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.

Kristin Murphy

Over the summer, I took a risk and left my job as a school mental health specialist, without a defined plan. I was commuting an hour each way and feeling completely burnt out with ongoing crisis situations at work. By the time I got home to my family each day, I felt exhausted and overwhelmed. I knew deep down inside something needed to change, but I wasn’t sure what I could do. My kids were 1 and 4 at that time, and I felt like I was missing so much of their lives. Childcare challenges and illnesses were frequent reasons I would have to call out or rotate with my husband. Read more>>

Tevin Johnson

For me I feel like being a music artist and personal trainer in spaces that are so heavily saturated is a risk in itself! Nowadays you have even more pressure on yourself to be creative & different but also authentic to who you are! The hard part is that sometimes you don’t know who you are! Ive been a music artist now about 7 years and my growth from when I started till now is night and day but I still have room to get better! I’m my design team, my management team, my road manager , my social media manager, honestly everything except for videographer and engineer! Read more>>

Amanda Young

My entrepreneurial journey feels like it’s been a series of one risky move after another. Being an entrepreneur is definitely not for the risk adverse. Probably one of the most uncomfortable risks I took was letting go of the business I had built as a nutrition and health coach in order to focus on working with women and the Goddess. I leapt from doing something that was identifiable and understandable to the main stream, into an area that was not clearly defined and could sound a bit woo woo to most. Read more>>

Rollo Papers

I abandoned a half-ride (50%) scholarship to attend law school in San Diego for an unpaid internship at a recording studio in Pittsburgh. It was the best decision of my life. A lot of people don’t know this, but I was accepted to law school at California Western in downtown San Diego. I would’ve been a member of the class of 2020. I was obsessed with the show Entourage and wanted to be the Ari Gold of the music industry instead of the movie business. The truth, though, is that the character I really wanted to be was Vinny Chase. Read more>>

Julie Merica

My life has been completely dependent on my ability to get face deep into my fears and take major risks in my life. It started with a major move after establishing a teaching career in Florida to Chicago without a job (or nearly enough savings) that led to me taking improv classes to get over my debilitating stage fright so I could ideally, try my hand in stand up comedy. Now I have a successful podcast, a dream job I didn’t know was as an option 9 years ago but paid my bills within 1 and a half of recording in my closet. Read more>>

Chris Johnson

Risk tolerance is a huge part of starting a business. They call it “taking the plunge” for a reason. I was fortunate to have a very steady job and clear career path in my first career in the technology space, but I lacked some of the passion for the space. Going from having a 401k, stable income and a clear future to essentially starting from scratch was certainly a mixture of excitement and fear. I had two young kids and COVID was at it’s height when I put in my notice at my old job. Read more>>

Alka Subramanian

We took a huge risk in early 2000’s when my husband and I quit our jobs and started working in healthcare provision for children living with HIV in Sub-Saharan Africa. In the early 2000’s, the AIDS pandemic was at its peak and thousands of adults and children were dying of AIDS related causes. The current pandemic is huge, but the AIDS pandemic was bigger. AIDS has claimed 40 million lives compared to COVID which has claimed around 7 million lives. Drugs to treat AIDS or ARV’s were very expensive and unaffordable for most people in Sub-Saharan Africa. Read more>>

Laura Yelin

As someone who doesn’t fear risks and actually gets excited about them, taking chances in life feels like a thrilling adventure that adds excitement and purpose to my life. The rush of adrenaline that comes with stepping into the unknown and challenging myself to do something that others may consider too risky or daunting is what I thrive on. I am motivated by the potential rewards that come with taking risks, whether it be financial gain, personal growth, or the satisfaction of accomplishing something that I thought was impossible. Read more>>

