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Mainstreet Financial Education

The learning library, open to anyone

Guides to the money decisions that come up around retirement, written in plain English. Read what you need, and take it to whichever advisor you trust.

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Common questions, answered

These are questions people actually ask me. Tap one and it opens the guide.
How to get all the tax relief you are legally entitled to?Read → How to maximize the value of your company pension plan?Read → How to invest so 50% to 100% of your return is tax-free?Read → Whether you should own an IRA?Read → How to pass your possessions to family with the least expense?Read → How to reduce or eliminate your estate tax?Read → How to increase the growth potential of your savings and investments?Read → How to avoid capital gains tax when selling real estate, stock, or a business?Read →
How to divert income-tax dollars into real estate investments?Guide in development
How rental real estate can lower taxes and increase income?Guide in development
Tax-advantaged ways to save for your children's education?Guide in development
How to manage family finances if a spouse becomes incapacitated?Guide in development
How to protect a disabled child's benefits after your death?Guide in development
The advantages of Medicaid and how to qualify a senior family member?Guide in development
What type of mortgage you should have on your home or rental property?Guide in development

The planning pillars

Income, investments, taxes, legacy, and risk usually end up with different people who never speak to each other. These five guides cover what each area handles and where the seams show.
Planning pillar

Retirement income planning

Your savings have to become a paycheck. How Social Security, a pension, and withdrawals fit together, and why the order you draw them changes what you owe. Start here for the income guides.

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Planning pillar

Investment planning

What your money sits in should follow from when you need it and how much of a drop you can watch without selling.

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Planning pillar

Tax planning

Most tax savings come from what you do in the years before the bill, not in April.

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Planning pillar

Legacy planning

Where your assets go when you are gone, and how much of the handoff gets eaten by tax and probate.

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Planning pillar

Risk management

One bad event can undo a good plan. What to insure, and what you can afford to absorb.

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Taxes in retirement

Tax planning · 2026

7 most generous tax rules for retirees

Retirees qualify for breaks most people never claim. Ranked by what they save, with a note on where each one collides with Social Security taxability or Medicare premiums.

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Tax planning · 2026

5 tax traps in the first 5 years of retirement

Between your last paycheck and your first RMD you have more control over your tax bill than you ever will again. Here is how people waste it.

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Tax planning · 2026

Long-term capital gains tax

Gains sit on top of your other income. That is why the same sale can be taxed at nothing one year and 15% the next.

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Tax planning · 2026

Self-employment tax

Where the 15.3% comes from, what it costs on real numbers, and the deduction that takes some of it back.

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Tax planning · 2026

Required minimum distributions, explained

At 73 the IRS starts pulling taxable income out of your accounts whether you want it or not. The penalty for missing one is steep, but the timing and the source are still yours to choose.

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Tax planning · 2026

How retirement income stacks for taxes

Two households with identical income can owe very different tax. What usually decides it is which accounts the money came out of.

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Income & benefits

Retirement income

Social Security break-even

Claiming at 62 instead of 70 is a bet on how long you live. The break-even is closer than most people expect, and it is rarely the only thing that should decide it.

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Annual planning

The 12-month money checklist

One task a month, starting with beneficiary forms in January and ending with a net worth snapshot in December.

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Retirement · Timing

5 timing decisions you can't undo

Some choices around your last paycheck cannot be walked back. Medicare's two-year income lookback is the one that catches people.

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Medicare & health

Medicare · 2026

Medicare Part A & Part B

Original Medicare comes in two parts. Here is what each one covers and what it costs in 2026.

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Medicare · 2026

Medigap basics

Original Medicare leaves gaps. Supplement plans fill them, but the window to buy one without medical underwriting closes faster than most people realize.

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Medicare enrollment

5 worst first-year Medicare moves

Some enrollment windows open once. Miss one and the late penalty follows you for the rest of your life.

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Medicare · 2026

Medicare & skilled nursing care

Medicare does pay for skilled nursing, but only under conditions most families never hear about until they are standing in a hospital hallway.

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Long-term care

Long-term care · 2026

Planning for long-term care: your real choices

Medicare does not cover custodial care. Families end up paying for it four ways, and this walks through each one with 2026 costs.

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Long-term care

No long-term care plan at 70?

By 70 the traditional insurance window has mostly closed. That leaves a shorter list, and this covers the conservative end of it.

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Retirement income

Income, long-term care & Roth: how they connect

These three decisions keep landing on the same dollars. Deciding them one at a time is how plans get tangled.

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Downloadable guide · PDF

Understanding long-term care (client guide)

Five printable pages on what Medicare will not cover and how families pay for it, with questions to bring to a conversation with your parents.

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For federal employees

Federal benefits · 2026

The FERS Special Retirement Supplement

Some FERS retirees get a bridge payment until 62. It is easy to lose to the earnings test if you take a job after retiring, and nobody warns you first.

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Federal employees · 2026

Navigating your federal benefits & retirement

The pension, the TSP, FEHB, and Social Security all move when you change your retirement date. This is how they move together.

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For business owners

Business owners

Should I be an S-corp?

The election can cut self-employment tax. It can also raise your payroll cost and shrink your Social Security record, which is why the salary number matters more than the election does.

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Business owners

How do I protect what I've built?

Entity structure, contracts, insurance, and how the assets are titled all have to hold. A gap in any one of them undoes the rest.

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Business owners

Turning a business into retirement income

Most of your net worth sits in something that does not pay you monthly. Here are the ways owners turn it into income.

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Business owners

Why a profitable business runs out of cash

You can be profitable on paper and still miss payroll. The gap is almost always timing.

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Choosing an advisor

Financial planning

8 questions before hiring an advisor

Ask these before you sign anything, mine included. I have written down the answers worth listening for.

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Prefer to learn in person?

I teach these same topics in person and online around metro Atlanta. Nobody sells you anything in the room.

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