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Matthew R. Harris

Two Retirees. Same $2M. Very Different Paychecks.


Happy Friday Reader ☀️

Stay tuned until the end of the email: I included a short overview of my Structured Roth Conversion Guide, which outlines a strategy for making Roth conversions more structured and tax-efficient.


Most people approaching retirement focus on one question:

“How much have we saved?”

But a better question is:

👉 “How much income can our savings actually produce?”

Because retirement doesn’t run on a portfolio balance.

It runs on income.

Two retirees could each have $2 million saved.

One generates $12,000 per month in retirement income.

Another generates $15,000 per month.

The difference usually isn’t investment performance.

It’s how the income strategy is structured.

Here are five ways thoughtful planning can increase retirement income without simply taking more risk.


1️⃣ Use an Age-Based Spending Strategy

Most retirees naturally spend 1–2% less per year after the first decade of retirement.

Planning for that reality can allow retirees to safely spend more in the early years, when travel, health, and experiences matter most.


2️⃣ Maintain Meaningful Growth Exposure

Being overly conservative can quietly reduce lifetime income.

A thoughtful allocation to growth assets helps a portfolio continue supporting income for decades, especially during longer retirements.


3️⃣ Delay Certain Income Sources

Some income sources grow significantly when delayed.

For example, Social Security benefits can increase roughly 8% per year between full retirement age and age 70.

Those guaranteed increases can translate into a larger retirement paycheck for life.


4️⃣ Use Dynamic Guardrails — Anchored by Safety

When part of a retirement plan includes market-independent income, it creates stability.

That stability allows retirees to spend more confidently from their investment portfolio.

🔒 Secure income creates flexibility
📈 Flexibility supports higher spending


5️⃣ Create a Personal Pension Strategy

Many retirees rely heavily on bonds for stability.

In some cases, replacing a portion of the lowest-yielding assets with a personal pension strategy can provide:

🔒 Market-proof lifetime income
📈 Higher sustainable spending
🛡 Protection from longevity risk

Research often shows allocating 25–40% of a portfolio to guaranteed lifetime income can increase sustainable spending while still preserving liquidity and legacy potential.


Retirement planning isn’t just about protecting assets.

It’s about turning savings into the highest sustainable retirement paycheck possible.

If you’d like to see how your current strategy translates into retirement income, you can learn more about my Retirement Income Review here.

Now as usual, all of the new resources of the week, are linked below. Enjoy!

Featured Resource of the Week:

The Structured Roth Conversion Strategy

Roth conversions can be a powerful way to reduce future taxes — but most retirees hesitate because of four major challenges:

How do I pay the taxes on the conversion?

What happens if the market drops while I’m converting?

How do I avoid the “phantom tax” risk of paying taxes on money the market later erases?

And how do I prevent the conversion from triggering higher tax brackets or IRMAA surcharges?

These challenges often make Roth conversions feel risky or inefficient.

In this week’s resource guide, I walk through an often-overlooked strategy that allows Roth conversions to be structured more deliberately and tax-efficiently. By coordinating how the taxes are funded, stabilizing assets during the conversion period, and managing tax bracket exposure, retirees can gradually shift tax-deferred assets into tax-free wealth.

The key is structuring the conversion so taxes are controlled, volatility is managed, and the long-term benefits of tax-free growth can fully compound.

👉 Access my full Structured Roth Conversion Guide here

As always, thank you for allowing me into your inbox.

The years leading into retirement are often the most financially sensitive. Small structural decisions can have long-term consequences.

If you would like to understand how your current income and tax strategy measures up, you can learn more about my Retirement Income Review process here:

Retirement Income Review

Additional resources and case studies:
Safe Wealth Planning

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8860 Westminster Blvd. , Westminster, CO 80031 Unsubscribe · Preferences

Matthew R. Harris

I help individuals and families transition from the accumulation phase of retirement to the income phase through structured income planning and tax-smart withdrawal strategies.

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