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.

Jax Atwell

In 2012, I took a big step in business by stepping away from a partnership of four principles and a partnership of two principles. Striking off on your own, with no safety net and no guarantees was tough. The landscape in the private investigations industry was changing rapidly. Many of our historical platforms, data, and techniques were under very big fire from the Obama Administration. At the time many investigators platforms were based on one or two things they did well. I was noticing investigators who began to struggle and some eventually left the industry. I was noticing the companies with more diverse platforms doing better through this hard period. Most of these run by investigators who were in their 60-70s and on second careers from military and law enforcement. Read more>>

Paula T Webb

“The original writer is not he who refrains from imitating others, rather he is the one who cannot be imitated by any others.” In today’s world of instant access across the Internet, many people today believe that if information is posted on the Internet, it is there to be used for free no matter who may “own” the materials. This is true for music downloads, along with movies and just about every other type of Intellectual Property. Since there is little recourse for the copyright holders to recoup financially from the Internet pirates posting materials owned by others, this poses a multi-dimensional challenge for artists and authors. Read more>>

ROICIA BANKS

As an Afro-Indigenous woman, I have always found it difficult for me to feel safe in different workspaces. I have learned to shrink myself when necessary, managed to shine here and there just enough to prove I am doing my job, occasionally wear my hair in curls; I am positive every Black woman can relate. I believe as a social worker for this entity, I advocated effectively for my families and kids, I gave my best every day. So much so that my days were starting earlier, ending later, and I was sacrificing my weekends of rest and life to conduct parental visitation. I transitioned into a different position that I thought would be less of a toxic work environment. Read more>>

Erica Hernandez

9 months into the pandemic I purchased a salon. It was a huge risk but we made it though our first year successfully! I had been working for the pervious owner for 6 years and because of an injury she was forced into retirement. She was a wonderful boss and amazing mentor. I loved being a part of the team she built. I had been planning on purchasing the salon from her in the future but when the pandemic hit and circumstances changed we had to make the decision to go through with the purchase of the salon a little sooner than expected. It has been the greatest risk we have taken. Read more>>

Michelle DiMuria

In 2017, I was finishing up my master’s degree in Criminal Justice through ASU online and I had just won a pitchfork award for best educational program from my mental health awareness week. I felt like I was on top of the world, when everything came crashing down in May of 2017. Without going into too much detail, my family and I tragically lost two important people, my aunt and uncle. It almost didn’t feel real at the time. Here I was getting ready to graduate with my master’s degree and my world shattered once again. I remembered everything that happened to me when I was sexually assaulted (raped). Attempting to process what had happened to me, I began working on my Pave the Way: Mental Health Summit. It was a huge success, with over 700 people in attendance and 50+ vendors/exhibitors. I knew this is where I belonged, in the mental health community. Read more>>

Sarah Hargrave

I think every entrepreneur feels, at some point, that starting a new venture is the riskiest decision of them all. Instead of taking the time up front to plan, analyze, and develop my strategy, I decided to jump right in and figure it out as I went. I simultaneously opened a retail storefront and art gallery, which immediately fed the interior design business, and the success of those two verticals supported my love for custom furniture design and manufacturing. The Collective became an umbrella for those three entities and that was not planned, however, each piece supports the other in many different ways. Read more>>

Steffie Notion

I love taking risks in general and especially with my embroidery. I love when I can use unconventional materials like latex, pressed flowers or rope, in a way that feel at odds with the fabric and thread. I am also a big fan of making mistakes. I am a perfectionist at heart so I took me a while to understand the value of your mistakes, and how really when something doesn’t work out the way you’d hoped, it is just an opportunity to do it different and better the next time. As long as you are learning, the mistake is always worth the effort. I find the more risks I take in my art the more chances I have of making a mistake and learning something valuable. Read more>>

Katrina Murphy

Moving to California has been a childhood dream of mine. It started with my obsession with The Beach Boys in 4th grade, and escalated into having a California themed bedroom painted bright yellow, filled with palm trees and surfboard decor. Although I am Wisconsin girl at heart and will forever be deep-rooted midwestern girl, my dream never faded and I decided to move post college graduation. Well, in terms of launching a career and moving cross-country, the timing of it was not necessarily ideal as this so happened to be in 2008 during the economy crash. While I ideally was hoping to continue my education and get my Master’s in Art History and teach, these jobs were being cut left and right and I needed to find a new path. Moving to California not knowing anyone was a risk in and of itself, but I knew it was something in my heart I had to pursue. Read more>>

