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.
Dan Dowding
We quit our full time jobs to pursue video art full time!
At first it was an obsession for collecting vintage electronics and mainly analog CRT video art. We worked our fulltime jobs as a video editor and head of electronics recycling for several years. It was just a side quest that we obsessed over and spent every morsel of extra time we had digging deeper down the rabbit hole of video art. As our obsession grew, so did the opportunities to display our art. We started realizing that everyone young and old gravitated towards this “nostalgia”. All of a sudden my friend calls me and tells us “David Hasselhoff wants to shoot a music video in front of your TV Wall.” Before you know it the Hoff is belting out his single “Open Your Eyes” in my live/work studio. We’re flying to Miami to work with Bad Bunny. Eminem wants us to make an installation for a museum in Detroit. Then the pandemic hit and everything stopped, but we didn’t. We kept making art for ourselves. We developed our website. We were lucky to pivot out of the pandemic successfully. All the investments we made into our hobby and obsession during the pandemic paid off tenfold. It still feels like we’ve captured lighting in a bottle or rather electricity in a tube. We’ve been at this full steam since 2017 and now we are a team of 10 with a mission to bring artists’ and brands visual identity to life by combining vintage and modern technology. Read more>>
Carmalita Af
This past spring, I went on a cross country roadtrip with my dear friend, Jenea who is a big sister to me. She’s a huge traveler and explores the most beautiful places all over the world. When Jenea shared her mapped-out itinerary of an adventurer’s dream cross-country road trip filled with hiking, glamping, sleepovers and exploration–I was happy to tag along. I had driven cross-country alone once, but didn’t get a chance to stop and explore between Los Angeles and New York. This time around, I was eager to be both driver and rubber-necking passenger. Read more>>
Jill Hall
In 2021, I made a bold decision to leave my corporate career and fully embrace creativity. After more than 20 years in real estate management—beginning as an administrator and ultimately becoming a Senior Vice President—I felt it was time to reconnect with the artistic side of myself I had too long set aside. My career had been fulfilling, and I was proud of everything I achieved. Yet, a part of me longed to follow my own creative path. So, I took the leap. I resigned and began dedicating my time to making art. To my surprise and joy, opportunities came quickly. My work was showcased in multiple exhibitions, both locally in Washington and out of state. Then, in October, a charming cottage on the main street of Edmonds became available. It felt like the perfect place to bring a long-time vision to life. I opened Bench & Board, an art and gift shop, and since then, I’ve spent three rewarding years combining my passion for creativity with the joy of curating a unique shopping experience. Read more>>
Laketa Entzminger
Starting this business involved taking huge personal and financial risks. I prefer to work behind-the-scenes and keep to myself, but my business has forced me out of my comfort zone. Financially, I used my own funds. I was an elementary teacher and enrolled in herbalism classes, so this did not allow for a lot of spending outside of bills and other necessities. I felt, at the time though, it was now or never. I was already making products for family and offering herbal consultations, so I decided to formally start a business doing just that. I made several products in addition to customized formulas for my herbal consultations. Today, my mission has leaned more towards providing education to children and families. Taking these risks has been worth it! Not only did I accomplish a childhood dream of writing and publishing a children’s book but seeing children excited about learning about herbalism genuinely makes my heart happy. Read more>>
Adriana Rodriguez-baptiste
Hi, my name is Adriana, and I am the founder of Healing Roots Together. I’m a licensed clinical social worker, psychotherapist, and a coach in NY. I’ve worked in community mental health for the last 20 years and became an executive at a nonprofit before the age of 40. I taught at an Ivy League school for 6 years and ran 2 New York City Marathons to cope with the grief of not being able to have kids. After serving my community for many years, I have decided to use my education and work experience to connect women who are childless and childfree to each other. I understand that it can be an isolating experience, and I know there are ways to find purpose beyond parenthood. I was able to cope with my grief by gardening and realizing that just because I couldn’t grow life on the inside didn’t mean I couldn’t grow life on the outside with Mother Nature in the garden, Read more>>
Kd Holmes
Straight out of graduate school, and after two additional years to earn my licensure, I leaped and started my own private practice. At the time, that was practically unheard of. How dare a young woman venture into private practice in a field dominated by seasoned therapists? But that’s my nature—I follow my gut, do what feels right, and give it everything I’ve got. For the next 12 years, I worked relentlessly, training, consulting, and immersing myself in my specialties to become the most informed and effective therapist I could be. Read more>>
Sophie Williams
