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.
Janelle Davison
Six years ago, in my late thirties, I found myself juggling multiple roles – a spouse, a parent to two children, a co-founder of a nonprofit, and running my own optometry practice along with an eyeglasses boutique. However, the reality of running my private practice started to take a toll on my life. I was overwhelmed, fed up, and craving a change. Read more>>
Sabrina & Dave Sauve
When we first made the decision to pursue music professionally in 2021, we knew that it wouldn’t be easy. We come from a small town in Northern Ontario, Canada, where pursuing the arts professionally is not very common, so we knew that we would be taking a risk. There were many aspects of the music industry that were new to us, and we had to learn as we went. Releasing our music to the world was scary, but we knew that our relationship had to come first no matter what. As a husband and wife duo, we learned that we had to put in the effort to maintain a healthy relationship, or there would be no music happening. Looking back, taking the plunge was the best decision we ever made. It has brought us on some of the most beautiful adventures that still seem unreal to this day. We can’t wait to see what’s in store for us in the future. Read more>>
Kat Costolo
I’ll be honest with you. I’ve put this off. Even though most of me is excited to share details of what the last year and a half has given (and taken from) me, all of me lacks the ability to sit still most days. Maybe by writing this I will learn if that’s a tick in the pro or con column. Or, maybe we need to make a new column. Risks. Why do we take ’em? More specifically, why do I continue to take ’em? Read more>>
Kelly Michelle Thomas
From 2017-2020, I was working as a shift manager at an arts and crafts store. At first, I loved my job because I was surrounded by my love for creating art, but over the years, I began to loathe it as new management was taking over. It started to become a nightmare. While working I would paint in my free time in my home based studio, called MICHESHART, and sell my art. When the pandemic hit it was a life changing moment for me. I couldn’t work from home and my job was demanding more and more from me. I was living with my mother at the time who is disabled and was among the high risk. Read more>>
Bri Luginbill
This end of June, we had the opportunity to rent a business space on our downtown village called Dimondale, MI. We decided to go for it and it was such a good decision! At the time I’m writing this, it’s mid July and we have sound many packages and memberships and have people drop-in to yoga class. The community support and interest has been incredible and it feels like we opened our yoga and creative studio at the perfect time. Read more>>
Ashley Smith
I’ve always felt drawn to the arts, and spent a lot of my youth trying every medium I could–acting, singing, flamenco dancing, painting, charcoal, costume design–yet none of those ever seemed to quite fit. I also had a great love of animals, so when it came time to pick a college and major, I initially planned to go into animal behavior, since chasing the artist’s life when I didn’t even know what kind of art I wanted to do seemed foolish. So, for my freshman year, I worked in a behavioral monkey lab and started down a science track. By the end of that year, I’d discovered that I loved studying behavior, but that the actual experience of doing science wasn’t for me. Read more>>
Jordan Pol
When I started my career almost 15 years ago I knew I wanted to become the best hairstylist I could. After working in Boston my hometown I knew i wanted more. I decided that New York City was where I needed to be so I packed up my aunts car and moved to New York not knowing anyone. I was lucky that a hairstylist in my apartment building was friends with an owner of a one of new York’s tops salons and helped me get my foot in the door. Read more>>
Kalisha Wilson
The biggest risk I have taken for myself is starting my business with only 3 clients. I was in a place in my life where I was discouraged. Wondering why i wasn’t in a further place in life. After praying and asking God which way to go I was brought an opportunity to chase my dreams and start. I started with only one to two clients one week to no clients the next week. Here today I speak a year later and I have a full clientele. It has definitely not been easy but with the support from my partner, family, friends and clients none of this would be possible. I will say I am still not where I want to be business wise and I still have a lot to learn but I am so proud of myself for taking the risk to get out there. Read more>>
Emily Kurth
After 9 years of running my art business out of my home with mostly an online presence, I opened an in person studio/shop in May. The opportunity came out of nowhere when a local interior designer reached out and asked if I’d like to sell my art in her new boutique. That was a no brainer, but that led to another opportunity…opening my own studio in her building. I had spent 9 years telling myself that I couldn’t afford an in person studio and let’s be honest, it’s a lot easier to hide out at home and to not really put yourself out there. I said to my husband, “I don’t know, it’s a big risk.” to which he replied, “Sometimes you have to take risks in life, Emily.” That was just the encouragement/challenge I needed to hear. My studio opened on May 5, 2023 in a building full of other creative women entrepreneurs. Read more>>
Jaia Robinson
Taking risk can improve your life tremendously, especially as a creative person. Throughout my career I’ve noticed when I try a new process or technique majority of the time I’m happy with the results. Growth is tied up in risk taking, I’m always searching for new ways to be uncomfortable, to challenge myself. During covid, I began cycling and had the bright idea to custom design my bike. I was new to cycling and had never designed/custom painted a bike let alone my own. Once I completed the project It lead me to several custom art opportunities. Read more>>