Ashley Godby

I moved to Los Angeles, CA right after high school to dance professionally and ended up staying for 17 years. I loved my life in California, but there was a part of me that knew I was ready for my next chapter in my journey. I auditioned to become a SoulCycle instructor in March of 2016 and after that day my life changed forever. I got into the training program and did a 10 week training in NYC and four months after that I was opening the Uptown studio back at home in Dallas, Texas. I experienced so many emotions through the process but every feeling was beyond worth it! I trusted the process and leaned into the journey. I’m so grateful that I did, because the reward was more than I could have ever imagined. Read more>>

Teresa Smith

I had been working in the nonprofit community for about 10 years. At the time, I was overseeing multiple programs that focused on ending poverty. I was growing increasing frustrated with the systems and policies that impacted the communities we were serving that had little impact and resulted in generational poverty. In essences, the programs were designed to teach people on how to deal with poverty while neglecting the notion of actually ending poverty. I experience strong resistance from community partners and supervisors when suggesting ways to bring more innovation and client centered work. We were in the heart of the Great Recession. Read more>>

Andrea Pasquale

The two risks I took are somewhat linked together. The first risk was leaving my job as an on-air announcer. I had worked in radio since my teenage years and was working at a single station for over 12 years. I was bored, there was no upward mobility and I was barely making enough money to get by after a divorce. After looking around for anotehr job for about a year I was hired to run a non profit radio reading service where I had been volunteering for 8 years. I knew radio, had volunteered at the reading service and had a little experience in fundriaising, but it was a big leap to suddenly start running this organization, m anaging some difficult people and being responsible for fundraising events, grant writing and raising money to keep it open. Read more>>

Ania Volovique

I was living the “American Dream”, checking off the boxes of good job, house, marriage…and then realized it wasn’t MY dream. I was not happy and was just moving through the motions each day. As scary as it felt at the time, I decided to recreate my life from the ground up. I quit the safe job, left the toxic marriage and started my photography business. For the first time in my life, I chose myself. The risk of staying the same far outweighed the risk I may fail. I dove head first into personal development to understand myself deeper and to strengthen my emotional intelligence. This led me into the coaching industry which I then connected with photography. Read more>>

Deborah Mosher

Starting my business was a risk or better said a leap of faith for me. In 2012 a chapter in my life ended and a new chapter began. For twenty six years I dedicated my life to being a wife and stay at home mom of six children. Unfortunately, my marriage ended in 2012. Being a Christian, I asked God for direction. Starting over in your 50’s and being a stay at home mom was a challenge. I continued seeking God in prayer. Without a doubt, God answered my prayers in his timing! I began volunteering as a clown twisting balloons but that ended due to a latex allergy. Later on, I volunteered at many charity events with my giant bubbles. As time went on, my ministry became a ministry/business. So the “taking a risk” or “leap of faith” for me was to believe God had a purpose for me. Read more>>

David Tribble

I hesitate to say “I took a risk”. and here’s why. Yes I am a dreamer so that puts me in a category of someone who doesn’t require security in a sense of a steady job w/ steady income w/ benefits. I haven’t seen benefits since I was a school teacher. Which, if I may, they deserve all the benefits and a raise for being in the trenches with the kids of today. But back to the risk taking, I knew early on that music was something that I connected with, which made everything else make that much more sense, therefore making all things better. Read more>>

Bryan Jimenez

Well, the biggest risk I’ve taken was dropping out of college and quitting my job to pursue my acting career. It was super difficult in the beginning because all the stuff that can go wrong, cross your mind. But I didn’t let that stop me! As a matter of fact I dedicated my whole life into Acting that I have refused to settle down in a relationship, refuse to go out and refuse to have a back up plan. I am really taking a big risk because I’ve invested all my money and time into my acting career. I’ve lost girlfriends and friends because of all the time I have occupied into my craft. Read more>>

Darlene Kearney

Years ago, I started my business from working out of my house. 5 years later received an opportunity from a friend to take over her office space. I was already renting a smaller office from her. I didn’t even think twice. I just did it. What a huge risk. But it was worth it. No matter the challenges I continued to remain open, and offer more services to expand my business. Read more>>

Duly Eldritch

The timing in which this is happening couldn’t be funnier to me. For roughly the last half year I’ve been displaced and haven’t had the space to make music or much art. That’s motivated (scared) me into taking an out-of-state job with a friend of mine. It’s an opportunity to make a good chunk of money, working a difficult job in a relatively small amount of time. Given the economic reality that myself and many people close to me have found ourselves in recently, this money made will give me enough leeway to set apart the time I’ve so desperately wanted to dedicate toward just making things. Right now, I’m currently in the planning process for that move. As far as how it turns out? I guess we’ll just have to see in about four months!. Read more>>

