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06/26/2026

Our Managing Partner Jeff Judge was quoted by Jenna Romaine in US News & World Report this week after Wharton released a new Social Security analysis.

The short version: Wharton projects the trust fund used for retirement benefits will deplete in February 2033. The official trustees report says Q4 2032. A few months difference.

Most of the coverage is focused on that date gap. Jeff's take cuts to what actually matters for people approaching retirement.

The depletion date is not the number to plan around. The number that should shape your strategy is the projected benefit cut under current law if Congress doesn't act: roughly 20-24%.

That is a real and specific planning input. It affects how you size your retirement account contributions now, whether Roth conversions make sense in your current income range, and how you build an income plan that doesn't rely too heavily on Social Security as its foundation.

A few months on a headline projection don't change any of that math.

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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.

06/26/2026

Your car just got a $3,200 repair estimate. You've had it for 11 years. It's paid off.

Do you fix it, or finally pull the trigger on something new?

Mike Winters at CNBC quoted our managing partner Jeff Judge this week on exactly this question.

Jeff's answer: the repair bill is a trigger to start the math. It's not the answer itself.

The comparison that actually matters is total cost to total cost. Not what your new payment would be vs. what the repair costs. Everything: repair history, projected maintenance, insurance difference, remaining equity, loan structure if you finance.

For a paid-off car, the math is direct. Its job is to cost less than replacing it. When it can't do that job, you have your answer.

For anyone in or approaching retirement, a new car payment is a fixed monthly draw. It competes with healthcare costs, travel, and the spending structure you've been planning around. That context changes the calculation in a real way.

Run the numbers before you decide. Not after.

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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.

06/26/2026

Founder Mark Rossbach on the five foods he can't live without:

• Crab cakes
• Steamed crabs
• White cheddar popcorn
• Polish galumpkis
• Fried chicken

Maryland roots and a little Polish heritage, no apologies. The people handling your retirement and tax planning are people first. No pitch, just clarity.

06/26/2026

Founder Jeff Judge on the foods he can't live without:

• 𝗣𝗶𝘇𝘇𝗮 — bad pizza still beats no pizza.
• 𝗡𝗮𝗰𝗵𝗼𝘀, 𝗳𝗮𝗷𝗶𝘁𝗮𝘀, 𝘁𝗮𝗰𝗼𝘀 — Mexican, all of it.
• 𝗕𝗼𝘅 𝗛𝗶𝗹𝗹 𝗰𝗿𝗮𝗯 𝗰𝗮𝗸𝗲𝘀 — as long as they're from Maryland.
• 𝗔 𝗴𝗼𝗼𝗱 𝗿𝗶𝗯𝗲𝘆𝗲 — bone-in or out, grilled at home or out, doesn't matter.
• 𝗣𝗶𝘇𝘇𝗮 𝗙𝗿𝗶𝘁𝗲𝘀 — fried dough in sugar, his grandmother's tradition, still made every Christmas and Thanksgiving morning.

That last one's been in the family for decades — the kind of tradition worth protecting. No pitch, just clarity.

06/25/2026

If you've ever left a financial meeting feeling talked over instead of talked to, this one's for you.

A lot of the women we work with came to us after years of being treated like a passenger in their own financial life.

Statements addressed to someone else. Questions answered to their husband. The quiet assumption that they didn't really want the details.

They wanted the details. Nobody offered them in plain language.

Here's what we believe. You should walk out of every meeting understanding your own money better than when you walked in.

You should be able to ask a question without feeling embarrassed.

And the person across the table should be working for you, not for a commission.

If you're navigating this alone, whether after a divorce, a loss, or just because you're the one who handles it now, a few questions are a good starting point. Do I know what I have? Do I know what it needs to last my lifetime? Do I trust the person helping me?

You deserve straight answers to all three.

What's one financial question you've wanted to ask but never felt comfortable asking? No judgment here.

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

06/25/2026

Employer 401(k) matches are shrinking, and a lot of pre-retirees are reacting to the wrong number.

Kerry Hannon at Yahoo Finance covered the new data this week, quoting Jeff Judge of Chesapeake Financial Planners. Fewer companies are offering a match in 2026 than in 2025. The average maximum dropped from 6.3% to 6.11%.

The real issue Jeff flagged? Most employees aren't even getting the full match they're already entitled to.

Before you start worrying about what your employer might cut, ask whether your current deferral is high enough to capture what they're offering right now.

If it isn't, that's the first fix.

Then raise your contribution slightly above the match threshold to keep your total savings rate steady regardless of next year's benefit changes.

Your own savings discipline outlasts any benefit package. That's the number to own.

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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.

06/24/2026

You had a great year in the business. So why doesn't it feel like it?

We hear this from owners all the time.

Revenue is up, the team is busy, the year looked strong on paper.

And yet the personal balance sheet hasn't really moved.

Here's what's often happening. The money the business generates keeps going back into the business.

Every available dollar funds growth, payroll, or the next thing, and very little of it ever becomes personal, durable wealth that exists outside the company.

That works right up until the day you want the business to support you instead of the other way around.

The fix isn't dramatic. It's deciding, on purpose, what the business owes you each year before it gets reinvested.

It's having your personal and business finances looked at together instead of in two separate rooms.

It's getting your CPA and advisor talking before the tax bill, not after.

Your business should be building something that outlasts your involvement in it.

Business owners: when you have a strong year, do you have a system for turning some of it into personal wealth, or does it all go back in?

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

06/24/2026

A client in his late 50s asked our managing partner Jeff Judge whether he should buy a Bitcoin ETF.

Kate Stalter quoted Jeff's answer this week in US News & World Report, and it's the same answer he gives anyone close to retirement.

He asks two questions. What is your thesis? And what happens to your plan if it goes to zero?

For a younger saver with real conviction and a long runway, there can be a case for a small, speculative allocation. A sleeve, not a foundation.

For someone three years from retirement, the time horizon doesn't leave room for the position to be wrong.

Bitcoin is volatile by design. Fidelity itself warns that its fund can result in significant or complete loss. That isn't a knock on the product. It's the nature of a single, highly volatile asset.

The real question was never whether Bitcoin is good or bad. It's whether it fits the plan you actually have, at the age you actually are.

If you're weighing a speculative position close to retirement, tell us in the comments what's making you consider it. That's usually where the real planning conversation starts.

https://skd.so/whyYU0

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

06/23/2026

Jeff Judge wrote a new piece for Kiplinger this week, and it opens with something we hear in almost every first meeting.

The couples who feel calm about money in retirement are rarely the ones with the biggest accounts. They are the ones who set a few clear rules and stopped second-guessing every decision.

Here is what that looks like.

They separate their money by when they will use it, so the cash for the next couple years is not riding on this year's market. They pick one withdrawal approach and follow it instead of guessing each month. And they put a real healthcare number on paper. Fidelity estimates a 65-year-old retiring in 2025 may need around 172,500 dollars for healthcare in retirement, not counting long-term care. That figure feels far more manageable once it is written down with a plan behind it.

None of this takes more wealth. It takes structure, decided before the worry sets in.

What is the retirement money question that is on your mind right now? We read every comment.

https://skd.so/U3LEDm

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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.

06/23/2026

Feedback like this from Kim W 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/zvPbTm - https://skd.so/2OiSbR -

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