Derrick Ortiz / Orlando Selllers
HOK : Taking a Risk was a big part of HOK&DJS merging together as one brand . We were by o Te h pushing our own brands and styles in the fashion industry , but we knew coming together would be something different. Merging our brands took alot of work to get our audience to see who we are separately but most importantly who we are together . Read more>>
Grace Brunette Stadler
Looking back I feel a bit like my entire journey from making my first piece of jewelry to creating a wholesale business to opening up a crystal shop, has been a series of risks. I would like to tell you where those risks started. I had been making crystal jewelry for a few months and had started selling my pieces at a few shows and farmers markets – whenever I had time off from my restaurant job. One day my bosses called me in for a meeting and I found out they were downsizing. This left me with the option of staying at the store in a part time position or choosing something else. Without a moments pause, I said, to their and my surprise, “I think I would like to leave then”. And with this, a combination of risk and the universes’ push; I jumped full time into my business. Read more>>
Sam Brooks
I truly believe anyone willing to pursue the arts is ultimately taking a risk. Artistic expression is beautiful, personal, and takes vulnerability to put ones self out there. That in itself can be a risk for most. Auditioning is my job as an actor. Taking risks that further distinguish the uniquenesses and authenticity in my work are the risks I enjoy taking. Read more>>
Krish Gutierrez
One of the biggest risks I’ve taken was quitting my job (literally packing my things and storming out) without a plan b. I was working for a terrible boss who didn’t pay us properly. It was going on 3 weeks without a paycheck. Mind you we were supposed to get paid weekly. It was a blessing in disguise because the same day I left, I went for a walk in my neighborhood and saw a “FOR RENT” sign on one of the local business store fronts. I called the phone number on the sign and the rest is history. My salon has been open for over 10 years now. Fully staffed with amazing team members and clients. Read more>>
Heaven Beam
I would say I’ve always been a “risk taker” when it comes to reaching my goals but one of the most recent risks, I’ve taken would definitely have to be starting Heaven Beam Beauty in 2021. This was after having gone through a traumatic experience that led me to develop a severe case of imposter syndrome throughout the pandemic. For me it was very difficult because it required me to once again be vulnerable and put myself “out there” after trying to protect myself by hiding in the shadows for so long. Read more>>
Bone One
Without risks, you will never know how far you can go, who you can become and what you can achieve. Sometimes the risk looks scary and in that moment, it means you gotta jump and go for it. You can’t be afraid to fail. It might just work out better than you imagined. Read more>>
Joseph Micacchione
The biggest risk I have taken thus far in life is/was definitely the decision to take my recent hobby turned passion full-time. During the pandemic I, like most of the world, was confined to my apartment for a long period of time. This forced me to focus my time and attention inwards. At the time I was working my corporate job in finance and prior to the pandemic I hadn’t realized just how unhappy I was with this career path. All that forced time alone quickly caught up to me…. I quickly slipped into a dark place mentally… I felt trapped… trapped in my job, trapped in my apartment… and with no outlet or positive thing to focus all this energy. Read more>>
Tenni King
Moving to Dallas was a risk for me back in the spring of 2015, I had been previously living in Los Angeles building a career in fashion PR, which I thought at the time was my dream job. But after having my first taste as an assistant at a PR firm, I quickly learned that that career path and I did not mix well. It was not the right fit for me at all. I ended up quitting my job and moving to Dallas to be closer to family. Once I arrived in Texas, I had no clue what I was going to do. PR jobs are few far and between in Texas, especially within the fashion realm. Read more>>
Hazel Owens
The biggest risk I have ever taken was taking a leap of faith to pursue ministry full time. What I discerned as full time ministry (at the time) was counseling as a marriage and family therapist and Bible teaching. I had a deep desire and passion to not only empower women but to help in restoring relationships. I wanted to be able to journey alongside people in becoming the best versions of themselves, for themselves first then for their families and communities. Read more>>
Chikeeh Talker
I always knew I would end up owning a business. My life has geared me towards being a leader and a boss of my own successes. When I decided to take the plunge and start off on my own after being very dependent on a 9 to 5 job, it was nerve wracking to say the least! I had blind faith in the beginning let’s say! Haha I quit…. took the plunge….created my brand and never looked back. Sometimes risks are scary, but it’s the scary things that really feel like you’re living. Read more>>
Michael O’Donnell
My wife and I took a huge risk starting our business. I was working for corporate America and had a good job but, didn’t love what I did. I was dog training part time on the side and absolutely loved it. I went to my Wife in our 1st year of marriage and while she was 6 months pregnant and asked how she would feel about me quitting my job and opening our own dog training company. She was extremely supportive and told me to do what I was passionate about and she would support me along the way. We then decided to take out my 401k, get a small loan, and open Sit Means Sit Dog Training Apex. Since opening in March of 2016 we have grown from 1 single employee to 11 full time trainers in apex and have open a second location in Charlotte North Carolina where we have another 10 full time trainers and continue to grow. Read more>>
