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.

Gail de Giron

I moved from Omaha to Colorado without having a job nor a place to live. Just got in the truck and moved. Read more>>

Eric ESH Hornsby

In 2014 I had been in my environmental career for 10 years and was looking for something. I had dreamed of running an eco tourism business for some time by then. In fact I was in the process of starting a customizable eco trip business. I had bought six kayaks and had several mountain bikes and was spending time at the small business association try to learn how to launch. Somewhere during this process I had a realization, I realized I really could pull this business off! And I also realized with this same focused effort I could probably do anything. Read more>>

Dominic Stephen

Success is a constant game of taking risk. How myself & 90% of people growing up the people around them never really took any risk. It was always stay in school, go to college for 4-8 years and get a “stable” job then retire when you’re 60 from your 401k. But I really opened my eyes and looked around me and saw that none of these people doing that were successful. Yeah they might be doing just okay with a J.O.B (Just Over Broke) but none of them drove the car they really wanted, could take trips at anytime, had the house they really wanted, still complained about their job and still had a negative mindset towards money. Read more>>

Josh McFadden

One of the biggest risks I’ve ever taken was directing and producing a feature film. I had been working professionally in the industry as an actor for about four years by the time I decided I was finally ready to get serious with a scrappy little 70 page screenplay I wrote towards the tail end of my high school years and had been carrying with me since. By then I had built up a respectable network of people locally from the various projects I had worked on but I knew if this was going to happen I was going to have to step outside of my creative bubble and try to build up an audience as a complete nobody to all of the people I was trying to reach. Read more>>

Josh Nagel

My voyage through the realm of video production spans over a decade, tracing its origins back to my role as a graphic designer within a law firm. What began as a remarkable position gradually transformed into a full-fledged commitment to video, affording me the opportunity to cultivate my unique style and acquire comprehensive knowledge of the intricacies that underpin the video industry. Read more>>

Hannah Patten

My life has pretty much been a rollercoaster of taking risks, right from the get-go. I still remember my college days vividly – a mere sophomore – when I kicked off the wild ride that’s been Hülya Swim. It’s kind of surreal to think about it, but fast forward to now, and I’m almost 26. The twists and turns I’ve navigated since then have taught me so much. Read more>>

Chase Yi

Risk has become a tremendous theme in my life over the past few years. And as I’ve thought about it and how it’s affected me, I’ve realized that I’ve been taking huge risks since I first moved to Los Angeles when I was 18 years old. I grew up in a small town in Kalamazoo, MI, and after doing some plays and feature films around the state, I packed up my car and drove across the country by myself to pursue my dream of being an actor. At first, I thought I would become this famous actor with all the money in the world to take care of my family. I thought I would become a big star and that my life would be this amazing success story, but that wasn’t the case. Read more>>

David Sweeney

It seems to be the received opinion that one does not grow without taking risks. It certainly is the case with me – and the older I get the more I find that the risks are worth taking, and the less I care about the consequences. Mind you – I’m not suggesting people take financial or personal risks that edge on ruin. Our society isn’t quite supportive of that, and there sure is no safety net should one fail. So a million caveats about the fact that what I’m talking about are creative risks, artistic risks – professional risks to break through a duller habit, perhaps, or upend a conventional “This is how we do it, because this is how we’ve done it, so this is how it’s done” mentality. Read more>>

Jessie Marcus

I once wrote a blog entitled “Life is change and I object!” and I still feel close to that sentiment. Don’t get me wrong, I’m not one to want a repetitious boring life but change has frequently felt overwhelming and sparked that holy @#$% out of control sensation. So how do I respond to opportunity or change when I clearly prefer a permanent address in the illusion of the safety zone? Only through experience have I come to know that taking a risk offers me benefits that far outweigh staying in my realm of comfort and supports my personal growth. Read more>>

Demetrice Lopez

When it comes to career, taking risks can be scary. In 2022 my husband (co-founder of Clair Em) and I decided to take a leap of faith and start our own consulting practice based on our years of experience in the legal as well as our personal lived experiences. To provide some context, we are normally both low-risk, practical, by-the-book type people so deciding to branch out was scary. Thanks to our faith in one another, our faith in God, and our commitment to being the change we wish to see in the world we started Clair Em Motivators, LLC. It has been one of the most fun and rewarding experiences of our lives! Read more>>

