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.

Nicole Bernard | Founder, manager and chief maker – NB Makes

Risk and I are definitely “frenemies.” Despite a lifelong interest in the arts, I was told even from a young age that perusing a career in the arts doesn’t offer the same certainty or financial security as a “traditional” career path (whatever that is). I never regret the choices I’ve made in my life because they’ve set me on the path I am today, but from the time I applied for college until I left my first corporate job, every decision I made was rooted in that fear. Study advertising instead of fine arts. Interviewing for established companies instead of startups. Staying in jobs I’m not passionate exactly about because they pay well. Read more>>

Lee Trowbridge | Realtor

Risks in my career have always been very calculated. I am a contingency planner by nature, so before I make a decision, I have ten back-up plans, even if they are just in my head. I don’t make any moves or decisions without extensive research, and have learned over the years to trust my gut. With all of that lead-up, by the time I make the jump, I feel prepared. Read more>>

Tasha Whitaker | CHW & Wellness Enthusiast

Taking risk in life is necessary for growth. We don’t always know what the outcome will be when we make a decision just because “we feel” it’s the right thing to do and we go for it. I believe the gray areas of life, the uncertain times are when we grow the most because you are committed to finding the solution. Taking risk has built my confidence to use my voice and speak up for issues that matter to me which led to The CHW Crew Podcast that I created to elevate the voices of community health workers around the globe. Read more>>

Dan Martini | Guitarist for the Band Surge

Risk is inevitable in the music business you have to be prepared for it. there is no guarantee or sure plan that’s what we love. Its thrilling. we believe as a unit that if something excites you enough its worth the risk! if you approach life and you always ask yourself “what if?’ are you really living? this concept pushes us to look at risk and tackle it head on. we understand that risk can make or break a career in the music industry, but you won’t know if you don’t try. Read more>>

Apree Clicque | Therapist

A couple of years ago, I had the opportunity to attend a leadership conference where the theme was: Retreat? Hell, we just got here. That has stuck with me more than most views on leadership. It has helped me to harness energy to make hard decisions and be willing to sit in discomfort. Hard things take work. Often times, our brain wants us to quit – not because we are incapable of hard things, but because it would feel more comfortable. Read more>>

Déraj Austin | Plant Dad/Model/Musician

Without risks, you won’t know whether if you’re great or bad at something, if something will work out or not, etc! So for me, I love taking risks; it’s equivalent to having faith. Back in 2017, I took a risk on moving to Dallas, from Mississippi. I had somewhat of a plan, but honestly, I didn’t have a strategic plan. Overall, that one risk, has gotten me to Dallas and I’ve met an abundance of dope people since I’ve been here. “Take that risk, but be smart about it!” Read more>>

Lisha Hackney | Actor, Spokesperson, & Voice-over Artist

In the past, I would often say that it was important to take risks, but when it came time to act on it, my fear of failing would cause me to play small. As I’ve grown as a woman and an artist, I realize that having the courage and faith to step out of your comfort zone is where all of the magic is. I now see taking a risk as a chance to go deeper in learning about yourself. As an actor, the times that I have taken risks have led to the biggest creative payoffs. Read more>>

Rebekah Hedges | Full-time Photographer & Podcaster

Taking risks is a big factor in the way life’s unfolded for me. I’ve been given so many different job opportunities, from working as a Crime/Events Reporter to teaching English in Tianjin, China. Each opportunity had a lot of risk involved, especially buying a one way ticket overseas for a dream job. Yet every career move allowed me to explore what was really my ultimate passion, which led me to my career in full-time photography! Deep down sharing my voice through the powerful medium of photography had always been my way of sharing joy in the world. Read more>>

Briana Pass | Journalist

Throughout my journey of starting my podcast and not afraid to put myself out there. I’ve learned that taking a risk was part of the process. How can you expect to be great if you don’t build yourself with some type of risk? Step out of your comfort zone and allow yourself to grow. I did it. Taking risks has turned me into a BELIEVER, a BOSS & a LEADER. Read more>>

Stephan Harris | Realtor & Digital Artist

In order to reap the most rewards you must take on high risk. As far as my Real Estate business goes im engaged in it full-time. it was risky in the beginning however in the long-term you’re able to take in more information and learn from your mentors. Leveraging your finances, experience, and resources is essential for a risky endevour to succeed. Read more>>