“I’ve been absolutely terrified every moment of my life—and I’ve never let it keep me from doing a single thing I wanted to do.”
1000 NO's Series: Leadership Lessons from Georgia O’Keeffe’s Art and Life
“There are things we want to say—but saying them is pretty nervy.”
—Georgia O’Keeffe
Who Was Georgia O’Keeffe—and Why Should Leaders Care?
Georgia O’Keeffe (1887–1986) was a pioneer in every sense.
A boundary-breaking artist, a woman who defied expectations, and the creator of some of the most iconic modernist works of the 20th century.
She was best known for her bold flower paintings, desert bones, and minimalist landscapes, she painted in a way no one had seen before in her time—and insisted on doing it her way.
In 2014, decades after her death, her painting Jimson Weed/White Flower No. 1 sold for $44.4 million—the highest price ever paid for a painting by a woman at that time.
But beyond the records and the worship, O’Keeffe’s life was a masterclass in reinvention, resilience, and creative power. And the more I walked through her museum in Santa Fe, the more I realised: her journey speaks to the very heart of leadership in this strange, demanding, transformative era we’re living in now.
The Journey of Mastery
O’Keeffe didn’t begin by breaking rules. She began by learning them. Drawing. Studying. Following technique. Her early works are structured, controlled, precise.
Then, gradually, she moved beyond imitation into exploration. What she felt. What she saw in dreams. What had no name.
That’s the journey of mastery. First, you copy. Then you question. Then you step into your own voice.
Leaders often want to skip to originality. But true mastery begins in the foundations, and only later evolves into freedom.
Owning Your Originality
Before she became Georgia O’Keeffe, the singular force, she tried on many styles. She was influenced. She experimented.
But eventually, she did something no one else had done: she made the intimate monumental. She painted flowers so close you could fall into them. Skulls that felt sacred. Mountains that belonged to her alone.
She was willing to be different. Willing to be misunderstood. Willing to become herself.
And that’s what bold leadership asks: not perfection, but courage. The courage to stop performing and start creating from your essence.
When Resilience Looks Like Flexibility
In 1923, after public critiques of her abstraction, O’Keeffe shifted her work, briefly, toward more representational forms.
Not as a retreat. As a recalibration. A way to stay visible while protecting what mattered.
Leadership isn’t always about defiance. Sometimes it’s about knowing when to flex, when to listen, when to adapt without erasing who you are.
The Shapes We Don’t See
“There are a few shapes I have repeated a number of times during my life and I haven’t known I was repeating them until after I had done it.”
This quote pierced me.
We all repeat shapes. Not just in art. In leadership, in relationships, in how we handle pressure, success, intimacy.
But here’s the thing: we don’t just miss our patterns. We often miss our power.
I’ve worked with leaders who couldn’t see the genius that came so naturally to them it became invisible. Repetition isn’t always dysfunction. Sometimes it’s your brilliance trying to get through.
What if the very thing you’re doing over and over is the seed of your unique voice?
The Nervy Truth
O’Keeffe said, “There are things we want to say—but saying them is pretty nervy.”
She knew. And still, she said them. Not in words, but in line and color. In scale. In silence.
She painted what others wouldn’t dare name.
That’s the kind of courage we need now - not noise, but nerve. The quiet, unshakable kind. The kind that tells the truth when it’s not convenient.
Leaders aren’t called to repeat what’s already known. They’re called to make visible what’s been hiding.
Stillness in the Storm
In the 1930s, amid personal tension and professional scrutiny, O’Keeffe began taking solo trips. Into nature. Into silence. Into the desert.
She wandered canyons. Collected bones. Painted Cross with Red Heart - a canvas full of sky and symbol, completely absent of human form, yet completely about humanity.
In the midst of chaos, she didn’t power through. She became still.
Stillness is not stagnation. It’s the ground clarity grows from.
Evolution and Return
O’Keeffe’s eyesight began to decline gradually over the years, but by the time she reached her 80s, her central vision was almost entirely gone. She could no longer paint with precision.
And yet, she didn’t stop creating.
She began working with clay. Her assistant, Juan Hamilton, helped her discover ceramics. She returned to earlier shapes and let her hands lead.
She didn’t abandon her voice. She just found a new way to express it.
That’s leadership: not clinging to tools, but staying loyal to the truth you’re here to express.
The Inner Critic and Celebration
O’Keeffe sometimes destroyed her own work. She was rarely satisfied. She moved from one piece to the next.
Sound familiar?
Many high performers build extraordinary things, then rush past them. They skip the celebration. They numb the pride. They never feel like it’s enough.
But resilience isn’t just pushing forward. It’s the ability to pause. To say: This mattered. To feel your own impact without deflecting it.
Companionship and Joy: The Cat Came Too
Let’s not mistake solitude for loneliness.
O’Keeffe lived in remote places, but she wasn’t alone. She traveled with friends. And her cats. Yes, even into the desert.
She knew the power of proximity. She chose people who sparked her creativity and respected her quiet.
It’s a leadership lesson too often forgotten:
Proximity is power.
If you’re the smartest person in the room, you’re in the wrong room.
You don’t need a crowd. You need a constellation, people who expand your sight, not shrink your spark.
Breaking the Mold
O’Keeffe didn’t just paint differently. She lived differently. She defied expectations. Refused labels. Became a woman creating work no one knew how to define.
She forged a life and body of work that didn’t fit inside the boxes of her time. She made the world widen itself around her truth.
And that’s what leadership asks of us now. Not more of the same. Not better versions of what’s already broken.
But something deeper. Wilder. More true.
The next era of leadership isn’t about domination. It’s about vision. It’s about reshaping the frame.
A Circle That Nothing Can Break
She once wrote to her husband: “A circle that nothing can break.”
Her life was a circle. Of return. Of transformation. Of essence rediscovered in new form.
And so is mine. Since leaving the traditional path of corporate leadership, I’ve stepped into work that feels truer, supporting bold, visionary leaders who are here to build not just success, but significance.
This is not reinvention. It’s remembering.
And maybe that’s what’s next for you too.
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