How Are You Measuring Your Life? — Beneath The Surface
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Jun 6, 2025
This thought-provoking discussion begins with a moment of reflection inspired by loss, prompting a deep dive into personal values and measures of success. It questions whether we chase societal scoreboards or align with our true selves. Listeners explore the contrast between achievements and meaningful connections, advocating for love and authenticity. The conversation encourages introspection, guiding us to define our own standards of fulfillment and navigate life’s direction with purpose and intention.
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insights INSIGHT
Question Your Life's Scoreboard
Most people measure their lives but rarely question if their metrics reflect their true desires.
Society often imposes scoreboards that don't align with personal meaning, causing emptiness.
volunteer_activism ADVICE
Evaluate Life Direction Now
Reflect on whether continuing your current life path will lead to fulfillment and success.
Assess the directions of your health, relationships, and joy to avoid wasting precious time.
insights INSIGHT
Soul Over Societal Metrics
A life truly worth living focuses on intimate connections, love, and authenticity over fame or wealth.
Measuring success by external achievements leads to a hollow feeling despite apparent accomplishments.
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Published in 1854, 'Walden; Or, Life in the Woods' is a series of 18 essays that reflect Thoreau's experiences living in a small cabin near Walden Pond from July 1845 to September 1847. The book is a personal declaration of independence, a social experiment, and a voyage of spiritual discovery. Thoreau details his life in the woods, discussing the construction of his cabin, his daily activities, and his philosophical reflections on economy, social relations, and the importance of living in harmony with nature. The work is considered a cornerstone of American literature and a foundational text in the Transcendentalist movement, emphasizing the benefits of a simplified lifestyle and the importance of individual freedom and self-reliance[2][4][5].
The question hit me at a funeral:
If I keep living exactly as I am… what will my life add up to?
This episode isn’t here to give you answers. It’s here to help you ask better questions.
How are you measuring your life?
Are you chasing a scoreboard someone else created?
Or are you living in alignment with what your soul knows to be true?
You’ll hear reflections from the Stoics, wisdom from David Brooks and James Hollis, the ache behind Rumi’s poetry, and the quiet clarity of your own heart. I walk with you through the dangerous gap between what society tells us to want… and what actually makes life feel worth living.
This is not about chasing more. It’s about choosing better and following what truly matters.
So I’ll leave you with three questions—ones worth returning to again and again:
How will I measure my life?
Who am I working to become?
What is the life I’m truly trying to create?
Connect with Sean:
👉 Explore Sean’s writing, books, and executive coaching at whatgotyouthere.com 📩 Drop a message, share your thoughts, or connect directly Info@whatgotyouthere.com 📤 Love the episode? Send it to a friend who needs it or share it on social