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)
June 23, 2026
Micro-Retirements Carry Macro Risks, Advisors Warn Clients
Health insurance headaches are among the potential problems with climbing off the career ladder temporarily.
June 23, 2026
Does NAPFA’s new fiduciary definition clarify or muddy the water for clients?
Some advisors say they already have a hard enough time explaining what a fiduciary is under federal law and that NAPFA's new definition for…
June 22, 2026
7 Best Fidelity ETFs to Buy Now
This asset manager's funds include bonds, stocks and niche strategies, although not all are suitable for every investor.
June 17, 2026
Advisors Wary of SEC’s Plan to Allow Semiannual Corporate Earnings Reports
Quarterly reporting helps inform clients, but it also encourages public companies to focus on the short term.
June 16, 2026
These life-insurance policies are booming. Here’s who should — and shouldn’t — buy one.
Indexed universal life insurance policies have a very specific purpose that can help families, if used correctly.
June 16, 2026
With inflation up, my friends are asking about TIPS and I bonds—here’s what I told them
TIPS and I bonds are designed to help protect savings from rising costs, but advisors say major portfolio moves in response to short-term news…
June 16, 2026
These life-insurance policies are booming. Here’s who should and shouldn’t buy one.
Indexed universal life insurance policies have a very specific purpose that can help families, if used correctly. These insurance products may be better for…
June 16, 2026
The biggest risk to your retirement isn’t a market crash — it’s a crisis you probably haven’t planned for
Health-related financial risks are the No. 1 threat to retirement security.
June 15, 2026
The biggest risk to your retirement isn’t a market crash – it’s a crisis you probably haven’t planned for
Health-related financial risks are the No. 1 threat to retirement security.
June 15, 2026
Advisors Don’t Mince Words on DOL’s Plan for Alts in 401(k)s
ThinkAdvisor polled advisors on their views about Labor's proposal. Here's what they said.
June 15, 2026
Kiyosaki escalates urgent warning about value of dollar
The author of “Rich Dad Poor Dad” says a hidden risk is hitting savings accounts and reducing wealth.
June 11, 2026
Gen X gets financial squeeze in key years for retirement saving
These demanding years are crucial for your financial future, but even if you neglected that 401(k), there's still time to catch up before retirement.
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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