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11/02/2026

Your bonus hit. In three weeks, half of it will feel like it was never there.

That's not a budgeting problem, it's a sequencing problem.

We see it constantly with households earning well into six figures: the bonus or the RSU vest lands, taxes take a bite nobody planned for, and the rest quietly absorbs into regular spending before a decision gets made.

The fix isn't complicated, but it has to happen before the money hits your account, not after.

Decide the split in advance: a fixed share to retirement accounts, a fixed share to any high-interest debt, and only what's left to discretionary spending.

If equity compensation is part of the picture, the vesting and the tax withholding rarely line up the way people expect, and that gap is where the real planning happens.

A specific decision beats a general intention every time money shows up in a lump sum.

If a bonus or vest is coming and you want a plan for it before it lands, a Fit Call is the right move.

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

10/31/2026

Picture yourself at 84. Is the money still there?

That's not a dramatic question. Women's retirements commonly stretch 25 to 30 years, often longer than their spouse's, and most retirement income plans were rarely built around that math.

We hear versions of the same worry constantly: years of not being fully involved in the household's financial decisions, followed by a sudden need to understand statements someone else set up.

That's not a knowledge problem. It's a timing problem, and it's fixable at almost any age.

The caregiving most women take on, for children, for aging parents, sometimes for both, also changes the retirement math in ways a generic plan rarely accounts for.

None of this means starting over. It means getting an honest answer to one question: at your actual spending, does the money last as long as you might?

That's a conversation worth having before 84, not during it.

What's the one question about your own retirement you haven't actually asked out loud?

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

10/30/2026

The costly Treasury mistake is not buying the wrong bond. It is selling the right one at the wrong time.

Jeff Judge, CFP and managing partner at Chesapeake Financial Planners, was quoted by Rachel Christian in U.S. News & World Report this week in a guide on how to buy Treasury bonds.

His example: a client bought long-dated Treasurys right before rates climbed in 2022. The price fell. A home repair came up. He sold to pay for it, and the loss locked in. Held to maturity, he would have gotten his principal back. He just could not wait that long.

Jeff's fix: match maturities to when you need the cash, or build a bond ladder so some bonds mature every year.

One more point from the article. A Treasury ETF has no maturity date, so its price moves with rates every day. TreasuryDirect wins on certainty.

If you want to see which of your dollars have a date on them, a Fit Call is a good first step.

Read the article: https://skd.so/Yfc8TN

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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.

10/30/2026

Mark Rossbach on the five people who shaped how he thinks about work, risk, and what actually matters.

• 𝗠𝘆 𝗗𝗮𝗱 — He was a hard worker down at the docks at the Port of Baltimore and instilled his work ethic in me.
• 𝗝𝗶𝗺 𝗥𝗲𝗶𝗻𝗲𝗿, 𝗺𝘆 𝗳𝗶𝗿𝘀𝘁 𝗯𝗼𝘀𝘀 𝗮𝘁 𝗮 𝗹𝗮𝗿𝗴𝗲 𝗖𝗣𝗔 𝗳𝗶𝗿𝗺 — He gave me increasing responsibility at a young age and hired me.
• 𝗪𝗮𝗿𝗿𝗲𝗻 𝗕𝘂𝗳𝗳𝗲𝘁𝘁 — He keeps things simple and still lives in the first house he bought and never showcases his wealth.
• 𝗠𝘆 𝗯𝗿𝗼𝘁𝗵𝗲𝗿-𝗶𝗻-𝗹𝗮𝘄 𝗥𝗼𝗯𝗲𝗿𝘁 𝗕𝗮𝗿𝗿𝗲𝘁𝘁 — He was always a risk taker and became the president of his company. This risk taking helped me get out of my comfort zone working as an accountant/auditor for a company to help advising people on financial matters.
• 𝗠𝘆 𝘄𝗶𝗳𝗲 — She always encourages me to pursue my dreams and to whom I am greatly thankful for.

No pitch, just clarity.

10/29/2026

A good year for your investments the year before Medicare can turn into an expensive year for your Medicare bill.

It's called IRMAA, the income related monthly adjustment amount, and it catches people off guard almost every year.

Medicare looks back two years to set your Part B and Part D premium. For 2026, that means your premium is based on your 2024 tax return, not what you're earning right now.

Cross $109,000 as a single filer, or $218,000 married filing jointly, according to CMS, and your premium jumps for the full year, even if your income has already dropped back down.

A large capital gain, a Roth conversion, or even a one-time bonus two years before you turn 65 can push you over that line without you realizing it until the Medicare letter arrives.

The surprise isn't the rule itself. It's finding out about it two years too late to do anything about it.

If you're within two to three years of Medicare, this is worth checking now, while there's still time to plan around it.

Has anyone ever walked you through how this actually works for your specific income?

