"Judge a man by his questions rather than his answers." — Voltaire
In the quiet moments between meetings, in the space between notifications, a question forms in the minds of many accomplished professionals: "Is this all there is?"
We've climbed the ladders we were told to climb. We've accumulated the symbols of success that society celebrates. We've dutifully followed the prescribed formula: good education, respectable career, comfortable home, reliable retirement plan.
Yet something feels incomplete.
The Questions We've Been Trained Not to Ask
From childhood, we're conditioned to provide answers. The educational system rewards correct responses, not thoughtful inquiries. The professional world celebrates solutions, not explorations.
But what if our obsession with answers has led us astray?
The most profound shifts in human consciousness have always begun with questions, not answers. Socrates didn't transform philosophy by proclaiming truths but by asking questions that revealed the limitations of conventional wisdom. Einstein didn't revolutionize physics through definitive statements but through thought experiments that questioned the very nature of reality.
As the ancient Zen masters understood, "In the beginner's mind, there are many possibilities; in the expert's mind, there are few."
The Financial Plan vs. The Purpose Plan
As a financial planner, I've seen countless spreadsheets detailing exactly how much money people need to accumulate by retirement. These plans answer questions like "How much?" and "By when?" with impressive precision.
But they rarely address the more essential questions:
· Why am I accumulating this wealth?
· What purpose will this wealth serve beyond securing comfort?
· How might my resources contribute to something greater than myself?
When I ask clients these deeper questions, something remarkable happens. The conversation shifts from numbers to meaning, acquisition to contribution, and security to purpose.
One client, a successful executive with more wealth than she could spend in three lifetimes, sat quietly when I asked her what she hoped her money would ultimately accomplish. After a long pause, tears formed in her eyes. "No one has ever asked me that," she said. "I honestly don't know."
That moment of not knowing began her journey toward purpose—a journey that eventually led her to establish a foundation addressing childhood literacy, a cause deeply connected to her early struggles.
The Art of Better Questions
"The quality of your life is determined by the quality of the questions you ask yourself." — Wayne Dyer
What questions might shift your relationship with success and purpose?
Consider these:
· If money were no object, how would you spend tomorrow?
· What problem in the world makes you angry enough to act?
· What activity makes time seem to disappear when you're engaged in it?
· What would you attempt if you knew you could not fail?
· Whose lives do you wish to touch before your journey ends?
These questions don't demand immediate answers. Rather, they invite contemplation. They create space for possibilities. They initiate journeys rather than destinations.
The Both/And Path Forward
The dichotomy between financial success and purposeful living is largely a false one. The most fulfilled individuals I know haven't abandoned material success for spiritual poverty. Instead, they've integrated prosperity and purpose by ensuring the former serves the latter.
As Marcus Aurelius reminded us: "Very little is needed to make a happy life; it is all within yourself, in your way of thinking."
The path forward isn't choosing between prosperity and purpose, it's aligning them so that your resources fuel your mission rather than becoming the mission itself.
Questions as Compass Points
When Lewis Carroll's Alice came to a fork in the road, she asked the Cheshire Cat which path she should take.
"That depends a good deal on where you want to go," said the Cat. "I don't much care where," said Alice. "Then it doesn't matter which way you go," said the Cat.
Without meaningful questions to guide us, any path leads nowhere in particular. But with the right questions serving as compass points, each step—whether advancing our careers or reshaping our priorities—moves us toward authentic purpose.
Begin With One Question
If you're feeling the tension between achievement and meaning, begin with just one question: What matters most?
Carry this question with you. Let it inform your financial decisions, career choices, and time use. Notice how it shifts your perspective from accumulation to allocation, from having to being.
The answer may not come immediately. That's perfectly fine. Remember, it's not about racing to answers but learning to live meaningfully with questions.
As Rilke advised: "Be patient toward all that is unsolved in your heart and try to love the questions themselves... Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now."
Live the questions now. The answers will emerge not as destinations but as signposts on your ongoing journey toward a life of purpose. In this life, prosperity and meaning aren't competitors but companions on the path.
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How has asking better questions changed your relationship with success and purpose? I'd love to hear your thoughts - please contact me by clicking here.