Bill Perkins’ “Die with Zero” has captured the attention of retirees and financial planners alike with its provocative message: optimize your life experiences rather than maximizing your net worth at death. While the book’s philosophical framework offers valuable insights about living a fulfilling life, its financial planning advice raises significant concerns that warrant careful examination. As a financial advisor, I believe in extracting the wisdom while recognizing the practical limitations—and potential dangers—of implementing this approach literally.
The Good: Philosophical Gold Worth Mining
Memory Dividends and Experience Investing
Perkins introduces the compelling concept of “memory dividends”—the ongoing returns we receive from experiences long after they occur (source)(source). Unlike material possessions that depreciate, experiences “actually gain in value over time” as we relive them through memories triggered by songs, scents, or photographs. Research in behavioral finance supports this phenomenon, showing that people form lasting positive memories from meaningful experiences that continue to provide psychological benefits throughout their lives (source)(source).
This insight challenges the traditional view that spending money on experiences is merely consumption. Instead, Perkins reframes experiential spending as an investment that pays dividends for decades. When you take that European vacation at 30, you’re not just paying for two weeks of travel, you’re investing in memories that will enrich your life for the next 50 years.
Time Bucketing: Age-Appropriate Experience Optimization
One of the book’s most practical contributions is the concept of “time bucketing,” which is aligning experiences with your physical and mental capabilities at different life stages. Research on aging and time perception confirms that older adults have different preferences and capabilities than younger adults, with increasing focus on emotionally meaningful activities as time horizons shrink (source).
The science supports Perkins’ intuition: studies show that as people age, they increasingly prioritize emotionally satisfying experiences over knowledge-seeking activities, and this shift may follow a non-linear pattern that accelerates after age 60. This means that adventure travel, physically demanding activities, and career-building experiences are better suited for earlier decades, while family time, cultural pursuits, and legacy activities become more valuable later.
Focus on What Truly Matters
Perhaps most importantly, “Die with Zero” challenges our cultural obsession with endless accumulation. The book encourages readers to consider whether they’re living fully or merely existing to build wealth they may never meaningfully use. This philosophical shift toward intentional living and conscious consumption has genuine merit, especially for those who sacrifice present happiness for an uncertain future.
Beware: The Financial Planning Pitfalls
The Hypocrisy Problem
Before examining the financial advice, we must address the elephant in the room: Bill Perkins continues to build wealth while preaching asset depletion. With an estimated net worth between $110 million and $500 million as of 2025, growing through his energy trading hedge fund Skylar Capital, Perkins embodies the opposite of his own advice (source)(source)(source). His recent purchases include a $15 million painting (viewed as an investment potentially worth $100 million) and a $22 million home (source).
This disconnect matters because it reveals the advice’s limited applicability. When you have hundreds of millions of dollars, “dying with zero” is aspirational (i.e., you could deplete 80% of your assets and still live luxuriously). For mid-to-high net worth retirees, following this advice literally could mean poverty in old age.
The Annuity Solution’s Hidden Costs
Perkins suggests that one path to dying with zero is simple: buy annuities and long-term care insurance to cover essential needs, then spend down your remaining assets freely. While these products can play important roles in retirement planning, his analysis oversimplifies their costs and limitations, particularly for middle-income families.
Long-Term Care Insurance: A Percentage Game
The cost of long-term care insurance isn’t dramatically different for Perkins versus a traditional retiree in absolute terms. However, as a percentage of net worth, the burden is vastly different (source)(source)(source). A $3,000 annual premium represents 0.0006% of a $500 million net worth but 3% of a $100,000 portfolio. This creates a fundamental trade-off that Perkins’ analysis ignores.
Mid to mid-high net worth families face difficult choices about funding end-of-life care:
- Insurance approach: Pay premiums for decades with no guarantee of needing coverage, facing potential rate increases that could make policies unaffordable (source)(source)
- Self-funding approach: Accept the risk of depleting savings if extended care is needed, potentially leaving a surviving spouse in financial distress (source)(source)
- Hybrid strategies: Use home equity, reduce current spending, or combine partial insurance with partial self-funding (source)
The Liquidity Trap of Annuitization
A true “die with zero” strategy would require annuitizing most assets through Single Premium Immediate Annuities (SPIAs), but this creates severe liquidity constraints (source)(source)(source). Early withdrawal from annuities often triggers surrender charges of 7-10% and tax penalties, making funds inaccessible for emergencies or changing circumstances.