Chef Irie

Now this s an interesting question. One that I’ve answered many times since becoming a chef. each time i tell it though I’m amazed that I made the decision I made. So.. I am from Jamaica and I’ve been here in the US nw 38years. Education in the islands is not only taken seriously by the institutions but also by the students as well. It’s a sense of pride to know that you went to primary shool, took an exam that placed you in one of the high schools of your choosing upon susccesfully passing then matriculating grade 7-11, take another exam that allows you to graduate and subsequently allow you go on to complete grades 12-13 should you choose to do so providing that you had passed enough exit subjects. Read more>>

Natalie Averill

About four years ago, right before the chaos of the Covid pandemic, I hit a point in my adult life that felt like a major life changed needed to happen. I was mostly home with my two small children acting mostly as a stay at home mom. I taught Pilates successfully over the prior ten years, but never completely committed my time to it. When I was home I realized I was beginning to lose myself and the sense of independence I once had. I took a big leap after a long conversation with my Husband. I was going to either purchase the current studio I worked at, or I was going to go out on my own. Keep in mind I had no savings and no idea if I could even get a loan.  Read more>>

Joy Bosley

Starting out as an aspiring model I learned that nothing comes easy in life. I also learned that if you have a passion for it you must take risks and go after what you love. I have battled through life obstacles and made investments that were risky. I started as a model at the age of 18 and went to auditions, castings and fell into scams that were disappointing at the time. Each disappointing scam led me closer to the real deals that I embarked on later in life. It all started when I risked everything at the age of 18 to drive from Alabama to Miami Florida with nothing more than a few dollars to spare by the time I arrived. The reason I drove to Miami was because of a casting call for Magic City that aired on Starz in 2013. Read more>>

Melissa Green

Starting a business was a risky move, but we were determined to make it work. We knew that we could keep our overhead low by operating primarily online, but we still had a lot to learn about running a business. In our first year, we focused on building our community with military spouses. We did this by attending vending events, selling coffee, and connecting with people on a personal level. Our efforts paid off, and we quickly built a strong following. Read more>>

Andrea Seider

Starting any kind of business endeavor involves some risk. Starting a business at a time when you are knee deep in the thick of raising two tiny humans is also pretty risky. What if all this time spent up at night and during nap times and in the wee hours of the morning ends up being a waste? What if the money I’ve invested ends up being lost? What if no one even likes what I’m doing? What if I should be spending more time with my kids instead of working on this dumb dream of mine? Read more>>

Lyrical

In 2012 I took a risk a left my corporate career as a Disability Case Manager for AT&T and stepped out on faith to start my own business. Lyrical Eyes Management I began managing different talent around the Chicago Land area and really made a name for myself. We are now in 2023 and I am stronger than ever. I have managed talent all over the world from Lil Durk, Tink, Ravyn Lenae who is now signed to my label at Three Twenty Three Music Group, Vicki Street, ChinaShadae, Freddie Old Soul, Kylin, Camari Gilbert and a host of so many more past and present. Read more>>

Chelsa Darling

Turning your art into your income is not all the sex, drugs and rock ’n’ roll I was led to believe. It’s actually a lot of taxes mixed with near-constant anxiety, met by endless decisions. There’s ever-evolving technology to adapt to and we live in the dawn of “Everything is content”, so you also need to film everything you do as a creator in hopes your audience will see you and hesitate just long enough on your art mid doom scroll. Read more>>

Tammy Adler Foeller

I would have to say one of my greatest risks has been disclosing that my daughter was suffering from substance use disorder. Our family had been hiding in the darkness for so long, it just seemed normal. I never wanted anyone to know. There is so much shame, embarrassment and isolation that is part of this disease, it just seemed best to keep it a secret. I was so concerned about the judgment that would follow. I feared our church friends would not want to associate with us. I didn’t want people to think I had been a bad mom, or that our family was somehow responsible for her disease. I wondered if we would lose our friends. Read more>>

Minoti Vaishnav

I moved to Los Angeles from India when I was 19 years old to work in the entertainment industry. I didn’t know a soul here, but it didn’t matter to me — I was going to make it no matter what. I hit the ground running when I got here, producing music, events, film and television all while getting my degree in Screenwriting. After college I worked in documentaries, then in unscripted television for every major network from Discovery Channel to Netflix, and finally found my way to my passion — scripted TV, which is the medium I currently work in. Had I not taken the massive risk of changing my entire life and moving here on my own, I wouldn’t have a career as a successful TV writer and producer. Read more>>

