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Chesapeake Financial Planners

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Chesapeake Financial Planners

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

09/01/2026

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.

08/28/2026

Founder Mark Rossbach shares his overrated and underrated takes — from German cars to the underappreciated value of a home-cooked meal someone else made for you.

• 𝗢𝘃𝗲𝗿𝗿𝗮𝘁𝗲𝗱 — 𝗚𝗲𝗿𝗺𝗮𝗻 𝘃𝗲𝗵𝗶𝗰𝗹𝗲𝘀 — I like my Lexus
• 𝗢𝘃𝗲𝗿𝗿𝗮𝘁𝗲𝗱 — 𝗙𝗮𝗻𝗰𝘆 𝗿𝗲𝘀𝘁𝗮𝘂𝗿𝗮𝗻𝘁𝘀 — I can eat casual and love diners
• 𝗢𝘃𝗲𝗿𝗿𝗮𝘁𝗲𝗱 — 𝗚𝗲𝘁𝘁𝗶𝗻𝗴 𝗱𝗿𝗲𝘀𝘀𝗲𝗱 𝘂𝗽 𝗶𝗻 𝗮 𝘀𝘂𝗶𝘁 — a polo and casual pants are more comfortable, no one cares that you wear a suit
• 𝗢𝘃𝗲𝗿𝗿𝗮𝘁𝗲𝗱 — 𝗚𝗼𝗶𝗻𝗴 𝘁𝗼 𝗹𝗶𝘃𝗲 𝘀𝗽𝗼𝗿𝘁𝗶𝗻𝗴 𝗲𝘃𝗲𝗻𝘁𝘀 — I like watching on TV and being comfortable
• 𝗢𝘃𝗲𝗿𝗿𝗮𝘁𝗲𝗱 — 𝗧𝗿𝗮𝘃𝗲𝗹𝗶𝗻𝗴 𝗼𝘃𝗲𝗿𝘀𝗲𝗮𝘀 — there are so many places to see in the US and nearby Islands

No pitch, just clarity.

08/27/2026

If your retirement plan is "sell the business someday," that's not actually a plan.

We hear this a lot from business owners, and we get why. Every extra dollar goes back into growing the business because that's what built it in the first place.

The problem shows up later, when the business is 80 or 90 percent of someone's net worth and retirement accounts have been an afterthought for years.

Here's the uncomfortable question worth asking now instead of later: if something happened to the business tomorrow, an industry downturn, a health issue, an unexpected competitor, what would you actually have?

A few things worth doing regardless of when you plan to sell: get an honest business valuation, not the number you've been carrying around from a conversation years ago.

Start funding retirement accounts outside the business, even in smaller amounts, so your future isn't entirely tied to one asset in one industry.

And get your CPA, attorney, and financial advisor in the same conversation at least once, because right now they're probably each working with half the picture.

The business can still be the biggest driver of your wealth. It just shouldn't be the only plan you have.

What's stopping you from getting a real valuation done this 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.

08/26/2026

She'd never once logged into the retirement account. Then she had to understand it in a weekend.

That's a real situation we've seen more than once.

A spouse passes away or a marriage ends, and suddenly the accounts, statements, and decisions that were someone else's job become yours, often on a tight legal timeline.

If that's close to where you are right now, a few things matter more than the rest.

First, get a complete list of every account, debt, and beneficiary designation before you do anything else. You can't make good decisions about money you can't see.

Second, don't rush into big investment or insurance decisions in the first few months. Temporary holding accounts exist so you don't have to decide everything at once under stress.

Third, check your beneficiary designations immediately. An old one can override even a carefully updated will.

And one more thing worth saying plainly: if an advisor shows up unusually quickly after a divorce or a death is finalized, that timing is not an accident. Take your time choosing who you work with.

You don't have to become a financial expert overnight. You just need someone who will slow down, explain things in plain language, and help you make decisions in the right order.

If you're in the middle of this right now, what's the question you keep circling back to?

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

08/25/2026

Jeff Judge was quoted by Cameron Huddleston in AARP this week on the true cost of buying a teenager a car.

Most parents plan for the price tag. They don't plan for what comes after.

Adding a 16 year old driver to your auto policy can raise your premium by $4,000 to $5,000 a year. Add gas, repairs, and a car loan, and the purchase turns into a multiyear expense, not a one time cost.

Jeff's own son doesn't turn 16 until 2028, and he's already running these numbers for his own family.

The parents who come out ahead here aren't the ones who found the cheapest car. They're the ones who checked the insurance cost before they went shopping.

A Fit Call is the right first step if you want to plan for this before it hits your budget.

https://skd.so/YGSz98

https://skd.so/wQfUQX - https://skd.so/2rBQMq -

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

08/25/2026

Jeff Judge - https://www.linkedin.com/in/jeffreymjudge -'s newest Kiplinger - https://www.linkedin.com/company/kiplinger/ - article rethinks how to choose a Social Security claiming age.

Most people decide based on longevity alone. Jeff's take: it should be a tax decision too. Up to 85 percent of your benefit can be taxed federally once your combined income crosses a threshold that has not moved since 1984.

His strategy: use the low-income years between retirement and claiming to convert to Roth and capture capital gains at rates you will not see again once benefits and required withdrawals arrive.

If you are within a few years of this decision, a Fit Call is the right next step.

https://skd.so/KQUliW

https://skd.so/WXbLLB - https://skd.so/ePGJYY -

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

08/25/2026

When clients like Andy share their experience, it reaffirms everything we stand for. If you're looking for a team that's genuinely invested in your future, we're here. https://skd.so/JbkDc1 - https://skd.so/aO0FPj -

08/24/2026

Chesapeake Financial Planners' Jeff Judge was quoted by journalist Beth Pinsker in MarketWatch this week, talking about sports betting as a budget line item rather than an occasional splurge.

Jeff's rule with clients who gamble: winnings that get swept into a brokerage account are the tell. That is someone treating it as spending money, not an investment.

One client caps gambling at 10% of income. It's budgeted and capped, and it never touches retirement savings.

What Jeff watches for is whether that number holds steady or creeps up after a losing streak. A number that stays the same is discipline. One that grows quietly is worth a conversation.

If you have a spending category in your own life that has never gotten a real conversation, that's worth looking at before it decides itself.

https://skd.so/aGSOqG

https://skd.so/L4WgSU - https://skd.so/JMNWXQ -

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

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

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