[Podcast Episode #26] The Unexamined Life Is Not Worth Living: Why Reflection Creates Results
Episode #26
Ready to turn reflection into a competitive edge? In this episode we unpack a year of wins and misses to show how small systems create outsized results—financially, physically, and strategically. No fluff, just the tools and stories we used to design a life and business that compound.
Some topics covered are:
- A 3-day calendar audit vs. a daily–weekly–monthly review loop
- Automating investments for steady wealth building
- Gold/silver habits, missed rallies, and better systems
- Redefining health around sleep, injuries, and family realities
- Execution frameworks that speed decision-making
- Digital boundaries with a “brick” phone and two numbers
- Turning every experience into value through reflection
- Daily story capture to turn life into lessons
- And more…
Episode Summary
Every December, between Christmas and the New Year, a sacred pause enters our calendar. It is not merely downtime, nor is it simply a break from the year’s hustle. For us, business owners, legacy builders, family stewards, this window is an invitation to examine, reflect, and recalibrate. As Cris and Philip opened this year’s first episode of Get Your House in Order, they offered a deeply personal and strategic look into their annual review processes and the timeless lessons extracted from 2025.
1. Reflection Is a System
Cris sets aside three full days to comb through his calendar. He revisits conversations, trips, highlights, and hardships, not only to savor the memories but to extract meaning from each moment. His process isn’t accidental; it’s ritualistic. Lists emerge: friendships gained, values tested, books read, and even a catalog of negative experiences that still carry hidden value.
Philip complements this with a journaling system that breaks the year into digestible daily, weekly, and monthly insights. The key lesson? Annual reflection is not an event. It is a system that, when practiced throughout the year, turns chaos into clarity.
2. Automate What Matters
Cris revisited a long-standing habit: buying physical silver and gold. Years ago, he had automated this as a weekly routine, a habit learned from his father-in-law, who witnessed the collapse of East Germany. Yet, over time, this habit faded. In 2025, Cris was reminded of the principle behind David Bach’s The Automatic Millionaire: wealth is built not by bursts of brilliance, but by systems of consistency. This revelation prompted a broader question: what other critical life systems need automation?
3. Health as Foundation, Not Accessory
For Philip, health was a cornerstone theme. Historically a high-performer who prioritized health to fuel productivity, 2025 disrupted that narrative. With two young children and recurring minor illnesses, he found his old routines faltering. Pain and fatigue replaced gym sessions and quiet mornings. His breakthrough came by returning to fundamentals, tracking daily habits on paper, covering physical, mental, emotional, and spiritual well-being. It wasn’t innovation. It was rediscovery.
4. Execution Is King
Cris brought up a powerful, if controversial, example: Donald Trump’s early executive actions. Whether admired or criticized, one principle stood out, decisiveness. For entrepreneurs and investors, the takeaway is clear. The world is moving too fast for prolonged indecision. Strategy without execution is daydreaming. In 2025, Cris felt the cost of delayed decisions and committed to tightening his execution rhythm in both business and life.
5. Redefining Digital Discipline
Philip confronted his addiction to the smartphone, an issue many acknowledge but few truly solve. After years of attempting discipline through willpower and productivity apps, his breakthrough came with a physical “brick” device that blocked access to distracting apps. This external tool became a boundary setter, allowing him to reclaim time, mental focus, and ultimately, creative energy.
6. Travel, Serendipity, and the Value of Presence
Though Cris logged countless travel miles, Estonia, Argentina, Uruguay, he didn’t always know if each trip would yield results. And yet, reflecting back, he found that nothing was wasted. A conversation on a plane turned into a friendship. A trip taken in uncertainty sparked new connections. It reaffirmed the value of showing up, of being present, and of allowing life to surprise us.
7. Capture the Mundane: It's Where the Magic Hides
Philip shared a favorite exercise: every day, write down the most story-worthy moment. Then record it. Using a journaling app and a morning walk, he memorializes life’s daily gifts, his child’s comment, a coaching insight, a passing thought. When you practice noticing, you find that even the ordinary contains seeds of wisdom.
Conclusion: Design the Life You Want, One Reflection at a Time
As Philip reminded us: “An unexamined life is not worth living.” But an examined life? That’s a designed life. And a designed life leads to legacy.
So whether it’s gold coins or grocery lists, new countries or new convictions, a year in review is never about nostalgia. It’s about noticing patterns, distilling principles, and taking strategic action. The past is not just something we remember. It’s something we use.
Make the reflection. Take the lesson. And above all, get your house in order.
Get a free copy of "Get Your House in Order"
Principles of success based on the life of Cosimo de’ Medici by Cris Auditore Zimmermann