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

06/04/2026

CNBC quoted Chesapeake Financial Planners' managing partner Jeff Judge this week on the new 529 plan rules in the One Big Beautiful Bill.
Jeff's warning: not every career training program qualifies. A coding boot camp and a community college certificate can have different eligibility outcomes from the same 529 account.
Before using 529 funds for adult education, verify the program is authorized under the Workforce Innovation and Opportunity Act or a recognized national credentialing organization.
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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.

06/04/2026

The Daily Upside featured Jeff Judge, CFP®, of Chesapeake Financial Planners this week on values-based investing and the growing demand from younger investors.
"Younger investors want portfolios that reflect who they are." — Jeff Judge
3 in 4 investors under 41 say they'd choose an advisor who offers values-based investing over one who doesn't.
If you want to talk through what this looks like for your situation, schedule a Fit Call.
https://skd.so/I6m6rb
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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.

06/04/2026

Two people retire with the same portfolio and the same average returns over 20 years. One runs out of money. The other doesn't.
Same numbers. Different outcome.
The difference is when the bad years hit.
If the market drops significantly in year one or two of retirement, you're selling shares at low prices to cover living expenses. Those shares aren't there to recover when the market comes back. The math compounds in the wrong direction.
This is called sequence-of-returns risk, and it's one of the most underestimated dangers in early retirement. It doesn't show up in the long-run average. It shows up in the first three years.
The good news: there are specific strategies to reduce your exposure during that window. They require planning before you retire, not after.
If you're within five years of your retirement date and haven't modeled this specifically, a Fit Call is worth scheduling.
What questions do you have about protecting your retirement income in the early years?

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

06/03/2026

MarketWatch featured our founder Jeff Judge this week on Treasury yields and what investors should actually do about them right now.
His quote says it plainly: a 20-year Treasury at today's yields looks completely different to a 40-year-old still accumulating than to a 68-year-old who needs income next year.
Both are reading the same headlines. Both need completely different strategies.
Jeff's approach for clients right now is a barbell: short-term T-bills covering 12 to 18 months of living expenses, plus a layer in intermediate investment-grade corporates yielding in the 5.5% to 6% range.
He's not extending duration until the rate trajectory settles.
Buy for the coupon. Not the price pop.
If you're in the years surrounding retirement and this question is on your mind, we should talk.
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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.

06/03/2026

Cybercriminals don't need to break into every account you own. They only need one.
That's the risk Jeff Judge addressed in Kiplinger this week, discussing whether splitting retirement assets across multiple institutions is a real security strategy -- or just added complexity.
There's genuine logic behind it. If a breach happens at one custodian, assets held elsewhere are protected.
But here's the part that often gets overlooked:
Every additional account is another login to secure, another statement to monitor, and another layer of coordination required at the exact time in life when financial complexity should be going down, not up.
For retirees managing RMDs across multiple accounts, the oversight burden is real.
The goal isn't more accounts. The goal is a clear, coordinated plan for who watches your money, how it's protected, and what happens if something goes wrong.
If that plan doesn't exist yet, book a Fit Call with the team.
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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.

06/03/2026

"We had a great year. So why doesn't it feel like we're getting ahead?"
This is the most common thing we hear from business owners in their second meeting with us.
Revenue is moving. The business is growing. The stress hasn't stopped.
What's usually happening: every dollar the business generates goes right back into the business. Owner compensation, equipment, payroll, the next phase of growth. Personal accounts stay flat.
This isn't a business problem. It's a coordination problem.
When your business finances and personal finances have never been looked at together, it's easy to optimize one and ignore the other. We've seen profitable businesses where the owner is behind on retirement savings, has no real emergency fund outside the business, and has no clear picture of what they'd actually have if they sold tomorrow.
Building a business is not the same as building wealth. The two can happen at the same time. But that takes a plan.
If this sounds familiar, a Fit Call is worth having. We work with business owners specifically on this kind of coordination.
What's the biggest gap between where your business is and where your personal finances are?

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

06/02/2026

Clients like Sharon L are why we do this work. If you’re ready to work with a team that puts your goals first, we’d love to connect. Schedule a complimentary Fit Call here: https://skd.so/6NmsDq - https://skd.so/7BAWOp -

06/02/2026

You want to retire at 62. Medicare doesn't start until 65. Those three years have to come from somewhere.
This is one of the most underplanned expenses in early retirement. Not because people don't know healthcare costs money, but because they haven't actually run the numbers.
ACA marketplace coverage in your early 60s can run considerably more than what you paid through an employer. The premiums alone can change your retirement budget significantly. And that's before out-of-pocket costs.
A lot of people discover this when they're six months from their target retirement date. At that point, you're not adjusting your plan, you're scrambling.
The fix is planning it early. Know the number before you make the decision. Build the healthcare gap into your retirement income model.
If you're planning to retire before 65 and haven't modeled the healthcare cost specifically, that's a Fit Call conversation worth having.
What year are you targeting for retirement?

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

06/01/2026

MarketWatch featured Chesapeake Financial Planners' Jeff Judge this week on alternative college savings strategies.
His insight: I-bonds are one of the most underused options for parents saving for education. They're inflation-protected, and the interest is federally tax-free if the money goes toward qualified education expenses.
If you've built your college savings plan around a single account and you're not sure what happens if your child's path changes, it's worth a conversation.
https://skd.so/AYPqeH
See if you're a fit: https://skd.so/xytore - https://skd.so/eVB48g -

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

06/01/2026

If you've ever run the NYC vs. smaller city salary comparison, you probably stopped at rent and groceries.
Jeff Judge at Chesapeake Financial Planners was quoted in Investopedia this week on why that's the wrong place to stop.
The question isn't just about purchasing power today.
It's about what your location is doing to your retirement accumulation window.
High-cost cities can carry real earning advantages early in a career.
But for clients in their 50s, staying in a high-cost environment during the decade when savings should be compounding hardest is often the most expensive financial decision they're not modeling.
If your location isn't part of your retirement plan conversation, let's fix that.
https://skd.so/GFnNvP
Book a Fit Call: https://skd.so/CbuO4X - https://skd.so/5Zcfvo -

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

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