98 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.
97 articles
Business Owners & Exit Planning
Your business is your largest asset and your retirement plan at the same time.
87 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.
84 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.
84 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
Estate Planning & Trusts
Estate planning protects your family, avoids probate, and ensures your assets go where you intend.
79 articles
Social Security Strategy
Your Social Security claiming strategy can add or subtract hundreds of thousands of dollars over your lifetime.
79 articles
Tax Planning & Strategy
A proactive tax strategy lowers what you owe across your lifetime, not just this April.
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.
33 articles
Medicare & Healthcare in Retirement
Medicare decisions made at enrollment are often permanent.
31 articles
Tech & Equity Compensation
Equity compensation is powerful but complex.
29 articles
Women & Divorce Financial Planning
Women face distinct financial planning challenges including longer retirements, career gap impacts, and higher divorce and widowhood rates.
23 articles
College Planning
Funding college without derailing retirement requires a deliberate strategy for savings accounts, financial aid positioning, and funding priorities.
18 articles
Behavioral Finance
Your biggest investment risk may not be the market; it may be your own behavior during a downturn.
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.
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.
Browse every article
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.
All (1076)
Basics (137)
Behavioral Finance (25)
Business Owners (136)
Charitable Giving (20)
College Planning (28)
Contributed (33)
Economic & Market Reports (1)
Estate Planning (138)
High Net Worth (89)
Investments (197)
Quoted (181)
Retirement Planning (394)
Risk Management (151)
Taxes (303)
Tech & SaaS (31)
Wealth Events (191)
Women (64)
June 2, 2026
Can Clients Have Principles and Performance? Younger Generations Think So
Survey data and advisors' anecdotal experience show an emerging interest among younger generations in values-based investing.
June 2, 2026
Is it OK for a financial adviser to get twice the fee when they manage $500K vs. $1M — even when I know that’s not twice the work?
Have an issue with your financial adviser or looking for a new one? Email questions or concerns to picks@marketwatch.com.
June 2, 2026
‘Worth paying attention to again.’ With Treasury yields near record highs, 5 financial advisers on how to smartly capitalize on this now
Rising inflation fueled by the war in Iran pushed 30-year Treasury yields to a 20-year high in May. Now at 4.98% through May 28…
June 1, 2026
What does property and casualty insurance cover for homeowners?
What Does Property and Casualty Insurance Cover for Homeowners? Last reviewed: July 2026 Property and casualty insurance covers two things: damage to what you…
June 1, 2026
How Do I Stop Lifestyle Inflation From Destroying My Savings?
How Do I Stop Lifestyle Inflation From Destroying My Savings? Last reviewed: July 2026 You stop lifestyle inflation by deciding what your raise is…
June 1, 2026
What should I do about a concentrated stock position?
What should I do about a concentrated stock position? Last reviewed: July 2026 If a single stock dominates your portfolio, you should build a…
June 1, 2026
Trump’s ‘big beautiful bill’ turned 529 plans into ‘lifelong education’ accounts, expert says: How to take advantage
New rules allow 529 plan funds to pay for eligible career training, certifications, licensing fees and continuing education costs.
May 31, 2026
When should I start working with a financial planner?
When should I start working with a financial planner? Last reviewed: July 2026 The right time to start working with a financial planner is…
May 31, 2026
What Is the Best Medigap Plan for New Medicare Beneficiaries?
What Is the Best Medigap Plan for New Medicare Beneficiaries? Last reviewed: July 2026 For most new Medicare beneficiaries, Plan G is the best…
May 31, 2026
How Do I Stop Lifestyle Creep from Destroying My Wealth?
How Do I Stop Lifestyle Creep from Destroying My Wealth? Last reviewed: July 2026 Lifestyle creep is the slow, almost invisible rise in your…
May 30, 2026
What do women need to know about investing for financial independence?
What Do Women Need to Know About Investing for Financial Independence? Last reviewed: July 2026 Investing for women starts with one fact that flips…
May 30, 2026
What is long-term care insurance and do I need it?
What Is Long-Term Care Insurance and Do I Need It? Last reviewed: July 2026 Long-term care insurance is a policy that pays for help…
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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