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.

Peri Heft

Most of us have heard the term “big risk, big reward.” And honestly, I don’t 100% agree with that, BUT, I do believe there is a lot of truth to it. When it comes to starting ANYTHING new, there is some level of risk. And when you’re developing, starting, and launching your own business as an entrepreneur, most people start out in debt due to the investments that have gone into the business before earning that money back. For me, diving into health and wellness was a moment of trust, vulnerability, and you guessed it, risk. Read more>>

Tania Van Pelt

We learn through failure. To take a risk is to flirt with or even succumb to failure. In my experience, a risk, a bet on oneself is nearly always worth it. My biggest successes rise from the ashes of my biggest failures, which were all risks taken. I wrote and co-produced a TV pilot, which in the end was not picked up by a distributor. That was a big risk. And ultimately, while I learned SO much, it failed. Still, it got me in the door, got a book, and then a second one published. Read more>>

Elisa Foster

Haustay was founded in January of 2020, during the start of a world-wide pandemic. Though it may sound crazy to start a property management business for vacation rentals at this time, we quickly realized that property owners needed assistance at this time more than ever. So even though it seemed risky at the time to start a vacation rental property management business, it proved to be beneficial and surprisingly needed at the time. Read more>>

Erica Comitalo

So much about business-building is about risk-taking—especially when you choose to niche down. From the moment I launched my business, I knew I didn’t just want to be a copywriter. There are plenty of those. I didn’t just want to be a copywriter for creatives. There are plenty of those, too. I wanted to be a copywriter who served a specific kind of creative, allowing me to master a way to serve them in all their unique needs. Read more>>

Natolie Warren

I literally started my private practice a month after I became a fully licensed professional counselor. At the time, I was doing contract work for a psychologist working as a psychometrist. She invited me to begin renting space in her office so I could start to see clients independently. Even though I was somewhat afraid, I took a huge risk and began the necessary steps to begin seeing clients. Starting my own practice was something that I knew I wanted to do one day but I did not imagine it would happen this way or this soon. I am so glad that I took the risk. It has been 14 years and I am still in business. Read more>>

Andrea Nied, PT, DPT

My family and I moved abroad to London, UK in 2018. At the time, my kids were 2 years old and 9 months old! Looking back, that was a pretty wild decision to move across the globe with two small kids, but it was an unbelievable experience. We were able to take them to some amazing destinations like South Africa, Mallorca, Barcelona, Greece, Switzerland, Germany, Belgium, Scotland, and Wales. I had just obtained my UK Physiotherapy license in 2020 when Covid struck. Rather than get a job at a large physiotherapy clinic or hospital, I decided to start my own business in order to serve my local community. Read more>>

Aria Lanelle

After I released my last EP “My Name Is”, I moved to Brooklyn on a whim and it changed the course of my life and music career. Before I moved, I’d still been living at home in Massachusetts making music. But after my grandmother passed, my mom decided there wasn’t anything left for her in Mass anymore and moved back to Texas. I didn’t want to go back to Texas (where I was originally born) at that point, so I saw a listing on Facebook from one of my old classmates to sublet a room for the summer in BK and took it. Read more>>

Matthew Collins

Quitting my job and starting my own business was a pretty big risk, now that I look back on it. I had a great job working with intelligent colleagues where I had the opportunity to work with a variety of different clients and patients with interesting issues to resolve. It was at this job that I really became a rehab specialist, rather than a run of the mill personal trainer. I would see 8-10 clients/patients per day and it was basically like drinking out of a fire hose in terms of how much I learned and how much value I got while working there. Read more>>

Liz Cook

When I first moved to Arizona, back in April of 2018- I took the biggest risk of all. I had just gone thru a divorce in January of that year, and I had started dating my now husband- all while just graduating from cosmetology school 8 months prior. I was working at a small salon, but was burnt out. I worked non-stop; 70-80 hrs a week. My boyfriend surprised me with a trip to Arizona for some relaxation, and we fell in love. Read more>>

Kayleen Shearer

If you would’ve told me even just a few years ago that I would currently be a full-time photographer I would’ve certainly laughed at you. I was all in on working in large corporate settings and saw my future in sales and tech. Stability and high earnings were the marks of success in my eyes, and I certainly willingly sacrificed other liberties to achieve just that. As cliche as it sounds, I found immense identity in the status and earnings of my job. Read more>>

