The Labor Day weekend marks the end of summer. Schools at every educational stratum are back in session, and yes, it’s time for football. Growing out of what historians call “the labor movement,” the holiday became national in 1894 and is observed the first Monday in September ever since.

The BBQ, football, golf, water sports, and a relaxing weekend with family and friends aside, all of us would be wise to have a “Labor Day” conversation with clients. When we ask about a client’s professional/work/labor life, what kind of responses do we get? Is there animation in the voice or smile? Does a spontaneous joy break out when the topic of work bubbles up? For some, work is energizing and rewarding. Such is not the case, however, with many.

So why go there?

Our work stories, work life, work attitudes, and work reward are hardwired into who we are and how we see the present and future. Doing a financial plan without having the work conversation would be like going through a physical where the physician never asked you about diet or exercise. What we “do” and what that labor means to us speaks to life purpose touching corridors of the heart that hold sway over the most critical decisions we make.

Start such a conversation by asking the “What do you do for a living?” question. Pay attention to voice inflection, body language, and emotion. No matter what you hear, respond by asking, “I’ve always wondered what a job like that involved. Could you tell me about your average day?” Then transition to a deeper place asking, “What is it about your work that is most challenging?” and then, “What is the most rewarding aspect of what you do?” Listen and learn no matter the answers.

These questions will lead you in any number of directions shedding light on issues like how much longer this person plans to be engaged in traditional work. Are there health issues that could shorten a career? If in a marriage or partnership, how does the other person feel about continued employment? And then, the ultimate planning question: Is a “work optional” lifestyle even possible?

When a moment in the conversation transitions, ask, “If money is no issue as you continue to work, what would you most like to do with the work years remaining?” It is at this juncture that you, as an advisor, will begin to see a change in voice, attitude, and perhaps emotion. Here is where your investment in the process goes to places others never consider. And yes, it is the gathering of this deeper data that will empower you to do your best planning.

So, have a restful, meaningful Labor Day. Then, starting next week, find ways to ask prospects and clients about work, its meaning, and how what they do feeds into the more significant issue of purpose. I can think of no more important conversation to have that will inform and shape all the numbers we can enter into a planning study.

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