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Chesapeake Financial Planners

Feel More in Control of Your Financial Life. Get Clarity and Confidence Without Doing It All Alone

09/07/2026

A high income isn't the same as a finished plan.

We work with a lot of households earning $300,000 or more who still feel behind. The pattern is usually the same. Contributions are maxed on autopilot, but nobody's checked whether the withholding actually matches the real bracket. Cash sits in an account earning nothing while a 401(k) hits its limit.

None of these are dramatic mistakes on their own. They're small gaps that add up quietly, year after year.

Have you had someone look at your income, accounts, and taxes together in one conversation, or has each piece been handled on its own?

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

09/06/2026

Jeff Judge was quoted this week by MP Dunleavey in Stanford Center on Longevity on the family conversation that stalls out for so many of our clients.

A recent Pew Research survey found most older adults have talked funeral wishes with their kids. Far fewer have talked about how they actually want to live if they lose some independence.

Jeff's point: families often treat aging parents like a checklist. Estate documents, done. Funeral wishes, done, conversation over. But the harder conversation, about a parent's dignity and their fear of becoming a burden, never really has a finish line, so a lot of families avoid it entirely.

A parent who won't discuss assisted living usually isn't being difficult. They're scared of losing control over their own life.

The families who handle this well ask a different question: not "what's the plan," but "what does a good future look like for you?"

A Fit Call is a good place to start if this conversation has stalled in your family.

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https://skd.so/omSiFC - https://skd.so/HUCHkU -

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

09/05/2026

Jeff Judge was quoted by Lorie Konish in CNBC this week, talking through one of the most common assumptions in retirement planning that turns out to be wrong.

Most people expect Medicare to cover long-term care when the time comes. For most families, it won't. Medicare may cover up to 100 days in a skilled nursing facility, and only right after a hospital stay. It doesn't cover the ongoing custodial care that long-term care usually means.

Jeff put it plainly to the reporter: people assume Medicare is their long-term care plan. It isn't, and finding that out during a crisis is the worst possible time.

The families who plan ahead do better. Starting the long-term care conversation in your 50s or 60s, instead of your 70s, means better pricing and access to protections that can be harder to get later.

We'd love to help you figure out where you stand before it becomes urgent.

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09/05/2026

The wire clears, and suddenly your business is a number in a bank account. That moment feels like the finish line. It's actually the starting line for a different set of decisions.

We've seen this play out a few different ways. Money sitting untouched in a savings account because doing nothing feels safer than moving too fast. Investment offers arriving within weeks, sometimes from people who found out about the sale before the seller had time to think. Family and old friends suddenly interested in the money.

The decisions made in the first six to twelve months after a wealth event, whether it's a business sale, an inheritance, or a settlement, are often the ones that can't be undone later. The inherited IRA has a distribution clock most people don't know exists. The settlement net is smaller than the number that got announced, once fees and liens are accounted for.

None of this means you have to decide everything immediately. It means the pace should be intentional, not driven by whoever calls first.

If you've recently been through a wealth event, what's felt like the hardest part to navigate?

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

09/04/2026

Five things most people do not know about Chesapeake Financial Planners founder Mark Rossbach — including a CPA background that still shapes how he works with clients today.

• 𝗠𝘆 𝗽𝗮𝗿𝗲𝗻𝘁𝘀 𝘄𝗲𝗿𝗲 45 𝗮𝗻𝗱 50 𝘆𝗲𝗮𝗿𝘀 𝗼𝗹𝗱 𝘄𝗵𝗲𝗻 𝗜 𝘄𝗮𝘀 𝗯𝗼𝗿𝗻
• 𝗜 𝘀𝘁𝗮𝗿𝘁𝗲𝗱 𝗯𝗼𝗮𝘁𝗶𝗻𝗴 𝗮𝗻𝗱 𝗹𝗼𝘃𝗲 𝗯𝗲𝗶𝗻𝗴 𝗼𝗻 𝘁𝗵𝗲 𝘄𝗮𝘁𝗲𝗿 — it is peaceful
• 𝗜 𝗮𝗺 𝗮 𝗖𝗣𝗔 𝗮𝗻𝗱 𝗮𝗽𝗽𝗹𝘆 𝘄𝗵𝗮𝘁 𝗜 𝗹𝗲𝗮𝗿𝗻𝗲𝗱 𝗳𝗿𝗼𝗺 𝘁𝗵𝗮𝘁 𝗰𝗮𝗿𝗲𝗲𝗿 𝗮𝗻𝗱 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝘁𝗼 𝗺𝘆 𝗰𝘂𝗿𝗿𝗲𝗻𝘁 𝗷𝗼𝗯
• 𝗜 𝗯𝗲𝗹𝗶𝗲𝘃𝗲 𝗶𝗻 𝗽𝗲𝗼𝗽𝗹𝗲 𝗮𝗻𝗱 𝘄𝗵𝗮𝘁 𝘁𝗵𝗲𝘆 𝗰𝗮𝗻 𝗮𝗰𝗰𝗼𝗺𝗽𝗹𝗶𝘀𝗵 𝘄𝗵𝗲𝗻 𝘁𝗵𝗲𝘆 𝘀𝗲𝘁 𝘁𝗵𝗲𝗶𝗿 𝗺𝗶𝗻𝗱 𝘁𝗼 𝗮 𝗴𝗼𝗮𝗹
• 𝗜 𝗹𝗼𝘃𝗲𝗱 𝘀𝗽𝗲𝗻𝗱𝗶𝗻𝗴 𝘁𝗶𝗺𝗲 𝗵𝗲𝗹𝗽𝗶𝗻𝗴 𝗰𝗼𝗮𝗰𝗵 𝘀𝗼𝗰𝗰𝗲𝗿 𝗮𝗻𝗱 𝗯𝗮𝘀𝗸𝗲𝘁𝗯𝗮𝗹𝗹 𝘄𝗵𝗲𝗻 𝗺𝘆 𝗸𝗶𝗱𝘀 𝘄𝗲𝗿𝗲 𝘆𝗼𝘂𝗻𝗴

