The chapters in our stories are often marked by wins and losses. Getting a new job, getting fired. Getting a life-threatening medical diagnosis, beating it and getting a clean bill of health. Too often, due to a societal expectation of modesty and humility we are discouraged from talking about the risks we’ve taken that led to those ups and downs – because often those risks draw attention to how we are responsible for the outcomes – positive or negative. But those risks matter. Those stories matter. We asked some brilliant entrepreneurs, artists, creatives, and leaders to tell us those stories – the stories of the risks they’ve taken, and we’ve shared them with you below.
Todd and Emily Olander

Opening a craft malthouse was by far the biggest risk we’ve ever taken. Malt, aside from water, is the biggest ingredient in making beer. It is made by taking a cereal grain, usually barley, soaking it until it germinates, then drying the germinated seed. This process produces chemical reactions in the grain that make sugars more accessible and turn it into a product suitable for brewing beer. Todd, a 5th-generation Colorado farmer, has been growing small grains, including lots of barley, for his whole life. His family has been growing it for decades. Read more>>
Taryn Becchina

The biggest risk I’ve taken was starting my business! I’m sure that’s the answer you were expecting but let me explain. I’ve always had a passion for photography but never thought it would or could take me anywhere. I was also passionate about exercise science, or so I thought. I graduated from ASU with a degree in exercise science and became a health coordinator for special needs adults & kids. While that job was extremely rewarding, my heart was pulling me in a direction I wouldn’t have ever expected, photography. Read more>>
Sherelle Reed

In June of 2021 I decided to retire from Corporate America as a Corporate Instructor to become a full-time entrepreneur! I have always had a love for motivating others to become their best. As a young girl I was the neighborhood peace maker. I would mediate disagreements between my friends and encourage to consider different perspectives to things. As I grew older, I took the same interest into my family structure. I began my career in Corporate America specializing in Customer Service as an instructor. I was responsible for training new hire associates who were beginning their careers in the call center. Read more>>
Crysy Allyson

Taking a risk. We often shy away from doing so due to fear, right? I’d been a full-time employee as well as part time entrepreneur for years. Did I want to work solely for myself? Absolutely. Did I know what was in store for the future if I took that risk? Absolutely, not! So, I continued to work as a full-time employee where things were stable, and I was comfortable. At work, I was stressed, overwhelmed and unhappy. I struggled with fear of stepping out on faith or staying in my comfort zone for years. At one point, I began therapy due to work related issues. I shared this personal information with my supervisor who I thought I could trust, In turn, she gossiped about me with my coworkers! I was so upset! Not that me going to therapy was out (therapy is essential!), BUT because I shared my personal information with this person, and they talked about me like what I was experiencing was a joke! Read more>>
Baily Roberts

Starting Vision Magazine was such a daunting risk in the beginning. I had worked as a curve model for over 3 years at that point, and I had witnessed (and myself experienced) discrimination in the industry. Discrimination from our differences in all of us artists that I thought made our industries beautiful. I wanted to create a platform that instead embraced and celebrated these differences and backgrounds for all talent in the fashion and arts industries. I had never started a business before, ran a production team, or been the creator of any kind of larger-scale community. I just felt so strongly called to begin the journey. I was terrified, but my instincts pushed me to embrace the uncertainty. Read more>>
Lou Marsella & Mario Piteo

Both Mario and I were in our 20’s working in a salon that was going out of business. We didn’t know what we were going to do. So we came up with an idea of opening up our own business. This way everyone in the salon would have a place to go. We search high and low in our area and could not find a space that would accommodate us. Either there was a salon already or they did not want a hair salon. We finally stumbled upon an office building that was in foreclosure. The Bank just wanted to fill it up with anyone they could get, so we went with that. Everyone told us well the space is on the second floor we shouldn’t do it. Read more>>
Aubrey Smith

All of my life I have wanted to be in the Entertainment Industry. I got my real start after I started my podcast “The Shake Up”. Someone at the local radio station heard it and asked me to come in for a live, on air interview. From there, I became a part-time Radio Personality. After a year, I took the riskiest leap of faith ever and quit my day job. I took a major pay cut from being a hospital administrator to live my dream as a full-time Radio Personality. So many doors have opened for me to be a successful business owner (Aubrey Shine Cosmetics), event host/promotor (Aubrey Shine, LLC) and singer/songwriter. I have become a published journalist and a blogger over the last couple of years, which is one of my childhood dreams. Read more>>
Mike Wird

Building my own business and brand to serve humanity by protecting, inspiring and pushing humanity’s evolution forward: As a youngster I always had this subtle feeling like I was meant to do something really big and important for the world…Like there was something more out there than what I was being taught and it needed to be brought into the awareness of many others worldwide. I didn’t know how I was going to do this or what it would look like at that time. Call it faith, call it a calling from a higher power, whatever it was, it seemed like an impossible task and as I matured through life, I just knew it was going to happen and had to be done! Read more>>
Float Like a Buffalo