Adrienne Wise, LPC, CCTP

The story that first comes to mind is how I had to put my life on hold after starting my business in December of 2018, to care for my mother who had a major stroke on March 31, 2019. I was still working a full-time job at a senior manager level and was only 4 years into my marriage. Not to mention being a parent to a child who was proving to be a rising athlete. This made it a challenge balancing attending events for my son, going on date night with my husband, and waking up at 5am and ending my day around 9:30pm to give my mother the extra care she needed. Read more>>

Da’Ron Collins

In 2012 I made the biggest decision and took the biggest risk of my life! I moved away from my entire family and relocated to Los Angeles. I’d received a calling in which I knew that if I wanted to reach another level I’d have to put myself in position to become more than who I was. When I first arrived to LA I was back and forth to the county food stamp line, having to share a car, and use public transportation when I had to. I was dependent upon financial aid from the local community college I attended and eventually graduated from. Read more>>

Donna Menne

The biggest risk I took was quitting my job in Minneapolis in the Medical Profession to move to California. I resigned from my job with the idea that I wanted to help more people in a different way. Covid hit and there was so much uncertainty in the world. I started life coaching people online during Covid and seeking jewelry. Once businesses opens up again I decided that I wanted to help people FEEL happier and live their best lives and I wanted to do it in person. Face to face. It was a huge risk but it has paid off and then some. There is nothing like face to face human connection to create community. Read more>>

CECILIA LEMES

When I was 17, I decided to move to another city to go to college and study Civil Engineering. It was 5 years of much learning, struggle, work. I have so much affection for everything I experienced in those years, for the people who passed through my life at that time, but despite choosing to study Engineering, music was always my passion, always what I wanted to do. When I finished college I decided to pursue my dream of living abroad and making music. It wasn’t easy and it is still not, but for me to feel in my heart that I was making the right choice for my life, I had to take the risk of leaving everything, family, friends, a possible career as an engineer. Read more>>

Damali Fraiser

After almost 20 years in a corporate career I decided to leave to pursue being an entrepreneur full-time now at 43 years old I am a full-time kettlebell and nutrition coach driving systemic change in the fitness industry to make kettlebell training more accessible to more diverse bodies. This might not be that strange if I had studied kinesiology in university but I actually studied materials science and engineering and spent the majority of my career in process engineering software development lifecycle and change management. Read more>>

Christine Ferris

Growing up I was always taught to not take risks. That pursuing anything creative was a huge risk. That ending up living out of my car was what happened to those who pursued being an artist. In the fall of 2020. I decided to take a risk. One that has lead to me growing as an artist. As a person. As a business owner. Having always been a creative a person. I enjoyed crafting and painting a lot. I knew that this is what I wanted. I just never had the confidence to take that jump to make something of it. At least not until I showed some online friends the project I was working on for myself. Read more>>

Demie Fultz

I think taking risks is a requirement to pursuing our really big dreams and goals. You may find yourself thinking that you can’t possibly achieve that really big goal of yours, but I think you can. I used to be someone who didn’t believe in myself. I saw other creators/influencers on social media and I thought to myself how amazing that would be. I read books, and I thought to myself how being a writer would be so cool. However, I never made the connection that I could be that also. So for me taking a risk, has been about diving into my greater mission to “Start Going Further”. Read more>>

Mike Feldman

I think getting into real estate in the first place was a huge risk. I didn’t have a very strong sales or entrepreneurship background, didn’t have a lot of money to start the business with and we knew that we’d be starting a family soon. I got into real estate full-time from day 1 and didn’t give myself the option to fail. We knew that once we had a kid that my wife would quit working so I didn’t have a choice but to success and provide for the family. That first year I worked harder than anyone I knew because I knew I had to establish a strong foundation for my business by the time my wife quit work and I was the sole income provider. I sold more houses that first year than any other new agent in my city. Read more>>

Margitu Adamo

I believe taking risks are you listening to your intuition and being true to yourself. It’s only considered a risk because it isn’t ideal, temporarily. I’ve given myself a new turn in life, and a new outlook. My entire life I thought I was going to be in the health field, go to medical school and become a surgeon. I used this goal as an excuse to dismiss myself. After loads of unsuccessful triumphs in school and not receiving the results that mirrored my efforts, etc. Read more>>

