Meet Lindsay Anderson

We caught up with the brilliant and insightful Lindsay Anderson a few weeks ago and have shared our conversation below.

Lindsay , we’re thrilled to have you sharing your thoughts and lessons with our community. So, for folks who are at a stage in their life or career where they are trying to be more resilient, can you share where you get your resilience from?

I believe resilience is both a creative act and an act of radical responsibility. It’s the ability to take full ownership of your experience—to stay grounded in your truth while continuously evolving how you meet the world. My resilience was shaped early, through exposure to responsibility and independence. I ran hot chocolate stands, mowed lawns, and sold crafts at the mini mart to buy my own school clothes—not just out of necessity, but from a desire to create freedom and choice. That mix of resourcefulness, curiosity, and drive became a throughline I’ve returned to again and again.

But resilience has also been built through the boldness of going after what I want. The more I’ve reached for—whether professionally, creatively, or personally—the more I’ve been tested. Each move, risk, and reinvention brought challenges I couldn’t have predicted. From leading teams through IPOs and acquisitions to leaving it all to travel and build a values-led life, every chapter has deepened my resilience by stretching my capacity to learn, adapt, and stay connected to my inner compass.

Today, resilience looks like staying in integrity with myself, even when things are hard or unclear. I cultivate it through practices that bring me home—meditation, time in nature, intentional reflection—and through a deep commitment to learning from everything.

Resilience, to me, is less about bouncing back and more about staying rooted as you grow, shift, and evolve.

Great, so let’s take a few minutes and cover your story. What should folks know about you and what you do?

I’m a leadership and growth coach, consultant, and entrepreneur based in Joshua Tree, CA. My work sits at the intersection of personal development and intentional living—supporting people in reconnecting to what matters most and resourcing themselves with the tools and clarity to lead with purpose.

After a decade building and leading teams across tech startups and Fortune 500 companies—through IPOs, acquisitions, and large-scale organizational change—I made a conscious and values-driven choice to evolve my career. I wasn’t stepping away from leadership—I was stepping further into it. I wanted to integrate my experience in business and team dynamics with my deeper purpose: helping people grow, lead, and live with more alignment, integrity, and impact. That journey led me to coaching and entrepreneurship, where I now guide executives, founders, and creatives through personal and professional transformation.

Through 1:1 coaching, consulting, and curated experiences, I help clients become more effective, conscious leaders—rooted in who they are and equipped to navigate complexity without burning out. I also co-run Stay With Terra with my husband—a boutique brand offering intentional stays in the Mojave Desert. These spaces have become an extension of my work—designed to support rest, clarity, and meaningful reconnection.

Right now, I’m focused on expanding both sides of the business—deepening my coaching work while creating opportunities to gather in person through retreats, creative collaborations, and nature-based leadership experiences that help people reset, reflect, and make their greatest impact on the world.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

Self-trust is the foundation. It’s what allows you to take bold, aligned steps—even when they don’t make sense on paper. Every pivotal move I’ve made—changing majors, launching businesses, shifting careers—required me to listen inward and act from a place of clarity, not just logic. For anyone starting out, I’d say: build your inner compass early. Reflect often. Ask yourself what’s true for you—not just what’s expected of you—and practice honoring that.

Curiosity has been a constant teacher. It’s what keeps me learning, questioning, and expanding. It’s the quality that’s helped me evolve—both personally and professionally—without getting stuck in a fixed idea of who I am or how things “should” be. Curiosity allows you to meet uncertainty with openness instead of fear. For anyone early in their journey: stay curious about yourself, your patterns, and the world around you. Curiosity doesn’t just lead to answers—it leads to alignment, growth, and possibility.

Bold, aligned action is what brings it all to life. You can have values, clarity, and insight—but at some point, you have to move. The most radical act is living a life that’s true to you, especially in a world that constantly asks you to play it safe. I’ve learned to treat every move as an experiment—whether it was evolving my work beyond corporate roles, launching something new, or building something more purpose-driven. Today, I get to bring that same mindset into my coaching and consulting with corporate leaders, founders, and creatives alike. And here’s the part that’s often overlooked: it doesn’t always require a massive overhaul. Start small. Make a shift. Try something new. Let boldness live in the tiny choices too—and let action refine your path.

What was the most impactful thing your parents did for you?

My parents gave me radical acceptance and the freedom to fully express myself. If I wanted to dance ballet, they supported me. If I wanted to try journalism, debate, or writing, they were my earliest fans. I never felt boxed in by who I was supposed to be—instead, I was encouraged to explore who I truly was. I remember asking my mom over and over if I was “skinny,” hoping for some kind of external validation. She’d always say, “You’re not skinny, you’re perfect.” It wasn’t just a compliment—it was her way of protecting me from internalizing the world’s narrow definitions of worth.

My dad, too, has always been my biggest champion. He instilled in me this deep belief that I could do anything—and helped me see that hard work was part of the magic. If I wanted to get better at ballet, he trained with me before class. If I wanted to learn photography, he walked the neighborhood with me, finding flowers to practice on. There was this constant balance of possibility and effort: You can do anything—and you have what it takes to get there.

My childhood was far from perfect, but these moments of presence, peace, and unconditional support instilled in me a fierce trust in my inner voice. They taught me that I could be whoever I wanted to be in the world—and that being myself was more than enough.

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Bry Penny

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