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.
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.
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Business Owners (118)
Charitable Giving (19)
College Planning (27)
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 7, 2026
Women often outlive men. Here’s how they should approach their long-term care needs
In addition to typically living longer than their husbands, women also are more likely to need long-term care, which can be costly.
June 6, 2026
A $5,000 wedding shows how millennials are rethinking life milestones
A 38-year-old's decision to forego debt offers a window into how younger generations are approaching marriage and money.
June 5, 2026
How Lenders Use Debt-to-Income to Evaluate Your Loan Application
Your debt-to-income or DTI ratio matters more than you may think. Do one thing: Don't rely solely on your credit score before applying for…
June 5, 2026
Chilling in Money-Market Funds is the Hot Retail Strategy Now
The stock market keeps setting records, yet one of the most popular trades is to sit in cash or money-market funds. The US money-market…
June 5, 2026
Fidelity lowers the bar for small investors to get in on SpaceX IPO
Small investors gain access to the SpaceX IPO as Fidelity lowers its customers' minimum account balance requirement to just $2,000.
June 4, 2026
These income funds offer double-digit yields – but come with cost and complexity. How they work
Autocallable ETFs offer attractive coupon payments, but investors should prepare to do some homework if they're exploring these funds.
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
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 29, 2026
Your Retirement Portfolio Might Need a New Kind of Diversification No One Is Talking About
AI and cyber threats to brokerages are growing. Will keeping your retirement funds in two or more institutions lessen your risk of getting wiped…
May 28, 2026
Should You Take a Buyout at Work?
Imagine if your company offered you six months' worth of salary if you quit your job right now. Would you go? What if they…
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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