Jennifer Shaw

‘No Risks, No Rewards.’ Early on in my adult life I recognized that what most people settle for as a safe, comfortable life just didn’t do it for me. I had checked all the boxes, but I was bored, unfulfilled and lacked purpose. I remember moving offices at my job at the school district and I was assigned the desk by the second story window. I had a view and natural light. My co-worker looked over at me and said, ‘You are so lucky that you get this view for the next 25 years.’ I felt as though she handed over a life sentence. Thankfully at this time I had already started building my doTERRA business on the side and was beginning to see a light at the end of tunnel. Read more>>

Christy Robinson

Actually I have two stories about risks I have taken with my business that turned out to be wonderful decisions. The first was NOT getting a degree and going into debt to learn jewelry making. Instead I worked and got paid to learn metal smithing and the jewelry business by working as a bench jeweler/assistant to two different established jewelers. The first jeweler I worked with specialized in contemporary art jewelry. While working for him, I learned what tools I needed to set up my metal smithing studio and also about how to run a contemporary art jewelry business with shows and collections and such. Read more>>

Winter Clark

Being an entrepreneur and following my passion is the biggest risk I’ve ever taken! It’s not for the faint of heart and it’s one of the most rigorous, soul-expanding, spiritually growing and heart-rending things I’ve done. Deciding to open my own practice with services that help people locally and globally has been endlessly satisfying and yet there are still moments that come up that challenge me to continue to transform. Whenever the energy of my business wants to evolve there’s a risk involved. The resistance that comes up with that risk reminds me of the reward on the other side of that uncertainty. Read more>>

Natasha Castillo

I think any entrepreneur can relate that the moment you step out on your own its scary. I was 21 when I took the risk of starting my own business, I decided to open my own salon, signed the lease the day before giving birth to my son. With about $500 in my bank account. THAT was risky. Right out of school I started at a salon working commission, after being there a year and growing a clientele I was still only making $600 a paycheck plus tips! I knew I couldn’t survive off this so I needed to make a decision, Take the risk and go on my own, or quit the industry. According to salary.com, The average hairdresser makes $27,132 a year. I was determined when I decided to go on my own that wouldn’t be me. Read more>>

Mason Aksamit

When I was in my first semester of College I decided to leave before the end. I knew it wasn’t what I wanted for my life, and it caused a lot of turmoil in my family. To this day my grandfather does not speak to me. But because of that decision I figured out how to test out of 3/4 years of my Bachelor’s degree earning nearly 90 credit hours with tests that give you direct college credit. I was able to receive my Bachelor’s degree at 19 for $10,000. I have since written a book and tutored 15 people on how to test out themselves saving a total of $1,500,000 on college tuition. I know if I could make my way onto a major news station, I could save millions of people thousands upon thousands of dollars on tuition and start destroying this ridiculous student debt crisis of $1.57 trillion. Read more>>

Wyatt Bell

Becoming an Artist full time was the biggest Risks I have taken. It meant I had to fully commit to my craft and to myself to be able to make it. Im still learning how to better myself and become more successful everyday, it is one of the hardest tasks to balance both mentally and in physical aspects. Working for yourself is most definitely the most complicated job to have and its hard to realize that until your fully in it… But the reward of knowing you determine your outcome in life is priceless and absolutely WORTH THE RISK. Read more>>

Ellen Hinton

Music has always been my passion, but pursuing it full time seemed risky. I had a full time job that I enjoyed, but it wasn’t chasing my dreams. I also had bills and responsibilities that made me afraid to step outside of my comfort zone. One of the first songs that I released was about leaving that job and facing my fears. My first songs did nothing for the first few years. I was wondering if I made a mistake. Then boom! One of those songs that I wrote was in a national commercial. Over the years, several songs have been on tv shows, movies, and commercials, and I was making a living doing what I love. Last year, I made TikTok’s top ten list as one of most duetted music artists and one of my songs on that platform is currently trending. Read more>>

Stephen Groce

“The person who never took a chance never had a chance, not in terms of risk, but of opportunity,” is a motto that has served me well across multiple sectors of my life. From my political aspirations running for a seat in the 8th largest School District in the US to bootstrap funding a new Financial Technology entering the United States. The risk is that I had never done either before. However, what I learned from each of those endeavors was only strengthened by the many risks I’ve taken with other ventures in-between. Let’s look at my decision to launch two different divisions under our corporate company BUILT By PN Industries, Inc., (Brands for Utility, Interaction, Learning & Thought). One channel operates in the apparel and accessory space, while the other is in professional services focused on business consulting, marketing, and strategy. Read more>>

