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💡 Rethinking Retirement: 6 Books That Redefine Wealth, Wisdom, and Well-Being
As we approach the end of 2025, a wave of fresh thinking is reshaping how we view money, meaning, and retirement. These six standout books offer more than financial advice—they challenge us to align our spending, planning, and life design with what truly matters. Whether you’re building your retirement roadmap or guiding others toward financial wellness, these lessons are worth integrating into your journey.
1. 🧠 The Art of Spending Money by Morgan Housel
Housel reminds us that money is emotional, not just mathematical.
• Key Insight: Spending reflects identity—how we see ourselves as secure, generous, or successful.
• FinFit Takeaway: Help clients define their “enough” and build budgets that reflect joy, not just restraint.
• Tool Tip: Use FinFit’s expense tracker to separate “must spend” from “like to spend” and visualize values in action.
2. 📉 1929 by Andrew Ross Sorkin
History repeats itself—especially when we forget its lessons.
• Key Insight: Market crashes stem from human behavior—greed, fear, and overconfidence.
• FinFit Takeaway: Encourage users to stress-test their plans, not predict the future.
• Tool Tip: Integrate downturn simulations into your retirement calculator to build resilience.
3. 🌱 A Richer Retirement by William Bengen
The creator of the 4% rule now emphasizes flexibility and meaning.
• Key Insight: Retirement is a life design challenge, not just a withdrawal strategy.
• FinFit Takeaway: Shift focus from fixed rules to adaptive planning.
• Tool Tip: Let users toggle withdrawal strategies and visualize evolving income flows.
4. 🍀 Lucky by Design by Judd Kessler
Luck isn’t random—it’s structured.
• Key Insight: Markets exist everywhere—from jobs to relationships.
• FinFit Takeaway: Help users identify hidden systems and navigate them with intention.
• Tool Tip: Map opportunity flows alongside financial ones—career pivots, sabbaticals, geographic moves.
5. 🧭 The Compass Within by Robert Glazer
A fictional parable with real-life clarity.
• Key Insight: Values alignment fuels energy, clarity, and courage.
• FinFit Takeaway: Anchor financial plans in personal values, not external expectations.
• Tool Tip: Include a “values check” in your onboarding quiz or journal prompts.
6. ✈️ Retire Often by Jillian Johnsrud
Why wait for one big retirement when you can take many?
• Key Insight: Mini-retirements offer adventure, rest, and reinvention.
• FinFit Takeaway: Normalize career breaks and build them into long-term plans.
• Tool Tip: Let users model sabbaticals and see how they affect savings, reinvestment, and retirement age.
🌟 Final Thought
Retirement isn’t just a financial milestone—it’s a reflection of how we want to live. These books remind us that planning with purpose, flexibility, and emotional clarity leads to richer outcomes. At FinFit, we’re not just crunching numbers—we’re designing lives.
📚 Reference:
Why Social Security Alone Isn’t Enough — And What You Can Do About It
