Leadership Lessons from a Motorcycle Trip

Last night we rewatched 𝙇𝙤𝙣𝙜 𝙒𝙖𝙮 𝘿𝙤𝙬𝙣 - the 2007 documentary following Ewan McGregor and his best friend Charley Boorman on their second major motorcycle journey. 

I thought it could be interesting to view the first 2 seasons again, through newer, wiser eyes - 21 and 18 years after they first aired.

In 𝙇𝙤𝙣𝙜 𝙒𝙖𝙮 𝘿𝙤𝙬𝙣, they were riding from the very top of Scotland all the way down to Cape Town, South Africa.

It was their second epic adventure. The first, 𝙇𝙤𝙣𝙜 𝙒𝙖𝙮 𝙍𝙤𝙪𝙣𝙙, had taken them east from London, through Kazakhstan, Mongolia, Siberia, then across to Alaska, ending in New York City. It was grueling, raw, and at times dangerous - but unforgettable. They were fully in it. Soaking in each culture. Tackling wild terrain. Savoring the wonder, fear, beauty, and absurdity of it all. They felt every mile, together.

But in 𝙇𝙤𝙣𝙜 𝙒𝙖𝙮 𝘿𝙤𝙬𝙣, something changed early on.

They rushed. They raced to ferry deadlines, barely pausing to meet locals or learn about the land beneath their wheels. And frustration built. The pace wore on their connection. And in Khartoum, Sudan, it boiled over - until they realized: this journey was no longer about presence. It had become a checklist. And they were missing the point.

Sound familiar?

Leadership today can feel the same. 

The calendar is packed. Pressure mounts. We move at lightning speed chasing KPIs, deliverables, and we get to the finish line of one project only to run to what’s next!

But when we don’t slow down, we lose track of why we started the journey in the first place.

We miss:

• the richness of our team’s perspectives

• the subtle shifts that tell us something deeper is going on

• the moments that could shape our leadership - but don’t, because we’re already on to the next meeting

Fortunately, after the blow up in Khartoum, Ewan and Charley got back on the bikes - but with a reset. They remembered the point wasn’t just the destination. It was the ride.

Leadership is the same.

𝙒𝙝𝙖𝙩 𝙢𝙞𝙜𝙝𝙩 𝙨𝙝𝙞𝙛𝙩 𝙞𝙛 𝙮𝙤𝙪 𝙨𝙡𝙤𝙬𝙚𝙙 𝙙𝙤𝙬𝙣 𝙟𝙪𝙨𝙩 𝙚𝙣𝙤𝙪𝙜𝙝 𝙩𝙤 𝙧𝙚𝙖𝙡𝙡𝙮 𝙩𝙖𝙠𝙚 𝙞𝙣 𝙬𝙝𝙚𝙧𝙚 𝙮𝙤𝙪 𝙖𝙧𝙚 - 𝙖𝙣𝙙 𝙬𝙝𝙤’𝙨 𝙤𝙣 𝙩𝙝𝙚 𝙧𝙞𝙙𝙚 𝙬𝙞𝙩𝙝 𝙮𝙤𝙪?

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