Day 27 of 40 Days of Story: Who’s your Sherpa? And why do great stories—including yours—need them?

Many years ago I fell in love with a Sherpa. Well, it was the idea of a Sherpa.


I was building out a leadership structure for a large group of volunteers. I searched for an inspiring vision for the leaders of my leaders.


The term coach felt overplayed. But when the metaphor of Sherpa came to mind it was magic! There’s the technical term for Sherpa that means “a member of a Tibetan people living on the high southern slopes of the Himalayas in eastern Nepal and known for providing support for foreign trekkers and mountain climbers[1]. But here’s the idea of Sherpa that entranced me: a skilled guide who has been where you long to go. It’s someone who has knowledge, resources and commitment to take you there.


However, a Sherpa doesn’t carry you or make the decision for you go further or quit.


The concept of Sherpa galvanized my leaders of leaders. And when I’ve paused to realize my own need for a Sherpa it has served me well. And when I haven’t, well there’s been some unnecessary suffering in my life.


Exhibit A: Four years ago I shoved my belongings in storage and headed to Cuba to chase a story. I became taken with Cubans’ creativity and grit. I couldn’t shake this sense I needed to do a film. But I had never independently directed a documentary.


I was torn. I had this desire—and drive—but was daunted by the process.


As my drive and then desire were on the brink of diminishing I went on search for my Sherpas. I connected with several accomplished filmmakers. They gave me practical advice…and told me the path would be very tough. I was so grateful for everyone’s helpful advice, but there was one internationally acclaimed filmmaker’s words that cut me to the core. She told me about the one film she never finished. In the midst of all her award-winning films, that story still haunts her.


I knew I couldn’t quit. I did an Indiegogo campaign to raise funds to return to Cuba for a month. I researched, threw parties on rooftops to meet great Cubans, found my Director of Photography. And yet…I realized I was only getting started.


I teamed up with a couple of friends to lead cultural-exchange trips to Cuba to fund the filming. It was such an invigorating experience to invite friends from the US to meet amazing new friends in Cuba. Yet, it eventually became clear this approach wasn’t sustainable for the long-haul.


If I didn’t get more resources and take a different approach this would be that unfinished project that would haunt me.


As I was wrestling with having made such progress—and others investing in me—and yet feeling stuck, a brilliant entrepreneur friend contacted me. We ended up co-founding a media company and he had a great sense that the project should become a series rallying a community, building an asset and not having just a one and done documentary. We got to Sherpa each other—he guided me in business and I got to guide him in storytelling.


If I hadn’t had my Sheraps on the journey I know Startup Cuba would have never existed.


So, who are your guides in this season? Perhaps a better starting question is: Where do you need guides?


I most need a guide when I am stuck. I know I’m stuck when my desire and drive are diminishing to accomplish an important goal.


Then I must ask, is there someone who has accomplished this goal I can ask for help? Who has the needed knowledge and resources and who has–or can be invited to have–a vested interest in me achieving it?


Now that we’re half-way through 2019, it’s a great time to assess your need for a Sherpa.


I’d love to hear about your search for a Sherpa and when one has served you well.


Do tell.


And I promise to let you know when I fall in love with a Sherpa!