Karlee Hart

Growing up, I knew I wanted to be an entrepreneur, thanks to family members before me who were business owners : my Father & Grandfather particularly. I always felt that I was chasing something in my early years, usually sports-related. When I got to college as a Freshman, for the first time in as long as I could remember, I wasn’t playing a sport and wasn’t being challenged physically or mentally like I was used to. I dived into extracurriculars such as a sorority, but didn’t necessarily feel I fit in to that lifestyle. COVID-19 hit during my sophomore year, so I found myself spending a lot more time at home / off campus than I would’ve ever imaged as a college student. Having this driven, business minded approach to life … I was searching for purpose in the not-so college years. Read more>>

Jerry & Deidre Vigil Cordova

We have both always had jobs that were in creative fields. Jerry majored in Graphic Design and spent almost 20 years working for Design firms. During that time, he was usually balancing playing bass in 2-4 bands, as well as doing studio and session work. Deidre spent 19 years in the Beauty Industry as a hairstylist, salon owner and traveling as a National Hair Color Educator. We were always on the go, running past each other in opposite directions. But then Covid happened. It sent our world into a screeching halt. During that time, we learned to slow down and see the many beautiful things in our world that we had been running past daily. Read more>>

ShaeisLove

Taking a risk for me was the day I decided to no longer live in fear of being a Sex Educator publicly. I can recount the hundreds of conversations I’ve had over the last decade and a half with my peers, both men and women from across the sexual spectrum. Those conversations were so powerful and impactful, because I was able to learn about the nuances of people, relationships, sexuality, and the way society and our upbringing shapes our belief system. Read more>>

Cesar Barrios

So growing up I remember always being told I need to have an idea of what career I wanted to pursue by the time i graduate high school. It put a lot of pressure on me and caused me to get a degree I have absolutely no interest in. After graduating college I realized I needed to make a change and pursue something that makes me happy, and decided I’d move to California to chase my DJ career. Shortly after making that decision, the Covid pandemic began and nationwide lockdowns began, and tons of people started to get laid off. I was a bit nervous of the risk I was about to take, but I was determined. Read more>>

Beth Herriman

In my mind, I’ve always been risk adverse. I’ve been a stay-at-home mom with kids and pets for many years, lots of ideas, but until inventing the dooloop I’d been reticent to take the next steps necessary to push any design idea forward. Not having had a career in a long time, spending family resources on the dooloop idea was terrifying. I’m not used to/comfortable with investing in myself. Also, it was scary because there was no start small and grow with this sort of item. It’s only affordable if you make a lot at a time – and startup costs were significant. Read more>>

Suzanne Elizabeth Murphy

Everything great that has ever come into my life has been a result of taking a risk or some giant leap of faith into the new and unknown. When I lived in NYC decades ago, I wrote the following for a weekly writer’s group I helped found. The words come from my first experience of scuba diving in the Netherlands Antilles. I was fearful during my training in a cold lake. The wet suit, big fins, mask, heavy oxygen tank, weight belt, breathing tube and regulator. All made me feel clumsy and not myself. I had to learn how to make it all part of me. After all, I was becoming a fish! Read more>>

Nadja Sayej

I take a risk every single day that I choose to pursue my career. Every flight I book, every meeting I attend, every event I go to is a risk–because I could always be somewhere else, or doing something else. I have to actively take steps to take a risk every single day, basically. It never stops. But it’s always worth taking a risk for your career. You have to keep hustling. Never give up on your dreams, no matter how big the obstacle is in front of you. You have to never stop believing in yourself. And let’s face it, if you’re a creative or an artist, you truly have a gift. Use it. Get out there and share your beauty with the world. You never know what’s next on your path if you pursue your passion. Read more>>

Sam Respass

So a little over a year ago I thought to myself “Why not start hormone replacement therapy?”. I’d heard estrogen is great for growing your hair out and I was dealing with a bit of thinning round the temples. Obviously I was aware that people would hear I’m taking estrogen and think I was trans, I am, but at the time I was just looking to grow some hair. When I went into Planned Parenthood and told them it “Seemed like it was time” I was able to get a prescription for estrogen the same day, that was awesome. I can’t remember the exact date but I’m almost certain I did it on April 20th because I thought it would be really funny, and it is. Read more>>

Sandra Lin

The biggest risk I took was walking away from a very comfortable career I had in the medical field to pursue being a tattoo artist. I made the decision to jump and risk it all. I knew I wanted this, I believed in myself harder and stronger than anyone else needed to. I knew that if I jumped, I would work harder than anyone around me, and I would make sure I didn’t fail. So I did. I had the incredible support of my now wife. But I knew that I had to take that risk if I wanted to change my life and live my dreams. Read more>>

