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Chesapeake Financial Planners, 2402 Scotlon Court, Forest Hill, MD (2026)

07/23/2026

Our managing partner Jeff Judge - https://www.linkedin.com/in/jeffreymjudge - was quoted this week in ThinkAdvisor - https://www.linkedin.com/company/thinkadvisor/ -, and Melanie Waddell - https://www.linkedin.com/in/melanie-waddell-1bb28511 -'s article on annuity compliance highlights a mistake we see often.

An advisor recommends an annuity before fully understanding the client's situation. Jeff described a case where a prospective client owned a variable annuity inside an IRA and nobody, not even the original advisor, could explain why. He was paying for tax deferral the IRA already gave him.

This isn't rare. It's what happens when a product gets picked before a plan gets built.

If you're holding an annuity and can't say in one sentence why it's right for you, let's talk it through.

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The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.

07/23/2026

He wanted to retire at 62. Then he actually ran the healthcare number for the three years before Medicare starts at 65, and the plan changed.

This is one of the most common mistakes we see in early retirement planning. The number in someone's head accounts for the mortgage, the car, even travel. It rarely accounts for the bridge years before Medicare eligibility.

Medicare Part B alone runs $202.90 a month for most people in 2026, and that's before adding a supplement, a Part D drug plan, or any bridge coverage before you're even eligible.

A few questions worth asking before you pick a retirement date.

Do you know what health coverage actually costs between the day you leave your job and the day Medicare starts?

Have you priced out COBRA versus a marketplace plan versus staying on a spouse's coverage?

Is your retirement date built around a paycheck ending, or around a plan that accounts for what replaces your coverage?

None of this means 62 is the wrong number. It means it's worth stress-testing before it becomes the date on the calendar.

What's thrown off your retirement timeline that you didn't expect? Tell us below. A Fit Call is a good place to run the real numbers before the date is set.

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.

07/22/2026

Can AI actually give you good money advice? Kiplinger decided to find out, and our own Jeff Judge weighed in.

The magazine ran five real financial scenarios past ChatGPT, Gemini, and Claude, then ran the same scenarios past certified financial planners, including Jeff, to compare.

One scenario hit close to home for a lot of our clients: someone in their mid-50s trying to retire on schedule while also covering two kids' college tuition. The AI treated it like a math problem. Cut the goal or cut the spending.

What it missed is that real families don't get to pick one clean answer. They need a plan that flexes when a semester's tuition bill lands the same month the market takes a dip.

Jeff put it this way in the article, quoted by journalist Chris Taylor: "One thing to note about AI is that it only answers the question that you ask. It's not asking for additional information or asking for clarification. It's not getting to know your personal situation."

That's the piece a chatbot can't replace. Knowing your situation well enough to ask the right follow-up question before giving an answer.

If you've been leaning on AI for financial guidance and want a second opinion from someone who knows your actual numbers, a Fit Call is a good place to start.

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𝘛𝘩𝘦 𝘰𝘱𝘪𝘯𝘪𝘰𝘯𝘴 𝘷𝘰𝘪𝘤𝘦𝘥 𝘪𝘯 𝘵𝘩𝘪𝘴 𝘮𝘢𝘵𝘦𝘳𝘪𝘢𝘭 𝘢𝘳𝘦 𝘧𝘰𝘳 𝘨𝘦𝘯𝘦𝘳𝘢𝘭 𝘪𝘯𝘧𝘰𝘳𝘮𝘢𝘵𝘪𝘰𝘯 𝘰𝘯𝘭𝘺 𝘢𝘯𝘥 𝘢𝘳𝘦 𝘯𝘰𝘵 𝘪𝘯𝘵𝘦𝘯𝘥𝘦𝘥 𝘵𝘰 𝘱𝘳𝘰𝘷𝘪𝘥𝘦 𝘴𝘱𝘦𝘤𝘪𝘧𝘪𝘤 𝘢𝘥𝘷𝘪𝘤𝘦 𝘰𝘳 𝘳𝘦𝘤𝘰𝘮𝘮𝘦𝘯𝘥𝘢𝘵𝘪𝘰𝘯𝘴 𝘧𝘰𝘳 𝘢𝘯𝘺 𝘪𝘯𝘥𝘪𝘷𝘪𝘥𝘶𝘢𝘭.

07/22/2026

The listing said 38,000 euros. That was not the price.

Hani Richter at Reuters wrote this week about young buyers going abroad for their first homes, and asked Jeff Judge what he made of it.

The woman in the story bought a studio in southern Italy for 38,000 euros. Where she lived in Dublin, the median is 395,000.

Here's the part that catches people.

Purchase taxes, notary fees, agent commissions. None of that shows up in the listing photo, and it's usually due the day you sign.

Jeff's take was direct: a cheap apartment overseas is a second country's worth of paperwork with a bed in it.

Cheap property abroad is rarely cheap by accident. Sometimes it's a local economy in decline. Sometimes it's work the listing skipped. Sometimes it's the paperwork itself.

That said, he gave her credit where it's due. She owns it outright. No lender. That's real.

