. I was fascinated by the director’s approach and the energy on set, which were completely different from what I had experienced in Japan. That’s when I realized that if I moved to the U.S., I could be part of more projects like this and learn new techniques. Even though I didn’t speak English at all, I decided to take the leap and move. Read more>>

Jamie Boulton

I studied Electrical Engineering and Communications at Northumbria University in Newcastle, UK I got a job straight out of university for Mercury Communications in London with full graduate training program. I worked for them for four years before taking voluntary redundancy in 1994 Using the pay off I took a year out and travelled around the world On my return I worked in telecoms to pay of my travel debts and worked on film sets at nights and weekends. After a year or so I had to decide between telecoms and film/tv industry when I was offered a great job at AT&T and a runner job in Soho on minimum wages! Thankfully I chose the runner job and a year later I was a freelance avid editor from 1998 until the present day Read more>>

Kenan Heppe

In 2017, I moved to China to pursue acting work in the Chinese film industry, without knowing a single person there. And I barely spoke Chinese. But, there had been enough signs. Indeed, it was finally time to take a calculated risk, bet on myself, and have the adventure of a lifetime. Quick rewind. In 2004/2005, I saw “Hero,” an incredible Chinese film directed by Zhang Yi Mou. It was playing in theaters in Hood River, Oregon, where my family lived at the time. This heartwrenching adventure/war/love story, full of expressions I hadn’t seen in my own culture, displayed through color and music in a way I hadn’t seen in American films, made me curious about China. I knew I wanted to go there one day. It’s 2012, now. I’m in college, studying Chemistry at Oregon State University. As a member of the Honors College, I was invited to go to China on a trip with a group of engineering students. I had remembered the impression “Hero” left on me, and I went on the trip. Simply put, I had an amazing time, and I wanted to learn Mandarin Chinese. When I got back to the States, I enrolled in First Year Mandarin. But, my chemistry work quickly became too consuming. I stopped studying Chinese, and went about my life. Read more>>

Tierra Graves

In 2014, my life changed in the blink of an eye. I was faced with the death of my father. This was a moment that I thought I would never recover from. In my weakness, my depression, and my grief I was encouraged by family and friends to write a book. Taking a risk, to share my struggles, dark moments and pain in a book brought many uncertainties and fear. I initially reached out to a publishing company in 2015. I didn’t know much about how to go about publishing a book and who I needed to contact. I found this company online. I was asked to give a large amount of money up front. During this time, I was in undergraduate school. I asked my school counselor who had written a book about this company. She immediately told me it was a scam and not to send them any money. I was disappointed and very scared. I continued my studies and put publishing a book on the back burner. Read more>>

Omotara James

It was the holiday season of 2015 and I was down bad. In addition to a heaping helping of holiday blues, I was involved in a long-term toxic relationship with an ex-girlfriend, who was also my boss, and a lousy boss at that. Although I didn’t know it at the time, I was about to receive extra confirmation from the universe that she was not for me. Having recently informed her that I was considering returning to school to get my MFA in poetry, instead of congratulating me she broke down in tears of frustration, citing her generalized anxiety that I would leave her. I had to console her. At work. On my lunchbreak. What I hadn’t told her at the time was that I had already attended an enrollment day at a local university and was waiting to find out if they would accept me into their program for the winter of 2016. Although I enjoyed the social work I was doing, it was draining and all-encompassing. I found myself feeling unsupported at work and extremely exhausted. Read more>>

Jannica Honey

Most of us, creatives find “risks” the most challenging aspect of being self-employed. Perhaps “taking a risk” is the hardest part of life, yet totally central to “being alive”. Perhaps it is only me and my luggage of trauma that makes me apprehensive and anxious each time I leave my comfort zone (what is that anyway?). Yet THIS is the only way creatives stay imaginative. We simply have to allow for that “flow” or creative river to move along our inner landscape. If that river of creation doesn’t swell we never know what the destination or the result will birth. It is like a forever process into the unknown… waters of creativity. Flowing rather than stagnant.  I googled risk, seems like something we all shy away from. Definition for risk. noun as in chance taken. Synonyms Antonyms. Strongest matches. danger, exposure, hazard, liability, opportunity, peril, possibility, prospect, uncertainty. Read more>>

Laura Viola Maccarone

Being a graphic designer has been my dream since I was eleven years old. Starting a design studio was fueled by my passion for creativity and a desire to help brands visually express their identities. The journey, however, was anything but straightforward. It was defined by taking significant risks, the first of which happened when I approached the owner of a boutique aromatherapy company, BC Essentials. I made the bold move of asking the owner who did their labels and had they ever considered a rebrand. Their brand didn’t quite capture the essence of their high-quality ingredients. The outside did not showcase or match what was on the inside. One day, I found myself in BC Essentials perusing all their products, in that moment is when I took a leap, a risk and approached the woman behind the counter. That woman happened to be the owner, Beverly Buccheri, and in that moment, I pitched the idea of rebranding their entire line of aromatherapy products, all 360 of them. It was a bold move, especially considering I was still establishing my business, but I believed in my vision and the potential impact of a refreshed brand identity. Read more>>

Hannah Hinton

Starting my photography business was life-changing. I have always been creative and had an eye for photography, but lacked the courage develop it into something greater. In 2020, I was in my last year of nursing school when I decided to finally take on the risk of opening my very own business. Despite having limited time and financial resources, I leapt in with my heart to pursue this dream. The start was a lot of work; slow going at times. Trial and error navigated me to find what worked and what didn’t. After becoming a nurse, I found this side passion to be even more rewarding. It was an outlet for me to spark creativity and put my “9-5”, or “7-7” in my circumstance, to the side. I am fortunate enough to be able to manage being both a business owner and a nurse PRN at the hospital. It is hard for me to imagine my life now without having taken this chance all those years ago! Read more>>

Orsolya Szabo Dr.