Balancing my career as a full-time professional dancer with Texas Ballet Theater while running Pointeworks has been one of the biggest risks I’ve taken. Starting Pointeworks wasn’t about stepping away from my dance career—it was about expanding my passion for ballet into new territory during the summer off-season and layoffs while creating opportunities for fellow artists. Launching Pointeworks in my hometown of San Diego was both thrilling and challenging. It was an opportunity to bring top-level ballet back to where I started, but it came with its share of late nights, constant problem-solving, and a steep learning curve. The key was staying open to advice from more experienced mentors while staying true to my vision: putting artists first and creating the kind of supportive environment I value as an artist. Read more>>
Marisa Baggett
For over 20 years, I built my career around sushi—teaching classes, catering, consulting, and even writing a couple of sushi cookbooks. Sushi was my passion, my livelihood, and a big part of my identity. But in 2024, I took an unexpected turn: I transitioned entirely to plant-based sushi. The decision didn’t come out of thin air; I think it was always lurking in the shadows. There was an “inciting incident” that pushed me forward. I was working on a once-in-a-lifetime sushi project, one that felt like the pinnacle of my career. I loved every part of it, but something nagged at me throughout. I realized after the project ended that I’d felt deeply conflicted about using certain seafood. Concerns about sustainability and my evolving kosher observance weighed on me. Read more>>
Deanna Carell
It’s 2011, I just graduated from Seton Hall University with my Bachelor’s Degree in Business Marketing and the country is digging itself out of the great recession. At the end of 2007 into 2008 America found itself in a subprime mortgage crisis which caused record breaking inflation and many people losing their jobs and businesses going bankrupt. Although the recession ended in 2009, many of those effects were felt, especially in lower income families like mine. I grew up in a single parent household. My mom worked and took care of my sister and I on a very tight budget. I learned at a young age from her the importance of hard work and saving money. Going to college was a dream, as the oldest I was the first from our family to graduate college after receiving scholarships and government grants for my academics. I graduated at the top of my class, from the Marketing Honors Society with a good job laid out for me. And I decided not to take it. Read more>>
Ray Beldner
The biggest risk I took was in 2021, after the Covid lockdowns, when I decided to devote myself entirely to my art practice. Before then, I’d always kept a safety net – a part-time job, consulting work, teaching gigs. But something about living through the pandemic crystallized things for me. I realized that if I wanted to succeed as an artist, I needed to commit fully. Making art itself involves daily risks: every blank canvas represents the possibility of failure, every exhibition opens you up to criticism or worse – indifference. Each piece reveals something deeply personal about who you are and how you see the world. But choosing to make art your sole source of income? That’s a different level of risk entirely. Read more>>
Podcasters Tanya Johnson And Jessica Parker
When we first decided to start Girl…Call Me with Tanya and Jessica, it felt like stepping off a cliff into the unknown. Neither of us had worked in the podcasting space before, and while we had plenty of ideas, we lacked the technical knowledge and audience-building expertise. Jessica hasn’t spent much time on social media since 2020, and Tanya didn’t know the difference between an Instagram Story and a Reel. It was both exciting and terrifying to commit to something so unfamiliar. Read more>>
Alyssa Burlingame
The biggest risk I’ve ever taken was starting Daisy & Dahlia Branding Co. I traded a steady paycheck, 401k, and health insurance for a flexible schedule, freedom of my time, and pure faith. To say it has always paid off would be a lie…but to say that I’ve stopped believing in this business would also be a lie. I have not yet reached the purely thriving stage of being a business owner, but I have learned so much about trusting the Lord, trusting other people, and about my own strengths and weaknesses than I ever would have learned at a 9-5. I am thankful that I took the risk and started my business…it is such a gift! Read more>>
Jessica Pierre-paul
One of the biggest risks I’ve taken was starting my own digital marketing business, Nicole Martin Digital. It wasn’t a decision I made lightly—I had a secure job with consistent income, and stepping out on my own meant leaving behind the safety net that came with it. The idea of building something from the ground up was both exhilarating and terrifying. The backstory is simple: I’ve always been passionate about helping small businesses grow. Over the years, I noticed a recurring theme—many small business owners, especially wellness professionals, were struggling to manage their online presence while juggling the demands of running their businesses. I realized there was a real need for someone who could step in and handle social media and digital marketing in a way that aligned with their brand voice and vision. It was this realization that sparked my desire to take the leap. Read more>>
Dawn Hull
My ventures, from OliverAlert and aKeKee to CandlestickCoasters, have always been driven by a desire to address a need, often arising from personal experience. Losing Oliver plunged me into the world of lost and found pets, where I encountered countless others desperately searching for their beloved companions. This fueled my desire to help, leading me to create OliverAlert. Next came aKeKee, the first vertical search engine dedicated to pets. Most recently, I’ve embarked on a more creative path with CandlestickCoasters, transforming repurposed candlesticks into unique and functional tables. I now find myself searching for the perfect pieces to add to my portfolio. Read more>>
Claudia Carreno