Marcie (MJ) Lakin

In the eighth grade, the principal asked me up on the auditorium stage to show an example of what a well-dressed female student looks like, shyly, I capitulated. I was wearing a 3/4 sleeve, just over the knee, semi fitted, wool plaid, Italian coat dress, self-belted with tall, heeled boots, that I am pretty sure my mom and I got for a hefty discount, at Loehmann’s Back Room. It was the proudest day in my reserved mother’s life and the last time I ever wore it. It felt like more of risk to me to lose my life to the status quo. Isn’t life all about risk? About being daring? If it’s interesting it is. Read more>>

Tiffaney Carr

Starting my business was one of the biggest risk I have ever done in my life. Before I started my business, I worked a restaurant manager at a hotel where I was responsible for the dining facilities at my hotel. While working there I knew I had a heart for starting a catering company, I was passionate about food and service and my business minor was in entrepreneurship. While talking to my AGM at the time, he pushed me to go for my dreams because a life of regret wouldn’t be fun. So I decided to take the leap, I started working another full time job to save money and starting a finance class at my church. I took out my 401k to help with starting the business and the rest is history. Read more>>

David Sodemann

I started Boho Camper Vans my friend, and now partner, Brett Ellenson. When we came up with the idea in March 2018, I knew in every fiber of my being that renting camper vans in Arizona would be successful. The problem was I didn’t have the money saved to purchase a van let alone the money for materials needed to turn the van into a camper. Most mentors or successful entrepreneurs would say something like, “put together a business plan”, or “start saving a little each month”, but that’s not the approach I took. The excitement of bringing Boho Camper Vans to life had overcome my thoughts. It was now my purpose, and I wasn’t going to wait. Read more>>

Jared Carrizales

Our company has always put a premium on values. Things like honesty, transparency, and general ethics. Before starting Heroic Search while working as a freelancer, I discovered that this approach was a big reason that companies would hire me. So I’ve always viewed that as an asset. A few years ago, we worked with a client that owned an ecommerce store. They sold products of varying designs for thousands of different types of products. One of these products happened to be a confederate flag. That particular design actually sold pretty well. One day, he asked me if that was that would be worth promoting (ads, SEO, etc). I gave him my honest thoughts: Read more>>

Steven Silver

The greatest risk I ever took, was leaving my families jewelry business, where I had a nice income and worked with mostly family and left without any preparation, plan, clients or idea of what I wanted to do I also had three (3) small children at home. However it was the greatest thing I ever did after figuring out what I wanted to do. I beat the pavement, made a zillion phone calls and presentations to get where we are are today, which is the most successful Jewelry Appraisal Business in Houston Texas. Read more>>

Giselle Climpson

The biggest risk I’ve taken was relocating to a new city with a really big dream, and not a really big budget. I’ve always been an open-minded artistic individual, but where I’m from, that status isn’t really a visible option or life path. You’re either this, or that, but never are you celebrated for creating your own lane. Mostly because the type of life path you have for yourself is something only you can see, the individual, the creator. I was wrapping up my undergraduate coursework and I knew that I would need hands-on training to be competitive in the industry of fine arts, writing, and communication. I didn’t realize I would need to have a drastic change of scenery, but I knew that was the only way I’d be able to make an impact. Read more>>

Joanna Zeiger

I grew up in San Diego, CA. I loved San Diego — the weather, the people, at that time San Diego was a sleepy town without a lot of traffic. I truly didn’t think I would leave Southern California. Swimming was my sport. I competed since the age of 7 and qualified for the Olympic trial (the first of 7 in three sports, swimming, triathlon, and marathon spanning 1988-2016). When I applied to college, I looked at schools both on the west coast and east coast; however, my heart was calling me to UCLA. During this time, I was recruited to Brown University for swimming. I went to Brown on a recruiting trip during a cold, bitter March weekend. It was grey and almost uninviting. It was across the country. I didn’t know anybody. Yet, I loved it there and felt connected almost immediately. All other recruiting trips paled in comparison. Read more>>

Jessica Davis

I was facing a lay off in September 2012. I was only half bothered for I had been unhappy there for a long time and I would have some unemployment to help me get through the transition. A turn of events took that away and forced me to make the decision to leave what I should have left a long time ago on my own. Another company bought the old company and offered me my job back. I just could not see voluntarily going back to being so miserable and instead chose to jump off the cliff and sprout wings on the way down. At that time, I had been licensed for massage for over 12 years but had let fear get the best of me when it came to actually working in the field. I had kept up with my massage license because I am a just in case girl. Read more>>