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.

Candis Garcia

Starting my own business has been one of the biggest risks I have taken. I wasn’t as prepared as I thought I was. I knew it was something that I wanted to do, and I just had to make a move. I had been working at Mary Dewalt Design Group for 6 years. I would say that I moved up the ladder pretty quickly and felt a little bit stuck doing the same thing over and over again. Not only was the job getting a little boring but the commute in was starting to take a toll on me and to top it all off I was a new mother. Read more>>

Dephree

We were not getting much traction in the music biz. Me and my day 1 road dog started the brainstorm. What can we do? How about a publicity stunt? What if you climbed up on a bus in hollywood? What about a freeway sign in downtown LA? – The idea was born. Read more>>

Marcella Laine

I was 23 when I quit my full-time job and pursued photography. I was a little over a year out of college, and had been working a few design jobs which were within my degree of graphic arts and design. I moved to a new city for a corporate job that was super comfortable, for the first time in my life I had financial security, and was experiencing tons of benefits of working for a large company. Read more>>

Stacy Johnson

I feel like my whole experience as a small business owner has been one big risk. From day one in 1998, when I quit my job as a designer at Cynthia Rowley in NYC taking the leap to start my own line, Stacia. And not just starting a clothing line, but opening up my very own boutique on a desolate, up-and-coming street in my Carroll Gardens, Brooklyn neighborhood, Smith Street. I had a lease and key in hand and the beginnings of a collection of designs. Read more>>

Jacqueline Castro

I have had quite a few changes in my life and professional career, but the greatest risk / change was to pursue art full time. When I was growing up, I always heard sayings like – You cannot make a living as an artist – you need to study something that will the pay the bills, etc. so I did, but even when I was doing something non art related, I always found a way to get back to it. It is something that is part of me and when I am looking to take a break from the busyness of life, art always gives me inner peace and helps me find creative solutions. Read more>>

Melanie Whitney

Starting a business felt like the scariest thing in the world to me at the time. Just flirting with the idea gave all the limiting voices inside my head the stage. Who did I think I was? Who would want to pay me for these services? Thankfully, I was supported by other business owners who were familiar with these voices. They encouraged me to just try it, give myself the chance to try. Read more>>

Judy Lane Boyer

It’s hard to quantify risk past a certain point. What are the criteria for measuring the risk of a life decision? Plus, what may look like a terrific risk from one viewpoint may, from another, seem like a surefire bet. Read more>>

Sharron Rouse

If you had asked me years ago what my life would look like today, I would have given a run down of how I wanted to move up the ladder in the field of education and eventually open my own school. I had a plan. It was safe. It was secure. But, life has a way of forcing you into spaces and places you never dreamed of. Read more>>

Alec Adams

I think there’s potentially a fine line between taking a risk and being unwise. I think we are only being unwise when we make decisions based on what other people think or say we should do despite knowing in our hearts what we are meant to do. Read more>>

Thomas Phillips

Starting your own business is always risky. I cashed out my 401K and invested not just in my own company, but in myself! There have been times I thought about going back into the workforce, where I could make a substantial income. But I would always have the what if’s. And seeing the change in people after they use my products, makes the hard work I put into providing a quality product at a reasonable price is the most gratifying experience I have have ever felt. Read more>>

Matt Anlyan

I guess I take a lot of risks. In 2016, I took a huge risk by leaving a well paying, comfortable job with an international non-profit to open a donut shop with a good friend of mine. I had two young kids at the time so it was a massive gamble to uproot everything and put all of our life savings into a venture that has a notoriously high failure rate. Read more>>

Molly Caskey

The real estate broker called and agree to show me the space that would eventually become The Hive PCFL- a boutique Coworking Space on the most beautiful street in Historic Downtown Panama City. Read more>>

Angela Solomon

I started my mission based, diversity search firm A. Solomon Recruits 17 years ago when it was unpopular and no big deal like it is today. It was a huge risk to quit my. agency recruiting job and venture out on my own for the unknown. As a Black woman, who has navigated white spaces most of my life, I saw the need for a staffing agency that highlights and advocates for the hiring of Black, Hispanic and Latino talent in Corporate America. Read more>>

