All of these questions lead to there. These questions lead to the mistaken assumption of the Destination Life--that there is a place or plot on the map where everything comes together, and that our job from that point on is to keep it together. The first ROL reality is to reject the Destination Life in favor of the Exploration Life.  

The Exploration Life is one where we realize that life is an unyieldingly dynamic proposition that makes no promise whatsoever about static happiness, i.e., "If you do this and get this, everything's going to be great from that point forward."

In conversations with clients, we talk to them about places they want to go, places they want to be--destinations that will ultimately disappoint if they do not get in touch with the place they are at in life.

People retire at 65 because they think that's what they are supposed to do. They buy a beautiful home in a gated community and, quite often, wake up miserable in a short amount of time. Why? Because they are out of the Exploration Life. While they were chasing the destination dream, they were in expedition mode. But as soon as they arrived, it was over. This is why my lawyer tells me he will never retire--he understands that it's really about learning something new all the time. He has shared with me that he can always tell when a lawyer is going into decline. They get intellectually lazy, they stop reading the journals--they are no longer curious. They have bought into the destination myth.

In life, when you are playing defense, you are no longer living--you are only surviving. The multimillionaire who lives only to play defense is in no better a place than the pecuniary miser who is vigilantly guarding every scrap and lives only to hoard.

Defensiveness is an essential element in a financial plan; but in life, defense is death in its earliest stage. It is a signal that the boards have been attached to the windows, the gate is locked, and the gun is loaded for looters. It is a gated community called Cape Fear. And people save up their whole life to get there. I have seen this deception play out a thousand times. Perhaps this was what Tennyson had in mind when he wrote, "How dull it is to pause, to make an end, (sic) to rust unburnished, to not shine in use, as if to breathe, were life."

We all know the old axiom, "It's not about the destination, it's about the journey." Yet in this industry, we treat the entire proposition as if it is about the destination. If a client's life means nothing more than a number, then the conversation should be about the destination. But if a client's life should be about more than that--relationships, usefulness, significant contributions, and meaningful engagement--then we need to begin asking better questions and start changing the assumptions about where the conversation commences. Because if money is intended to help your clients live a more meaningful life, then they are not going to get there with the old destination maps we've been using. Like the farmer said, "If I were you, I wouldn't start from here."

"Where has your journey taken you so far, and what role has money played?"

"Where do you find yourself at the moment, what would you like to change, and what would you like to keep?"

"What are the potential scenarios that could play out in your future, and what role does money play in them?"