It seems like we take risks every day when it comes to pursuing this dream of making a living off of music. The biggest risk we’ve taken over the past few years is to take the leap from playing exclusively in Colorado to touring nationally much of the year. We were supposed to start touring nationally in Spring of 2020. We had a beautiful, 5-week tour planned that covered much of the midwest and southern United States. We got two stops into that tour before everything fell apart due to Covid. We didn’t even make it out of Colorado before our shows started cancelling and we had to make the very difficult, but right, decision to return home to keep everyone safe. This was a bad day. We were heartbroken… but it was also a blessing in disguise. Read more>>
Liliana Barrera

Before becoming a professional dancer, I used to work full time for a company that gave me financial stability and great benefits, as well as the opportunity to travel the world. When I first thought about quitting my job to become a professional dancer and Pilates instructor, it was kind of an insane thought: who in the world would leave a secure job with good salary and benefits plus the opportunity to travel for work? I shared that thought with some of my friends and they told me I was crazy; they all suggested to keep dancing as a hubby and maybe teaching some Pilates classes to make some extra money. I was so in love with belly dancing that I decided to proceed my professional career was a bellydancer, Read more>>
JJ Moreno

For most of my life, I had been in the rock scene, making music that had nothing much to do with my traditional Mexican culture. I never saw myself playing Latin music, let alone Cumbia style. And, after many years of being in the Dallas area rock scene, I felt the need to do something different from what was being done at the time. I had travelled to a couple of cities in other states and noticed it was just not Dallas, but other cities as well that played the same songs from 20 years ago. I didn’t feel like I wanted to do that anymore, so I took a risk and started a Cumbia band. That alone is not the risk, many bands play cumbia, but the risk was to do my own music, not covers, which I enjoyed, but got tired of playing week after week. Read more>>
Vinnie + Jess Mai

We both currently operate Tipsy Oak full-time, but this wasn’t always the case. We worked full-time jobs in retail while managing and expanding Tipsy Oak on the side for years. This led to long nights and using up any extra time we had towards the business. We had dreams of making it our main source of income, but feared giving up the stability of our full-time employment. In March 2020, the Pandemic happened and we were both furloughed. Despite the unfortunate circumstances, we used this time to focus on our business at a full-time level. While people were spending more time at home, we gained more traffic to our Etsy shop and began to see an influx in sales. Read more>>
Cheri Anderson

There are always opportunities surrounding you. The question that haunts us all is if we’ll take the risk and try something different or new. Are we smart enough? Strong enough? Carry enough determination? All these questions flash through our brains before taking the leap. Well, at least for me they did when considering launching my own photography business. Although I’ve had formal education in photography, I was the mom of three young children and had spent the last several years taking care of them; being their personal assistants, chef, and chauffeur. It was after one of their sporting events that a dad suggested that I get back into photography professionally. Read more>>
Sara Ahmad

2021 was a very challenging year. It was the year that was forced to realize many things and take a big risk that I didn’t know I was ready for. At the start of 2021, I was working for a corporate marketing agency. In February, I decided to move to a different team within the same company. In this new team, I would be managing higher-budget paid social ad campaigns on a variety of platforms. I was ready and hungry to learn and grow. I didn’t realize was how quickly things would escalate. Read more>>
Nathan Hallford

I had never planned to open my own BJJ Academy but I knew I enjoyed teaching. I had been helping with and covering classes for several years when the opportunity to teach twice a week at another martial arts school presented itself. It was the “easy” way to dip my toe in the pool of running a school without actually having to take the plunge. After a few months of this I had another opportunity come up where I could open my own school but I had big reservations. Would I have enough money to cover rent and expenses? Would I be able to re-coup my investment in mats and deposits? How would I attract new clients as the majority of people I knew in the industry ALREADY had a school they trained at. Read more>>
Kai Collins

I once moved to Chicago and auditioned for Second City on a whim. I didn’t know anyone there and aside from layovers at O’Hare, I’d never actually been to the Windy City. I’d literally taken one improv class in my life and had recently gone through a bad breakup. I was in the middle of transferring all of my worldly possessions into a storage unit, preparing to move back in with my parents at the age of 26, when I ran into a good friend from college. After I filled him in he asked what I was going to do. Without thinking I said, “I’m moving to Chicago.” And when he asked why, again without pause I said, “I’m going to do improv at Second City.” Read more>>
Aline J. Milfort

