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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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)
July 14, 2026
Vanguard, Envestnet Team Up to Curb Tax Risks on Model Portfolio Conversions
Envestnet and Vanguard are expanding their partnership to tackle one of the biggest obstacles to broader adoption of model portfolios: the tax bills that…
July 14, 2026
Can mortgage rates fall without another Fed rate cut? Here’s what experts think
Mortgage rates could fall, but they could also rise or remain the same, regardless of the Fed's policy rate decisions. Experts explain the factors…
July 14, 2026
AI vs. robo advisers: How they stack up against each other — and human financial advisers
Robo advisers are getting smarter as AI capabilities increase — but how much control are investors willing to hand over?
July 13, 2026
A New Custody Rule Is on the SEC’s Agenda. Here’s What to Know.
The agency plans to issue a proposed rule that would address questions raised by advisors about holding crypto.
July 12, 2026
Retirees have questions for financial advisers. Here’s what they want to know.
Increasingly, retirees are turning to financial advisers for the first time to help navigate an array of issues as they step out of the…
July 10, 2026
What clients miss about HSAs — and how advisors can help
Health savings accounts cover a broad range of medical expenses, but the boundaries of what those tax-advantaged dollars can be spent on are not…
July 10, 2026
Advisors, Take Note: SEC Rule Revamps Are on the Way
The SEC released its spring Reg Flex agenda Tuesday. All items on the list are proposed rules, with custody and off-channel communications changes slated…
July 10, 2026
1,500 Americans filed for bankruptcy each day last year. They should have done this instead.
Personal bankruptcy filings surged 47% between 2022 and 2025. Here's what you should do before deciding to file.
July 10, 2026
‘Trump accounts’ are great — if you’re already rich
'Trump accounts' are great — if you're already rich. They're a poor deal for most other people.
July 8, 2026
Why State Street’s SPYM Is Treasury’s Top Choice for Trump Accounts
A handful of products were selected for the new government-sponsored accounts, including products from Vanguard and BlackRock.
July 7, 2026
SpaceX IPO Left Financial Advisors With a Blueprint for the Next Mega Offerings
With OpenAI and Anthropic waiting in the wings to go public, pre-IPO wealth planning is suddenly urgent.
July 7, 2026
Haven’t Saved Enough for Retirement? Here’s What Not to Do. ‘It’s Usually Wrong.’
Financial experts on how to handle it if you started saving late and now haven't saved enough for 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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