Kei-Ella Loewe

In 2020 I found myself at a crossroads. As a 27-year-old I had left my previous career as a theatre-maker and stage manager back home in South Africa, immigrated to The Netherlands and was starting over. I needed to reimagine a career for myself in a country where I didn’t speak the language and had no money or network. A month later the global pandemic hit. Later this blank slate would be a blessing, but at the time it felt like a jail sentence. I felt I needed to protect myself by choosing a financially safe career where I could earn a living without going back to University. Read more>>

Thomas Riccio

In 1988 I was hired as an Assistant Professor of Theatre at the University of Alaska Fairbanks. I had left my job as artistic director of the Organic Theatre in Chicago, resigning disillusioned and spiritually exhausted. The theater had become increasingly corporate and took from me without giving in return. I had the same feelings I had when I was a teenage window clerk for McDonald’. I felt trapped in American theatre’s bloodstream, only to find I was an industry worker selling a consumer product. In my heart, I knew theatre had to be more than subscription series, grant hustles, good reviews, and cocktail parties with corporate sponsors. Read more>>

Tracey Tischler

I’m 57. My daughter, Jessie, is going to be 22 this month and is graduating college as a teacher and also working in special needs. I have been a single mom since she was 1. She graduated summa cum laude in high school and she has a 4.0 at Pacific Lutheran in Tacoma, WA. She is also the coxwain and captain for the Lutes rowing team. I did a good job and my parents were all helpful and very supportive. I’m the youngest of six kids, 5 girls and 1 boy. Here is the order, oldest to youngest: Sandy, Chris, Pam, Al, Kim and Tracey (me). My sister Chris found out in October, right before I turned 28, that she had an aggressive form of cervical cancer. Read more>>

Alison Miller

I am not a risk taker. I’m not impulsive and I was raised to save, and hoard my pennies. Because of the aforementioned saving and hoarding of pennies I was able to realistically consider purchasing the fledgling, failing lingerie store where I’d been working for a year before it started to go under. I opened my first adult store for $10,000 (paid over the course of ten months) when I was 23. For moral and financial issues, my family didn’t support me. I did find support in my boyfriend at the time who promised he could provide for us both with his anticipated, and never realized, inheritance from a tattoo mogul. I got lucky, I say, but I also worked my ass off, and my business quickly prospered and grew. Read more>>

Jessica Stahl

Booking a one-way ticket to Amsterdam, a city I’d never been to before, after a sudden breakup and without a job was the biggest risk I’ve ever taken. I’ve always loved traveling and exploring new places, so when my boyfriend dumped me out of the blue, I thought, “screw it, let’s go.”The truth is, big risks like this have never felt like risks to me. It’s more like following a neon sign that reads “THIS WAY” with an irresistible pull. Read more>>

AJ Grey

I had never been out west before, so my partner, Taylor, and I decided to hit the road in our van back in 2021. We both felt a desperate need, after being cooped up in or home during Covid, to get a good shot of nature on steroids. Savannah, Georgia has a natural beauty of its own breed, with its grandmother oak trees cloaked in spanish moss that seem to be slow dancing to jazz with each small note of humid breeze, but we needed a vast nothingness so we could exhale. We started our route up north and made our way to Badlands and Yellowstone, Moab and Flaming Gorge, all the way down to Gila National Forest. Read more>>

Tiffany Ramm

The biggest risk I every took was staying in Los Angeles after surviving infidelity, financial abuse, and a devasting divorce which left me estranged and abandoned with only $37. I had always wanted to leave the Midwest, being a native Minnesotan, and live in a warmer climate, so despite my huge setbacks I insisted on staying and making it in Los Angeles. Prior to moving to Los Angeles, I was a full-time school social worker, part-time non-profit Executive Director, and part-time talent (tv hosting and modeling). My then husband got a new job which moved us to Sacramento. Read more>>

Stephanie Olivo

I was a business owner with my late husband for 10 years and when he passed- I closed that business and realized I didn’t know what I wanted to do with my life as a career/business. I decided to get my Real Estate license, but something was missing- I felt I couldn’t express my true creativity with real estate because I was so involved with medical- felt I still needed that to be in that world. Read more>>

Marcus Bruggom

May 1st, 2004 I turned 18. I was legally allowed to sign the loan papers for a wakeboard shop in Okoboji. Iowa. This is the story of Warped Incorporated. Growing up, you couldn’t keep me on the ground. I climbed anything and everything since I could walk: trees, buildings, rocks, boulders, rope, no rope. The details didn’t matter, I just wanted to go up. Sitting still was never a strong suit of mine. I got my first skateboard when I was 6 and skinned half my face off on the first day. 30 years later, I still skate. The only difference; now my skateboard has a motor and goes 22 mph. Read more>>