Research confirms that annuities with delayed liquidity can provide higher returns but at the cost of flexibility (source). While this forced discipline helps some retirees avoid overspending, it can be catastrophic when life throws curveballs such as medical emergencies, family crises, or changes in living situations that require immediate access to funds.
The Irreducible Uncertainty Principle
The fundamental flaw in the “die with zero” financial strategy is its assumption that we can predict lifespan and expenses with sufficient precision to optimize asset depletion. This ignores what I call the irreducible uncertainty principle: no matter how sophisticated our planning, we cannot eliminate the basic uncertainties that make precise timing impossible.
Longevity Risk: The 10-15 Year Problem
What happens if medical advances or genetic luck extend your life 10-15 years beyond your “die with zero” planning horizon (source)? Retirement planning research shows that longevity uncertainty alone can require 25-100% more savings than deterministic models suggest (source). A retiree planning to deplete assets by age 90 who lives to 105 faces 15 years of potential poverty—a risk not worth taking for most families.
The Quality of Care Question
There’s a profound difference between being able to afford quality long-term care versus relying on Medicaid facilities. When your assets are depleted, you lose the ability to choose where you receive care, potentially affecting both your quality of life and your family’s willingness to visit. This isn’t just about comfort—it’s about dignity and maintaining relationships during your most vulnerable years.
The Alternative: Probability-Based Planning with Guardrails
Instead of the binary choice between endless accumulation and precise depletion, successful retirement planning embraces uncertainty through probability-based approaches with dynamic guardrails (source)(source). This strategy acknowledges that we cannot predict the future perfectly but can create systems that adapt to changing circumstances.
Risk-Based Guardrails vs. Asset Depletion
Modern retirement planning uses risk-based guardrails that adjust spending based on portfolio performance and market conditions (source)(source). For example, if your portfolio falls below certain thresholds, you reduce spending by 10%. If it performs well, you can increase spending. This approach provides the flexibility to enjoy life while maintaining financial security (source).
At Calculated Wealth, we implement tactical asset allocation strategies combined with spending guardrails because we believe this provides the greatest probability of navigating an unknowable future successfully. This approach may not result in dying with zero dollars, but it maximizes the chances of living comfortably throughout retirement while preserving dignity and choice in your final years.
The Balanced Approach: Living Fully While Planning Wisely
The genius of “Die with Zero” lies not in its literal financial advice but in its challenge to examine our relationship with money and experiences. The book’s value comes from asking better questions: Are you deferring too much happiness for an uncertain future? Are you so focused on accumulating that you’re missing opportunities to create meaningful memories with family?
However, these philosophical insights don’t justify abandoning sound financial planning principles. Instead of choosing between endless accumulation and reckless depletion, consider a middle path:
- Embrace time bucketing: Align your spending with your life stages, prioritizing age-appropriate experiences while you can enjoy them
- Invest in memory dividends: Spend intentionally on experiences that will provide lasting value, especially those involving relationships
- Maintain financial security: Use probability-based planning with guardrails to balance current enjoyment with future security
- Plan for uncertainty: Accept that you cannot predict your exact lifespan or expenses, so maintain buffers for the unexpected
- Choose quality over quantity: When it comes to end-of-life care and experiences, preserve the ability to maintain dignity and choice
The ultimate irony of “Die with Zero” is that its best insights have nothing to do with the dollars in your bank account at death. They’re about recognizing that life is finite, experiences matter, and relationships are what we truly retire on. You can embrace these truths while still planning for the reality that uncertainty makes precision impossible—and that’s okay.
A successful retirement isn’t about timing your final dollar perfectly; it’s about maximizing fulfillment while maintaining the security to face whatever the future brings with dignity and choice. That’s a goal worth planning for, even if it means you might not die with zero after all.