Carey sat in my office to discuss an investment in his retirement. During our time together, I suggested a long-term strategy with incremental short-term steps. “I’ve been thinking a lot,” he said, “about a question you asked me months ago.” I leaned in a bit as he continued. “You suggested I ask myself not what I am retiring ‘from,’ but what I plan to retire ‘to.’” I nodded and asked him to tell me more.

In the next several minutes, Carey talked about options he was considering for the retirement chapter of his life six years in the future. An active professional his entire career, he realized that moving “from” the work he had known for decades was only half of the retirement equation. He longed for something to draw him forward, a “to” if you please, shaping the season that could well consume his next 20 years.

A Baby Boomer myself, I am keenly aware that a significant chunk of any advisory practice is with men and women born between 1946 and 1964. We were, until recently, the largest cohort of the country’s population, now eclipsed by the millennials. The retirement conversation looms large. But positioning investments, creating a plan, and managing risk cry out for another, dare I say more invaluable, aspect of our work.

How do you set up a “from-to” conversation? Like the Greek god Janus who looked forward and back at the same time, we must include the “from-to” topic in planning conversations. 

In my experience, the best place to start is to learn as much as you can about a client’s work, family, lifestyle, and future. Make notes and ponder their import. In a nutshell, doing our best work only begins when we have both the financial and life-story pictures in focus. Find a way to say, “Would you imagine with me your life ten years from now? Health is good; you retired from your career. What do you envision a typical day or week being in that season a decade from now?” And listen.

When I have asked these questions, most clients say, “I haven’t thought about it.” Even those who tell me they plan to play golf three times a week, travel, and spend more time with their grandchildren eventually add, “But you can’t do that every day.” Hearing these sentences reminds me why I am their advisor in the first place. Few in the Boomer generation are asking these vital questions. What a client is retiring “to” is a future space most have not even imagined.

The offshoot from the conversation positions you to probe other matters and to affirm the personality, gifts, and interests you know the client already has. Applaud their community involvement. Encourage them to begin thinking about a unique, “preferred future,” and keep the conversation going. What you learn and how you respond will only enhance your value, positioning not only their assets but their lives for what can be their best chapter. “From” and “To” frame life-changing choices. It’s a question clients need us to ask, the answers to which could well change their lives for the better.

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