The risk of starting this brand was real. But the reward? It’s in every small victory, every new customer, and every step forward I take. I’m still learning, still growing, and still working hard to make Dream Wear Boutique everything I’ve always dreamed it could be. It hasn’t been easy, but taking that risk was the best decision I could have made. Starting Dream Wear Boutique was a risk. A big one. When I first had the idea, I wasn’t sure if it would succeed or if it was just a fleeting dream. But something inside me told me to go for it to take the leap and turn that vision into reality. Little did I know, the road to building a well-known brand would be much longer and more challenging than I ever imagined. Read more>>
Flawless Finish Artisrty, Llc
It’s hard to believe it’s been 10 years since we launched our mobile bridal business! It all began with the three of us—Marisa, Melissa, and Tiffany—freelancing as hairstylists and makeup artists. We kept crossing paths at weddings and soon realized we shared a common vision. At that time, the traditional bridal routine involved brides/bridal parties getting up early, driving to a salon—often battling traffic and parking—and then spending hours getting hair and makeup done, all while racing against the clock. It became clear to us that there was a gap in the market. Read more>>
Mallory Mundy
I’ve always loved the saying, “That risk you’re scared to take might be the one that changes your life.” I’m a big believer in taking risks and making changes when you’re following your bliss. For years, I led the flagship office of the largest real estate company in the world alongside my two partners. My life revolved around work—nonstop. Then, in 2020, everything changed. My husband became seriously ill, and we discovered he had cancer in one of his lungs. He underwent surgery and faced emergency complications. It was a wake-up call for both of us. We realized that life isn’t meant to be spent behind a desk, staring at a busy highway. Read more>>
Candice Plewik
As far back as I can remember, I have visualized, and fantasized, about my future success. I distinctly remember playing with my Barbie dolls, imagining I was the main character in the dramatic story I was acting out. When I was Barbie, I was either a famous Hollywood actress, a New York City high fashion model, a big city architect, or just the overall “big boss” of a company. What is success? To my 6-year-old self, success meant making lots of money, living in a mansion, and having an in-ground swimming pool. It was having cable television with hundreds of channels and having a personal chef. It was dressing in fancy clothes and driving a red sports car. At that age, success was accumulating “stuff.” Read more>>
Dallas Anselmo
Risk taking plays a big role in life. Before taking any risk, I like to weigh both the risk and the potential reward. If the potential reward outweighs the risk of the action, it’s a no brainer. Sometimes, you just need to dive into something and simply see how things will play out. My life would look completely different if I hadn’t taken the risks that I have and to further better myself, I’ll continue to take risks. You never know when a random decision you make could change the entire trajectory of your life! Read more>>
Jenifer Renzel
Every time I work on a painting I ask myself to take risks. With my sort of crazy style, I’m flying without a plan and must rely on spontaniety and intuition. Sometimes I find myself losing inspiration and just staring at a piece, or becoming frozen because a piece is almost done and I’m afraid of ruining it. I’ve come up with techiniques for overcoming these blocks. One thing I do is put at least three painting in motion at the same time. When I get stuck, I work on a different piece for awhile. If I’ve rotated through the working pieces many times in a session and nothing is happening anymore, it’s time to quit. Read more>>
Celina Voelker
Most of my life I played it safe. I went to college, finished my degree and obtained a doctorate to start practicing clinical pharmacy at the age of 23. After fourteen years of practicing in the medical field, my heart was being tugged into a different direction. For years, in my free time I would help design friends and family’s spaces, focusing on the story of their family and the heart of their home being reflected throughout the design. My husband was very in-tune with where my heart was being lead and he encouraged me to start a business where design, functionality and budget align. Read more>>
Shonmarra “miss By-polar”
I have come to realize that each day I am choosing to take a risk by relying on myself to provide for my family, manage HR and accounting for my business, and act as my own marketing team. I am currently taking a chance by living solely off my business, which means I may not always be able to give all my money to it. There are times when I have to risk my sleep and happiness in order to pursue my vision of creating passive income and generational wealth through my business. It requires a high level of focus and discipline to avoid taking risks that could result in losing everything. I often question the path I have chosen and the sacrifices I make daily in order to succeed. However, I am constantly reminded that my mission is greater than the risks I face each day. Read more>>
Pc Worldwide Ent
Starting our entertainment company was definitely a leap of faith. We knew it would be challenging, but we were ready to bring our ideas to life. One of the biggest lessons we’ve learned is that working with various businesses means adapting to different styles, needs, and expectations. Each collaboration teaches us something new about communication, trust, and compromise, which is essential in entertainment where everything is dynamic. Read more>>
Megan Cullen
