You’re working hard, things are going well, piece by piece you’ve built a life you are proud of, you’ve overcome obstacles and challenges, beat the odds and then you find yourself at the center of an unexpected dilemma – do you risk it all to keep growing? What if growing means leaving the job you worked so hard to get or the industry you worked so hard to break into? How we approach risk often has a huge bearing on our journey and so we’ve asked some of the brightest folks we know to share stories of risks they’ve taken.

Ryan Kline

I’m a huge advocate of taking risks. Whether or not you fail it’s always an opportunity to learn. I did that very thing when I decided to start shooting photos as a paid professional. I was a FedEx driver at the time and wasn’t exactly enjoying my job. I was overwhelmed with my work load and honestly drinking way too much to cope with the stress. Read more>>

Marisa Lowenstein

This’s the story of when I decided to leave my full-time job as a Senior Designer in NY to finish my studies so I could teach Vedic Meditation to other Creatives. As humans, we think that risk comes from change, but the key is to realize that it is safer to keep evolving than to hold on to something that is no longer serving us. Read more>>

Meg Sutton

I launched my company – Belle & Union Co. – in the late spring of 2012, at a wholesale trade show called the National Stationery Show. I had never sold a single greeting card, but I believed in my work, and knew that wholesale was the way to go to create volume and longevity for my new company. I had saved every penny I had made from custom wedding invitations to exhibit at that show – a huge risk in and of itself – but walked away with 52 orders, and the confidence that I had made the right decision. Read more>>

Annie and Ginger

We stepped into working with a population that often goes ignored or overlooked at best, oppressed and exploited at worst. Women and children who have experienced the atrocities of human trafficking and journey with them to bring Jesus, love, life and hope in the darkest spaces. Read more>>

Wendy Douthett

One way I have Taken risks with my business is the decision to direct and coordinate a fashion show. I recently had the opportunity to put together a festival and fashion show at Macy’s at Centerra in Loveland. I feel the fashion show went amazing! I took the risk, and it paid off with a successful fashion show, showcasing my talents as a personal fashion stylist. Read more>>

Marc Edward Winer

I took my first risk after working for other skincare companies opening my own solo skincare office I went from one room and 5 years later opened two rooms and 5 years later opened three rooms so I could offer more facials and rented the other rooms out but it became too much to manage then I simplified and went back to one facial treatment room and one skincare product retail room . Read more>>

Michael Kerley

Deciding to follow my path and pursue bladesmithing full-time is the biggest risk we have ever taken. I had been working full-time as a bladesmith since February of 2022, but Alyssa (my business partner and girlfriend) still worked a full-time job to help us through slow times. In September of 2022, Alyssa lost her job and it became apparent that the decision in front of us was going to be life-changing. Read more>>

Jill Magoffin

For 25 years, I found myself immersed in the corporate world, embracing the familiarity of regular paychecks and a sense of security. But deep down, I knew those positions weren’t where my true fulfillment lay. The dissatisfaction grew, and I yearned for something different, something that would ignite my passion. Read more>>

Ray Roselia

My family experienced a whirlwind of changes over the past handful of years – I became a mom & welcomed my son into the world in 2019, and then the pandemic immediately turned our lives upside down. Faced with some difficult decisions, we decided to take a big risk… my partner quit his job of 10 years to be a full time stay home dad, while I decided to grow my part time business into a full time endeavor. Read more>>

Tiffiny Wiley

In late 2014 I was diagnosed with a rare form of breast cancer and underwent surgery and subsequent treatment. The treatment nearly ended my life due to an allergic reaction to one of the chemo drugs. This reaction was also rare! A day before my surgery, I was laid off from the company I was working for at the time. Many years before my diagnosis, I knew it was time for a change. Read more>>

Nancy Williams

I’m a big believer in enjoying the journey and detaching yourself from the results of your efforts. So when I was really disappointed after not receiving a call back for a job I thought I was perfect for, I knew I needed a mindset shift. Each rejection is proof of putting yourself out there and taking a risk, so I decided to take a full semester to see how many rejections I could get, and to start celebrating them. Some results I expected – to be more willing to take risks and to have less of an emotional response to rejection, for example. Others were a surprise. Read more>>

Linda Espinoza

In the beginning of the year, I took a risk and decided to make my full time job as a therapist for a telemedicine company to work part time (about 7 hours a week!) to pursue my own full time private practice. The push to make this long thought out plan was a company restructure that was leaving me burned out and with low pay. Read more>>

Jacqueline Schmidt

When I was thinking of opening my own beauty boutique I really had no money to do it. At the time I had my three kids, debt, and a dream to be my own boss. I had the idea for my shop, what I’m passionate about, and the whole vision. With the little bit of money I had I put that towards the rent and deposit and I basically put the rest in God’s hands and told myself “If it works out then it’s meant to be”, and “If it doesn’t well at least I tried”. My husband is a carpenter/builder and built out the whole shop for me which saved us alot of money! Read more>>

Alison Woods

One of the biggest risks I have taken as an artist was spending nine months working on a technically challenging 8 x 11 foot painting. It was the first time I had ever worked on anything of this scale. The painting required a steep learning curve in researching and acquiring new technical skills. Read more>>