His rule if you're tempted: rent there six months first. One full winter and one full tax year before you commit to anything.

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𝘛𝘩𝘦 𝘰𝘱𝘪𝘯𝘪𝘰𝘯𝘴 𝘷𝘰𝘪𝘤𝘦𝘥 𝘪𝘯 𝘵𝘩𝘪𝘴 𝘮𝘢𝘵𝘦𝘳𝘪𝘢𝘭 𝘢𝘳𝘦 𝘧𝘰𝘳 𝘨𝘦𝘯𝘦𝘳𝘢𝘭 𝘪𝘯𝘧𝘰𝘳𝘮𝘢𝘵𝘪𝘰𝘯 𝘰𝘯𝘭𝘺 𝘢𝘯𝘥 𝘢𝘳𝘦 𝘯𝘰𝘵 𝘪𝘯𝘵𝘦𝘯𝘥𝘦𝘥 𝘵𝘰 𝘱𝘳𝘰𝘷𝘪𝘥𝘦 𝘴𝘱𝘦𝘤𝘪𝘧𝘪𝘤 𝘢𝘥𝘷𝘪𝘤𝘦 𝘰𝘳 𝘳𝘦𝘤𝘰𝘮𝘮𝘦𝘯𝘥𝘢𝘵𝘪𝘰𝘯𝘴 𝘧𝘰𝘳 𝘢𝘯𝘺 𝘪𝘯𝘥𝘪𝘷𝘪𝘥𝘶𝘢𝘭.

07/22/2026

She'd been looking at the same statements for two years and still didn't know what they meant.

Not because she wasn't capable. Because no one had ever sat down and actually walked her through them.

That's one of the quieter money mistakes we see, especially for women stepping into managing their own finances after a divorce, a loss, or just deciding it's time to take the wheel. The accounts were set up by someone else, in someone else's shorthand, and asking feels harder than it should.

A few signs the fog hasn't lifted yet.

You know roughly what you have, but not what it actually means for how long it needs to last.

You've avoided opening an envelope from an account you're not totally sure you understand.

You've made a financial decision recently and haven't told anyone you're not sure it was the right one.

None of that means you're behind. It means nobody's translated it into plain language yet.

What's one financial question you've been sitting on and haven't asked out loud? We'd like to know. A Fit Call is a low-pressure place to finally ask it.

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.

07/21/2026

Nearly half of the retirees who went back to work last year did it to cover basic living expenses.

Andrew Shilling at MarketWatch asked Jeff Judge why that keeps happening. His answer: un-retirement usually isn't about running out of money. It's about running out of confidence in the plan.

The mistake underneath it is usually structural, not dramatic.

A fixed 4% withdrawal rule doesn't care that the market just dropped 20%. It takes the same dollar amount anyway, which turns a temporary loss into a permanent one. That rule was built for a different era and it doesn't flex when things move against you early.

What works better: guardrails. Spending adjusts up in strong years and down slightly in weak ones, so principal gets protected automatically.

And keeping two to three years of near-term spending in cash and short-duration bonds means a downturn never forces a sale at the bottom just to cover the grocery bill.

If retirement is close, ask what your plan does in a bad first year. If the answer isn't clear, that's worth a conversation.

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𝘛𝘩𝘦 𝘰𝘱𝘪𝘯𝘪𝘰𝘯𝘴 𝘷𝘰𝘪𝘤𝘦𝘥 𝘪𝘯 𝘵𝘩𝘪𝘴 𝘮𝘢𝘵𝘦𝘳𝘪𝘢𝘭 𝘢𝘳𝘦 𝘧𝘰𝘳 𝘨𝘦𝘯𝘦𝘳𝘢𝘭 𝘪𝘯𝘧𝘰𝘳𝘮𝘢𝘵𝘪𝘰𝘯 𝘰𝘯𝘭𝘺 𝘢𝘯𝘥 𝘢𝘳𝘦 𝘯𝘰𝘵 𝘪𝘯𝘵𝘦𝘯𝘥𝘦𝘥 𝘵𝘰 𝘱𝘳𝘰𝘷𝘪𝘥𝘦 𝘴𝘱𝘦𝘤𝘪𝘧𝘪𝘤 𝘢𝘥𝘷𝘪𝘤𝘦 𝘰𝘳 𝘳𝘦𝘤𝘰𝘮𝘮𝘦𝘯𝘥𝘢𝘵𝘪𝘰𝘯𝘴 𝘧𝘰𝘳 𝘢𝘯𝘺 𝘪𝘯𝘥𝘪𝘷𝘪𝘥𝘶𝘢𝘭.

07/21/2026

Here is a mistake we see people make right before retirement: they assume the bonds in their portfolio are protecting them from inflation.

When CNBC's Darla Mercado asked how to prepare a portfolio for rising prices, our Managing Partner Jeff Judge pointed to a tool most retirees overlook: Treasury inflation-protected securities.

An ordinary bond pays a fixed coupon. If inflation climbs, that fixed payment quietly buys less every year.

A TIPS bond adjusts its principal with inflation, so what you get back keeps pace with prices instead of falling behind them.