Joan DiGiovanna
At 57 years old I decided after much research and deliberation to become a realtor. I had gone through a series of events that had left me financially strapped. A friend who believed so strongly in the idea of my being a realtor paid for my schooling. I was working 7 days a week and going to school at night 5 nights a week. It took everything I had to learn a completely new career. My entire life was spent in the hospitality industry with the highlight being a restaurant I owned called Pasquale’s. Now I was learning about square feet, mold, listing agreements, purchase agreements, math in ways I had never applied it before, it was overwhelming but I passed and got my license! Read more>>
Maya Harris
The year was 2021. It was a late August warm day in LA and I decided to dance outside of the monotony and take myself on a date. Why? Because we were still living in the obscurity of; long grocery lines, hand sanitizer more valuable than water, and a collective energy of exhaustion and precariousness that filled the air like a lingering aroma you just can’t put your finger on. At the time, I had been laid off and living off of my dwindling savings, so the date had limits. I took myself to Huntington Gardens in Pasadena. A friend of mine had briefly mentioned rose gardens and grassy patches of shade for a low cost and I thought that sounded exactly like what the therapist… and the financial consultant had ordered. Read more>>
Zineb Baaout
4 years ago I flew away from my country to the United States to study a masters without knowing anyone in that country and taking a loan that I didn’t know if I’d be able to pay back or not. This was my first time ever on an airplane and my first time living on my own. I had to take this risk in order to grow as a person and find what else is out there to have a choice and an ability to compare between the pros and cons of my home country and this new country I went into. I gotta say, that was the best decision I made because I learned to appreciate many things I was taking for granted such as family and community. I was able to meet the love of my life in this new country and also found a great job that helped save money to enjoy life a little more. Read more>>
Sandra Camacho
In 2018, I said goodbye to a stable job at Google to pursue my passion for designing for social impact. After nearly 5 years of several experiments to “redesign” my career at Google around human-centered design and ultimately burning out, I had reached a dead end. Over the span of a nearly a decade, I witnessed the company veer away from its startup essence and toward the inevitable realities of a big company: process, structure and standardization. I had depleted my energy for an unsatisfactory payoff: feeling undervalued and underutilized across my full skill set because of my inability to “fit” into a rigid job description. Read more>>
Giovanni Lodigiani
Back in 2008, I decided to move to California. Music composition and filmmaking was my field. But during that time I had to move on my own while continuing to provide for my family in Italy. It was a considerable risk to invest everything in this adventure also because it was the year of the economic crisis. But I saw no alternative. I am grateful that I took that perhaps somewhat risky step because today I would very much regret not having done it. I was a music conservatory graduate and had a concert career in europe. The film & TV production was what I felt the most. At the beginning of the American adventure I was also used by pimps who took advantage of me but mostly I always managed to get to know and work with people of great value. Which allowed me to learn a lot, build an international catalog used all over the world and especially in the most important US television channels. I think the best weapon is always persistence. Read more>>
Joe Jaeger
Taking a risk is everything in business. When the fear of failure has you up all night I think that’s when you know you’re making the right decision. And in the end if it’s not the right move you get something more valuable then a return on investment – a lesson! It was last year actually that I took one of the biggest risks of my life. I closed on a commercial property next door to one that I purchased two years prior. It was double the size, double the price, and double the risk. I had no idea what it needed – but I knew we needed it in order to expand our business. Read more>>
Piper Byers
Recently, I’ve decided to make the transition back to creating country music and it’s honestly one of the biggest risks I’ve taken creatively so far. I grew up performing as a country artist in DFW and sang at rodeos, dive bars, two-step venues, you name it. And I loved it so much and loved the country community. But as I got older, my tastes changed a little and I also realized that country music was not the ‘safe space’ for everyone the way it was for me. I realized it had become alienating and not welcoming to lots of groups of people, including some groups that my closest friends and loved-ones were in. Read more>>
Lana Arana
The biggest risk I’ve ever taken is deciding to start my business completely on my own. I was 24 and was faced with the decision to either keep working in a toxic environment or leave and open my own place. I decided to rent out a tiny salon suite and put my entire life savings into starting it up. I opted for the most basic equipment and furniture to start because I was so broke. I also had 0 clientele. I was terrified but I knew I didn’t want to spend my life working under someone else. Now, almost 2 years later, I can say that risk has completely paid off. I’m in my own storefront building, have 2 employees, and see 40-50 clients a week. Read more>>
Wayne D Burdette Jr.