Liana Sonenclar

I think the biggest risk I’ve taken was leaving college to pursue the arts. I worked myself into the ground in high school. I did my first year of college at the University of Chicago, and once I was there, I think I realized I had worked my entire life for something I didn’t want. I’ve always loved theater, but growing up (probably due to a lot of fear,) I never pursued it. And then at 19, I think it hit me, if I didn’t go after it then, I probably never would. So I left Chicago and moved to New York. Read more>>

Sophie Makowski

Baking has always been a passion of mine since I’ll was a child baking with my mom. When I went to Michigan State I worked at the MSU Bakery for my work study. It was one of my favorite parts of my 4 years at state. After graduating I would decorate cakes and cookies for family and friends but never thought to turn it into a business. Fast forward to getting married and working at an Assisted Living in their Marketing Department I had my daughter. I loved working with seniors but I desperately wanted to be home with my daughter, so I made the decision to be a stay at home mom and grow my home bakery business. Read more>>

Christine Wiethop

I was teaching high school math when I launched Baking Sweet Scents online. A year and a half later, I had become very involved in the wedding industry as a baker while also going through a second round of burnout in education. Financially, it was not time to leave my job, but I felt led to take the leap of faith and give the business my full-time attention at the end of that school year. Read more>>

Noelle Johansen

When the pandemic hit in 2020, my business gained attention and support like it never had before. I was working full-time at a daycare, and when I went home, I was constantly embroidering and creating art. After about 6 months of consistent sales, I quit my job to be a full-time artist and moved across the state to be closer to my family. I didn’t have any savings, but my mantra for years was “I’ll figure it out.” And that’s what I did. Read more>>

Drewgotgamee

When I was 18 in college studying Mechanical Engineering and still making content on the side, I found myself in a place where I wasn’t enjoying my major and over time in college I would slowly begin to create videos more than studying for my major. So I decided to take the risk of dropping out of college to put all my energy into making content full-time and to be completely honest that was one of the best decisions I’ve made because that risk basically forced me to bet on myself and to strive to achieve my goals. The risk of dropping out of college with worth it, since then I’ve gained a great following and met a lot people along the way. Read more>>

Wheres Dank

I was working construction and I really hated it completely. If it was 99 degrees or 0 degrees, I’d most likely be outside working. I told someone I was thinking about quitting and working the studio full time and he told me that’s the stupidest thing they ever heard. It took my back a little but once I lost my benefits at work I was pretty much forced to quit. I wasn’t going to do that crappy job with no benefits. I decided to rent out a room at the studio I was working at and put everything I had financially into when I only had 2-3 clients I was working with. Read more>>

The Black Boy King

As an musician, artist, rapper, whatever you consider yourself in your position in the music business, you are always taking risks. For me, I’ve lived a life that is full of risks that I’ve taken to succeed. I grew up on Tropicana Ave in Sin City so you learn the value of understand the risk versus reward mentality. When you gamble, you understand that you can win or lose. You are mentally prepared for it, and take the risk anyway because of the old saying “fortune favors the bold”. And if you want to be successful in life, you simply have to take risks. Read more>>

Heather Neff

The risk I took was starting my business Heather Neff Wellness. To take on this endeavor I had to leave my super secure but also super toxic job as a server which felt incredibly risky considering I would be taking a large initial paycut as I created momentum. Not only was the financial burden a risk but I also clung to the comforts of my hospitality community, my addictions, and my identity. I knew in my bones that these had to shift if I were to be the face of this new business but I had a really hard time letting go of my attachments. Read more>>