I took the most significant risk on February 19, 2021, at 8:05 a.m. I will say it was more of a “forced” risk than optional; however, I will forever be grateful it happened. This decision led me to move from the only place I ever knew, Florida, to Texas, where I would learn more about myself beyond just professionally but personally. National match day occurs in February every year in the psychology world. This is the day every psychology doctoral student around the nation learns of if and where they are matched via email to complete the last phase of their academic career before graduation. Months of filling applications, asking for letters of recommendation, and experiencing various emotions lead to this moment. So on February 19, 2021, I remember running through the house screaming, “I matched! Read more>>
Nikko Smith

Taking a risk is literally my whole career. Entrepreneurship has tons of ups and downs, so it’s a major risk to wake up and choose myself everyday. I haven’t always been an entrepreneur and honestly, I became one before I was fully prepared. Back when the pandemic first started I was working a full time job. It became a remote position and then eventually I wasn’t working at all. I was worried about what my next move would be. How would I make money? Instead of me applying for other jobs, I poured into myself and my own brand. During those months of not working, I truly invested in myself. I honed my craft, I bought my LLC, I did test shoots to build my portfolio, etc. Read more>>
Adam Olsen

During the beginning stages of the pandemic in 2020, business owners had two options; adapt to what the changing laws and regulations for what would be an unidentified period of time or slow down/close their business with the hope it would all blow over. The Real Estate market was very unpredictable at that time, and with how my team operated, very social media marketing driven, we were met with two options. The less risky route, cut back significantly on all marketing expenses, work with our current deals and hope the market returns to normal. Read more>>
Kendall James

In October of 2021 I took the big leap out of the 9-5 to pursue my creative endeavors. It’s been one of the most freeing, yet terrifying things I’ve ever done with a wife and a 5 year old to support. Aside from fronting Neon the Bishop, I started a video production company called Reel Flamingo. Now, my main source of income is performing music both solo and with the band, as well as video production. It’s a dream for sure, but definitely a grind. So far, the risk has brought some pretty incredible rewards. Just three months after stepping out Neon the Bishop won Channel 93.3’s Hometown for the Holidays, bringing some pretty great opportunities in 2022. The video production company has snagged some cool contracts as well. We haven’t landed completely stable financially yet, but definitely heading that direction. Read more>>
Nkosi Gomez

I closely associate the word risk with another word; gift. I see them having a reciprocal relationship. Recently, I’ve reached a milestone in life. The last time I aligned with the Voyage team I was a working artist earning a full-time living through creative expression. A new variable has emerged in my life since then. His name is Sol Ashai Gomez, my son. Now, the reason to live and create is even more dense than before. This path is perhaps my biggest risk at 27. It has been clear for as long as I’ve called myself an artist that I would soon start my journey to parenthood. There has been lingering fear associated with providing for a family however, I’ve understood it as the mind being unsettled as to what the future holds, giving me more of a reason to stay present & confident in not knowing. Read more>>
Maggie Mae

In 2014 I decided to relocate to Eureka Springs AR from Denver CO. I was ready for a change in lifestyle. Going from a city of 700K to one of 2K was a huge change and allowed me to open Blossom Beauty. I’ve always loved styling hair and doing makeup and a traditional cut and color salon just wasn’t for me. When I opened Blossom Beauty I figured the wedding hair and makeup market would be over saturated since Eureka Springs is the “wedding capital of the south”. But I quickly found my niche in proving luxury, on-location wedding hair and makeup services. I’ve loved every minute of it (even the difficult parts). Since adding my first assisting beauty artist in 2016 the team of artists has grown to seven and we are able to serve over 100 brides per year. Read more>>
Hillary Bell

The biggest risk I have taken is making the decision not to be average. The reason many people stay stuck is because they refuse to admit they don’t want to be average. I have learned that whether you want to fit in with the crowd or venture out to fulfill your own purpose and potential, you use energy. Why do you choose to use your energy to remain average when you can shift it into something greater and bigger? When are you going to stop letting fear block you from the greater life you deserve? Overcoming fear is taking a big risk but are you not risking your success when you decide to not overcome it? I was asked in a conference, “What would you gain if you just said yes.” Well, while taking this risk to overcome fears of not being average I have let go of shame, embarrassment, Read more>>
Miranda Torres

I was born and raised protected and loved unconditionally. For that, I am ever-grateful-but now in my 27th year, I feel the true heaviness of the blanket I still bare to this day.. As an artist, I long for more-for it all. I watch others from a screen or from a near and far distance and I ponder: “Is that the life for me, as well? What will I become? What have I already become? Am I complete?” I have these constant inner conflicts as a pansexual woman and a modern artist in 2022. Read more>>
Jene Kapela

Honestly, the idea of being self-employed was terrifying to me at first. I never planned on being a business owner. While I have many friends who intentionally set out to start their own businesses, I did not see myself as an entrepreneur. In fact, it took other people asking me to do work for them and insisting on paying me for it before I even considered the possibility of working as an independent contractor – and I only planned on doing that part-time. Read more>>
Nasa Lamode

