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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 Income
Strategies for creating sustainable retirement income from Social Security, pensions, investment accounts, and other resources.
When a Roth Conversion Is a Mistake: Tax-Smart Alternatives
Is a Roth conversion always the right move? For many households, prepaying taxes can be a costly mistake due to negative tax arbitrage. Large conversions can also trigger hidden penalties like the Medicare IRMAA cliff, Social Security tax torpedo, and ACA subsidy losses. Learn when to pause a conversion and discover superior, tax-free alternatives like Qualified Charitable Distributions (QCDs) and Donor-Advised Funds to maximize your lifetime after-tax wealth.

John Macy
Aug 16
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
Roth vs. Traditional: Which Makes More Sense for You?
When should you make Roth contributions and when should you choose to contribute to a Traditional IRA/401(k)? Key rules of thumb and decision factors.

John Macy
Aug 13


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


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


Longevity Risk in Retirement: Will Your Money Last?
A longer life is something most of us hope for—but it also means your retirement savings may need to last 30 years or more. This article explains longevity risk, why average life expectancy can be misleading, how living longer compounds other retirement risks, and the practical strategies that can help you build a more resilient retirement plan.

John Macy
Jul 20


How to Create a Sustainable Retirement Paycheck
Creating a retirement paycheck is one of the biggest challenges of retirement. Learn how to combine Social Security, pensions, annuities, TIPS ladders, dividend income, and flexible portfolio withdrawals into a reliable retirement income plan that can help you cover essential expenses, manage market volatility, and enjoy retirement with greater confidence.

John Macy
Jul 17


Building a Global Dividend ETF Portfolio for Retirement Income
Ready to bring your dividend strategy together? In the final part of our series, we map out how to combine complementary U.S. and international dividend ETFs into a single, resilient retirement portfolio. Discover our 6-fund global model portfolio—featuring SCHD, DGRO, VYM, and more—designed to balance current cash flow, long-term growth, and downside protection without chasing dangerous yield traps.

John Macy
Jul 15


Best International Dividend ETFs for Retirement Income
Looking to diversify your retirement income beyond the U.S. market? International dividend ETFs offer attractive valuations and global diversification, but they also bring unique currency and tax risks. In Part 2 of our series, we review 10 top international dividend funds—including LVHI, DIVI, SCHY, and VYMI—using our custom scoring model to help you find the right fit for a resilient, globally diversified income portfolio.

John Macy
Jul 15


Best U.S. Dividend ETFs for Retirement Income and Growth
Looking for reliable retirement income? Simply chasing the highest dividend yield can be a costly mistake. In Part 1 of our dividend series, we analyze 10 top domestic dividend ETFs—including SCHD, DGRO, and VYM—using a professional multi-variable scoring model. Discover how to balance current cash flow, long-term growth, and risk to build a resilient, low-volatility portfolio tailored to your unique financial goals.

John Macy
Jul 15
How to Manage Sequence of Returns Risk in Retirement
Market volatility is inevitable, but it shouldn't dictate your retirement lifestyle. In Part 2 of our series on Sequence of Returns Risk (SoRR), discover five actionable, defensive layers to insulate your wealth. Learn how to construct a dedicated volatility buffer fund, establish flexible spending guardrails, maximize your guaranteed income floor, leverage uncorrelated assets to protect your principal against volatility, and rebalance periodically.

John Macy
Jul 8


Sequence of Returns Risk: What It Means for Retirees
When transitioning from saving to spending, the math of retirement shifts completely. Discover what Sequence of Returns Risk (SoRR) is, how an early market crash can hollow out your portfolio, and why static withdrawal strategies can introduce additional risk in your retirement.

John Macy
Jul 8


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


How I Invest My Own Money as a Retirement Income Coach
Ever wonder how financial professionals invest their own money? In this post, I pull back the curtain on my family’s semi-retirement portfolio to demonstrate true diversification in practice. Moving far beyond a traditional 60/40 mix, I break down our exact allocation across equities, real assets, private credit, and managed futures. Discover how we balance growth, reliable cash flow, and inflation protection to design a resilient financial future.

John Macy
Jun 20


Dividends, Interest, and the 4% Rule
How do dividends and interest fit into the classic 4% Rule? Many retirees think investment income is "extra" cash on top of portfolio growth, but it's actually just one part of your total return. Discover the origins of safe withdrawal rates, why modern research supports a 4.5%–5% baseline, and how a tax-smart withdrawal sequence—spending your taxable income first—can drastically cut tax drag and maximize the life of your retirement nest egg.

John Macy
Jun 19
Bonds or Stocks for Income Investing?
Should you rely on bonds or dividend stocks for retirement income? While bonds offer a steady paycheck, they leave you vulnerable to inflation. On the flip side, dividend stocks provide vital growth and inflation protection but carry higher market risk. The real magic happens when you combine them. Discover how a strategic blend of stable fixed income and rising dividend growth creates a resilient, inflation-proof stream of cash flow to secure your retirement.

John Macy
Jun 18
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
Retirement Withdrawal Strategies to Make Your Money Last
Following the old rule of thumb to spend taxable accounts first and save your Roth for last can backfire, triggering massive tax spikes, IRMAA surcharges, and the "widow's tax trap." Discover a better way to coordinate your Traditional, Roth, and brokerage assets. This guide explores three tax-smart alternatives—Bracket Filling, the Withdrawal Waterfall, and Blended Withdrawals—to help smooth your lifetime tax bill and protect your hard-earned retirement wealth.

John Macy
Jun 18
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
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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