The biggest risk in my opinion that I have ever taken without doing one ounce of research was back in 1998/1999 when I decided against everyone’s wishes to attempt to purchase a NASCAR Race team from Cale Yarborough. It was one of the biggest life changes that not only affected me but those around me especially in my immediate family. The quick story is I saw it posted in the local newspaper as we were in the same area in South Carolina and by the afternoon was sitting in front of him making a deal. Read more>>
Adri Maria
I took a risk by leaving my steady 9-5 job to build my own company. It was a leap of faith, driven by my desire for freedom and the pursuit of my passions. Financial challenges arose, and I had to take on contract jobs to make ends meet. Despite doubts and setbacks, I continue to persevere, gaining clients and growing my business. I may not be where I know I can be yet, but I am enjoying the process of building and learning in the meantime. Read more>>
Meghan Holton
Last September, I quit my well-to-do corporate job in digital marketing to pursue writing and producing music full time. I realized that spending my days in banal meetings, running advertising campaigns for these conglomerates to increase their quarterly profits. That’s not how I wanted to live. I’d rather have less money and spend my time working on meaningful projects that I will forever hold dear. Read more>>
Michael Rundberg
I think everything in life has risk. We risk by doing and not doing, so why not try? If you are someone who is passionate about something, who has an idea and does the work, what is stopping you? The only risk is putting yourself and your work out there. The bigger risk could be not acting and missing out. Don’t think of it at first as a business. It’s not a win/loss situation. It’s an opportunity to do what you love and love what you do while hopefully offering something new to the world it maybe wants or needs. Then worry about the business. Be rational, realistic, practical and most importantly, patient. But always try to move forward. Read more>>
Collin Pape
When I first graduated from high school in 2007, I took the path commonly traveled on—school, sports, find a job. I played college football in AZ for 2 years at Glendale community college. In 2009, I moved to Denver where I had originally planned to finish my last two years of college football at a D2 school. However, plans changed, and I decided to go to the Metropolitan State University part time while I worked as a chef for 2 years. During that time, I joined the Glendale Raptors which was a rugby team. After two years I moved to Bolivar Missouri where I finished playing my last two years of college football before moving back to my home state of Arizona earning my bachelor’s degree in Sports Management at Grand Canyon University. Read more>>
Kyle Pemberton
I became a Barber back in 2017 and graduated from Boise Barber College with no real plans other than to learn the craft and making an income. Barbering was something I pursued after a long career in the culinary industry that started at a young age. Growing up with a single Father, food was always on the table and a roof was a put over our head. But, times got tough in the 2008 economic collapse and it was time for me to step up and help out financially as well. Read more>>
Heewon Jeong
The biggest risk I have ever taken goes back to my high school years. Full of youthful enthusiasm and eagerness, I decided to take on a journey into the world of animation, a passion that continues to drive me today. However, I was unaware of the realities of the practical world and had no idea of the challenges that awaited me. My decision to attend an American college and make a name for myself in the animation field must be a shock to my mother, who took the responsibility of caring for my sister and me. Read more>>
Crystal Winfrey-Ellington
I would like to say its a blend of taking a risk and having faith! After getting myself established in the health and fitness industry of what it really is like after graduating college and then going and applying in the real world, I found out that in order to find my potential, I would have to step out in faith and take some risks. My first risk and step in faith occured after an unexpected circumstance involving a unique fitness facility I worked for, shut down. I was dealt with the decision if I should look for another gym to work in or what y next move would be. Read more>>
Erin ONeill Armendarez
In 2019, I was a tenured Associate Professor of English on a small branch campus of a large university. I had worked hard to build that career but was bored and frankly somewhat disillusioned by so much of what the job entailed. I loved my students, my subject, and I was proud that I served on the board of a national organization and participated in things like writing white papers that solidified best practices in the profession. I had written some chapters for some books. I was passionate about my teaching. Still, I began to feel stagnant, as if my choices were about safety, not growth. I had gotten married in 2012 to a man who lived in a different town. Read more>>