Jeff uses them as a small, deliberate slice of the fixed income side, not the whole plan, and pays close attention to the term, because a 5-year and a 30-year behave very differently when rates move.

If you are close to living off your savings, it is worth checking whether your safe money is actually keeping up with the cost of living.

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𝘛𝘩𝘦 𝘰𝘱𝘪𝘯𝘪𝘰𝘯𝘴 𝘷𝘰𝘪𝘤𝘦𝘥 𝘪𝘯 𝘵𝘩𝘪𝘴 𝘮𝘢𝘵𝘦𝘳𝘪𝘢𝘭 𝘢𝘳𝘦 𝘧𝘰𝘳 𝘨𝘦𝘯𝘦𝘳𝘢𝘭 𝘪𝘯𝘧𝘰𝘳𝘮𝘢𝘵𝘪𝘰𝘯 𝘰𝘯𝘭𝘺 𝘢𝘯𝘥 𝘢𝘳𝘦 𝘯𝘰𝘵 𝘪𝘯𝘵𝘦𝘯𝘥𝘦𝘥 𝘵𝘰 𝘱𝘳𝘰𝘷𝘪𝘥𝘦 𝘴𝘱𝘦𝘤𝘪𝘧𝘪𝘤 𝘢𝘥𝘷𝘪𝘤𝘦 𝘰𝘳 𝘳𝘦𝘤𝘰𝘮𝘮𝘦𝘯𝘥𝘢𝘵𝘪𝘰𝘯𝘴 𝘧𝘰𝘳 𝘢𝘯𝘺 𝘪𝘯𝘥𝘪𝘷𝘪𝘥𝘶𝘢𝘭.

07/21/2026

Feedback like this from Charles G is what drives our team every single day. If you're ready to get serious about your financial future, let's talk. https://skd.so/MOnd8i - https://skd.so/QbOzuB -

07/20/2026

The riskiest moment in retirement isn't the market. It's the week you move a large balance.

Rolling over a 401(k). Funding a new account. Wiring the down payment on the place you're retiring to. Those are the transfers worth watching, and attackers know it.

Grace L. Williams reported in Financial Planning this week on SonicWall's mid-year findings, and quoted our Managing Partner Jeff Judge. Cyberattacks on financial firms are down in the first five months of 2026. That reads like progress until you learn why. Attackers got selective. One security executive described intruders who sit inside a system for months, ignoring small transactions, waiting for the seven-figure one.

The average time to patch a high-severity vulnerability in financial services is 102 days.

Jeff treats cybersecurity the way he treats a financial plan. One document isn't enough, and it's useless if nobody updates it. So we keep a written policy, a continuity plan reviewed annually at a minimum, a managed services team on the technical side, and multistep verification on anything involving money movement.

That last piece is the plainest one. It's also the one that does the most work.

If you're approaching a rollover or a large transfer this year, it's worth asking who verifies it before it goes out.

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𝘛𝘩𝘦 𝘰𝘱𝘪𝘯𝘪𝘰𝘯𝘴 𝘷𝘰𝘪𝘤𝘦𝘥 𝘪𝘯 𝘵𝘩𝘪𝘴 𝘮𝘢𝘵𝘦𝘳𝘪𝘢𝘭 𝘢𝘳𝘦 𝘧𝘰𝘳 𝘨𝘦𝘯𝘦𝘳𝘢𝘭 𝘪𝘯𝘧𝘰𝘳𝘮𝘢𝘵𝘪𝘰𝘯 𝘰𝘯𝘭𝘺 𝘢𝘯𝘥 𝘢𝘳𝘦 𝘯𝘰𝘵 𝘪𝘯𝘵𝘦𝘯𝘥𝘦𝘥 𝘵𝘰 𝘱𝘳𝘰𝘷𝘪𝘥𝘦 𝘴𝘱𝘦𝘤𝘪𝘧𝘪𝘤 𝘢𝘥𝘷𝘪𝘤𝘦 𝘰𝘳 𝘳𝘦𝘤𝘰𝘮𝘮𝘦𝘯𝘥𝘢𝘵𝘪𝘰𝘯𝘴 𝘧𝘰𝘳 𝘢𝘯𝘺 𝘪𝘯𝘥𝘪𝘷𝘪𝘥𝘶𝘢𝘭.

07/20/2026

The retirement income number most people aim at is too high.

The mistake we see most often is a couple delaying retirement to hit an income target they were never actually going to spend.

Here's what that math misses. A big share of your paycheck was never spendable income. Payroll taxes came off the top. So did your 401(k) contribution. Both stop the day you retire.

Then the costs of working life fall away too. The commute. The extra car. The work clothes. The childcare years that already ended.

Our founder, Jeff Judge, broke down eight of these disappearing expenses for Kiplinger this week.

Build your plan around what you'll actually spend, not the salary you used to earn.

If you're a few years out and want to know your number is right, a Fit Call is the right first step.

https://skd.so/yy5Rgc

https://skd.so/ssI3Jn - https://skd.so/eaVW3P -

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.

Chesapeake Financial Planners

07/23/2026

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07/22/2026

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