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.

Bridget Green

In 2017, I obtained my real estate license. After passing the real estate exam I signed on with a Keller Williams office and began learning to become a Realtor. In January of 2018, I decide to leave my full time job and focus completely on being a full time Realtor. I really wanted learn a new profession and make my mark. Little did I know the lessons and rewards I would learn from taking such a big risk. Read more>>

Dimple Bhanushali

One of the biggest risks I’ve taken was making a bold shift from a stable and well-established career in finance to the fast-evolving, unpredictable world of fashion. I had built a solid foundation in finance and a clear upward trajectory. But I felt unfulfilled, and I wanted to create something rooted in sustainability and inspired by my cultural heritage from Kutch, India known for its traditional craftsmanship. Read more>>

Mac & Paige Carpenter

 

One of the biggest risks that we’ve taken as a creative pair was also one of the choices that came the most naturally – the decision to pursue making stained glass full time. Although we both studied art in college at SCAD, Mac had been working as a recruiter for years until he was abruptly let go in the fall of 2022. Despite hating the job, he had held it for years as I (Paige) worked as a graphic designer, changing throughout our relationship from working a corporate job to freelancing and working with small businesses. We had already started to make glass, but on a smaller scale, and once he was fired we both agreed it was worth it to give stained glass a full chance, and we decided to give it til the end of the year to start with. Read more>>

Laurie Larsen

I write novels. Conventional wisdom has always been, in order to build and grow your audience, keep writing the same types of books so the reader knows what to expect from you. Each book should be the same, but different. Different characters and plots, but the same type of reading experience to make your readers comfortable. After spending ten years writing contemporary romance, I felt a call from God to switch to Christian romance. The two genres are similar with a compelling romance, a conflict that the two people work through, a “dark moment” in their relationship where it looks like an insurmountable problem, and then a satisfying resolution leading to a Happily Ever After. The differences were: 1) no sexy scenes in Christian fiction — just clean and wholesome and 2) a faith journey for at least one of the characters in addition to the romantic journey. Read more>>

Gary Saperstein

I have taken 2 major risks when starting Out In The Vineyard. The first risk was making the decision to “go for it” and leave the day job. I was working in the restaurant business as a General Manager of numerous establishments for 25 years. It’s what I knew and was passionate about. But, I was going through a change and losing the passion for the biz. Once you lose that passion for the hospitality business it’s time to get out of it. Read more>>

Paula Rivero

In acting you have to take risks, make choices for your character, for the story. That´s how you put your own print in the work, the way you build and shape the different roles through your acting.
Taking risks means to grow, to dare to go beyond, and keep looking for more. For me being a performer/choreographer brings me joy, it’s my passion and I can not just settle down with one thing, one win, one achievement….there is something inside of me that drove me into this profession and I like to honor and fulfill that feeling, and in order to do that I have had to put myself out there and try new things. Read more>>

Kim Marie

For years I beat myself up for floundering through life, feeling so unsure of what was mine to do and experimenting with so many different things. By the time I came to the work I do now as a Life and Spiritual Coach for holistically empowering women, I realized that I wasn’t floundering at all, but rather taking risks to align with my Soul’s longings. Many reflected back to me how courageous (and sometimes how crazy) I was to do what I did, which helped me to see my path from a new and much more empowering perspective. Read more>>

Aimee Gochinski

Let’s talk about this from an archetypal point of view, seeing as how our psyche speaks this language best. Archetypes are universal symbols or character types that recur across cultures and stories, helping us understand human behavior and motivation.

The Risk Taker archetype has played a strong role throughout my life. I have always felt that I have strayed from the crowd, not necessarily because of them, but because of me. My solitude has always been my sanctuary. My ways of thoughts and actions have seemed to differ from the societal theme. I will not choose a particular situation to speak about, I would rather talk about this pattern and how it comes together as a whole to form what one could call a personality trait. Read more>>

Gabrielle Padilla

One of the biggest risks I took in my business was deciding to go full-time as a hair and makeup artist. At the time, I had a stable job working in a hair salon, but I wasn’t creatively fulfilled. I had built a small client base on the side, but it wasn’t guaranteed income. Still, I trusted my skills, my passion, and the relationships I was building. It was during Covid that I decided to take the leap and left my salon job to pour everything into my business. It was scary, but that leap allowed me to grow, expand my brand, and eventually work with dream clients and on creative projects I never would’ve had time for otherwise! That risk taught me that betting on myself is always worth it and also having the right people around you and supporting you is everything ! Read more>>

Briana Reed

I think the most important thing as an artist is to not only take a risk but consistently take risks, the fear of the word No and/or perceived failure at something we desire, has the power to keep us stuck or only seeking that which is comfortable. As a freelance choreographer I am always looking for opportunities to create and whether applying for grants or sending in choreography submissions the risk is always rejection. Taking the risk to continuously hone your craft in the midst of rejection, essentially betting on yourself, your gift, and the vulnerability of that is risky; yet I have found in putting forth the effort and taking the risk to continuously put myself and my work out there the opportunities that have been right and most fulfilling for me and my growth as an artist have shown up. Read more>>

Tayla Green

In 2022, I took a leap that changed the entire trajectory of my career and my life. At the time, I was working in a comfortable role outside of cybersecurity—one with stability, predictable routines, and benefits. But deep down, I knew I had the drive and passion for something more impactful, something that matched the way I think, solve problems, and see the world. That “something” was cybersecurity. Read more>>

Briannon Kelley

One of the biggest risks I took was leaving the stability of a full-time role to launch my own boutique PR agency, BK-PR. I had spent years honing my craft, securing press for high-profile clients across entertainment, sports, and lifestyle industries, but stepping out on my own meant betting entirely on myself — without the safety net of a larger company’s infrastructure. I made the decision because I deeply believed in my ability to not only deliver results, but to build authentic, lasting relationships between brands and their audiences. Starting my agency meant doing everything from client acquisition to pitching, strategy, and execution, often while balancing financial uncertainty in the early stages. Read more>>

