What Would Gandalf Do?

A Lesson from the Wizard: Look ahead, but don’t forget to look behind

The first lesson in this set comes to us from the behavior of Gandalf the Wizard in the Hobbit, which was the prequel to the Lord of the Rings trilogy.

In the book, Gandalf, has recruited the Hobbit Bilbo Baggins to travel with the 13 dwarves to the Lonely Mountain on an “adventure” to claim their long lost treasure, which is being guarded by the evil dragon Smaug. Sound familiar? Anyone who has been recruited on an entrepreneurial adventure to "find the treasure" can surely relate!

Like many “adventures” in the business world, at first the journey goes along swimmingly – they sing songs, light campfires, and otherwise enjoy themselves on the road. At some point, Gandalf leaves the party, and they suddenly find themselves without their leader.

How do they handle this situations? This "first adventure" has many implications for an entrepreneur who is just beginning his or her journey and the team of "adventurers" that he or she is leading.



NOTE: This is the first of a set of lessons about business, entrepreneurship, and life from my favorite fantasy and science fiction, such as the Lord of the Rings and the Earthsea chronicles – it’s from a book I’m working on tentatively titled: “Wizards at the Helm”.

It is a cold, rainy night, not even the dwarves are able to light a fire. Without Gandalf, the party is left in the dark to fend for themselves when suddenly they spot a fire in the woods. The party sends Bilbo to investigate, and they get into trouble with a set of monstrous trolls, who capture the hobbit and the dwarves and threaten to “eat them”.

This is their first “true adventure” on what I think is a very archetypal heroic journey, and as you can see it’s not an inconsequential one – their very lives are put into mortal peril!

Gandalf’s departure allows the party to “test its mettle” – and though they are found lacking and need to be “bailed out" of this incident, the episode represents an important point in the development of both Bilbo and Gandalf as characters and heroes.

Many early stage business ventures also face death when they first try to make it on their own. But it’s the trials themselves which harden up the group and prepare them for the challenges which lay ahead. It is important to get through this first set of trials, even if you have to rely on a board member, or a mentor, or a wizard who knows the terrain.

And in fact it is Gandalf, who has dealt with Trolls before, who shows up in time, plays a clever trick on the Trolls, and rescues the party. After they are rescued, the dwarves naturally ask Gandalf: “Where were you?”

He answers, “Looking ahead”

The next question from them is: “And what made you come back?”

“Looking behind.” said Gandalf.

What can this teach you as you go on your own “heroic journey”?

To truly be a wizard you have to be able to anticipate what’s going on ahead of the curve, and sometimes this means scouting out into the future and leaving others behind to take care of present tasks.

But even when you do that, no matter what you see, you can’t ignore what’s happening in the present. You need to not only be able to scout ahead, but also bring those with you on the journey safely through the "road of trials". But it's not enough to do it all yourself. You also need to give them room to develop their own abilities as “heroes” and not lean on you as a crutch. This will serve you in the long run.