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

10/14/2026

Picture a couple in their mid 70s.

They give to their church every year and write the check from their bank account.

Every year they also take a required minimum distribution from the IRA and pay income tax on it.

Jeff Judge, a CFP and managing partner at Chesapeake Financial Planners, told Yahoo Finance's Rachel Christian he is a fan of qualified charitable distributions.

"Starting at 70½, a qualified charitable distribution lets you give up to $111,000 per person in 2026 straight from the IRA, and it counts toward your required minimum distribution."

That means a gift can go from the IRA directly to a qualified charity, and it counts toward the required amount.

Jeff also described how he thinks about legacy. When he works with clients, he steers traditional IRA money to charity and Roth or other assets to heirs.

Two accounts, two different jobs.

The IRA can fund the giving. The Roth and other assets can go to the people you want to leave money to.

If you are approaching required minimum distributions and give to charity each year, that is a conversation worth having before the year ends.

A Fit Call is the right first step to map your distributions and your giving together.

Rachel Christian's full guide on Yahoo Finance:

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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.

10/14/2026

The check clears, and the first week is when most of the damage happens.

Not because anyone does anything reckless. Because excitement and relief make good decisions feel urgent when they're actually not.

An inheritance, a settlement, or a sale of property. The money shows up, and there's suddenly pressure, real or imagined, to do something with it right away.

Here's what we tell people instead.

Park it somewhere boring for ninety days. A high-yield savings account is fine. The goal isn't growth yet, it's a pause.

Figure out the tax picture before you spend a dollar. An inheritance and a settlement are taxed completely differently, and guessing wrong gets expensive.

Resist the urge to pay off every debt at once. Some of it makes sense. Some of it trades flexible money for a problem you could have managed another way.

Tell fewer people than you want to. Good intentions from well-meaning relatives have derailed more windfalls than bad investments have.

None of this is about being cautious for its own sake. It's about giving yourself ninety days to make a plan instead of a dozen decisions in a single week.

What would you add to this list?

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

10/13/2026

Paying off the smallest card first feels like progress. It may not be the cheapest route.

Jeff Judge was quoted by Mallika Mitra in Money this week on how to pay off credit card debt faster.

Here is the math from the piece. A $10,000 balance at 21% APR with a 2% minimum payment is $200 a month. About $175 of the first payment goes to interest. At that pace, payoff takes roughly 10 years and costs nearly $14,000 in interest.

Jeff's planning view is simple to state. Rank every card by APR, not by balance size. Send extra dollars to the highest rate first, because that is where interest builds fastest.

He also suggested a look at fixed costs that rarely get a second glance. Subscriptions. Cell phone plans. Internet bills. A few calls and a quick audit may free up money that can go straight to the balance with the highest rate.

If you are carrying more than one card, the order you pay them in deserves a deliberate decision.

A Fit Call is a useful place to rank your balances and build a payoff order.

Full article in Money: https://skd.so/hVSRQc

Book a Fit Call: https://skd.so/C82bXR - https://skd.so/cl2Adq -

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

10/12/2026

Working past 65 doesn't mean Part B can wait.

Jeff Judge of Chesapeake Financial Planners wrote about the Medicare enrollment trap for Kiplinger this week.

The short version: whether you can delay depends on your employer's size.

With 20 or more employees, the group plan can stay primary and Part B can wait without penalty. With fewer, Medicare may be primary once you turn 65, and skipping Part B can leave gaps in coverage.

The cost of a wrong guess is what lasts.

Medicare adds 10% to the Part B premium for each full 12 months you could have enrolled and didn't. Three years is 30% more, every month, for as long as you have Part B.

Part D has its own late penalty if employer drug coverage isn't considered creditable. And signing up for any part of Medicare, even Part A, ends new HSA contributions.

Before your 65th birthday month, write down your employer's headcount and your enrollment dates. If they don't line up, that's worth a second look.

Book a Fit Call to review your Medicare timing before you delay Part B.

Full article: https://skd.so/5omwqw

Book a Fit Call: https://skd.so/cf12og - https://skd.so/xBArDr -

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

10/12/2026

Here's a Required Minimum Distribution mistake we see almost every single year.

Someone turns 73, remembers they have to start withdrawing from their retirement accounts, and assumes any amount pulled out satisfies the requirement.

It doesn't work that way.

The IRS calculates your RMD separately for each account type, based on the prior year-end balance divided by a life expectancy factor. Pull too little from the right account, and the shortfall gets penalized even if you withdrew plenty from a different one.

There's a second version of this mistake for people with several IRAs. You can combine multiple IRA RMDs and take the total from just one of them. But a 401(k) RMD can't be satisfied by an IRA withdrawal, and if you have more than one old employer plan, each one typically needs its own calculation.

A third version shows up with inherited accounts. The rules for an inherited IRA are different from the rules for your own, and mixing up the two is one of the most common errors we see corrected after the fact.

None of this is complicated once someone walks through it with you. It's just easy to get wrong the first year, and the deadline doesn't move for an honest mistake.

If you turned 73 this year, or know you have one coming, save this post before the December deadline sneaks up on 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.

10/11/2026

Turning down $7 to $8 million felt right to one business owner.

The owner, a government contractor, believed the business was worth $12 million.

Three years later, it sold for $6 million.

Jeff Judge wrote about why this happens for the Baltimore Business Journal this week.

Emotionally attached owners tend to value their companies 30 to 50% above what comparable businesses sell for. They count the sweat equity. A buyer's spreadsheet doesn't.