No pitch, just clarity.

09/03/2026

A business owner sat across from us recently. Twenty-two years building the company. Zero dollars in a retirement account separate from it.

That's not unusual. Every available dollar went back into the business, because that felt like the higher-return move at the time. And for a long stretch, it probably was.

The problem shows up later: the business is now the entire retirement plan, and the math behind that plan has never actually been stress-tested. What happens if the sale takes longer than expected? What happens if the number is lower than the one in your head?

This isn't an argument for pulling money out of a growing business. It's a nudge to build something outside of it too, even modestly, so the plan doesn't depend entirely on one outcome.

If you own a business, how much of your retirement plan currently lives outside the business itself?

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

09/02/2026

You signed a letter of intent to sell your business for $6M. Congratulations, and also, a lot of the tax decisions that mattered most were already made the moment that document was signed.

Whether the deal is structured as an asset sale or a stock sale changes what you actually keep, often by a significant margin. Whether the proceeds come as a lump sum or an installment payout changes when the tax bill hits. And by the time the LOI is signed, some of those levers are already gone.

We've sat with owners who found out after signing that the structure locked in a bigger tax bill than it needed to. It's not that anyone did anything wrong. It's that the tax conversation happened after the deal terms, instead of before.

If you're in the early stages of a sale conversation, even before terms are finalized, that's the right time to loop in a coordinated tax and planning conversation, not after signing.

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

09/01/2026

Michelle's experience is the standard we hold ourselves to with every client. Ready to see what that looks like for you? Book a Fit Call: https://skd.so/VEmQrB - https://skd.so/2itfdy -

08/31/2026

A client turned 73 this year and delayed her first RMD to the following April, thinking she was buying herself extra time.

What she hadn't realized is that the delay means taking two RMDs in the same calendar year: the delayed one plus the regular one for that year. Both land on the same tax return.

That can push someone into a higher bracket than they expected, right in the year they're trying to settle into retirement.

A few things worth knowing if you're approaching this deadline: the rule only allows that one-time delay for your very first RMD. After that, the deadline is December 31 every year. You can combine RMDs across multiple IRAs into one withdrawal, but not across 401(k)s. And a qualified charitable distribution can satisfy the RMD without adding to your taxable income at all.

If you're getting close to your first RMD, has anyone walked you through what the two-withdrawal year actually looks like for you?

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

08/29/2026

Myth: the market always recovers, so it doesn't matter when the drop happens.

Reality: timing matters a lot in your first year of retirement.

This is one of the more counterintuitive parts of retirement planning.

If your portfolio drops 20% the year before you retire, you still have time to recover before you start drawing on it.

If that same drop happens in your first year of retirement, while you're also withdrawing money to live on, the math changes completely.

It's called sequence-of-returns risk, and it's one of the most underestimated risks in retirement planning.

Two retirees can have the exact same average return over twenty years and end up in very different places, depending purely on the order those returns happened in relative to when they started withdrawing.

The good news is this is plannable. A cash reserve to cover a year or two of expenses so you're not forced to sell investments during a downturn.

A withdrawal strategy that can flex based on market conditions instead of a fixed amount no matter what. And a plan that's actually been tested against a bad first year, not just an average one.

If no one has walked you through what a down year would actually mean for your specific plan, that's worth doing before you're living it in real time.

Has anyone shown you what your plan looks like in a bad first year?

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

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2402 Scotlon Court
Forest Hill, MD
21050

Opening Hours

Monday	8am - 5pm
Tuesday	8am - 5pm
Wednesday	8am - 5pm
Thursday	8am - 5pm
Friday	8am - 5pm

Website

https://chesapeakefp.com/, https://outlook.office.com/book/[email protected]/?ismsaljsauthen

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