91 articles
Wealth Events & Sudden Money
A sudden influx of money creates a narrow window to make decisions that will affect you for decades.
Financial Planning Library
Perspectives
Guides for the financial decisions that shape your life, work, and retirement.
What financial planning topics does Chesapeake Financial Planners cover?
Chesapeake Financial Planners publishes practical guidance across financial planning topics, including retirement income, tax strategy, estate planning, Social Security, Medicare, investments, business planning, equity compensation, divorce, and federal benefits. Each topic begins with a complete guide and expands into focused articles about the decisions within it.
Explore by pillar 17 guides
Every article we publish sits inside one of these financial planning topics. Start with the guide closest to your situation, or explore its complete library.
83 articles
Investment Strategy
Your investment strategy should reflect your actual goals, time horizon, and tax situation, not a generic model.
Start here
Asset Allocation by Age and Risk Tolerance
81 articles
Business Owners & Exit Planning
Your business is your largest asset and your retirement plan at the same time.
80 articles
Financial Basics & Planning Foundations
A strong financial foundation starts with the basics: emergency savings, the right insurance, a clear debt plan, and a savings priority order.
78 articles
Social Security Strategy
Your Social Security claiming strategy can add or subtract hundreds of thousands of dollars over your lifetime.
78 articles
Tax Planning & Strategy
A proactive tax strategy lowers what you owe across your lifetime, not just this April.
75 articles
Estate Planning & Trusts
Estate planning protects your family, avoids probate, and ensures your assets go where you intend.
75 articles
Retirement Planning & Income
Build a retirement income strategy that covers healthcare costs, Social Security timing, tax efficiency, and portfolio withdrawals, guided by a CFP professional serving Forest Hill and the greater Baltimore metro area.
45 articles
Maryland & Local
Maryland has its own estate tax, unique pension exclusions, and county-level income taxes that affect retirement income strategy in ways generic national advice misses.
31 articles
Medicare & Healthcare in Retirement
Medicare decisions made at enrollment are often permanent.
29 articles
Women & Divorce Financial Planning
Women face distinct financial planning challenges including longer retirements, career gap impacts, and higher divorce and widowhood rates.
22 articles
College Planning
Funding college without derailing retirement requires a deliberate strategy for savings accounts, financial aid positioning, and funding priorities.
20 articles
Tech & Equity Compensation
Equity compensation is powerful but complex.
16 articles
Federal & Military Benefits
Federal and military benefits are among the most valuable compensation packages available, but only if you understand how all the pieces fit together.
15 articles
Behavioral Finance
Your biggest investment risk may not be the market; it may be your own behavior during a downturn.
8 articles
Firm Brand & R.U.D.D.E.R. Method
The R.U.D.D.E.R.
6 articles
Advisor Practice Acquisition & Succession
Transitioning a financial advisory practice requires the same rigor as any complex business sale, with the added stakes of client relationships and career legacy.
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Prefer to scan everything at once? The full archive is below, filterable by category and sorted by date. The pillar guides above are the better starting point if you are new to a topic.
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Contributed (27)
Economic & Market Reports (1)
Estate Planning (131)
High Net Worth (86)
Investments (195)
Quoted (160)
Retirement Planning (374)
Risk Management (139)
Taxes (274)
Tech & SaaS (22)
Wealth Events (186)
Women (64)
September 7, 2026
What expired in the TCJA sunset and what did OBBBA make permanent?
What expired in the TCJA sunset and what did OBBBA make permanent? Last reviewed: July 2026 Most of the 2017 Tax Cuts and Jobs…
September 7, 2026
Should My CPA, Attorney, and Financial Advisor Talk to Each Other?
Should My CPA, Attorney, and Financial Advisor Talk to Each Other? Last reviewed: July 2026 Yes, and for most business owners they almost never…
September 6, 2026
What Is the RSU Tax Withholding Gap and How Do You Close It?
What Is the RSU Tax Withholding Gap and How Do You Close It? Last reviewed: July 2026 The RSU tax withholding gap is the…
September 3, 2026
What Is a Social Security Claiming Strategy for High-Net-Worth Retirees?
What Is a Social Security Claiming Strategy for High-Net-Worth Retirees? Last reviewed: July 2026 The conventional Social Security claiming strategy says to wait until…
September 2, 2026
Does Maryland tax my retirement income, Social Security, and pension?
Does Maryland Tax Retirement Income? Social Security, Pensions & IRAs Last reviewed: July 2026 Does Maryland tax retirement income? Partly. Maryland does not tax…
September 2, 2026
Do I have to take my RMD before doing a Roth conversion?
Do I have to take my RMD before doing a Roth conversion? Last reviewed: July 2026 Yes. If you are 73 or older, you…
September 2, 2026
Why is Maryland the only state with both an estate tax and an inheritance tax, and how do I plan for it?
Maryland Estate Tax 2026: Why Does Maryland Have Both an Estate and Inheritance Tax? Last reviewed: July 2026 The Maryland estate tax 2026 threshold…
September 2, 2026
How can Roth conversions and RMDs trigger higher Medicare premiums (IRMAA)?
How can Roth conversions and RMDs trigger higher Medicare premiums (IRMAA)? Last reviewed: July 2026 Most people think of Medicare as a fixed cost.…
September 2, 2026
What is a mega backdoor Roth, and how do I use one?
What is a mega backdoor Roth, and how do I use one? Last reviewed: July 2026 A mega backdoor Roth is a strategy that…
September 2, 2026
How does Maryland’s $2,500 529 state tax deduction work?
How Does Maryland's $2,500 529 State Tax Deduction Work? Last reviewed: July 2026 Maryland's 529 tax deduction lets each taxpayer subtract up to $2,500…
September 2, 2026
Who pays Maryland’s 10% inheritance tax, and how do I protect non-lineal heirs?
Who pays Maryland's 10% inheritance tax, and how do I protect non-lineal heirs? Last reviewed: July 2026 Maryland's 10% inheritance tax is paid by…
September 2, 2026
How do Maryland’s new income tax brackets and 2% capital gains surtax affect high earners?
How Do Maryland's New Income Tax Brackets and 2% Capital Gains Surtax Affect High Earners? Last reviewed: July 2026 Maryland high earners now face…
Written and reviewed by Jeff Judge, CFP®, AEP®, ChFC®, CLU®
Managing Partner of Chesapeake Financial Planners in Forest Hill, Maryland, serving families and business owners across Harford County and the Baltimore metro area.
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