Risk-taking is at the heart of making a difference, but often we’ve been conditioned to avoid risk as much as possible. So, we asked some successful risk-takers to talk to us about how they developed their comfort with taking risk.

Rakel Kieding

My father taught me. An early memory comes to mind: I’m probably about 3, at home in Sweden. My father lifts me up on the shed roof, says “turn around, and fall backwards. I’ll catch you.” I did, I trusted him. He was an unusual father, for better and for worse. Growing up with a mentally ill parent is hard and comes with a cost, but I have also received the gifts of his deep soul. He taught me about beauty and reverence, and planted the seed of an adventurous life, not risk-free, rich in failure and learning about discernment, self-worth, love, grief and acceptance. Read More>>

Heather Van Dyke

My evolution as a tattoo artist has been deeply intertwined with the willingness to embrace risk and learn from every experience. For me, a ‘risk’ isn’t a negative, but rather a new opportunity for artistic growth and innovation.

Stepping outside of familiar styles and experimenting with new techniques, color palettes, or design concepts, its all a risk. There is always the possibility of a less-than-perfect outcome, but I view each attempt as invaluable data. Every ‘mistake’ becomes a powerful lesson, refining my understanding of skin as a canvas, ink behavior, and the nuances of different approaches. Read More>>

Josh Rech, Seth Deming, Garrett Black, Dan Kapper, Lucas Mroz, Ariel Báez

Josh: There have been some risks that have been pretty scary for me to do. But when I image a life without taking risks seems boring. I’m such a future thinker, so I’m always looking further down the road for my decisions in life. I kind of play that movie in my mind when I think, should I just work a steady job that I know can pay well, or should I take that risk and do what I really want to do and feel made to do? And that paired with the foundation of my life, which of my relationship with God, I feel freedom to make those choices, because I know He will take care of me and my family. And it’s really helpful to take risks from this place even when I’m terrified. Read More>>

Ruthie Harvey

To be honest it took time to just go for it confidence can be built, in my case it was a hobby that has turned into a mobile nail spa. Something that if you would have told me I’ll be making a career change in my 30’s I wouldn’t have believed you. Now that I’m on this journey I’m excited to see what the next chapters have in store for me, launching a mobile nail business in the city of Jackson, MI will be the first. Read More>>

Amy Schissel

I’ve developed my ability to take risks by trusting my creative process and embracing the unknown. Some of my most successful art installations have come from taking major risks, often under tight, time-sensitive deadlines. Once I decide to go forward with a large-scale project, it’s a full-on-no-turning-back commitment, even if I don’t yet know exactly how to get there. I thrive on the excitement of facing new challenges, both with the material that I usually engage with, paper, and learning new equipment and software to push myself beyond what I’ve done before. Read More>>

Corina Walsh

When I announced I was leaving a secure job to start a business, many people in my life thought it was a huge risk. I didn’t see it that way. For me, the risk was staying in a situation that made me miserable. Yes, entrepreneurship has a high failure rate but my mental health was at risk by staying in a soul-crushing career and job. When you are the one taking a risk, your perspective is different from others watching you from the outside. Read More>>

Natalie Valencia

I developed the ability to take risks through experience—both in life and in the studio. Participating in artist residencies abroad and exhibiting during Art Basel Week pushed me out of my comfort zone in the best way. Being in unfamiliar places, working with new materials, and sharing vulnerable work with an international audience taught me that risk is part of growth. In the studio, I challenge myself to experiment—whether through scale, color, or concept. I’ve learned that following your intuition and trusting the strength of an idea can be the most powerful risk of all. Read More>>

Heather Penny

Risk taking does not come natural to me. However, I do not enjoy feeling stuck or unproductive. Taking risks is what I have found that leads me into engaging with my life, my purpose, and my passion to the fullest. Without risking, am I really living?

First, I had to recognize this is how the world works. All of us want a big beautiful thriving life, but not everyone recognizes the cost required to achieve this. Taking the risk is that leap of faith required to go after a big life. But I need CLARITY on what I want. Read More>>

Laura Sauber

I wish I could point to a single moment, but as I reflect, taking risks has always been part of who I am. Even as a child, I felt a deep pull to stand up for what was right. I remember marching down the street, scared, to knock on a neighbor’s door and tell a bully to stop picking on my younger brother. I had an innate need to act. Read More>>

Bella Matasic

I was 18 when I made one of the craziest decisions of my life.
Skydiving alone with just two days’ notice.
But that was nothing compared to quitting my internship, which felt like death.
Not even joking.
It felt like shutting the door on my entire future with no way back.
Everyone thought I was insane.
They told me so to my face. Read More>>