The chapters in our stories are often marked by wins and losses. Getting a new job, getting fired. Getting a life-threatening medical diagnosis, beating it and getting a clean bill of health. Too often, due to a societal expectation of modesty and humility we are discouraged from talking about the risks we’ve taken that led to those ups and downs – because often those risks draw attention to how we are responsible for the outcomes – positive or negative. But those risks matter. Those stories matter. We asked some brilliant entrepreneurs, artists, creatives, and leaders to tell us those stories – the stories of the risks they’ve taken, and we’ve shared them with you below.

Brittany Garrett

Overall being a makeup artist is a risky job, we don’t have job security most times because makeup is still an unappreciated art for most. We often times are only celebrated in the movie and entertainment spaces. Read more>>

Scott Bruckner

My day job was as “in the box” as you could get. I worked in the insurance industry for a Fortune 500 country based in the East, the wing tip capital of the financial sector. I was once told I needed to ditch my wingtips because they had tasles on them. I thought they were stylish. Read more>>

Andrea Vargas Moreno

Back in 2020 during the Covid-19 pandemic my friend, and now business partner, and I decided to start our own company. This was a huge risk at the time due to how devastating the virus was, and it ultimately shut down the world. Read more>>

J Y

At the beginning of 2023, I decided to leave Los Angeles for a year to develop a more solid plan. I felt that I was moving way too fast in life and at the same time it felt like no time had passed at all. Read more>>

Eric Goins

After many years of working in the corporate world, my friends took me to an improv theatre on my birthday in 1998. I was amazed by the players on stage, so I signed up to audition for improv classes. That’s right, I had to audition to take a beginner’s improv class. Read more>>

Jaxyn Troy

In 2021 I decided to transition from fashion to music. Both arts have been a love of mine since childhood, but over time I let self-doubt, shame, and fear control my ability to pursue a music career. Read more>>

Vaishali Jha

In the realm of leadership, I discovered a profound truth—one that underscores the imperative of taking risks, being vulnerable and compassionate as a fundamental catalyst for positive change. Read more>>

Big V

I started working at UPS in 2003, solely because i needed a job in college to pay bills and help fund my music career. I hated it everyday and i was there for 10 years. Read more>>

Neva Leoncini

I am a full time Opera Singer from Florence, Italy. Spring 2022. I am singing in my hometown and I have a fulfilling career, I live close to my family and friends, I am content, but still something is missing and I don’t get what exactly. Read more>>

Erica Cope

The biggest risk I’ve ever taken was the decision to take over the lease of the Alt Theatre back in 2013. I was just out of grad school, did not have a job, or any income, or any business plan, but that didn’t stop me from opening an aerial studio anyway. Read more>>

Aleksandra Kay

I graduated college in May of 2020 with degrees in Psychology and Criminal Justice in the middle of the Covid pandemic. I had to figure out something to do to earn money, but with job-hiring being at a complete standstill, nothing was available. Read more>>

Erica Balk

At the age of 25, I found myself standing at the pinnacle of my career dreams. I had climbed the corporate ladder within a company I had devoted years to, and I had finally landed the coveted role of a manager. Read more>>

Shandra Davis

After completing my doctoral internship, I worked at an community outpatient program in their children and adolescents department. I loved working there, but it was made clear that upon getting licensed, they could not afford to keep me. Read more>>

Katie Fenske

I was a classroom elementary school teacher prior to becoming a mom. Being a working mom was a very challenging transition to me. I moved to an independent study charter school when my oldest son turned one. Read more>>

Ava Samuel

At Hotbox, every month we have a studio-wide focus. For February, our studio-wide focus is the second law of transformation (derived from Baron Baptiste’s 12 Laws of Transformation), “Be Willing to Come Apart.” I think this theme is very fitting when I think about taking a risk. Read more>>

Stephanie Urbina Jones

At the age of 33 I was a successful songwriter, living my dream, carving out my heart in song. I had a long ago given up my dream of being an artist performer. I had had a vision when I was four years old. Read more>>

Amanda Adams

I was a pediatric therapist most of my career. I owned a private practice with some friends, and I thought that was what I was going to do the rest of my life. However, at the beginning of 2020 I found myself super burned out, experiencing strange symptoms, and having debilitating panic attacks. Read more>>

