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.

Emilee The Visionary

The biggest risk I’ve taken is changing career paths to pursue modeling and styling. In 2019, I moved to small town Mississippi for college to pursue ministry. Amidst the quiet and calm nature of Bible school, I felt closer to God than I ever had. Read more>>

Christi Love Idavoy

In 2020 the world was faced with the unknown. My husband and I were both self-employed. With 2 businesses in the USA and one in Costa Rica, we lived and worked between the two countries. Read more>>

Megan Mendes

I had been working as a massage therapist for a busy chiropractic office for about 7.5 years. Over those years, I had worked my way up to being the lead therapist. Read more>>

Lena M Sleyster

It was Q3 of 2023, Urban Bounty Farms was in 11 grocery stores, delivering to consumers and restaurants around the KC metro, and I was still managing a full-time corporate career. Read more>>

Dakota Ramppen

In 2017, I eagerly began my journey as a sexuality educator, driven by a deep passion to educate and empower young minds. I would travel around Newark, New Jersey as a naive 20 year old with a bag filled to the brim with arts and crafts and the other with dildos, dental dams, and plush vulvas. Read more>>

Talon Frazier

With now becoming a television director/producer and Entrepreneur, its all about my creative expression and putting out my best work. Some times as an artist ” different types” we tend to want to create and publish are best meaningful projects. Read more>>

Crystal Ash

In 2022, I was burned out from a working extremely long hours as a Program Director at a startup organization. I was constantly stressed out and my nervous system was in shambles. Read more>>

Elizabeth Even

Six months after launching my business, I was considering all the different ways I could get my message out there and reach my nurses. I had lunch with a friend of mine and when he asked me about my business, I launched into a 7-minute stream of consciousness. Read more>>

Xavi De Guzman

My whole life has been about risks, but the biggest I’d have to say was moving to the west coast to pursue my art. As a former muay thai fighter – lightweight champion and Team Canada athlete, my only option to further my talents would have been to leave Toronto, but I chose to stay. Read more>>

Farhaan Hussain

let me take you on a journey through the chapters of my own story, a tale of risks, rewards, and a whole lot of pixels. You see, I’m a business grad who always had a soft spot for the arts. Read more>>

Jalena Hay

A defining risk in my life was pursuing art in college and receiving my BFA. Raised in a deeply traditional household in Southern California, where my Iranian father upheld traditional values, I often found myself restricted because of my gender. Read more>>

Shameka Jones

In 2014, I embarked on a new chapter in my career journey, joining a large IT & Business consultancy firm. With nine years of consulting experience under my belt, I approached my role with confidence and dedication, consistently meeting client expectations and contributing to the growth of my practice. Read more>>

Judy Penz Sheluk

It was 2003, and the firm I worked for was struggling. In an effort to stay afloat, several positions, mine included, were eliminated. I had an impressive record in the corporate world, but instead of looking for another job, I used my severance package to fund my journey into something I’d always wanted to try: journalism Read more>>

Taelor Jaye

Title: The Courageous Journey of a Young African American Entrepreneur: Turning Adversity into Opportunity Backstory: At the age of 23, Taelor, a young African American woman, found herself in a situation that seemed insurmountable to many. Read more>>

Shyra Divine

I had to make a choice to take a risk with myself and my career despite the outside influence from others. I live in a homeless program and one of their requirements is to work a job to provide savings for an apartment or other needs before leaving. Read more>>

Daniel Luckett

I left college after two years of school, hungry to become something more. I had a vision/ dream of being an entertainer of traveling and performing on stages, being on television, & building a team that would allow me to dream beyond myself. Read more>>

Alexandra Watkins

When I look back at the most amazing times in my life, it all began with the ability to take a risk. Taking a risk on myself, the opportunity…..walking in completely blind with nothing but faith in my heart. Read more>>

Sara Barrett

One big risk that stands out in my mind was submitting a collage I made to a local juried art show. Since having our daughter about 9 years prior, my artwork had taken a back seat to everything else. Read more>>

Christy Drescher

In my early 30s, I had the makings of the so-called “American Dream”: happily married with 2 beautiful kids, my husband held a steady job, I was able to see a few Pilates clients part time but still stay home with my very young children, we owned a home in a nice neighborhood, and had a good community around us. Read more>>

Dr. Simone Lewis

Eight months ago, I packed up my sedan and drove 613 miles from Florida to Georgia, without ever setting foot in Georgia before. Why? Because I wanted more for my life and my son’s life. Read more>>