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

10/28/2026

Most business owners we meet have no idea how much they're allowed to put away for retirement.

They assume it's the same number as a W-2 employee's 401(k) limit. It isn't, and the gap is bigger than most people expect.

A solo 401(k) for a self-employed business owner allows a total combined contribution, employee and employer, of up to $72,000 for 2026, according to the IRS.

Most owners we talk to have rarely contributed anywhere close to that, because every spare dollar went back into payroll, inventory, or the next piece of equipment.

That's understandable in year one. It's a problem by year ten, when the business has grown but the owner's own retirement account hasn't moved much at all.

This isn't about finding more money. It's about redirecting money that's already there once the business can actually support it.

If you haven't checked what you're actually eligible to contribute, that's a conversation worth having before the next tax deadline, not after.

When's the last time you checked your own retirement contribution against what you're actually allowed to put away?

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

10/27/2026

A couple retires in January. By spring, the market is down.

They saved well for decades. Now every withdrawal means selling shares at lower prices.

That is sequence of returns risk, and it is one of six ways the drawdown phase catches new retirees by surprise.

Our Managing Partner, Jeff Judge, wrote about all six for Kiplinger this week.

A few takeaways from his piece:

Dollar-cost averaging works in reverse. Falling prices that once bought more shares now make you sell more of them.

Cash gets a job. Holding roughly one to two years of expenses in cash can keep a downturn from forcing a sale.

Spending is its own skill. Some lifelong savers can't spend. Others spend too freely before they know how long the money has to last.

Retirement runs on different rules than saving. The transition deserves its own plan, ideally before the last paycheck.

If you are a few years from retiring, a Fit Call is a good first step to map out how you would draw from your accounts.

Read the full article:

https://skd.so/98HDt1

Book a Fit Call:

https://skd.so/w83hZM - https://skd.so/d8Auuq -

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

10/26/2026

If your husband passed away tomorrow, do you know which Social Security check you'd actually keep?

Most widows assume both checks continue in some form. That's not how survivor benefits work.

When one spouse passes away, the survivor generally keeps the higher of the two benefits, not both added together. The smaller check goes away.

For 2026, Social Security benefits carry a 2.8 percent cost of living adjustment, according to the Social Security Administration. That adjustment doesn't change this rule. It just means the number itself is a little different than it was last year.

We've sat with women who found this out during one of the hardest weeks of their life, not before it.

This is worth knowing while you can still plan around it, not while you're grieving and trying to read a government letter at the same time.

If you want to know which benefit you'd actually keep, that's a conversation worth having now.

Have you and your spouse ever actually looked at this together?

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

10/24/2026

Picture a couple about to retire. They have a solid nest egg and one nagging question: what do we do with all of it?

Someone mentions an annuity with a payout rate that sounds great. Now they are comparing it to the stock market, and nothing about that comparison feels clear.

That is because it is really two separate questions.

Jeff Judge was quoted by Brett Arends in MarketWatch this week on exactly this. His point: higher payout rates make income annuities worth a fresh look, but only for the part of your money that has to turn into a paycheck. Money meant to grow has a different job.

So start with the bills. Housing, insurance, groceries, health insurance premiums. Then see what Social Security and any pension already cover. That gap is what an income annuity would be asked to fill. Everything else can stay invested for growth and for the unexpected.

One thing to check before you sign anything. Payments depend on the claims-paying ability of the insurance company that issues the contract, so its financial strength matters. So do the fees and how much you can change after you buy.

If you are not sure where that line sits for your household, a Fit Call is a good first step. We will work through it together.

https://skd.so/xA5TX9

https://skd.so/2f0lDG - https://skd.so/vFTNUX -

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

10/24/2026

The Social Security raise for 2026 is 2.8 percent, according to the Social Security Administration. Your grocery bill did not get the memo.

Cost of living adjustments are meant to help benefits keep pace with inflation, and most years they do a reasonable job of it. But a 2.8 percent bump on a fixed benefit is still a small number next to decades of retirement.

This matters more for women than the averages usually show. Women tend to live longer than men, which means a retirement that might stretch 25 or 30 years instead of 15 or 20. A small annual increase, compounded over three decades, adds up to a very different number than the same increase over one decade.

We talk to a lot of women who are managing a household's money for the first time, often later in life than they would have chosen, after a divorce or the loss of a spouse. The math is rarely the hard part once someone sits down with it. The hard part is not having anyone to sit down with in the first place.

A longer retirement isn't a problem to be afraid of. It's a number to plan around, the same way you'd plan around any other known fact instead of ignoring it and hoping it works out.

If nobody has run your specific numbers against a 25 to 30 year retirement, that's one of the first things we'd look at together on a Fit Call.

Where does your own retirement timeline feel the least figured out right now?

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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