I firmly believe that taking calculated risks is a fundamental requirement for any successful entrepreneurial journey. Without embracing a healthy level of risk, there’s no opportunity for growth or advancement to the next level. One of the most significant risks I took was when I decided to pivot my career, transitioning from being a lawyer to becoming a location-independent consultant. It was a major leap into the unknown, one that brought with it countless challenges but also tremendous opportunities. But my journey of risk-taking didn’t stop there. I took another bold step when I decided to expand into new markets, while still living in Europe. I opened my business to new regions, moving from Hungary into the DACH region and beyond. Breaking into these markets required me to adapt to different business cultures, understand new customer bases, and continually evolve my approach to meet the needs of entirely new audiences. Read more>>

Jill Boyd

Oh, boy. So, there are many choices in this life as far as careers go. From attending college, receiving a certificate, training under a professional, or building from the ground up, there are many options. I wish more young people knew this. When I was younger, I was told I couldn’t make any money from music. Risk is an interesting word; based on context. I played “the safe side” for the first few years of my career. I attended business school and eventually landed a few “regular jobs:” one at a University helping students enroll into school, another in the customer service dept. for a big online store, etc. The decade from 20-30 was me floating through the “norms” of what others might expect of me. Before I turned 30, in that last week of being 29 I realized I hadn’t explored my dream: becoming a music composer. I decided right then and there to dedicate my next decade to music, and wrote down 5 things to accomplish in my music career over the next 10 years. I finished those goals in 2.5 years. I then wrote “bigger goals…” such as “win a competition, write for a full orchestra, hear it performed live..” I accomplished those within the next year and a half. I found myself at age 34, having finished all of those, and deciding “I’m going to make composing my full-time job.” Read more>>

Carissa Mattern

My artistic and professional careers have been interesting. At the end of 2016 I was halfway through my Master of Fine Arts in Studio Arts with a specialization in Design and Photography degree when I realized several things: I no longer wanted to teach art, and painting horses and other equestrian scenes is what made me happy. My work previously was heavy–a lot of dark imagery with emotionally taxing undertones. The work was important for me to get out there, but it was no longer fulfilling me in the way it had previously. When my work started to take a turn towards horses, quite frankly, I started to question what I was doing with my life. Prior to going for my Master of Fine Arts, I thought that the only way for me to have a fulfilled life was to be working in the arts full-time. I had only ever gone to art school from middle school through graduate school; it was the only thing I really knew. So when my work was shifting and the MFA program I was in wasn’t allowing me to make those drastic shifts, I started to think about what else I was interested in other than art and horses. This was around the time that Trump was running for President and my husband and I became very involved in politics; and my 9 to 5 was getting very involved in academic policy. Read more>>

Eileen Smith

The biggest professional risk I have taken (aside from temporary duty in danger zones including Afghanistan, Lebanon, and Tajikistan during its civil war) was leaving my diplomatic career after over 20 years, but well before my retirement age. At the time, I had spent over 20 years as a United States diplomat and had the adventure of a lifetime. I also had a busy home life with two kids, a dog, and a husband who also had a demanding career with lots of travel. Our work life balance fell apart and something had to give. I took personal leave from work and intended to come back once I got our ship righted at home again. But something shifted for me in my several months focused on my family and home. Suddenly, this dream that had been calling me since I was in high school – wasn’t calling me anymore. I spent the next few months thinking about what else I would like to do and talking to people who ran their own businesses. Read more>>

Bethany Kerr

When I was in college, I started to post my quick healthy meals on Instagram. My account was called @itsrainingveggies. My account grew quickly and I started getting free marketing gifts. This was very exciting for a college student trying to eat healthy on a budget. I started this account because I met a lot of college students who would tell me that eating healthy was too expensive and time consuming. My theme for this account was to make inexpensive, healthy dinners that are easy for college students to make. I had a lot of fun running and managing this account until the haters came out. A lot of my followers started following me because they thought it was a vegan recipe account (my account was not vegan) so people complained that my name for the account was confusing. At the time, I was interviewing for grad schools, applying for jobs, figuring out what my life would look like after college, and ultimately decided to sell @itsrainingveggies. I sold the account within a couple of days, and I was shocked at how many people were interested in my content. Unfortunately, @itsrainingveggies has been deleted, but I learned a lot about social media and creating a theme and voice online through that experience. I took a social media break for a year before I started to make health dinners and charcuteries boards on my new account @thebethiek. Read more>>

Rowena Sutherland

In 2016, at 33, I became the youngest person to ever hold the position of Executive Director of Culture for the Bahamas Government. It was a milestone moment, one that carried the weight of high expectations and an immense sense of responsibility. Consulting directly with the Prime Minister, I had the platform to amplify the voices of my community at the highest level of government. But the significance of the role didn’t come without its challenges. Being young and female in this space meant that I often faced pushback, particularly for my out-of-the-box thinking as a creative. Read more>>