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Financial Coaching for DIY Investors Approaching or Living in Retirement
Creating Sustainable Retirement Income, Optimizing Social Security, and Reducing Retirement Taxes
Building a Resilient Retirement Income System
Practical guidance for DIY investors approaching or living in retirement—covering retirement income, taxes and healthcare, portfolio construction, and the risks that can derail a retirement plan.


Retirement Readiness Checklist: 10 Things to Assess
Retirement is more than a financial milestone—it is a major life transition. A successful retirement requires a strong foundation of financial security, health, relationships, purpose, and adaptability. This retirement readiness assessment examines 10 essential areas to help you evaluate your preparation, identify potential gaps, and create a plan for a fulfilling and resilient retirement.

John Macy
Jul 27


Building a Retirement Plan That Withstands Market Crashes
Retirement isn't about predicting the future—it's about preparing for it. This capstone article in the Retirement Risk Management Series brings together the key lessons from the previous eight articles into a practical framework for building a resilient retirement system. Learn how secure income, diversified investing, flexible withdrawals, tax planning, insurance, and healthy living work together to strengthen long-term retirement security.

John Macy
Jul 26


Retirement Behavioral Risks: Panic Selling & Overconfidence
Successful retirement planning is not just about choosing the right investments — it also requires managing human behavior. This article explores the psychological risks that can derail retirement plans, including panic selling, chasing performance, excessive confidence, and failure to adapt. Learn how to create systems that help you make better decisions through market cycles.

John Macy
Jul 25


Healthcare Costs in Retirement: Medical & Long-Term Care
Healthcare is one of retirement’s greatest financial uncertainties—but the biggest risks are often misunderstood. This article explores the three phases of healthcare risk: bridging the gap before Medicare, managing healthcare expenses after Medicare, and preparing for the potentially high costs of long-term care. Discover strategies to protect your retirement savings and maintain your financial independence.

John Macy
Jul 25


12 Retirement Tax Strategies to Reduce Your Tax Bill
Taxes can quietly become one of the largest expenses in retirement—but thoughtful planning can significantly reduce their impact. Learn how Roth conversions, strategic withdrawals, asset location, QCDs, tax-loss and tax-gain harvesting, and other proven strategies can help minimize lifetime taxes, increase after-tax retirement income, and preserve more wealth for your family and charitable goals.

John Macy
Jul 24
Retirement Spending Warning Signs
Market volatility isn’t your biggest threat in retirement—the chronological timing of it is. Known as Sequence of Return Risk, a sharp downturn right before or early in retirement can permanently drain your nest egg if you are forced to sell assets at a loss. Learn how to spot critical withdrawal rate red flags and build a bulletproof income plan using safe withdrawal baselines, strategic emergency funds, guaranteed income floors, and flexible spending guardrails.

John Macy
Jun 18


Rethinking Retirement Income: Beyond the 60/40 Portfolio
Ready to trade decades of saving for a reliable retirement paycheck? While the traditional 60/40 index fund strategy is popular, it often exposes retirees to hidden market risks and the psychological stress of selling shares in a downturn. In this post, we explore alternative cash-flow strategies—from dividend growth stocks and REITs to BDCs and MLPs—to help you build a resilient income floor, improve portfolio diversification, reduce price volatility, and protect your hard-e

John Macy
Jun 14
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