Marisa Franco

Back in 2019, I was a 29 year old woman looking at the crossroads in my life. I saw two roads in front of me, two choices that determined my fate. Read more>>

Anna Lee

I received the Daniels Fund Scholarship after graduating High School, and attended Colorado State University. This was a full ride scholarship, and I decided to risk it on the Fine Arts, specifically Printmaking. Read more>>

Jennifer Barrett Fajardo

The biggest professional risk I’ve taken is making the leap to entrepreneurship and building a business when leaving my dream job in a state of burnout. Read more>>

Douglas Kenney

Sure. My name is Douglas Kenney. I’m a young social media figure known for the “R-U Relentless and Unstoppable?” YouTube channel, which has 3 podcasts behind it – Relentless and Unstoppable, Stories From Motorsports, and Stories From Motorsports international. Read more>>

Katelyn Camero

At the end of 2021, just a few months after my husband and I got married, I felt a tug to leave my job. At this time, it just didn’t seem like a logical decision, but I simply couldn’t shake the feeling which I know now was the Holy Spirit. Read more>>

Victoria Camp

Without risk, we stand losing the chance of what could have been. Read that again. Most associate the statement “taking a risk” with nervous connotation, an action that should be avoided if you desire security & safety… Read more>>

BMusique

Taking risks are important parts of living a your life on purpose. No of us asked to be and we were born into a life full of inherited circumstances. Read more>>

Eliabeth Frere

The biggest risk I ever took was giving up my full time job as a high school teacher (13 years) to stay at home with my children. Read more>>

Christian Wolf|

Growing up in a blue-collar town one finds oneself planning the trajectory of life through a large scope. The community is always in need of tradespeople, firefighters, mechanics, small business owners, and the list goes on. Read more>>

RACHEL NELSON

Starting Concetti was the biggest risk I’ve ever taken, because I wanted to create a business that does both residential and commercial design differently, more intrinsically tied to the human experience. Read more>>

Lisa Richardson

I would have to say my first risk happened during my undergrad when I decided to change majors from business to graphic design. I never knew what I wanted to be “when I grew up.” Read more>>

Kerrie Faye

I wouldn’t call it a midlife crisis because I’m not quite there when it comes to age. But in 2017 I survived a violent crash and after pushing through recovery, I found myself a year later ready to make a change–ready to take a risk. Read more>>

Caleb Kruse

In September 2023 I decided to leave the company I had been working at for 6 years. I worked my way up from a senior media buyer to the director of paid social, managing a team of 8 media buyers. Read more>>

Ashley Sargeant Hagan

Publishing my first novel was life and death to me, which is ironic, considering I write mystery novels! I was starting out older, having waited until my children were in school. Read more>>

Patrice Simpson

So, a few months ago I left my 9-5 to pursue a digital entrepreneurship course. That was a huge risk for me because it was a slow season for my virtual writing service and my 9-5 would normally help me out financially when being self-employed couldn’t cover all my expenses. Read more>>

Leslie Muhlbach

I have always been a risk-taker. Some healthy, some not-so-healthy. But it seems that when I was younger the curiosity of the consequence was so alluring. Read more>>

Dhwani Shah

My twenties have been characterised by taking risks. I switched multiple jobs, wearing the hat of an editor, producer, director and screenwriter, which allowed me to hone my skills and also find what I do best – directing. Read more>>

Caitlin Crooker

As a creative, the path I have chosen in life has always been seen as a risk. Not only by others but by myself as well. One of the biggest risks I have ever taken was changing my major to Motion Media Design at SCAD. Read more>>

Kalaija Mallery

Taking risks– and having faith in process– has been the single most defining force in my career. When I was an undergrad studying photography, I had only photographed women. Read more>>

Denise An

I am a part-time artist and a full-time Chinese medicine doctor/acupuncturist, who is planning a full-time future in art. I started making art as a child, and my parents gave me paint-by-number kits to calm my over-active mind. Read more>>

Jane Lowe

For as long as I can remember, I’ve always struggled with being comfortable with myself, believing in myself and self confidence was absolutely non-existent in my life. Read more>>

Jamar Root

If I had one mission to describe what I do, or who I am, it would be to inspire the world to do what they are passionate about and find success within it. Read more>>

Milan Zoe

Any business you ever start in your life will be a risk however for me they were all measurable risk. I have always been clear about what I was willing to invest – this includes not only money but also time, energy, and non material resources. Read more>>

Alexander Dupuis

When I get an idea for an animation that really excites me, there’s usually a little voice saying “that’s nice, but you’re not quite ready for that.” Read more>>