Diane Schindlbeck

In 2019 my husband Eric and I purchased a restaurant located in rural Michigan. We did not own the real estate, we leased the building but owned the restaurant operations. This restaurant was located at a golf course with a long history owned by the Gerber Family in Fremont Michigan. My husband left his job of nearly 40 years and I left my secure career in sales and marketing to own and operate this restaurant. 6 months later – the pandemic hits and our business was forced to close its doors to on premise dining. Read more>>

Timbrel Chyatee

I don’t think there is one moment that lead me to start my entrepreneurship journey. I think it was many small moments that come together to help me take a big leap to start my entrepreneurship journey. From a very young age I wanted to be in the fashion world. I just didn’t have the courage to follow my passion and go against my parents aspirations for my life. Being a child of a first generation immigrant means carrying so many of your parents dreams for your life, because you know all they sacrificed to give you better than what they had. Read more>>

Bee Golding

I opened Deep Cuts in August of 2020, which in and of itself was a pretty sizeable risk. Opening a new business in a new city during the heart of a pandemic was scary, but within a few months I had built some momentum as a safe haven for LGBTQ folks to get their hair done in a fun and friendly environment. However, I still had not come to terms with something very big within myself. Read more>>

Maria Von Losch

Taking a risk should be my tagline, LOL. I’ve been a risk taker my whole life. At age 22, my last semester in art school I decided to open a vintage clothing store at the beach. I had no experience, little money, I was still in school. This was definitely a HUGE risk. But I had a vision and a calling and nothing was going to stop me from doing it. I had it for 3 years and then closed it to move onto bigger things. Another entrepreneurial risk I took at age 28 was a novelty item I created and had one specific chain store in mind that would be perfect to sell it in. Read more>>

Nina Glazer

At first, following my passions felt like a risk. I have a great and successful career and I wasn’t unhappy but I felt a calling to do more and to align with what enlivens my spirit. I wanted to experience more, feel more, and paint more. Read more>>

Michele Huff

Believe it or not, taking a risk does not come naturally for me. I’m sure it doesn’t for most. But, once this business was created, I knew it was the only way to grow. I had to do the hard stuff and that meant asking for new customers to take a risk on us. It’s not always easy walking into a potential customer and asking them to take a chance on you (me), a new business owner and purchase my candles for their shop. But, I did. Read more>>

Paige Bond

I started out my career on the basis that I wanted to be the best couples therapist around town. Little did I know, that really doesn’t make me stand out and marketable. I did the trainings and certifications to gain the skills to be seen as the “the expert couples counselor” but realized that was still too general. There are TONS of expert couples therapists. At the beginning of this year I joined a business coaching program, which helped me redefine the population who I do my best work with. Read more>>

Paola Leon

In 2016 I was living in Venezuela, studying fashion design because it was the only fashion career path that was available in the country. I started feeling unsatisfied with the major because my dream was to open my own fashion business. An opportunity to relocate to New York City came up, and I knew that was my moment to take a risk in life!. Read more>>

Claire Walley

Setting up my company, The SEN Expert was the biggest risk I have ever taken professionally and to some extent personally. After working in education for 14 years in schools in the Uk and US I had progressed to senior management and had enjoyed the security and to some degree the inevitable promotions and ‘climb to the top’. Read more>>

Emily Hall

My entire life was planned. I was a good student – honor roll, clubs, goals. I knew I would go to a four year university (go noles!) and major in education, start my teaching career, get married, and start a family. Check, check, check, and check. Read more>>

Bailee Shaffer

The biggest risk, yet best life changing reward was to open Simply Peached Boutique. Ever since we were younger, we have wanted to open our own business. During COVID, we had several hours on our hands and thought “why not open a boutique now while we have the time, we have nothing to lose”. There have been some bumps in the road but, this has been one of the best decisions we could have made and we cannot be happier! We have had lots of support from friends, family and customers and we would not be where we are today without all of them. Read more>>

