By far, the topic that comes up most in our conversations with entrepreneurs and creatives is risk. We’ve had conversations about risks that worked out and risks that did not. We’ve seen eyes light eye sharing about career-trajectory changing risks as well as folks sigh about the risks they wish they had taken. Below, we’ve selected and shared some of those thoughtful conversations.

Michelle Angelic

Risks are chances made with destiny. We only have control of making the decision to take the risk, then destiny alters everything you thought you knew. It will change your life. Your insight changes. Your reasons for your drive change. Read more>>

Ashley Paige | Model & Model Coach

Risk, with discernment and caution, is an essential part of being an entrepreneur- human really. It allows you to break certain barriers you may have (or haven’t) noticed. I can recall a few moments where the risk taking value fed into both life and career. Read more>>

Pouono Valentino Malauulu | Bartender | Content Creator

In my life and career, risk has been a fundamental element, not just as a factor, but as a catalyst for growth and innovation. My approach to risk is shaped by my unconventional journey—dropping out of high school in the 11th grade propelled me into a world where taking calculated risks became second nature. Read more>>

Jessica Feldman | Senior Digital Marketing Manager & Integration Specialist

For many entrepreneurs and innovators, taking calculated risks can lead to significant achievements and advancements. However, it is important to balance risk with caution and thoughtful consideration of potential outcomes. Read more>> 

Zach Wetzel | Fine Arts Teacher and Singer/Actor/Director

Working in the Arts is a risk. Period. You never know where you’re going to work next. But that’s the fun of it. Fortunately, I have a day job teaching Music at BASIS Charter Schools and now Instrumental Music on weekends. Read more>> 

Jim Middleton | Songwriter, guitarist and singer

Risk is everything: In life are well as work. Anything that you love involves risk–to your ego, your finances, to your time and effort. Risk is what turns opportunity into reality. There are a lot of people out there who aspire to be musicians, to write and play music and get some appreciation back from the audience as evidence that they have something meaningful to say. Read more>>

Dr. Stacy Shepard | CEO, Author, and Principal

I am a huge risk taker, but I do not like to look at it as if I am taking a risk. I prefer to look at it as I am stepping out on faith. Every single decision I have made career wise thus far has been with the direction from God. I spend time with Him, so I am comfortable taking risks because no matter what happens and how hard things get, I know that with God I will not fail. I received my Ph.D. because I stepped out on faith. Read more>>