North Star or Dead End? 🌌 The Hardest Choice Every Leader Must Face
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🚨 The Leadership Shift: From Bosses to Stewards 🚨
True leadership doesn’t come from shouting orders—it comes from carrying others through the dark
It is the dead of night. The air is thick with fear and silence, broken only by the crunch of hurried footsteps on damp earth. A small group of people moves quickly through the woods, every sound amplified by the danger that stalks them. At the front, a woman pauses, listening—not just for pursuit, but for the faint promise of safety ahead. Harriet Tubman knows every rustle could be a patrol, every shadow a trap. Yet she presses forward, guiding others along a path she has walked before.
She carries no title, no rank, no army behind her—only trust, courage, and the unshakable belief that freedom is worth the risk. This is not the story of a boss demanding obedience. It’s the story of a steward who shares the danger step for step, leading not with orders, but with presence and sacrifice.
Harriet Tubman: The Archetype of Steward Leadership
The silence of the forest should have been safety—but it was not. Every mile north brought hope, but it also tightened the noose of danger. Posters offered rewards for Harriet Tubman’s capture, hunters and hounds patrolled the borders, and betrayal could come from a whisper in the wrong ear.
She had already risked her life escaping once, therefore returning to lead others was not just bravery—it was stewardship embodied. She didn’t stay behind in comfort; she chose to walk the perilous road again and again, each journey a test of shared sacrifice.
Context & Credibility:
Tubman escaped slavery in 1849 and returned ~13 times to free about 70 enslaved people. Nicknamed “Moses” for leading others to freedom.
Leadership Style vs. Boss:
Bosses rely on rank and orders; Tubman had none of that. She led by trust, vision, and action.
Stewards share the risk: Tubman didn’t send people north while staying safe herself—she walked the same dangerous road, facing capture or death alongside them.
Poll 1: Leadership Styles Today
👉 Which type of leader inspires you most?
🌟 The Visionary – paints the picture and walks with the team
🛡️ The Protector – shields people from risk and shares it equally
🎯 The Strategist – plans carefully, adapts quickly
💡 The Innovator – experiments boldly, learns fast
🤝 The Steward – puts mission and people first, ego last
The Strategy of Stewardship
The group reached a riverbank under cover of darkness. The current was swift, the night colder than anyone had expected. A boss would have ordered them across and stood back. But Tubman waded in first, showing it could be done, disguising her own fear so the others would believe. Her meticulous planning had already prepared them—songs sung in the fields had carried secret directions, a lantern’s flicker signaled when the way was clear, the North Star kept them true.
Some stumbled, panic threatening to unravel the journey. Tubman steadied them, whispering that freedom was only steps ahead. Her calm turned chaos into courage. Again and again, she proved the path was survivable because she walked it with them.
When doubt gnawed at the edges of the group, some talked of turning back. However, Tubman’s famous stance cut through hesitation: “Go on or die.” It was not cruelty—it was stewardship. Turning back meant capture for them all. Standing firm meant survival. In that moment, trust was forged not through speeches, but through action and results. She never lost a passenger, and every step forward deepened their faith in her care and competence.
Stewardship in High-Stakes Moments
The year was 1863, and the Civil War was tearing the country apart. Tubman was no longer guiding small groups through forests and fields—she now stood at the helm of an armed expedition. On the banks of South Carolina’s Combahee River, Union gunboats waited in the fog. Soldiers readied themselves, but all eyes turned to Tubman. She alone knew the lay of the land, the waterways, and the hidden paths where the enslaved waited.
The boats pushed forward under cover of night. The mission could easily collapse—but Tubman’s foresight had prepared the way. She had gathered intelligence from locals, mapped every bend in the river, and timed the raid with precision. Her empathy became strategy: she knew mothers would hesitate, clutching children too frightened to board. With unwavering calm, she sang familiar hymns across the water, her voice carrying assurance that it was safe to come.
Chaos erupted as plantations burned and Confederate forces scrambled. Panic could have scattered the people fleeing to the boats, though Tubman positioned herself at the crossings, guiding hundreds to safety. Step by step, she protected the vulnerable, urging them aboard while soldiers covered their escape.
By dawn, over 700 enslaved men, women, and children had boarded the boats—an exodus led not by a general with orders, but by a steward who fused courage with care. Tubman had built not just a daring raid, she built a system where others could finally thrive in freedom. It was stewardship at its most audacious: empathy sharpened into strategy, foresight executed with unshakable resolve.
What Modern Leaders Can Learn from Tubman’s Stewardship
The power of Tubman’s story is not locked in the past—it’s a mirror for the choices leaders face today. She had no title, no badge, no office with her name on the door. But her credibility was unquestionable because every action she took matched her word. Modern leaders don’t earn loyalty by handing down directives; they earn it by showing up, sharing the same risks, and proving that their word is bond.
Tubman’s success was never accidental. She studied terrain, listened deeply, and adjusted in real time. The lesson is clear: plan carefully but be ready to pivot quickly. In a world of shifting markets and unexpected crises, adaptability is not optional—it’s survival.
Most of all, she embodied shared sacrifice. A boss says, “You go.” A steward says, “We’ll go together.” That single difference is the heartbeat of trust. It transforms fear into courage and uncertainty into momentum.
And in every decision, Tubman chose people over ego. Today stewardship means protecting the collective, not polishing the leader’s image. Mission before self. Care before control. Service before status.
For any leader—whether guiding a team through quarterly targets or a company through sweeping change—the Underground Railroad still whispers its truth: real leadership doesn’t demand followers; it carries people forward, together, into freedom.
Closing: The Legacy of Stewardship
Harriet Tubman’s life proves a timeless truth: leadership is not about titles or authority—it’s about stewardship. She didn’t shout orders from the back. She stepped into the darkness first, carried the weight, and bore the risk. Her courage was contagious because it was shared. Her vision was trusted because it was lived.
Poll 2: Lessons from Harriet Tubman
👉 What’s the biggest takeaway from Tubman’s stewardship?
🚶 Lead by Example – “I’ll go with you”
🗺️ Plan Meticulously – strategy is freedom’s compass
🎶 Communicate Creatively – songs, signals, trust
⚖️ Share the Risk – never safe while others are in danger
🛶 Build Systems – pave the way for others to thrive
“Harriet Tubman wasn’t a boss. She was a steward. She didn’t just lead people—she carried them, step by step, into freedom.” That is the essence of leadership we hunger for today: a model where strength is measured not in command, but in care; not in control, but in the courage to walk alongside.
If you’re tired of the boss mentality—the barking, the ego, the detachment—there’s another way. In Collaborate Better, I lay out how to leave behind that outdated model and step into true stewardship. Because teams don’t thrive under bosses—they flourish under stewards who protect, guide, and build systems where people can do their best work.
✨ Preorder today and join the shift. Together, let’s rewrite leadership—not as command and control, but as stewardship and shared success. ✨
Next Blog in the ‘Collaborate Better’ PreSale: If Everything’s a Priority, Nothing Is