Latonya Littlejohn

I found my biological family in 2010. My adoption was supposed to be closed but as fate would have it,I learned who my parents were and where I came from. I took this information I had and went to facebook where I found two of my biological mother’s sisters. Read more>>

Julie Sestrich

I grew up in the small town of Baker, MT (population < 2,000) as my parents came over as refugees from Cambodia in 1980. Looking back at my childhood and circumstances, some presume that an environment like this lacks significant opportunities because there aren’t high profile activities and there are limited programs and resources. Read more>>

Ram Agrawal

Taking a risk is part of any activity you do. When we first had this idea of bringing Indian arts, music, dance form at one place, we thought of arranging a small event but in a central place and keep it for free to the public. Read more>>

Tim Hall

Taking risks is something we all must do. 2 reasons why… #1 Our ego wants us to stay in our comfort zone in what we know and can easily handle.  What your ego doesn’t realize by taking risks, you learn so much more about who you are when under pressure and how you handle new experiences. Read more>>

Chance Kittle

When I first graduated from Boise State and moved out to Austin, I set a goal of reaching out to Coaches or Trainers that I looked up to and would set the task of shadowing them no matter where they were in the world. Read more>>

Ashley Temaat

In 2019, my husband Paul and I were working in the real estate industry together as a team. Economy was great, business was great but after you’ve been in real estate for several years, you realize it ebb’s and flows. Read more>>

Donnabelle Casis

I was scheduled to have a solo exhibition of my paintings and prints at the Amy H. Carberry Gallery in March of 2020. It was up during the beginning of the pandemic, and ended up having to be deinstalled after only 3 days, when the gallery shut down because of the spike in COVID cases. Read more>>

Susan Gonzalez

My dream was to be an amazing Deaf teacher of Deaf/DeafBlind/DeafDisabled/Hard of Hearing/LateDeafened (Deaf*) children. Or so I thought. I worked for San Francisco Unified School District (SFUSD) for almost 13 years. Read more>>

Felix Werner

The greatest professional risk I have have ever taken is the project I am working on right now. It’s a crazy idea (or maybe not) with a crazy name, derived from the dutch painter Hieronymus Bosch. Why Bosch? His fantastical images seem so fitting in today’s complex world and they still inspire some 500 years later. Read more>>

Aki Sano

I don’t know where to start, so I will just begin typing. I am writing this from my new flat located in the beautiful city of Marrakech, Morocco. For those who may not know, Marrakech is situated in North Africa below Spain. Read more>>

Lauren Perna

The biggest risk I’ve taken is starting my business during the middle of the pandemic with no actual plans in place–just a far-off dream that I didn’t intend to execute for a while. But the universe had other plans, so I leaned in and made it happen. Read more>>

Jillian Jensen

Embarking on my entrepreneurial journey with the launch of Jillian Jensen Events in 2015 was an absolute leap into the unknown. I had only been in the full-time working world for 5 years and on top of that was expecting the arrival of my first child. Read more>>

Pamela Mitchell

Last year my husband and I decided to uproot ourselves again after 9 years living in Los Angeles, and we moved back ‘home’ to NYC. I’ve been very fortunate to be a working actor for the last 8 years with no other survival job, and a large portion of that truthfully has come from SAG-AFTRA commercial work in LA. Read more>>

Monica Brooks

I vividly remember sitting in a meeting with VPs, listening to information that I had no interest in. That moment was a turning point for me; I knew that I didn’t belong there. Fast forward to 2021, I finally decided to leave my corporate job, but the journey started in 2018. Read more>>

Nicole Leffler

The road to entrepreneurship has been filled with risk and change for me. It began with a radical shift from the construction industry (where I ran a residential remodeling firm and was a Licensed Builder) into the holistic and alternative health fields. Read more>>

Carla J Lawson

The biggest risk that I ever took in my life was deciding to be a full-time visual artist and acting on it. I had worked my entire life in retail and customer service jobs that paid me quite well. Read more>>

Jeremiah Cobbs

Every time I drop a product I take a “risk”. To produce a quality product on a small scale is not cheap. Most factories MOQ for a small order is 300 units. It’s truly an investment. Read more>>

Lari Shantrice

Risk taking was never a thing of mine unless it was small and calculated. I’ve always had big dreams and ideas but never executed any that required to take on big risks. Read more>>