LaTasia Wright

November 2019 I made the decision to leave a job and take a break from working to hear from God. I heard a call to rest and to leave where I was working. I worked in fitness studios and had my own wellness/fitness business. I had over 10 years experience in the health and fitness industry. I loved and was good at what I did from teaching classes, managing, and coaching others. Read more>>

Maria Viviana Colmenares

Living abroad. I was 22 years old when I decided for the first time not only to leave my home, but also my country (Venezuela). One of the main reason could be our political situation, but first we wasn’t that bad in 2010. It was a gut feeling which was trying to taking me away from where I was and what I was doing. I had the desire to grow, wanted another way to live, far from any comfort and also to see other ways to create. It sounds excited and it was! but also when I see the letter of acceptance from one of the company which I wanted to work with, kind of scared me because the plan now, became a reality. Read more>>

Anaregina Frias

I feel like every single big decision I’ve made since May 14th, 2015 has been a risk. I witnessed my dad die on a Thursday at 12;30 pm on May 14th, 2015. I promised him the day before that I would pursue my dream as an author but something more happened inside me that day. I realized how short life can be. I dove head first into spirituality. I decided to live my life as if though this year could be my last year. I learned fear cannot hold me back because death is coming for me anyway. And yet… Read more>>

Eduardo “Gualo” Jaramillo

Pusha Preme

One Risk I took that change my life forever would be when I left college after my scholarship ran out to go to New York City. I didn’t have a job, I didn’t having anything in saving except for my work study money and I didn’t have the proper clothes for the weather due to my school being in Mississippi. It taught me the importance of patience and being resilient. I took the time I was stuck filling out apps to do youtube blogs, learn how to record and mix on pro tools and develop my song making skills by studying rhyme patterns and lyrics. Read more>>

Theresa Kwong

After obtaining a Bachelor of Arts in Architecture from University of California, Berkeley, I practiced and earned my architect’s license in the state of California. It was a very traditional path in a male dominated field, at least in those days. My life was quite stressful, being challenged everyday not just on technical issues. As a double minority, it was a downright uphill battle especially on construction sites, on top of the usual dealings with clients and jurisdictional officials. I looked around and most of my women school friends either left the field, worked in related or unrelated fields. I was underpaid and overworked. Read more>>

Sandra Coker

If you ask me, choosing to give up my 20s and hundreds of thousands of dollars to pursue a dream that no one else in my family had dared dream was quite the risk. The sacrifice is the risk on this journey. Becoming a doctor was always my goal, but I had no idea what it would take to accomplish this goal nor did I have any idea that this dream would give birth to many other dreams along the way. I took the risk of taking the hard route and making the decision to pursue a career in medicine when there were many other easier routes to take. Read more>>

Dr. LaKisha James

I have always been a risk taker. Not sure why but I think it was because life is full of risks. A person does not know if something works until they try it. In 2015 I had my last child. I was on maternity leave and I was thinking about not going back into the corporate world. So, I spoke it over with my then spouse. We both agreed we did not want our baby girl being raised in day care. We also agreed I would start my business and he would be the sole provider in the household. I know he was thinking, why now? We just had a baby and here I was talking about starting a business. Read more>>

Lea Saccomanno

If you would have told me just a few years ago that I’d be embroidering “full time”, I would have laughed. Taking a chance on myself and giving myself the opportunity to really go after something I believe in has been one of the scariest yet most rewarding decisions I’ve ever made. Sippin’ and Stitchin’ started eight years ago on my living room floor with the same goal that I still hold to today – to share what I love in a fun, laid-back way. I’d have friends come over and we’d drink wine, eat snacks and I’d show them how to stitch. Read more>>

Jazmin Frias

The biggest risk I’ve ever taken was during the pandemic. I lived in Dallas at the time and after being shutdown for 2 month I decided to move back to my hometown in Laverne, Oklahoma and buy a restaurant. I had waitressed before but other than that had no prior experience running a business much less a restaurant. For context I’m a hairstylist. I had no clue what I was getting myself into but I had a vision. I loved that in Dallas anywhere you go it’s an “experience”. I wanted to bring that to my hometown and also create a place where my family could work at. Read more>>

Josie Cross

I graduated college May 2021, I was dying to get my hands on the clay as I finished my degree in Advertising and Graphic design. I always felt un-passionate about my degree, but felt it was a safety net in the corporate world while still staying true to my creative nature. When I returned home the Summer after college I worked in my parents garage in a beautiful outdoor make shift ceramics studio. I was very lucky to have such supportive parents and a beautiful space to work in. Read more>>

