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.

Taylor Broen

In 2020 I remember seeing a post that stated, “Be the girl who just went for it.” That spark was one of the factors that contributed to my idea of going into business on my own. I didn’t have a business plan; I hadn’t even envisioned myself using my cosmetology license to be a wax specialist let alone being a business owner. Read more>>

Rachel Ballard

In March 2019 at the age of 39, I got up one morning and couldn’t lift my arms to put the dishes away in the cabinet. Everything felt heavy. Within 24 hours my feet felt like they were on fire–the kind of burn you feel when you’ve spent too long in the snow and have to come warm up. Read more>>

Denise Simmons

Nine years ago, I was sitting in my cubicle having a moment. I was frustrated, stressed, and honestly embarrassed that I had to train my own boss — who later became the biggest micromanager ever. She wanted to know when I went to the restroom and even made me email her about it. I felt like I was in jail. Read more>>

Kami Smith

When I started my first business at 22 years old, I had absolutely no clue what I was doing. I just had audacity. That same boldness led me to co-found BBLA, a daycare, in 2016 – stepping into an industry I knew nothing about simply because the opportunity presented itself and I trusted myself to figure it out. For years, that audacity carried me. Read more>>

Tyler West

One of the biggest risks I’ve taken in my life was walking away from my job at the Marriott. I had spent years in hospitality, showing up for everyone except myself. Eventually, I realized that if I didn’t take a stand for my own creativity, I would be sacrificing the very thing that made me feel alive. Read more>>

Jayme Watts

Opening our restaurant, Sassafras, was the biggest risk my husband, Tony, and I have ever taken. Anthony Fish, my husband, has been cooking since he was 14 years old. He worked in many popular, cutting-edge restaurants in San Francisco for many years. I had only ever worked in offices all of my life. I was introduced to the restaurant business by Tony. Read more>>

Anna Rezan

I moved to New York City from Athens as a teenager… Like people used to do in the 70s.. to pursue an international acting career…. to be a part of American cinema that I loved since I was a kid…While still appearing in Greek projects, I guess I moved to the U.S. Read more>>

Meg Stolt

Owning a business is a risk. Being a coach can be a safe place. Embracing the fact that I am the CEO of my business, and not just a triathlete that coaches runners, marathon swimmers and triathletes, is the game changer. As an athlete turned business owner, I have learned how to take calculated risks, as I do when racing. Read more>>

Crissi McDonald

I’m an established professional in the equine industry, as a trainer, instructor, and Masterson Method equine bodyworker. I dreamed a story that featured killer whales as part of the main characters. I thought it would be one book, but it turned into a trilogy and pulled me out of the 2020 depression that was so prevalent for many of us. Read more>>

Mary Jean Ruhnke

Honestly, becoming a full-time artist was the biggest risk I’ve ever taken. At the time, I was a mom of two little kids. I had a solid corporate career, a husband, a home, and even a farm that depended on my income. Read more>>

Elijah Wickerham

The biggest risk I’ve taken was co-founding a video game studio, JollyWare. I’m a lifelong illustrator and artist. That’s why it came as a shock to some when I started attending college for video game programming. But it wasn’t a strange choice to me. I believe the most important thing an artist can do is branch out and learn other skills. Read more>>

Kendra Waddy

I often feel like my entire life has been shaped by taking risks. If you had asked me years ago, I would’ve told you I preferred the path of least resistance—why make life harder than it already is? But even then, I knew deep down that “just enough” never felt aligned with my value or the dreams I carried. I wasn’t satisfied with simply surviving. Read more>>

Alessandro Garbagna

I think the biggest risk I’ve ever taken was moving to New York City all by myself to pursue my acting career. I left behind my friends, my family, my culture, and my entire comfort zone. It was a journey into the literal unknown. I don’t think I was truly scared until it became real. Read more>>

Nicole Sheldon

My journey to becoming a salon owner wasn’t a straight line. It all started in 2010 when I stepped into cosmetology school in California, knowing that I wanted to run my own show one day. But life had other plans. After getting my license, I moved to Michigan and faced the harsh reality of building a clientele from scratch. Read more>>

Max Wasa

The music industry is an ever changing landscape. When I started in the 80’s it was a very label heavy format. Where the label made an investment in the artists but the artists was in debt to the label for the bulk of their careers. I wanted to make a company that was for artists by artists. Read more>>

LYNDSAY HOFFMAN

Picture this… It’s October 2024. Before anyone ever walked into LTH Beauty… before the room was finished… before the events, the community support, the pop-ups, the partnerships, the gratitude… It was just me. Sitting in my car after my last day at a job that had drained me for far too long. Read more>>

Shelley Simpson

Some individuals refer to this as pursuing the allure of shiny objects, but my career paths have all started with unconventional decisions. When I embarked on law school as a mother of two adolescent boys, people thought I was crazy. Similarly, when I transitioned from law to politics and subsequently to health policy, my choices were again met with skepticism. Read more>>

Morgan Godbee

I would say leaving a salaried position to become self-employed/an entrepreneur was a big risk for me. I had been so lucky to basically stumble into full-time work after being laid off from another salary job just 10 months prior, but I knew that there was more out there for me professionally. Read more>>

Jordana Herman

2017 was the first ‘risk’ opening Roc Pilates. The studio had a combination of refurbished equipment and new equipment from Tecno Pilates in Italy. it was located off Main Street in an old commercial building. Just as the studio was finding a rhythm, the Covid Pandemic started. That was 2020. Like everyone, we were in a state of shock. Read more>>

Good Times Roll

One of the biggest risks my husband Chris and I ever took was deciding to buy a beat up 1973 Volkswagen bus and turn it into what is now the Good Times Roll Bus. At the time, it didn’t feel like a business plan. It felt more like chasing a dream. We both loved vintage cars, events, and anything that brought people joy. Read more>>

Ben Sturdivant

When I started Legacy Property Media, it was the biggest risk I’d ever taken because I stepped into an industry I didn’t actually know how to work in yet. I’d always wanted to build something that could scale. My family has a long history in real estate, and after years in the music industry, I realized the one thing I missed most was creating. Read more>>

Gregg DaCosta

The biggest risk I took was saving up a good amount of money and investing it on myself. I bought my camera gear, many times I paid for a crew and paid for the cast when it came to creating a film’s. The risk here was simply if I place this money into my craft, will I make this back? Read more>>

Deanna Jackson

In July, I experienced a moment that many people fear—being laid off from corporate America. What could have been a setback became the turning point of my life. Instead of rushing back into a familiar system, I chose to honor the vision that had been calling me forward. Read more>>

Cindy Van Pelt

Today, as co-owner, pastry chef, and COO of The Source Café, I lead our operations, guide an incredible team, and foster the mission of integrity at the core of everything we do. None of it happened overnight. It grew from one bold decision, a risk that quietly rerouted the entire course of my life. Read more>>

Hannah Dobek

In 2013 I answered a late night phone call from someone I barely knew. I was a barista and part time artist then, and full time single mother. I was up late working on a piece when suddenly, the phone rang. I almost didn’t answer it, but something told me I should. Read more>>

Grace Ashworth

Before I became a Massage Therapist, I worked at a locally-owned shop in Chico for three years. The hourly wage was decent, but the hours were limited, and it was difficult to make ends meet without roommates or very cheap rent. I knew I wanted more for myself, but I didn’t yet know how to achieve it. Read more>>

Karina Wenker

In 2022, when my oldest son was a year and a half, I took a big risk and left a marketing career I had spent more than ten years building. I had worked in agency and corporate roles for large companies on three continents, so stepping away from that path was a major decision. Read more>>