I feel like I'm driving off a cliff. I'm leading my company's expansion into a new market. No one at our company has done this before. The board approved the project based on my proposal, but honestly, I was guessing at a lot of the numbers. Now I have a team of 8 people who relocated for this opportunity. They trust me. But every week brings a new problem I didn't anticipate. Costs are higher than projected. The regulatory environment is more complex. Our timeline is slipping. I'm torn between admitting uncertainty (which might undermine confidence) and projecting confidence (which might be lying). My team needs to believe this will work, but I'm not sure it will. How do I lead into the unknown without either deceiving my team or paralyzing them with my own doubts? — Navigator Without a Map in Nashville
Leading through uncertainty. Magellan's bold vision meets Cook's meticulous care.
I feel like I'm driving off a cliff. I'm leading my company's expansion into a new market. No one at our company has done this before. The board approved the project based on my proposal, but honestly, I was guessing at a lot of the numbers. Now I have a team of 8 people who relocated for this opportunity. They trust me. But every week brings a new problem I didn't anticipate. Costs are higher than projected. The regulatory environment is more complex. Our timeline is slipping. I'm torn between admitting uncertainty (which might undermine confidence) and projecting confidence (which might be lying). My team needs to believe this will work, but I'm not sure it will. How do I lead into the unknown without either deceiving my team or paralyzing them with my own doubts? — Navigator Without a Map in Nashville
Ferdinand Magellan
"The sea is dangerous, but obstacles have never been sufficient reason to remain ashore"
36 votes
James Cook
"Ambition must be tempered by meticulous care for those who follow you"
40 votes
76 votes total
Full Positions
From The Story of Magellan and The Discovery of the Philippines
"The sea is dangerous, but obstacles have never been sufficient reason to remain ashore"
I led men around the world through mutiny, starvation, and uncharted waters. They did not need certainty—they needed my conviction that the journey was worth the risk. Share the challenges openly, but never waver in the mission. Doubt is human; despair is contagious.
From Captain Cook's Journal During His First Voyage Round the World: Made in H. M. Bark "Endeavour", 1768-71
"Ambition must be tempered by meticulous care for those who follow you"
I charted more of the world than any man before me by preparing obsessively and adjusting constantly. Your team does not need false confidence—they need transparent leadership. Share what you know, what you don't know, and what you're doing to learn. Trust is built on honesty, not bravado.