Makala Fields

One big risk that I just took was leaving the classroom after 18 years! I’m using this time to rest, create artwork, and really pour into my business. I’m excited and a tad bit anxious because I am stepping out 100% on faith. I started teaching in my hometown of Providence in 2002 at The Met School, which is a project-based school. It was a whole new world for me and such a beautiful 4-year journey! After moving to Atlanta in 2006, I started working as a 6th grade social-studies teacher at KIPP South Fulton Academy and stayed for seven powerful years. Read more>>

Jonathan Bradley

Over the years I have worked many retail and restaurant jobs while studying, practicing and performing my artistic passions. One of the biggest risks I’ve taken in my life was letting go of my day jobs, investing in myself and most importantly, trusting the process of entrepreneurship. Being my own boss, allows me to run my business how I want, work from home and help my wife Lauren raise our three children. My family is my inspiration and motivation so everyday is confirmation that I made the right choice. It’s nice to watch my kids grow along with my business. Read more>>

Zulmy Mancia

I think the biggest risk I have taken so far in my life has been changing my career path from an allopathic to a naturopathic doctor. I had always envisioned myself becoming an allopathic doctor, there was never an alternative choice in my mind. In college, I was on the pre-med track, taking all the classes I needed for allopathic medical school as well as being involved in all the common pre-med activities such as volunteering as a medical translator, clinical research and pre-med student clubs on campus. Read more>>

Heather Arnold

Makeup artistry is my second career. I had always worked until I gave birth to my twin sons 24 years ago. At the time I decided to stay at home so that I could focus on being a mom, ending a three year stint as a pharmaceutical rep. I really enjoyed my job but felt that I would be spreading myself too thin if I tried to raise twins and work at the same time, Read more>>

Phoenix Sohl

There comes a time in life when you have to take bold risks and not be afraid to go off the beaten path. I’m a recording artist and yet behind closed doors for years I’ve studied, expanded my mindset and healed myself and community through wellness. Often you hear that you have to pick a lane and stay there, but I’ve never wanted to live inside of a box. I recently decided to step forward and re-introduce myself not just an artist/award winning performer or psychologist/ wellness expert but as both. Read more>>

Kari Monk

I worked for corporate America for most of my career, but never felt fully satisfied. I was behind the scenes, and didn’t really get to see the fruits of my labor. I also just felt like a warm body doing a job that paid the higher ups a bunch of money while I was held down by their thumb. When I had my daughter, I quit corporate America making a decent amount of money, and shortly thereafter started with the small family like Title office. Having a baby is not cheap, but I risked the financial piece for a more satisfying position that allowed me flexibility to be able to be present in my family life! It gave me the balance I needed which I couldn’t obtain in corporate America. Read more>>

Amber Mykaels

6 Years ago I would say I was a completely different person, living a completely different life and a single decision changed everything for me. I was living in New Jersey, dealing with a lot of health issues both mentally and physically and I was in a deteriorating marriage. I just felt completely stuck. I really had no idea what I was doing with my life. I had flown out to San Diego to meet my family for a weekend trip and I was having a hard time enjoying myself because of how unhappy I was with everything going on. Read more>>

Justin Grey

Despite the negative connotation surrounding the word risk, it is the only way to achieve success in life. There is a popular saying that goes “ no risk no reward” this simply means , if you’re not willing to take a chance or do something outside of your comfort zone you will never achieve greater heights or levels of success. I’m not only firm believer in the popular saying but I am also living testimony of success through risk-taking. Read more>>

Alexis Jackson

One risk that I have always been down to take is quitting my job and trying out a business idea! Don’t get me wrong, I definitely plan everything out; I made sure all my bills are paid up and that I have the resources and clients I need for my new business before quitting. Read more>>

Nikki Stoops

Righ after high school I went to college to pursue a psychology degree. I loved learning about it and also wanted to be a therapist to help people. I was also taking a bunch of art classes since I have always loved art and been into drawing and painting. After about two yrs of going to college I was feeling lost in my career path. I knew I wanted to do something that I would love and something that was my passion. Read more>>

Erin Johnston

In my past, I was a special education teacher for five years, a school counselor for seven years and a special education counselor/behavior specialist for one year. Having invested a handful of years in the education field, I felt somewhat comfortable and secure but always knew in the back of my mind and heart that I was being pulled in a different direction. I dabbled in private practice on the side to get my feet wet and to see if it was something I was interested in after all. Read more>>

