Chesapeake Investment Planning, LLC

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Chesapeake Investment Planning, LLC

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In 2009, Todd created Chesapeake Investment Planning with the express purpose of preserving that increasingly elusive personal client relationship.

With his more than 20 years’ experience in the financial industry, Todd is quite adept at financial development, investment management, and insurance planning. His passion for helping his clients create a path to financial independence rests at the heart of Chesapeake Investment Planning’s mission. Todd’s idea was quite simple: To create a Wall Street-competitive company while retaining a hometown touch. With this philosophy—coupled with our outstanding team members who share more than 50 years of combined experience—Chesapeake Investment Planning is striving to rise to the top of the financial advising community while providing that personal touch that our clients need and want. Securities and advisory services offered through LPL Financial, a registered investment advisor, Member FINRA/SIPC. www.finra.org
www.sipc.org. The registered representatives associated with LPL Financial may only discuss or transact business with residents of the states in which they are properly registered or licensed. No offers may be made or accepted from any resident of any other state. Third-party posts found on this profile don’t reflect the views of LPL Financial and haven’t been reviewed by LPL Financial as to accuracy or completeness.

11/03/2026

One investment gained 270 percent in the first five months of 2026. Two months later, it gave back 67 percent. 😳

Why do smart people chase numbers like that? Psychologist Daniel Kahneman said it best: "Stories trump statistics." 🧠

A hot streak always comes with a story. The story is what sells. The math is what stings.

Riches to rags is an old pattern, and so is the reverse. When a return looks too good to be true, give the story the same scrutiny you'd give the number.

If a market headline has your attention, run it past us before it runs your portfolio. 💬

10/31/2026

Not every monster wears a costume this month. Some show up as a text pretending to be your bank. 👻

Three cybersecurity myths worth burying this October:

🎃 "Some of my accounts are too small to bother with." False. Most attacks aren’t personal. Automated bots test thousands of accounts at a time, looking for a weak spot.

🎃 "Only older adults fall for scams." Absolutely false. FTC data has consistently shown adults in their 20s are reporting fraud, too.

🎃 "I'd know a phishing email if I saw one." Maybe once. AI-generated phishing has erased the classic tells: broken grammar, misspellings, and awkward phrasing.

This time of year, it's worth taking a moment to look past the obvious scares and pay attention to the sneakier ones, too.

10/29/2026

Nationwide's 2026 study surfaced three key lessons from parents:

🎯 Not starting early enough.
More than 25 percent of recent retirees wish they had started sooner. Fifteen years of compounding early in a career can make a HUGE difference.

🎯 Not raising the contribution rate as your income grows.
Thirteen percent of recent retirees wish they had contributed more to their savings each year.

🎯 Claiming Social Security at 62.
More than a third of boomers plan to claim benefits the moment they become eligible, even though doing so cuts the monthly benefit by 25 to 30 percent for life.

According to the SSA, waiting past full retirement age adds 8 percent per year, up to age 70.

Across the research, three things seem to matter most:
1️⃣ Starting early
2️⃣ Getting an outside perspective rather than relying on instinct alone
3️⃣ Treating retirement as something that unfolds over decades rather than a single date on the calendar

10/26/2026

How many years before you are ready to be "retired"?

It's one of the most important numbers yet.

TIAA's 2026 longevity literacy research found that workers who expect a shorter retirement save less consistently than those who expect a longer one.

That makes sense, but it also means the people who assume their retirement will be short are the same ones who may be building portfolios with shorter time horizons.

Once someone has already reached 65, the numbers shift.

According to Social Security Administration data:

📌 A 65-year-old man has roughly a 24 percent chance of living past 90

📌 A 65-year-old woman's chances are higher, closer to 35 percent

📌 For a 65-year-old married couple, there is about a 50 percent chance that at least one spouse lives past 90

The practical implication is not "assume you will live to 100."

It's that a retirement income strategy built around the "average lifespan" often assumes a person will die on schedule. Most people do not.

If retirement is on your horizon, the question to ask is, "What happens to my income strategy if I live to 95?"

10/23/2026

Trust & Will's 2026 Estate Planning Report found that 56 percent of adults don't have core documents in place, including:

📝 A will: who gets what, and who is in charge of making it happen

🏥 A healthcare directive (or living will): what you want if you cannot speak for yourself

✍️ Two powers of attorney, one for medical decisions and one for financial decisions, each naming a specific person

📄 A letter of instruction: the practical map to where accounts live, who your professionals are, and what your kids or pets need

The friction is that estate work forces a family to sit with mortality, name specific people for specific roles, and make decisions that feel too permanent to rush.

Without something in writing, though, families are left improvising during one of the most difficult moments of their lives.

Most say they fully intend to get to it, but too many put it off until it's too late.

Don't put it off. Talk to a financial professional who can help.

10/14/2026

Learn how tax loss harvesting can reduce your capital gains taxes, offset ordinary income and position your portfolio for long-term growth entering 2027.

10/13/2026

The Treasury Department auto-enrolled 70 million children into Trump Accounts on Oct. 1.

10/12/2026

It’s often the stuff you haven’t even thought of that can create the biggest divisions for your family after you're gone.

10/11/2026

With mortgage rates above 7%, shopping around can pay off: identical borrowers may receive offers more than half a percentage point apart.

10/10/2026

Long-term Treasury yields hit their highest level in 24 years as inflation, Fed policy, heavy borrowing and global rate pressure push interest costs higher.

Address

Stevensville, MD
21666

Telephone

+14432493514

Website

https://www.cipadvisor.com/

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