The Sandwich Audit

Last Thanksgiving my mom slid a folded piece of paper across the kitchen counter and asked if I could "take a quick look."

It was her Medicare drug plan notice. Her premium was going up, one of her prescriptions had moved to a more expensive tier, and her pharmacy was dropping out of the network. She'd received it in late September. The enrollment window to do anything about it had closed on December 7th. It was November 27th. We made it with ten days to spare, mostly by luck.

That was the moment I realized I'd spent years building systems for my own money and exactly zero for the people who raised me.

If you're somewhere between 35 and 60, there's a decent chance you're in the sandwich: kids or obligations on one side, aging parents on the other, and your own retirement somewhere in the middle getting squished. This week's Playbook is the audit I now run with my parents every October. It takes two sittings, it saves real money, and it turns a fall of nagging into one organized afternoon.

The timing isn't an accident. Two dates are about to hit back to back.

Wednesday, October 14th. The Social Security Administration announces the 2027 cost-of-living adjustment. The Senior Citizens League has been projecting around 3.6 percent, compared with 2.8 percent for 2026. Inflation has run hot this year, so a bigger number is likely. Payments with the new amount start in January.

Thursday, October 15th. Medicare's Annual Enrollment Period opens and runs through December 7th. This is the window to switch Medicare Advantage plans, switch drug plans, or move between Advantage and Original Medicare. Changes take effect January 1st.

Here's why those two dates belong in the same sentence. Most retirees have their Medicare Part B premium deducted straight from their Social Security check. So the raise they hear about on the 14th is not the raise they'll actually see. The 2026 standard Part B premium is 202.90 dollars a month, and the 2027 premium usually gets announced in November. The COLA headline is the gross. Your parents live on the net.

In a normal year, a lot of people let their plan roll over. This is not a normal year, for three reasons.

Plans are disappearing. Medicare Advantage insurers are pulling back hard. Humana told investors its 2027 exits will affect roughly 600,000 members. UnitedHealthcare has flagged a preliminary list of counties it's leaving. KFF found that about 2.6 million Advantage enrollees lost their plans going into 2026, double the year before. If your parents' plan isn't renewing, they should have received a separate notice by early October. If you see one, don't panic, but don't sit on it either.

Drug costs are shifting. The Part D out-of-pocket cap rises from 2,100 dollars in 2026 to 2,400 dollars in 2027. The maximum deductible goes from 615 to 700 dollars. And a temporary program that held down standalone drug plan premiums is ending, so many of those plans are expected to cost more next year.

Formularies and networks change every year. A drug that cost 15 dollars a month this year can land on a different tier next year. A doctor or a pharmacy can leave the network. The plan name stays the same while the plan underneath it changes.

Every one of those changes is spelled out in a document called the Annual Notice of Change. It should have arrived by September 30th. In my experience, most of them are sitting unopened in a kitchen drawer right now.

I split this into two sittings. Checks one and two happen this week, before the 15th. Checks three through five happen in one longer conversation before Thanksgiving, ideally in person.

Start with the Annual Notice of Change. Find it, read it, and pull out four things: next year's premium, the deductible, any change to their specific drugs, and any change to their doctors or pharmacies.

If the ANOC reads like a tax code written by lawyers who hate you, that's normal. I take a photo of each page, strip out the member ID and anything personal, and drop the text into Galaxy.ai with a simple prompt: "Here's my mother's 2027 Annual Notice of Change. List every change from 2026 that affects cost, drugs, doctors, or pharmacies, in plain English, in order of how much money it could cost her." Five minutes later I have a one-page summary I can actually talk through with her.

Then run the real comparison. On or after October 1st, the Medicare Plan Finder on medicare.gov shows 2027 plans. The trick most people skip: enter their actual drug list, with exact doses, and their actual pharmacy. Without the drug list, the tool sorts by premium, and the cheapest premium is often not the cheapest plan once you add the drugs. With it, the tool estimates total annual cost, which is the only number that matters.

If you want a human, every state has a free State Health Insurance Assistance Program, usually called SHIP. These counselors don't sell plans and don't earn commissions. Book early. They fill up fast in November.

One more drug-cost tool worth knowing: the Medicare Prescription Payment Plan lets someone spread their out-of-pocket drug costs into monthly bills instead of paying a big chunk at the pharmacy in January. It doesn't lower the total. It does keep a 700 dollar deductible from wrecking a fixed-income budget in the first month of the year.

Once the COLA is announced, do the actual math. Take their current gross benefit, apply the percentage, then subtract the 2027 Part B premium once it's published, plus any drug plan premium. That's the real raise. Write it down.

Then check whether they're paying the high-income surcharge, called IRMAA.

IRMAA adds money to Part B and Part D premiums for higher earners, and it uses a two-year lookback. For 2026, the surcharge kicks in above 109,000 dollars of modified adjusted gross income for single filers and 218,000 for married couples filing jointly, based on 2024 tax returns. The first tier alone raises the Part B premium from 202.90 to 284.10 dollars a month. Per person. The 2027 surcharge will be based on their 2025 return.