Summer Owens

In June 2010, I published my first book. It was my memoir detailing my journey which included becoming a mom at 15 by someone I didn’t know. A forced sexual encounter that changed my entire life. However, it also included my unexpected extreme success. As a teen mom, I graduated number 8 in my class of 302 students and was selected Most Likely to Succeed. I earned a full leadership scholarship to college, graduated magna cum laude, and was named Miss University. My son by my side through it all. I started my career with the Memphis Grizzlies (NBA team) in marketing and earned an MBA. Read more>>

Daniela Campos

Four days after I graduated college, I packed up my life from a little town north of Corpus Christi, TX and moved to Austin, TX. No concrete job prospects, no certainty or any ideas of how I was going to turn my Communication (with an emphasis on Media Production) degree into a career. Just me, my loving and supportive boyfriend, a surprisingly (and kinda depressingly) small amount of belongings, and the over-inflated confidence of a gal freshly graduated. I was convinced I was gonna run ATX one day, and I can proudly say that today, I am not and probably never going to. Read more>>

Bryan Tucker

My big risk. My first big risk started back in 2016 when I graduated high school and moved to Atlanta to be with a man that I had only known for less than a year. It all started back in December 29, 2016. Me and my family was staying in Paris, Tx. Witch a small circle in the middle of no where. I had just left football practice and was headed home for the night. As the night was coming to a end, my cousin rushes into the room asking me for a late night favor. She was my ride or die family member at the time so i couldn’t say no. Read more>>

Lauren Dickson

The biggest risk I’ve ever taken was starting my business on my own. At the time, I had a client turned mentor who mentioned to never start a business without a years worth of savings to live off of. I was 100% commission at the time and I was doing quite well at 27 years old, to most people it would have seemed crazy to leave that behind. But I had big dreams that I would never achieve where I was. I saved up a years worth of income and the week I hit that number I had two choices: pay off my student loan debt or start my own interior design business. I quit my job, took a month to sort through life and get the business set up, and immediately went to work. I don’t come from money, I don’t have a wealthy family member to catch me when I fall, and I didn’t take out a business loan. Read more>>

Whitney Ingram

In December 2019 I put in my notice at my job and a vacation request so that when I came back from my trip I would be done with that job. I went to Hawaii in January 2020 and came back without a safety net. I was so ready to begin my adventure as a freelance photographer! I had never really believed in myself before then and I still struggle with reassuring myself from time to time, but as soon as I got back I was landing client after client and sustaining myself! I was so confident for the first time in a very long time. Then Covid hit. Read more>>

Zipporah Cooper

The Risk I took was Betting on myself, with my charm, my own survival tactics and inner knowing. After my car accident in 2015 I went back to delta airlines for a brief stent when I was in the office not doing much of nothing “I started to work on a book Queens vs Concubines based on The Principles of the Bible. Then after I left Delta, I started my own Full Wave marketing and Movie production Company and also establish my own Foundation Called Upon This Rock Foundation World a Cross globally supporting Foundation always looking for more donations and support to keep being a vital organization for Charites to get funding from and then I began to take my brand image on social media more seriously.” Read more>>

Suzanne Sendel

I spent most of my professional career catering to architects, designers, hotels and property owners. I had a sales agency that provided interior furnishing to various installations, across North America. On a vacation, my sunglasses broke and as I was having them repaired, I discovered a very cool pair of hand painted eyewear, that I simply couldn’t resist purchasing. A year later, I wrote the manufacturer and then scheduled a Skype meeting, (10 years ago, there was no Zoom!) Read more>>

Natalie Ellison

I was always the shy girl. You can ask my family and they will tell you They never thought of me being a comedian. Even I can Tell I never thought of a path like this it was just something that was for fun but the more i developed this drive this thought process of entertainment. I needed to take the risk no matter what friends and family said. It became more then this “WANT” that want grew into a “NEED.” But What is life without taking risk? Read more>>

TORY KEIT

Starting the Oasis Community Foundation was not just a dream; it was a leap of faith—a calculated risk taken with the hope and determination to make a tangible difference in the lives of the underprivileged and marginalized. I moved to Atlanta in 2006, fueled by a burning desire to create something monumental that would leave a lasting imprint on the world. After years of networking, learning, and laying the groundwork, I took a significant financial plunge by investing a considerable portion of my savings to establish the foundation. Read more>>