The 25 Mistakes That Quietly
Drain Retirement Wealth.
And The Framework To Stop Them.
Every retirement plan has gaps its owner doesn't see — until the cost is no longer recoverable. Most families discover their exposure to taxes, probate, care costs, and income disruption only after the window to fix it has closed. I wrote The 25 Biggest Retirement Mistakes and built the PILOT Process Scorecard so you can find your gaps in 60 seconds — while there's still time to close them.
Get My Scorecard + Free Book →
A perfect accumulation plan is
a guaranteed distribution disaster.Most American families spend 35 years mastering one game — growing assets. Then retirement begins and the rules silently change. The portfolio that built your wealth is the wrong tool to protect and distribute it. The advisor who got you here is rarely the one who can get you through. And the gaps between disciplines — legal, tax, investment, insurance — are where families lose what they spent a lifetime building. The families who keep their wealth aren’t lucky. Someone found the gaps and closed them before they compounded. That takes a system.
5 layers. 1 score.
The complete diagnostic.That system is the PILOT Process™. It stress-tests your plan against the five risks that actually sink a retirement — before any of them cost you. Five layers, one score, in 60 seconds:
Portfolio Positioning
Designed for distribution — or still built for accumulation?
Income & Tax Strategy
RMDs, Roth conversions, withdrawal sequencing, bracket management.
Longevity & Stress Tests
Does your plan hold under market crashes, widowhood, or inflation?
Ownership & Control
Trust structure, beneficiary designations, and probate exposure.
Transfer of Risk
Long-term care, income floor, and risks that shouldn't sit in your portfolio.
All 25, laid bare.
Organized by the PILOT layer where each one lives.Every mistake families make falls inside one of those five layers. These are the 25 we see over and over working with families worth $1 million to $25 million — and most plans have at least six open right now. The Scorecard tells you exactly which ones are open in yours.
- Portfolio designed for accumulation, not distribution
- Cookie-cutter design with no distribution architecture
- Hidden fees layered through retirement accounts
- Sequence-of-returns risk ignored in the Red Zone
- Overexposure to volatility entering distribution
- No accumulation-to-distribution transition plan
- No written retirement income strategy
- Poor withdrawal sequencing across account types
- Ignoring RMDs and the tax bomb that follows
- Claiming Social Security too early
- No multi-year tax plan or Roth conversion window
- Ignoring Medicare IRMAA premium thresholds
- Underestimating life expectancy
- Ignoring inflation over a 30-year horizon
- Underestimating volatility’s impact on income
- No widowhood planning (the widow’s tax trap)
- Lack of accessible liquidity for emergencies
- Not stress-testing for future tax increases
- Assets fully exposed to probate court
- Outdated or contradicting beneficiary designations
- No will, trust, or power-of-attorney in place
- Improper asset titling for the family’s goals
- No guaranteed income floor
- No life insurance or risk-transfer strategy
- No long-term care plan
Find the gaps
before they find you.You’ve seen the problem, the framework, and all 25 mistakes. The only thing left is the one question that matters: which of them are open in your plan? The Scorecard answers that in 60 seconds — with your risk score, your personalized findings, and the free book that shows you how to close every gap it finds.
Get My Free PILOT Score →No cost · No obligation · Instant results
Gregory S. DuPont, Esq., CFP®
Estate Planning Attorney · Certified Financial Planner®One of fewer than 3,000 Americans who hold both credentials. Thirty years of planning through three estate tax overhauls, four market crashes, and a full generational cycle of clients whose plans have already played out — not modeled, not projected, lived.
Greg is the founder of DuPont Law Group and Advocate Wealth Solutions, creator of the PILOT Process and the 4D Estate Plan™, and author of The 25 Biggest Retirement Mistakes, The Retirement Tax Trap, The Probate Tax Trap, and The Long-Term Care Tax Trap. His March to a Million™ movement is on a mission to help one million families save a collective one billion dollars.
The PILOT Process and this Scorecard are how that standard reaches your family — the same five-layer review he runs for private clients, distilled into 60 seconds and a free book.