Here's the part almost nobody knows. If their income dropped because of a life-changing event, they can ask Social Security to use a more recent year with Form SSA-44. The qualifying events include stopping work or cutting hours, a spouse's death, divorce, and the loss of a pension. The classic case: Dad retired in 2025 after a big final working year, and in 2027 he's getting billed like he still has a paycheck. One form can fix that.

And if they're still working, the same lookback runs forward. A big Roth conversion or property sale this year shows up in their 2028 premiums. That's not a reason not to do it. It's a reason to know the number before they do.

This is the uncomfortable one, and it's the one that matters most if something goes wrong.

If your parent had a stroke tomorrow, could anyone legally talk to their doctor, pay their bills, or call their bank? For a lot of families, the honest answer is no. And the fix after the fact is often a court process that costs thousands and takes months.

The documents to confirm:

That last one is free and takes ten minutes per account. Brokerage firms are required to make a reasonable effort to collect one. It's a person the firm can call if they suspect fraud or diminished capacity. It doesn't give that person any authority over the money. It just means someone gets a phone call before a disaster instead of after.

The legal documents need an estate planning or elder law attorney in their state. Don't use a generic online template for these. State rules vary and a rejected power of attorney is worth nothing in the moment you need it.

Older adults are the number one target for financial fraud, and it isn't close. The FBI's internet crime report found that people 60 and older reported about 7.7 billion dollars in losses in 2025, roughly 37 percent of everything reported, from one age group.

So whatever you did on your own security, do it for them.

Freeze their credit at all three bureaus. Set up a family safe word for phone emergencies, because the "grandson in trouble" call now comes with a cloned voice. Turn on transaction alerts on their accounts, and with their permission, have alerts over a certain size copy you too. Write the callback rule on a card by the phone: nobody ever moves money because of a call they received. They hang up and call the number on the back of their card.

Framed right, this comes across as you sharing what you learned, and telling them that even people who run security teams for a living got fooled by these calls this year. Because they did.

The last check is a single page. Not a binder. One page.

Every account, institution, and approximate balance. Every insurance policy. The attorney, the CPA, the financial advisor, the primary doctor, the pharmacist. Where the original documents physically live. Who to call first.

Store it somewhere secure that the right people can reach. A shared, locked note in a password manager works well. A printed copy in a fire safe works too.

I keep my parents' professional contacts in Clay, tagged by family member, with notes on the last time we talked to each person. When their CPA calls me in March, I know who she is, what we discussed last year, and what she needs. It's a small thing until it's a big thing.

Most adult kids never have this talk because they're afraid it'll sound like they're circling the inheritance. So lead with you.

Something like: "I just did a full security and paperwork review on my own stuff because of all the fraud lately, and it was eye-opening. Can I walk you through what I did and see if any of it makes sense for you?"

Then let them lead. Ask questions instead of giving instructions. And do it in two sittings, not one. Nobody wants to discuss powers of attorney and drug formularies in the same afternoon.

With their permission, I record our planning sessions with Fathom. Partly so I don't miss details. Mostly so my sister, who lives three states away, gets the summary and action items the same day instead of a garbled game of telephone. Fewer family fights start with "nobody told me."

Then set a reminder so this happens every year without anyone having to remember. I use a small Make.com scenario with three dates: October 1st to look for the ANOC, the morning after the COLA announcement to rerun the income math, and November 20th as a hard stop to finalize any plan switch before December 7th. Each one sends me and my sister a short message with the checklist link. Fifteen minutes of setup, and the audit runs itself every fall.

This week: Find the Annual Notice of Change. Summarize the changes. Pull together the exact drug list and pharmacy.

October 14th: COLA announced. Run the real raise math.

October 15th through mid-November: Compare plans on the Plan Finder with the real drug list. Book a SHIP counselor if needed. File SSA-44 if a life-changing event applies.

Before Thanksgiving: Have the access, defense, and map conversation.

December 7th: Enrollment closes. Aim to be done two weeks early.

Being in the sandwich is mostly a calendar problem. You're never going to have a calm, free afternoon to deal with all of it, so the only way it gets done is if it's scheduled and broken into pieces.

The upside is bigger than it looks. A better drug plan can save a few hundred to a few thousand dollars a year. An IRMAA appeal can save more than that. And the documents and defenses in checks three and four protect the thing that matters most, which is the people.

My mom still has the folded piece of paper from last year. She calls it "the list." This year she called me in September to ask when we were doing it.

Want the whole audit ready to go?

I built The Sandwich Audit Kit for exactly this window. It includes the two-sitting audit checklist, an ANOC decoder prompt that turns the notice into a plain English summary, a Plan Finder walkthrough with the drug list worksheet, a COLA and Part B net raise calculator, an IRMAA and SSA-44 decision guide, a family access documents checklist to bring to an attorney, the one-page family map template, and the conversation starter scripts that keep it from getting weird.

Reply to this email with the word SANDWICH and I'll send it over.

See you Friday.

Alex Rivera, Wealth Architect at Wealth Grid