Aleyna “Lele” Jones

During the pandemic, I took the biggest risk by following my dream – to dive deep into holistic healing practices to improve my mind, body, and soul. As a small business owner, I received a loan from the U.S. Small Business Administration to invest in becoming a health coach in October 2020. Using the loan to pay tuition, I spent the rest of 2020 studying at the Institute for Integrative Nutrition, the world’s largest program. After a full year of working toward my goal part-time, I became a certified Integrative Nutrition Health Coach on October 5, 2021. Since then, I’ve taught 20 community yoga classes, received five yoga certifications, and worked in a hot yoga studio! Read more>>

Nikkey Creative

One of my main challenges is not having a blueprint. I came into the Art business world without a mentor or any guidance. Art school taught me the technical side of things when it came to my art. However, I had to teach myself how to market and sell art. I have spent countless hours researching and experimenting with art materials & testing out new products/vendors. I am still learning every day when it comes to my art. I have been using acrylic paint over the past 8 years. However, recently I obtained my first set of oil paints, that I am slowly learning how to use. Read more>>

Brad Erickson

Definitely the biggest risk I’ve taken in my professional and creative life was leaving my 19 year position as executive director of an arts service organization, Theatre Bay Area, in San Francisco, selling my home there, and moving to South Carolina to create an artists residency. Fortunately, my husband was on board for this major change as well — although as he likes to relate, each of us, on our long road trip across the country, was silently wondering “What the hell are we doing???” The result, so far, has been more than we could have hoped for. Read more>>

Jerry Roberts

A life risk that I have taken in life is starting my own business after deciding that I want to work for myself. I want to be an independent entrepreneur be my own boss doing the things that I love to do which is being an artist, creator, producer, comedian, Photographer etc. Read more>>

Sally Stewart

Owning and operating a specialty wine shop was something I’ve wanted for many years prior to finally opening my own shop. I was 32 when I received my ALS diagnosis, ALS a terminal and progressive disease that effects motor neurons in the brain that weaken eventually causing full body paralysis, with an average life expectancy of 2-5 years after diagnosis. I was forced to quit my job as a sommelier in my fine dining restaurant in Manhattan shortly after my diagnosis, due to my increasing difficulty walking. I was starting to fall more often and feel unsafe on the commute to and from work. Read more>>

Andy Zhu

Creating and leading a dance club on my own was unthinkable to me at the time. I was a freshman during the fall of 2019, and I was eager to find a dance/K-pop club that I could join to hopefully make new friends, explore my passions, and to just establish myself as a member of the Jasper HS community. My junior high boasted about their numerous and inclusive organizations that would make anyone “feel at home”. Read more>>

Philandis Stovall

As with life, anything worth having and lasting is a challenge! However, it is worth the effort as the reward and satisfaction will be great! Though my life hasn’t been easy, I’ve faced different difficulties. Like building a house, even with a solid foundation and the right tools, it takes time and dedication to construct something lasting and beautiful. I’ve persevered and come out stronger, knowing I can accomplish anything with the right attitude and diligent work. Taking risks is part of life and something I am comfortable with. I have learned to embrace risks and accept failure as part of the process. Read more>>

Halover

I think my 2 biggest risks were deciding to move to the US to study at Berklee College of Music and then moving to Los Angeles with $300 in my pocket to pursue my music career. I’m originally from a small town called Barnaul located in Siberia, Russia. I used to think that there is no way I can achieve anything with my music so after graduating high school I decided to study Linguistics instead. I thought writing songs and singing could be my hobbies while I have a”real job”. Read more>>

Kim Peretz

One of the most life-changing risks I have taken was when I decided to travel solo to Costa Rica to complete my 200hr yoga teacher training. This was a dream of mine for many years. It was something deep down in my heart that I really wanted to do. But for a long time, I didn’t take the leap and it felt like there was so much resistance. Traveling alone to a foreign country at such a young age seemed so daunting. Until one day, I decided: “this is it, I am going to do it” and so a couple of months later, I packed a suitcase, gathered the courage, and finally took a leap at my dream. Read more>>