I come from a small city, Milwaukee. I was raised in a small neighborhood, in a small home. Even though I would skate out to Chicago often, which was only an hour and a half away, I never actually realized exactly HOW humble my roots was. I mean HUMBLE. We had curtains and bedsheets for doors. All my uncles was gang members and drug dealers. Some of the women in my family and hood was sex workers and this is the life I knew. I didn’t know anything else. I was always different though. I was a nerd. I was always into nerdy stuff. I always had a passion for music too and kept my focus on that. Read more>>
D. Will

Takings risk comes in hand with everyday living. I often find myself in a position to where I have to take a chance. No matter if it’s working a job, relationships, or just creating music in general. The direction of opportunity is what I rely on when it comes to taking chances. Therefore, the biggest risk I took was transferring what I went through with and outside of football to creating music and pushing it. I never knew the amount of friends and family that would gravitate by doing so, due to me having success with football. Hearing any type of feedback whether it’s constructive, positive or negative criticism motivates me to never give up. Creating is an outlet for me to speak on what I don’t speak about with others. Read more>>
Elizabeth Cruz

Right after I started my own practice I came to my wife and business partner, Tina Nunziato and expressed my concern about how I was running all kinds of tests on patients and wasn’t finding the cause of their issues. I was putting them on tons of medicines only for them to continue to get sicker not healthier and I was seeing younger and younger patients in my office with digestive issues that I was used to seeing in older people. I wanted answers and was tired of telling patients I couldn’t figure out what was wrong with them. She and I took a risk and went on a two-year journey to learn about things my medical degree didn’t teach me. We’ve turned that learning into a podcast, online home study program, 3 books, and a line of private label supplements that are helping patients get better and get off of prescription and over the counter medicines. Read more>>
Kim Muench

I was certified as a parent coach through the Jai Institute for Parenting in 2016. Shortly thereafter, my husband left corporate to pursue his passion for adventure and helping others by opening a travel franchise. This required me to find a job that included health benefits for our family. I was fortunate to be hired to a job I loved, while it didn’t involve coaching parents, it did offer me a way to use my skills and learn and grow as a human being. Read more>>
Tarnesha Miller

There is a quote by Charlie T. Jones ” Unless you try to do something beyond what you have already mastered, you will never grow.” One story I enjoy sharing is that when I decided, on a whim, to enter into a pageant at the last minute; with no experience. One of my previous jobs had instilled in me the importance of self-development. Always be a student in life, continue to learn and grow. If you are in a room where you know everything, you are in the wrong room. Read more>>
Marnina Reid

I originally had a small massage therapy and somatic therapy practice. One that was building slower than I would have liked. I still needed to have a side job to survive financially. I was subleasing a space in a suite with two other more seasoned practitioners and colleagues that had well established businesses that were thriving. One day in the summer of 2018, Charlene Handel (Owner of Skin Fitness Etc). said to me that she wanted to retire and thought I should buy and take over her business. “Huh?” I thought. “I’m not an esthetician.” I was a longtime client and colleague of Charlene’s. She gave the most marvelous facials and had the best organic, edible products on the market today. Read more>>
Cadynse Love

In 2010 I hired a band for a fashion show fundraiser I was hosting in St. Helen’s OR. After hearing this band I was impressed & wondered more about their journey & why they seemed stuck. I’d never dealt with the music industry in any professional level but business I have always been good at. They asked if I could help them, I agreed walking into it blindly. This small risk taught me so many lessons about bands, rehersals, recording studios, bookings, etc. I loved every second and was honored to be able to watch them blossom. As time went on we mutually decided to part ways but my internal music bug was bitten. I’ve loved music since the 3rd grade! Read more>>
Robin Baker

In the early 2000’s my life circumstances changed, and I went from living in a huge Victorian home to a small apartment. I went from having a huge studio space to a tiny corner in my bedroom and when I talked to people or showed pictures of my art, they would say, “Where can I view it in person?” And my answer would be, “Um…in my bedroom.” It wasn’t an answer that was conducive for generating patrons, sales were sparse, and I struggled financially. Then in late 2015 I heard from a friend that a studio space in Hardy & Nance was available. It was one of the smallest studios in the building and while the rent was certainly reasonable, I knew it was still out of my range, but I took a leap of faith and rented it. Read more>>
Art Friedrich

Running Farmers Markets, and aggregating produce from many farms to sell at those markets, is taking a big risk every week. We spend thousands of dollars each week on perishable products that are only good for sale for a few days, and then have to hope that the weather cooperates, the people come out, that theres no major disruptions that are going to keep us from connecting. We also have to have a solid gauge on just how much we can move each week, because produce margins are very slim and we’re always trying to get the customers a good deal while paying farmers their fair due for their very hard work and all of their risk. Read more>>

