Leading With Courage and Curiosity

Written By BONNIE LESTER

On Staying Open in Moments We Cannot Control

“Be patient toward all that is unsolved in your heart and try to love the questions themselves.”
- Rainer Maria Rilke

Every January, leaders are encouraged to set goals that sound reassuringly measurable. Revenue targets. Hiring plans. Expansion roadmaps. I’ve made lists like that for most of my career. They have their place. They help us steer the ship.

But as I enter 2026, I find myself less preoccupied with what we will achieve and more concerned with how we will move toward it and who we are becoming in the process.

The world around us is increasingly defined by volatility and acceleration: AI systems that move faster than our norms and laws, social feeds that reward outrage over understanding, and economic and ecological pressures that expose every weak seam in our institutions. In this environment, leadership is less about having the right answers and more about developing the inner and collective conditions that allow better questions, better choices, and better relationships to emerge.

This year, I’m setting a different kind of resolution for myself, less like a checklist and more like a compass.

They are not promises of perfection. They are directions I want to face, again and again, especially when it would be easier to look away.I’m sharing them here in case they serve as a point of reflection for you, too.

The first direction I want to face is courage and curiosity.

There is always a moment, just before an important decision, when fear offers the easiest path: retreat into skepticism, stay on the sidelines, and critique from a safe distance. As leaders, we can become very skilled at using our intelligence to justify inaction.

This year, I’m committing to leading with courage and curiosity: to stay open, constructive, and possibility-focused, even when it’s more comfortable to close down.

Courage, in this sense, is not the absence of fear. It is the choice to keep our hearts and minds available to what is unfolding, to step into conversations we cannot fully control, and to admit when we don’t yet know. Curiosity is its twin: it is the willingness to ask, What else might be true here? What am I not seeing? Whose perspective is missing?

In a culture that often confuses leadership with certainty, choosing curiosity can feel like a risk. Yet, without it, organizations slowly harden around their own assumptions. Innovation becomes cosmetic. Strategy becomes theatre.

So I’m asking myself:

• When tension arises, do I default to shutting it down or leaning in?

• When someone challenges my approach, can I stay with the discomfort long enough to learn from it?

• Can I let my questions be as visible as my convictions?

Leading with courage and curiosity is how I want to meet challenges and opportunities this year. Not with bravado, but with a willingness to stay open.

Over the coming weeks, I’ll spend time with each of the new directions on my list, not as conclusions but as ongoing inquiries. If one of them meets you where you are, you’re welcome to sit with it here. And if it raises questions of your own, I’d be glad to hear them.

BONNIE LESTER

FOUNDER & CEO

I’m a writer and creative strategist whose work is grounded in strategy, sustainability, insight, and inspiration. I help businesses, non‑profits, foundations, and governments align profit with purpose and communicate in ways that are honest, human, and effective. I’m driven by a passion and purpose to dedicate my talent to the creation of a more just, equitable, and sustainable world. The stardust of our planet and our shared humanity.

For more than two decades, I’ve worked across the for‑profit and non‑profit sectors, helping organizations find the language, stories, and strategies that are true to who they are and meaningful to the communities they serve. My background spans brand communications, youth platforms, arts and culture, cause marketing, and social impact initiatives.

My work lives at the intersection of inner life, culture, and creative practice. I bring a musician’s ear and a writer’s sensibility: listening closely, asking questions, and treating every project as a dialogue. Whether I’m working with a bank, a start‑up, a cultural institution, or a grassroots non‑profit, my focus is to surface what matters and build communications and collaborations that feel grounded and alive. As a writer and creative director, I’ve led integrated campaigns in financial services, technology, healthcare, travel, consumer goods, sports, beer and spirits, and more. I helped develop award‑winning studentawards.com, co‑founded Uthink, a youth marketing and online research firm, and founded Art of Jazz, a not‑for‑profit dedicated to jazz and education. My work has received multiple gold and silver RSVP and Promo! awards—proof that careful listening and clear thinking can create results that resonate.

Today, through Higher Ground, I focus on authentic, cause‑driven brands grounded in profit, purpose, and sustainable impact. We help organizations clarify and articulate social purpose, design strategies that support sustainable development goals, build cross‑sector partnerships, and develop campaigns that reflect both values and realities.

Outside of client work, I’m a published author, pianist and jazz vocalist, arts advocate, and mother of two grown children who continue to show me what creativity and courage look like in everyday life. If you’re exploring how to align strategy and sustainability or how to bring more depth and meaning into your brand or initiative, I’d be happy to be in conversation.

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