Shoot your shot? Take a chance? Society bombards us with messages, phrases, examples and stories of how taking risk is the key to success, but is anything ever that simple? We asked some of the brightest folks we know to tell us about how they think about risk. We’ve shared their responses below.

Tom Sless | Singer-Songwriter, Artist, & Multi-Instrumentalist

When I think about risk, I consider two things: (1) risk doesn’t solely apply to “risky” activities and (2) risk is a factor not just in our actions, but also in our inactions. Risky activities are obvious: skydiving.. bull-riding.. passing up a secure corporate career path to co-produce a debut album (that was me).. but even in my day-to-day life, I’ve been presented with choices that are not obviously “risky” but involve risk. I risk failure in my career when I choose an extra couple hours of sleep instead of consistent morning meditation, reading, and writing. I risk a sense of loss when I let friends fall out of touch, rather than rekindle those burnt-out flames. I risk clarity when I prioritize a late night out over feeling fresh the next morning to tackle my goals. Read more>>

Michelle Gable | New York Times Bestselling Author

I am not generally a risk taker, but my career has definitely required a leap. Though I’d always wanted to be a writer, I knew my parents weren’t going to support any starving artist lifestyle. So, I did what any aspiring writer would, and majored in accounting! I figured I could write on the side. When I gave up my “day job” in 2016, I already had two published novels (including one New York Times Bestseller), and the third was written but hadn’t come out yet. Most people assume I left that job because I was finally making more money writing. Not true! I was the head of Investor Relations for a billion-dollar publicly-traded company and I was definitely making more in that job. But, it was no longer feasible to juggle both. Read more>>

Kristin Royster | Resin Artist

I have taken a lot of risks in order to get where I am today, and I have learned a lot from it. I took some really large risks, like starting my business full-time, signing contracts with stores to sell my work, and buying large amounts of supplies for new projects I wasn’t sure were going to be popular. Some of these risks took my business to the next level and some of them wasted a lot of my time and money. Overall, I have learned that it is best to take small risks frequently, rather than the occasional big leap. If I hadn’t started taking numerous, smaller, risks , my products wouldn’t have become as unique as they are. You don’t need to start off with a lot of products in large quantities in order to grow. It’s better to take small risks, see how successful they are, and then take the next risk. Read more>>

Lily Nicole | Master Life Coach & Content Creator

Taking risks is the only reason I am where I am today, with a 6-figure business, living in San Diego with more flexibility and time freedom than I’ve ever experienced. I’ve always been the type of person to “jump now, think later”, and while that mentality has gotten me into some interesting situations (like bank accounts in the negative and wondering where I was going to be living the next week) it’s how I quit my teaching career, made money from my computer while getting to be creative, moved across the country from Jersey to San Diego with 3 suitcases and a month’s notice, met my amazing boyfriend during a pandemic which led to a brand deal with Bumble… I can’t imagine not taking risks in my life. I honestly don’t believe that my style of risking taking is for everyone, but learning to listen to my intuition and jumping before all of the pieces of the puzzle are together is what allows me to have a birds eye view to PUT the pieces into place. Read more>>

Camryn Eakes | Dancer/Choreographer/Production Design

I learn the most from taking risks and, in turn, I love forcing my brain outside its defaults. And, a lot of what risk does for me is show me how or how not to achieve what I am going for. I’ve been greatly disappointed in myself after taking risks, but accepting that choice and moving on to your next venture is THE process. It’s part of my journey as an artist, and maybe the hardest part. Risks keep my life and career vibrant, and they keep me curious. Asking myself if I want to take a chance on something new is one of the first things I do when starting on a project. Being a dancer my whole life, I’ve learned to make choices on the spot and on stage, but through that I’ve learned that the choices that are “risky” are the most fun choices. Read more>>

Judyth Brooke Curtis | Actress & Producer

Calculated risk is a necessary part of growth and success. When I packed my bags and moved to Southern California, sight unseen, it was a risk. But I knew with every fiber of my being that I was supposed to be here. When I chose a creative career, I knew it was a risk. But it’s one I had to take. I think if you listen to your intuition, that quiet voice inside, you can sort out the bad risks from the good ones. And you have to be brave enough to fail, and brave enough to succeed. You can’t do either without risking something. Both are costly, but the rewards are far greater than never trying. Even failure brings reward, if you look for the lessons. Read more>>

Marissa Kay | Tattoo Artist/ Mixed Media Artist

In general I’d say that going into almost any creative or entrepreneurial field is a bit risky. I see risk-taking as a necessary and unavoidable part of my career, both in art and tattooing. I believe that longterm tenacity is the key to succeeding at most things despite how risky they are or aren’t. It’s not about taking a risk one time- It’s about choosing to take that same risk every morning you wake up. Read more>>

Mike Sheehan | Artist/Educator

You always have to be open to pushing yourself into challenging situations. It’s scary sometimes, but it’s essential to my growth as an artist/educator. It’s been a big part of my career. Putting myself in situations where I can absolute fail is what pushes my skill set. Read more>>

Nikki Neumann | Freelance Photographer

Life is a constant stream of calculated risks, some are more thought out than others, but every day we encounter risks. Some of the biggest risks I’ve taken have brought back some of the best rewards. Pulling myself out of complacency. Even moving to a new neighborhood in your city can change your life, probably not drastically, but it changes up your daily routine which can propel change in other areas of your life. I recently moved to a new neighborhood in LA and I’ve definitely been inspired by the local community here. I took a risk two years ago moving to LA. I decided to start my full-time freelance photography career and move to a new city at the same time. I felt like I was a little bit crazy at the time, but I like getting used to that feeling. I gave myself permission to go do what I wanted to do. Read more>>

Audrey Hermes | Owner, Frost Me Cafe and Bakery

Starting a business has plenty of risks involved, especially in the food industry. As I think of risk taking I weigh out who and how it would affect other people. If I truly feel as if the risk could only negatively impact my own life, I am more than willing to jump on it. When it starts to affect other people, I am much more cautious about my decision making and tend to lean on the side of safety. Now that we have a team of employees who depend on our company for their livelihood, every decision that is made has them at the forefront. I truly believe that their successes are my successes and vice versa. Read more>>

Julie Tremblay | Artist

Risk is the possibility of something bad happening. By that definition, almost anything you do has an element of risk to it. Risk is fluid. These days, just going to the supermarket is risky. That said, I have defied what people around me thought as reasonable or the “right thing to do” quite a few times, both in life and career. Of course I didn’t see it as such. It really comes down to intuition and how in tune with it you are. Every time I took a “risk”, I saw a clearing, something felt right all the way, like a flashing light that read “ALL SYSTEMS GO”. Every time, it turned out to be a great decision. That’s how I launched my career, by doing something that everyone “in the know” thought was “a very bad idea” but I knew better and had everything to gain. Read more>>

Renée Christensen | Director of Marketing at Léon & George

No risk, no reward! We’re all about risk. Read more>>