My career was set in motion after taking a big risk. I had just finished studying photography at university, but was still working at my day job at Clinique doing over-the-top makeup for high schoolers for their prom, while also trying to make sales targets for something I wasn’t really interested in. During one shift I was standing in between my boss and the second in charge. Each was bitching about the other to me. This was not where I wanted to be. When my boss wrapped up her shift and went home, it just struck me – if I want to be a photographer, I just have to be one. So I wrote my boss a note saying, “thank you but I’m never coming back” (I was about 19 or 20 at the time – I wouldn’t do that now.). I handed it to the second in charge and walked out. Read more>>
William Sena
The biggest risk of my career is yet to come. In April, of 2025 I plan to leave my job and move to LA to pursue my music career. Just being honest, this scares the life out of me, and that’s exactly why I have to do it. Life’s biggest blessings come outside of comfort. I’ve always felt that I perform best under pressure, and I plan to do just that. From a kid that started playing piano in church, to the artist I have become. I am immensely proud of my accomplishments, big or small. I am very optimistic for what the future holds. If you’re seeing me for the first time, come join me on this journey, we’re just getting started and you won’t want to miss it. Read more>>
Kyle Kleege
My spouse and I own a film company called Dirty Sweater Productions LLC. We mainly focused on short films for the first few years while slowly transitioning towards feature films, music videos, and advertisements. We managed to gain enough experience in those initial years where we decided that the time was right to put money and effort into a feature film. Obviously, you can figure out how to make a film via the experience of filming shorts but nothing can really prepare you for attempting to figure out how to get the film released into the world. What goes into it? How does one get it in the hands of a distributor? Things like that. Read more>>
Daniel Kalban
All creative works are, from the start, a risk. The first big risk is actually taking a chance on yourself. I could have stuck with writing fan fic with friends, but that would not have gotten me towards where I want to be. If I didn’t (with some encouragement) start to write my own stories with my own characters, I would not have gotten anywhere. The second big risk is finding out your team. I’ve been fortunate to work with good people. Others haven’t. People are the ultimate random factor. Read more>>
Krissy Strode
If you had told me years ago that I’d one day be a full-time entrepreneur and a Visual Storyteller, I would’ve laughed. That wasn’t the plan at all! My journey started at Sinclair Community College, where I enrolled as an Architectural Engineering major. Since middle school, I dreamed of becoming an architect, but after a few semesters, I realized it wasn’t for me—too much designing on computers and not enough hands-on work. So, I switched to Electronics Engineering Technology (EET). Read more>>
Xinzhen April Yang
During the production of Broken Finger, I stepped into one of the most challenging projects of my career—a film that dared to explore the intricate themes of East Asian identity, societal expectations, and the emotional complexity of LGBTQ+ relationships. This wasn’t just a creative challenge; it was a logistical and emotional risk at every turn. The casting process itself was a formidable obstacle. Finding actors willing to take on roles that required deep psychological vulnerability and authentic representation of LGBTQ+ experiences proved almost impossible. My executive producer, only half-joking, warned, “You might need to act in it yourself.” Faced with rejections and setbacks, I was forced to rethink my approach, leaning on my ability to connect with people and inspire their trust in the story. This delicate balance of persistence and sensitivity was a risk in itself—one that could have jeopardized the authenticity of the entire project. Read more>>
Melissa Velasco
I spent many years “playing it safe,” scared to take risks. In time, I grew out of that person, thank goodness. Bottom line, I was bored with complacency. I got busy realizing a dream I’d had since I was sixteen- a series, set in Hollywood, about a bunch of misfits attending one of the most famous schools in the world, which I attended in real life. Dropping back into my high school past didn’t scare me because my books are purely fiction. What isn’t fiction is my deep understanding of each of my characters. I infused parts of myself in them, and not all the parts are pretty, polite, or accepted by the more couth of society. Each new little indiscretion inserted into the series seemed okay in the moment. “Eh. It’s just my irrational anger. It’s human, right?” Wrong. . . When the smoke cleared, and the first book of the Hollywood High Chronicles series, Intuition, was ready to publish, I was raw. Read more>>
Christine Parker
One of the biggest risks I have taken as a mompreneur was opening my brick and mortar fitness business in 2015. I had just turned 40 and had given birth to my 4th daughter a little over a year before. At this point I had been working in the fitness and wellness space for about 15 years. I started as a personal trainer and group fitness professional in Los Angeles where I would often train 40+ clients a week. In 2007 I returned to my hometown of Pittsburgh, gave birth to my 3rd daughter, Ashlynn, and started to rebuild my career as a fit pro. I was offered a job at a physical therapy facility operating their personal training and fitness programing while at the same time I Ibegan organically building a fitness community in my own zip code. Read more>>