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Mainstreet Financial Education

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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?Read → How rental real estate can lower taxes and increase income?Read → Tax-advantaged ways to save for your children's education?Read → How to manage family finances if a spouse becomes incapacitated?Read → How to protect a disabled child's benefits after your death?Read → The advantages of Medicaid and how to qualify a senior family member?Read → What type of mortgage you should have on your home or rental property?Read →

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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Long-term care · Georgia 2026

Medicaid for long-term care: how it works, who qualifies

Medicare pays for recovery. Medicaid pays for care. The 2026 Georgia limits, what the at-home spouse keeps, and why the five-year look-back makes early planning the whole game.

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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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Fillable worksheet · PDF

Who pays for care (worksheet)

Price care where you live, then work out how the bill would get paid: a policy, a hybrid, or your own assets. Ends with the family questions most people skip.

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Life insurance & annuities

Fillable worksheet · PDF

What is it for? (life insurance worksheet)

Start with the jobs the money would need to do, count what you already own, and see whether there is a gap before anyone mentions a product.

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Fillable worksheet · PDF

Know your annuity (worksheet)

What to gather, what your contract actually says, and the questions to ask before you sign one. For people who own an annuity and people considering one.

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Real estate & your home

Tax planning · 2026

How real estate turns tax dollars into equity

Depreciation, the 1031 exchange, the home-sale exclusion, and opportunity zones let money that would have gone to the IRS stay invested. Each one has a bill attached later, and this shows both halves.

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Income & tax · 2026

Rental real estate: lower taxes, more income

A rental can send a check every month and a tax loss every April. How that happens, the passive loss rules that decide who can use the loss, and whether you want to be a landlord at 78.

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Home & property · 2026

Which mortgage belongs on which property

A loan on your home is a cost of living. A loan on a rental is a cost of doing business. How tax rules, risk, and your stage of life sort out which loan goes where, including paying the house off in retirement.

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Family & special situations

Education · 2026

Tax-advantaged ways to pay for a child's education

The 529 does most of the work and the 2025 tax law made it more flexible. How it compares with the other accounts, what Georgia adds, and how grandparents can help without hurting financial aid.

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Family & legacy

If your spouse becomes incapacitated, who runs the money?

Being married does not give you the right to manage your spouse's IRA. The four documents that do, the account settings most couples never turn on, and what to do in the first weeks if it has already happened.

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Family & legacy · 2026

Protecting a disabled child's benefits after you are gone

An inheritance left the ordinary way can cut off SSI and Medicaid. How a special needs trust and an ABLE account keep the benefits intact, and what federal families need to know about survivor benefits and FEHB.

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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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Fillable checklist · PDF

Questions to ask before you hire a financial planner

Ten questions to take into any first meeting, with room to write down what each advisor said. Use it on us first.

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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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