KC Garcia

Taking a big risk in something you’re not one hundred percent sure about is a pretty scary thought! At a young age we are taught skill sets to make sure we succeed in whatever job we decided wether that be medical, teaching or field jobs. To think that being a business owner is also an option wasn’t really talked about growing up. My entire adult life I worked with children and knew that’s something I always wanted to do. Read more>>

Megan Gillikin

As much as I like to think I tend to shy away from taking risks where I don’t know if success is the guaranteed outcome, I look back on my career and see that the decisions I’ve made have definitely been full of unknowns and risks at every turn. One of the biggest risks I took was leaving a full-time job with a guaranteed paycheck, and becoming an unexpected entrepreneur. Read more>>

D. Jones

Before starting D. Jones Reviews I literally had zero presence on social media but I decided to take a risk and launch the D. Jones Reviews IG page and fashion line “D. Jones Collections”(www.djonescollections.com). I know this decision is a huge risk as I am completely deviating from the life I’ve lived the past 21 years and it’s also a significant financial risk as well. Pursuing these endeavors requires a lot of investment in materials, production, equipment and marketing. Read more>>

Natalie Dungey

I always think about how the hardest choice is usually the best one for you in my experience. With difficulty and challenge, there comes growth. Hardly ever have I started something that changed my life in a positive way and thought “oh this is easy”. Even when I have tried to choose the easier path I get pushed in the direction of the road less taken anyways. Read more>>

Alyssa Farmer

Life! It’s the BIGGEST risk to take; learn yourself, learn what you like, learn what you will accept and won’t accept. It’s all about the lessons and how you react to them is the chance you take. Every day is a new opportunity to go after what you want! So I wake up everyday and take the risk with promoting myself, elevating and going after the life I want! The life I chose is creating each day, and pushing out all these visions I have in my head onto the canvas. Read more>>

Sheena Rae

The biggest risk I had ever taken was jumping both feet into working full-time as a hair and makeup artist. In January of 2020, I was working as an architectural designer at a job that I went to school for over 5 years for. I was working part time as a makeup artist at this time. I was balancing both jobs, taking time off from my day job to do makeup jobs. It came to the point where I had to pick. Read more>>

Kai Strachan

I think that often times in life, a lot of people are afraid of the unknown and are afraid to take a risk. My entire creative career has been about risks and just pursing what I love. It isn’t all flowers and sunshine, but that’s the fun in it. The biggest risk for me was packing up my entire life and moving to LA. I moved here in pursue of being a creative and ever since I made the decision to take the risk, it’s been a fun journey. Read more>>

Sadia Crosby

When I first began oyster farming, I thought it would just be a fun little side project that would allow me to spend more time on the water and share fresh oysters with friends. I should note- prior to starting my farm I had only eaten an oyster once and I was not a fan. Regardless, I loved gardening and land-crops so I thought it would be a fun new challenge. After my first few harvest, I received raving reviews from friends and family. Read more>>

Lisa Kellner

As a visual artist, you can be “known” for one type of work. Once you get momentum around that work it is exciting and gratifying. People request you for exhibitions, galleries begin to notice and sales start to happen. All part of the dream of being an artist. You work hard and start to see the payoffs. Read more>>

Jazmine McFadden

It is truly a pleasure to speak with you about risk taking. For me, I take risk daily as an artist and entrepreneur, however my first big risk was the day I became a full-time artist and small business owner. You see, I had spent 11 years in Corporate America as an Auditor with KPMG and with Bank of America in New York and Charlotte. Read more>>

Brandi Bass

Stepping outside of my comfort zone has always helped me achieve healthy goals. Starting my business with no help was a huge risk – financially, mentally, and emotionally. I had no idea what I was doing so I did tons of research and stalked similar businesses websites to get an idea of what I needed to get the ball rolling. I had to vet vendors and risked spending money on items that may or may not be great quality. Read more>>

Steven Revland

Growing up a musician….first performing on local television in 1963 as a 9 year old, I felt I was destined to be a performer, not really understanding how difficult that would be until a decade later. After taking 2 years of “wood shop” in high school in 1969 and 1970, I realized I may have a potential long term interest in furniture making as well. Read more>>

Lois Lambert

Every new business takes a risk. 35 years ago when I opened the Gallery of Functional Art, my first gallery, there was nothing like it in the US. There was 1 gallery in New York called Art et Industrie. They did some similar exhibits but they were not doing exactly what I had imagined. I had never worked in an art gallery. I had been around art all my life but this was a real business, and I had no experience running one. I was not a “rich kid” with backing. Read more>>

K Cornell Kellum

Interesting question, our biggest risk was launching a major Studio conglomerate, and as it turned out, the month before a pandemic. We have had several deals that fell through because of the timing such as an International $600M Funding / Distribution deal but we have still remained true to our goals, vision and focus. Read more>>

Melody Pourmoradi

When I first conceived The GiRLiFE Academy, I felt like I was embarking on a journey filled with uncertainties and risks. It was a business model that had never been tried before, and I had no idea if it would fly or not. But I was driven by a deep desire to make a positive impact, to create a program where women could learn how to empower girls using a curriculum that I had created. Read more>>

Deb Silver

Take the risk or lose the chance. The eureka moment? The Pandemic of 2020! During the pandemic I discovered an amazing gift that was always available, but eluded capture because of everyday tasks and responsibilities. I am referring to the gift of togetherness. Personally, togetherness is sharing a finely prepared meal at my dinner table with friends and family. Read more>>