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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Basics (132)
Behavioral Finance (12)
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)
May 19, 2026
Digital Custodian Altruist Takes On Schwab, Fidelity With New RIA Model
The affiliate model itself is nothing new, but it's novel for a custodian.
May 19, 2026
How to Keep Client Couples’ Simultaneous Retirements From Going Wrong
Couples who leave the workforce at the same time may be surprised when expectations don't meet reality.
May 18, 2026
Nearly 1 in 10 mortgages is now ‘non-qualified’ — here’s what that means
Financial experts weigh the benefits and risks of this niche loan option
May 18, 2026
SEC Wants to Stop Requiring Quarterly Earnings. Why Some Advisors Don’t Like It.
The proposal to allow semi-annual reporting could create information gaps that make it harder for financial advisors to do their jobs.
May 17, 2026
Why Advisors Are Betting on AI Infrastructure Over Apps
Even legacy tech companies like Intel and Dell Technologies are riding the AI wave with major stock gains this year.
May 16, 2026
Want a Hot Pre-IPO Company in Your Portfolio? Proceed With Caution
Adding a sliver of the hottest private companies to your portfolio can be far more tricky than buying stocks.
May 15, 2026
5 Ways Moving to a Low Cost-of-Living Area Can Cost You More
Moving to a low cost-of-living city to save money sounds smart, but lower pay, higher insurance, taxes and commute costs can quietly eat up…
May 15, 2026
Mamdani’s $12 Billion Debt Wipeout Plan Has a Lesson for Your Finances
Small savings are worth capturing once the income floor is stable, but you can't cut your way to wealth.
May 15, 2026
Steal these smart analogies to simplify planning for clients
Financial planning can be complex to regular investors. Advisors shared the analogies and stories that bring ideas into focus with clients and prospects.
May 14, 2026
Most people make this retirement mistake. You might still have time to fix it.
Nearly 60% of retirees left the workforce earlier than planned. Financial planners and researchers explain the steps workers can take now to prepare for…
May 13, 2026
How FAs Can Take Advantage of Expanded Pass-Through Voting Options
Large asset managers including BlackRock, Vanguard, and State Street are expanding pass-through voting programs that let investors direct proxy votes on indexed holdings, but…
May 13, 2026
How to Help Grown Children and Aging Parents With Tough Talks
Advisors can move a conversation in 30 minutes that a family has avoided for 30 years. Planner Jim Crider says facilitating estate planning conversations…
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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