Michele Daulton

In 2016, I took one of the biggest risks of my life: I left everything familiar behind and moved to the United States with my husband and two children. The transition was both exciting and terrifying. I didn’t have any friends or a support system, and everything—from the culture to the daily routines—felt brand new. Read more>>

Ruthie Bowles

Diving into narration was probably the next biggest risk after quitting my full-time six-figure job. I quite my employment to become a freelance writer, and that grew into content marketing consulting. Just before COVID, I narrated an audiobook for fun as a side thing. During COVID, I became disillusioned with my chosen career path. I wondered, if a virus might end my life here and now, what would I feel like I had done? Not to mention, getting bamboozled by some business coaches definitely soured me on the whole industry. Read more>>

Dr. Lisette Sanchez

One of the biggest risks I’ve taken was launching my own private practice. At the time, it felt huge and life-altering. I was burned out from my job, carrying a high caseload with little flexibility. I’d come home exhausted, day after day, but kept pushing through because I didn’t see another way. What finally gave me the courage to take the leap was realizing something simple but powerful: the risk wasn’t as big as I thought it was. I had always believed I didn’t have a safety net, but then I realized I did. If things didn’t work out, I could always return to a salaried position. That mindset shift changed everything. Taking that step taught me to bet on myself. Read more>>

James Miller

Any time you decide to venture out, pursue a dream, and start your own business, you are taking a huge risk. There are so many variables, so many obstacles, and so many rough times, that it can become very discouraging. I took a major risk by putting absolutely everything I had both financially and physically into the pursuit of owning and operating my own small brewery. I ran down a dream and committed 100% to it. I accepted the risk through dedication. I continue to risk so much, and have lost so much in my pursuit, yet my dedication has not faltered. I have failed in personal relationships, made so many sacrifices, and have paid a high cost by making that jump, taking that risk in building my business from the ground up. Read more>>

Aidyn Mancenido

It was the day of a new moon in April of 2018 when I gave my boss my 2 week notice. I had been fantasizing for some time about making art. And just making art. I didn’t want art to be a side hobby, or an afterthought, or a theoretical exercise, or fodder for engaging dinner conversation. I wanted it to be the center of my existence. I had never called myself an artist before, but I knew without a doubt that I wanted to become one. And I felt that desire with a similar level of simple clarity and conviction that a child evokes when asked “what do you want to be when you grow up?” “I WANT To BE AN ARTIST!” Full stop. Read more>>

Krysta Huber

The first was choosing an untraditional path for my career. I graduated college in 2016 with a degree in journalism, and at the time, I thought I’d end up as a financial newscaster—maybe on CNBC or Bloomberg. That goal initially led me into finance. I spent less than two years working at big banks and asset management firms, and very quickly realized I was not built to sit behind a desk all day. Read more>>

Eric Andrews

The biggest risk I’ve taken was quitting my job of 11 years to become an entrepreneur full time. I’d worked my way up in a property management company working many different facets and positions, but decided that Corporate America wasn’t for me. I had savings but they were exhausted in a matter of months. Nothing went as planned and almost, and I do mean almost everything took longer than planned. Building my business, staying focused, and finishing renovations all at the same time as dealing with real estate clients and the overall chaos that real estate is inherently. Read more>>

Sara Austin

I used to have a stable job—something people would call “secure.” But I felt overwhelmed, stuck in a world that didn’t leave much room for creativity or peace. Eventually, I hit a point where I couldn’t keep pushing through. So, I packed up my bike with what I could carry: a sketchbook, some snacks, and a lot of uncertainty. I didn’t have a big plan—just a deep need to breathe, to move, to see the world in a different way. Read more>>

Shyanne Gubler

Honestly my life has been full of risk taking ideas and not all of them have turned out well; especially when it comes to my business ventures. My poor husband can attest to all my attempts. My biggest cheerleader and logical advisor. My husband has been through all my risk taking but he has helped me while heartedly each and every time.
I’m going to tell you about my most recent and currently on going adventure. The purchase of my Percheron. Read more>>

Sarah Kugelman

When I started my first company i was 34yrs old and i was in a corporate job at a big company. I was making a good salary and i had been granted options in the company. The stock split 3 times while i was there so i was sitting on an illiquid asset that would vest in August 1999, my third year with the company. It was more money than i ever thought i would have in my life. It was money i could invest and would take care of me in my retirement as i had no savings. Read more>>

Sarah Patterson

It was a simple post on the “share your latest” virtual community platform, Pillar, where National Board Certified Health and Wellness Coaches hold membership to access industry resources, engage with research and hear about job postings. Read more>>

Rosa Castillo

Putting myself out there on social media has been the riskiest thing I’ve ever done—sharing my work with millions, opening myself up to both praise and criticism. But without a doubt, it’s also been the most rewarding. Like they say, no risk, no reward. Thanks to social media, I’ve had the opportunity to go on incredible press trips, connect with people I never would’ve met otherwise, and experience countless positive moments—all because I took the leap into content creation. Read more>>

Brooke Velazquez

The biggest risk I’ve taken was walking away from a company I had been with for 18 years to open my own recruiting firm, while raising three young kids and serving as the primary breadwinner for our family.

It wasn’t a decision I made lightly. So much of my identity and security had been tied to my former company. But over time, the culture and leadership shifted, and I reached a point where staying simply wasn’t aligned with who I was anymore. I knew I needed to make a change, not just for my career, but for my long-term fulfillment and the example I was setting for my children. Read more>>