Carey sat in my office a couple of weeks ago to discuss an investment in his retirement. During our time together, I suggested a strategy not only for this contribution but for those that would follow in the next several years. Once he decided, he said, “I’ve been thinking a lot about a question you asked me months ago.” Leaning in a bit, 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 share his thinking.

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 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 may not be the most valuable service we offer our clients.

How do you set up a “from-to” conversation? The only starting point I know is to inject into client visits conversational topics that ask about work, family, lifestyle, and the future. Jot down those notes and ponder their import. In a nutshell, doing our best work only begins when we have 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 is asking these necessary questions.

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 to what you hear will only enhance your value, positioning not only their assets but their lives for what can be their best chapter.  “From” or “To” is a haunting choice. It’s a question clients need us to ask, the answers to which could well change their lives.

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