The gap can get big. In the example Jeff uses, a firm that sells at 6x EBITDA now but waits and sells at 3.5x three years later gives up $5 to $8 million in proceeds.

Owners who handle this well start early. About five years before a sale, they step back from day-to-day operations. They get a third-party valuation. They work out what life looks like after the business, and where their involvement ends.

If you own a business, it's worth asking where your own number comes from.

We're glad to go through your exit timeline with you. Book a Fit Call and we'll review it together.

https://skd.so/jeyzVs

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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.

10/10/2026

Picture this: the kitchen is dated, a contractor quotes $60,000, and the bank offers a home equity line at 8 or 9 percent.

It feels reasonable because the house is an asset.

Jeff Judge was quoted by Cameron Huddleston in AARP this week on why that math deserves a second look.

Renovations rarely return dollar for dollar when you sell. The payment, on the other hand, starts the month the loan closes. For Gen X, that lands when fixed costs should be shrinking ahead of retirement.

The same article covers the smaller leaks too. Americans spend about $1,332 a year on subscriptions, and roughly $252 of that goes unused, according to CNET. Jeff's take: they survive every budget review because no single one feels big enough to cut.

Neither fix is dramatic. One is a ten minute look at your card statement. The other is putting a loan payment next to your retirement contributions before you sign.

If you want help sorting out which spending is worth keeping, a Fit Call is the right first step. We'll look at your actual numbers together.

Full article: https://skd.so/fD4Bf7

Book a Fit Call: https://skd.so/sCXDYQ - https://skd.so/dJECqW -

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

10/10/2026

A business owner asked us a simple question recently: if I stopped tomorrow, would I actually be okay? He'd never run the math to find out.

That question comes up constantly, usually years before anyone acts on it. The business is generating real revenue, but very little of it has ever been diverted into a retirement account separate from the company itself.

When we ran the numbers with him, three things showed up: retirement accounts funded at a fraction of what's actually allowed, no real estimate of what the business is worth to a buyer, and no plan for what happens to his income the day the business paycheck stops.

None of that is unusual. Most owners are heads-down running the business, and long-term planning gets pushed to "someday." The problem is that someday tends to arrive faster than expected, through a health scare, a partnership change, or simply exhaustion.

If you've never actually run this math for your own business, a Fit Call is a good place to start, before someday picks the timeline for you.

Where do you disagree with this?

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

10/09/2026

Founder Jeff Judge on his five biggest money mistakes — and the lessons that came out of each one.

• 𝗕𝘂𝘆𝗶𝗻𝗴 𝘁𝗼𝗼 𝗹𝗮𝗿𝗴𝗲 𝗼𝗳 𝗮 𝗵𝗼𝘂𝘀𝗲 𝗮𝘀 𝗼𝘂𝗿 𝗳𝗶𝗿𝘀𝘁 𝗵𝗼𝘂𝘀𝗲 — We should have gotten a smaller house and saved more in our 20's.
• 𝗕𝘂𝘆𝗶𝗻𝗴 𝗮 𝗵𝗼𝘂𝘀𝗲 𝗶𝗻 2006, 𝗿𝗶𝗴𝗵𝘁 𝗯𝗲𝗳𝗼𝗿𝗲 𝘁𝗵𝗲 𝗯𝘂𝗯𝗯𝗹𝗲 𝗯𝘂𝗿𝘀𝘁 — Became our family home for 16 years. Sometimes great things come from a bad situation.
• 𝗥𝘂𝗻𝗻𝗶𝗻𝗴 𝘂𝗽 𝗱𝗲𝗯𝘁 𝗼𝘂𝘁 𝗼𝗳 𝗰𝗼𝗹𝗹𝗲𝗴𝗲 — Just because they will give you credit doesn't mean you need to use it.
• 𝗣𝗮𝘆𝗶𝗻𝗴 𝗰𝗮𝘀𝗵 𝗳𝗼𝗿 𝗮 𝗰𝗮𝗿 𝘄𝗵𝗲𝗻 0% 𝗳𝗶𝗻𝗮𝗻𝗰𝗶𝗻𝗴 𝘄𝗮𝘀 𝗮𝘃𝗮𝗶𝗹𝗮𝗯𝗹𝗲 — Free money always beats money that could be working for you.
• 𝗦𝗽𝗲𝗻𝗱𝗶𝗻𝗴 𝗺𝗼𝗻𝗲𝘆 𝗼𝗻 𝘁𝗵𝗶𝗻𝗴𝘀 𝗜 𝗱𝗼𝗻'𝘁 𝗻𝗲𝗲𝗱 — 'It seems impossible for a man to learn the value of money without first having to learn to waste it.' — William Faulkner.

No pitch, just clarity.

10/08/2026

He retired at 62 and claimed Social Security the same month, mostly because that's what felt like the natural next step. He didn't realize what that decision locked in for the next 20-plus years.

Claiming early isn't automatically wrong. For some people, it's exactly right. The mistake is claiming on a timeline instead of a plan, without ever running what the difference actually looks like over a full retirement.

The maximum Social Security benefit at full retirement age in 2026 is $4,152 a month. Claim before full retirement age and that number drops for life. Wait until 70 and it climbs. Neither answer is universally better; it depends on health, other income, and whether a spouse's benefit is part of the picture too.

The couples who feel best about this decision are the ones who saw the actual numbers side by side before choosing, not after.

If you haven't run those numbers yet, a Fit Call is a straightforward way to see where you stand.

Save this if it hit home.

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

10/14/2026

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