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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.
When Should You Do a Roth Conversion? 5 Guiding Principles
Roth conversions are a powerful retirement tool, but timing is everything. Do them at the wrong time or tax rate, and you could end up worse off than leaving the money in your Traditional IRA. Discover the guiding principles for getting it right, how to find the tax bracket "sweet spots," and how to avoid costly hidden complications like Medicare IRMAA surcharges, NIIT, and the Widow's Tax Trap. Learn how to ensure the tax math always works in your favor.

John Macy
Aug 15


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


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


What Is IRMAA? How Medicare Surcharges Affect Retirement
Are your Medicare premiums about to spike unexpectedly? Discover the rules of the Medicare IRMAA tax trap, understand its strict two-year lookback mechanism, and learn eight strategies to safeguard your retirement income.

John Macy
Jul 8
Living on Dividends and Interest in Retirement
Is living off dividends and interest the ultimate retirement dream, or does a total return strategy offer greater security? Discover the true pros and cons of an income-focused portfolio, including how to spot high-yield traps and protect your wealth from inflation erosion. Plus, see a 10-year scenario breakdown comparing dividend growth versus total return investing to help you choose the most resilient, sustainable income plan for your long-term goals.

John Macy
Jun 18
How Much Do I Need to Retire? The 4% Rule Explained
Forget generic, one-size-fits-all "magic numbers" like $1 million or $2 million—true retirement planning is about calculating a custom target tailored directly to the specific lifestyle you want to live. This guide delivers a clear, three-step retirement formula to determine your exact target savings by mapping out a bottom-up budget, subtracting guaranteed income to identify your true "spending gap," and selecting a custom multiplier based on your retirement timeline.

John Macy
Jun 17
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