Diane Strand

Leaving my successful career in the Entertainment Industry to become an entrepreneur in 2003, was a leap – but I knew I was packing my own parachute, so I had faith because I was betting on myself and my partner for life and now business, my husband Scott Strand. I came home from working in reality television, missing dinner, bath time and putting my 2.5-year-old to bed, again. My husband who was a working actor who went back to school to finish his BA degree in Film and TV was about to graduate from CSUN said to me what if…. Read more>>

Miu Haiti

Being an artist inevitably comes with taking risks on a regular basis. That being said, the biggest risk I’ve taken was to move to a new country and start my life all over from scratch 4 years ago. I was fortunate enough to build a beautiful music career in Haiti thanks to my loving fans, but I realized that I couldn’t reach my full potential there, I wanted to accomplish more on the international stage, and what better place to pursue that, than the United States, the land of dreams. Read more>>

Letisha Bereola

I retired from the TV news industry after 11 years to start my own media and coaching business. Leaving a successful career to go and create a new one is quite the risk but I had faith the bold move was preceded by God’s calling on my life. I always knew TV news wasn’t the complete vision for my life but I didn’t have another piece of the puzzle until 2020 when I heard about coaching on a podcast. Right away I knew this was the next step for me. Read more>>

Juan Licon

Back in December of 2005 I graduated college with a Masters degree in Mechanical engineering with a specialization in aerodynamics and spacecraft propulsion. Soon after that, I started working for Raytheon Intelligence and Space located in McKinney TX. I was always financially responsible, so 10 years later in late 2015, I had managed to save enough money to do something big. My original plan was to use that money as a down payment for a big house, plan B was to take an unpaid year off from work and travel the world, Read more>>

Jaymee Wins

I believe in the saying, “Greater risk, higher rewards”. But along the path of being risky, you always get discouraged and wonder if all that you’ve been doing is worth it. I’ve always taken calculated risks even as at a young age. Although I graduated with a bachelor’s degree in my home country, the Philippines, my heart was never into the traditional path of landing a safe and secured job. Read more>>

Annette Coleman

In my art career I have continued to take risks. I’ve excepted work that I only had a fraction of the knowledge needed to complete the project. From an informational video for a client to a large stained glass installation. I acquired the skills on the job from hiring a coach to instruct me in video editing skills to investigation of methods for a 20 foot by 24 foot stained glass on glass installation. I knew I would succeed by sheer determination, collaboration with other creatives and hard work. And, the best part is that I would have additional skills to bring to the next project. Read more>>

Corinna Young

Opportunity favors the bold, and that requires taking risk. The biggest risk I have taken is betting on myself and starting my own private therapy practice. As a black mental health advocate I felt the need to create a safe, non-judgemental space for my clients to begin the journey of healing. My practice “Hues of Healing Therapy” is not only a passion project, but also my life’s purpose. Taking such a risk required me to feel the fear of failing, but not allowing it to hold me hostage. By taking such a risk, I hope that I inspire others to believe in themselves and to walk in their purpose fearlessly. Read more>>

Mahaley

During the pandemic I realized that my full time work in the opera business for 12 years was one that served me well for a long time, and brought me much joy and some of my best friends and experiences I have had- but I was feeling a pull for many different reasons to close that chapter and re-invent. Strangely that reinvention was more of a homecoming, as I started to write my own music again, which is something I had done naturally since childhood. Read more>>

Robert McDavis

After the chaotic year that 2020 was I took a risk by investing in laser engraving as well as the time it’d take to learn a new craft. Now after two years of experimental projects I can see I had really invested in myself so with the skills learned I could take the biggest risk now by reopening the shop. Read more>>

Stella Vidal

My life has been full of decisions some may see as controversial or risky. I consider those decisions bold moves, which have brought huge successes and some failures. But at the end of every day, I know that I’ve pursued life with passion and conviction. My first memory of taking a big risk started when I “left” my home in Colombia when I was 10 years old. Yes, I “had enough”and felt constricted by my parent’s upbringing, which was very traditionally Latin. Children are told to do as they’re told, no questions asked. This, however, went completely against my curious spirit. Read more>> 

Joshuah Jones

Helping musicians and local bands that I enjoy has always been a passion of mine. My band that I’m currently in, The Obsidian Resurrection, actually broke up back in 1999 and last year reformed to finally release our album that has been collecting dust this entire time. Back then I helped organize a very large group of bands in our area that made our local underground metal scene explode. Read more>>