Amberlyn Bonavita

I want to start this off with a quote from one of my favorite authors: “No one ever ascended a mountain without risk.” – Liane Moriarty If you were to tell me 5 years ago that at 33 years old I would be the owner of my own business, doing what I love every single day, I would have thought you were insane. I was comfortable in my career and was figuring out my work/family balance. Read more>>

Isaac Crawford

I grew up in a small town at Lake of the Ozarks. Population 133. My father was an electrician and my mother worked in a factory. The push to do something more than what was available to us in our small town was very minimal. I knew that the small town life wasn’t for me but how could I create a path for myself to navigate to a more exciting future. Read more>>

Carissa Bowser

February of 2020 I took a leap. One of faith but unfortunately one that quickly was followed by lies of fears and of failures. To make the decision to pursue art more full time was not easy. I sat at the kitchen table in tears at the thought of not feeling worthy or qualified or good enough to call myself an artist, let alone make it a career. But that’s the thing about faith. We are not given a promise of what the future holds but we are called to be obedient in doing what we have been called to do. Read more>>

Kedran Brush

I subscribe to the saying, “Nothing great comes from comfort zones.’ And that sums up the biggest risk I took in starting my own company. I’m a goal-oriented person and each year on January 1st, I write down 5-7 goals for that year. Some goals are big (like run a marathon) and some are smaller (like clean out the attic). That year, I took out a separate index card and I wrote “12-31-2018” on the card and I taped that card to my vanity mirror. I made a promise to myself that by that date I would be in a position to jump from the corporate world and into fulltime entrepreneurship. Read more>>

Diego Garcia

I have had my fair share of ups and downs in life. I was born in a small town in Mexico and the motivation for a proper education made me move to Texas at age 13 with my brother. After college, I experience multiple jobs and started working as a financial analyst at a business consulting firm. I was making good money and felt like my life was coming together. But then things started going south and I lost my job. I also lost my car, maxed out my credit cards, and was living at my brother’s house trying to find a way out. Read more>>

Lynda Fraser

I was in the top 2% of a direct sales company, earning a nice FT income and six all-expense-paid trips to various world locations when I felt a shift in sales and the economy nearing the end of 2019. I enjoyed having my own business and working from home, so I knew I needed to do something else before all my bills started piling up. So I took a risk and went back to school (online) to change my business direction. Read more>>

Jessica L. Sparrow

It’s funny because I never think of myself as a risk taker. A risk taker, almost immediately in my brain is someone who jumps out of airplanes or loves roller coasters-like my husband. However, when I think back on all the risks I have ever taken to pull myself out of my comfort zone and to break generational curses, I sort of surprise myself. I have taken several risks most were reactive or active and others were proactive, I guess. Read more>>

Claire Dees

Getting involved as the co-founder of Spectrum was a life changing experience for me. I got involved to assist, thinking that having a 10 year old with autism had given me some experience to share and support others on the journey and I ended up as the primary leader in the first few years. Our first meeting drew over 100 people so there was no doubt a need for support in our community. People wanted more than just support group meetings. Read more>>

Coco Miletti-Hall

I am going to share the story of a significant, life-changing risk I took back in 2019. In 2014, I started on my path as a freelance makeup artist by doing makeup and hairstyling for runway shows in fancy clubs in San Francisco. This led to many TFP (trade for print) photoshoots, which led to getting published in several magazines, which led to several paid editorial shoots, Napa Valley wedding jobs, and headlining an underground Indie art showcase for RAW. Read more>>

Renauld Lucius Porter

Besides starting my business in the face of covid, I also found the courage to leave my job. At the time we had been operating out of our home, seldom a ghost kitchen, or work whatever space deemed good enough to cook in. Caterings both private and event sectors were picking up as well as operation days. The natural separation was clear and I made my move. It was the greatest because for once I knew I was moving out of love and not survival. Read more>>