Before rushing to do something about a problem you are facing, take a moment to reflect on the nature of the issue first!

In a wide-ranging and at times NSFW ​interview with Andrew Ross Sorkin ​at the DealBook Summit 2023, Elon Musk spoke of the impact philosophical thinking has had on his trajectory in life. 

His personal philosophy, which he summarized as – a philosophy of curiosity – has been a driving force behind his various innovations and businesses. It emerged through the study of religious and philosophical works and was triggered by an intense desire to understand life’s big questions (What is the meaning of life? Why are we here? Where are going? Where are the Aliens (and do they even exist)?). 

In the realm of coaching, where practicality and results often take center stage, I’ve found that some of the most transformative sessions I’ve ever experienced (as a coach and as a client) are those that are philosophical in nature. 

It might seem surprising for a career-oriented coach to embrace philosophical discussions, given the perception of the coaching field as quintessentially pragmatic and action-focused. Yet, in my experience, it’s these deep and thoughtful exchanges that leave a lasting mark.

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When I refer to philosophy, I’m talking about an exploration into the nature of one’s experience and life, in pursuit of a deeper understanding of how it really works. Philosophical conversations involve uncovering and prodding at the fundamental beliefs and principles that appear to govern life, using analogies and metaphors to articulate insights that might be challenging to express otherwise.

Far from being time-wasting endeavors, these conversations serve as catalysts for authentic and lasting change, guiding the mind toward a deeper understanding of how life (and one’s career, relationships, etc.) really operate. It’s about discerning what is more true and less false.

A coaching conversation becomes philosophical when the tone shifts from “Here are the 7 steps you should follow to solve your problem…” to “Let’s explore the nature of the problem and truly understand it…“. 

Ironically, a better understanding of a problem (and more generally, how one’s world operates) paves the way for more effective solutions as the mind is able to reason from something that is more fundamentally correct. Sometimes, miraculously, problems may simply dissolve as they are seen with greater context, clarity, and wisdom. 

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History’s great leaders understood the transformative power of philosophical thinking in their pursuits, especially when there was a lot at stake. Often the starting point was the study of religious and philosophical works whereas the ending was always found by taking the insights gleaned by others and filtering it through one’s personal understanding of how life works and how it should be lived to achieve one’s specific goals. 

Take Marcus Aurelius, the Roman Emperor and Stoic philosopher, who believed that comprehending life’s fundamental principles and embracing virtues like wisdom and courage were crucial for effective leadership.

Similarly, Mahatma Gandhi’s philosophy of nonviolence, inspired by Hindu/Vedic principles, became the cornerstone of his leadership and fight for India’s independence. Gandhi believed in the transformative power of love and truth, guiding his approach to conflict resolution and social change.

Nelson Mandela, during his years of imprisonment, engaged deeply with philosophical works that shaped his vision for a free and democratic South Africa. Principles such as forgiveness and inclusivity allowed him to lead a divided nation successfully.

The lesson here is clear: philosophical thinking is not merely theoretical contemplation; it can serve as a guiding force shaping insights, actions and ultimately: legacy.

Leaders like Steve Jobs, guided by Eastern philosophy, showcase how incorporating philosophically derived principles (that were interpreted and filtered through his personal understanding of life and applied to his unique contexts) can inspire profound change, leaving a lasting impact on societies and the world. 

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Reflecting on your life and career from a philosophical perspective can be a transformative exercise. It’s not a waste of time, though it might appear so at first. As the mind starts to dive deeper into the nature of things and reflect on bigger questions (instead of fixating on what to do about a given issue) clarity grows, better solutions emerge, and correct actions unfold and intrinsic motivation is found.

You also benefit from avoiding unforced errors that come from solving problems with solutions that just create more (often worse) issues in their wake. It’s like fixing a leaky roof with strategically placed buckets throughout your home instead of replacing the roof! The best solutions address the root cause of a problem, which is exactly what philosophical thinking and reflection help you do. 

Have you taken a philosophical approach to thinking about your life, work and how to progress? If so, what benefits have you experienced?

Leave a comment below to let me know!