One planning insight. Two charts that caught our eye. Helping you stay the course in under three minutes.

Planning Insight | November 2026

The Cost of Convenience: Medicare and Open Enrollment Deadlines Are Here

Most of us are paying for at least one subscription we have forgotten about. A streaming service, a gym membership, possibly something that arrives in a monthly box. They renew quietly because that is what renewal is designed to do.

Your health coverage works the same way. The difference is that an unwatched documentary costs you twelve dollars a month, and this one can become far more meaningful (and expensive) in a hurry.

Two enrollment windows are open right now, and they share that quiet feature. If you do nothing, you get automatically re-enrolled in whatever you had last year. That sounds harmless, even convenient. The catch is that the plans change every year even when nothing in your life does. You are not renewing last year’s plan, you are accepting next year’s version of it, sight unseen.

If you are on Medicare

The window closes December 7. What you choose, or fail to choose, takes effect January 1 and generally holds for the full year. Three things shift underneath you in the meantime:

• Drug formularies get rewritten annually. A medication sitting comfortably in a low tier this year can quietly move up a tier or fall off the list altogether.
• Advantage networks get renegotiated. The doctor you have seen for a decade may be out of network in January.
• The costs reset. Premiums, deductibles and out-of-pocket maximums are all repriced for the new year.

Here is the number worth sitting with: roughly 65% of Medicare beneficiaries did not compare their coverage against other available plans during the most recent measured enrollment period. Two out of three people renewed without checking whether the plan still fit.

That is not laziness. It is a reasonable response to a sixty-page document that arrives unannounced in September and appears to have been written in a second language. But the comparison itself takes about fifteen minutes. Pull up your current plan, enter your actual prescriptions, and look. If it still fits, you have confirmed it for another year at no cost. If it doesn’t, you found out in November rather than at the pharmacy counter in February, holding a prescription that now costs four times what it did in December.

If you are still working

Your employer’s window usually closes in mid to late November, and the same auto-renewal logic applies. Most people give the entire process about ten minutes, which is less time than they will spend trying to find a movie to watch on that barely-used streaming service.

The 2027 figures, for reference:

• HSA contributions: $4,500 individual, $9,000 family, plus another $1,000 if you are 55 or older
• Health FSA: $3,500, with up to $700 carrying into the following year
• High deductible plan minimums: $1,750 individual, $3,500 family
• High deductible out-of-pocket maximums: $8,700 individual, $17,400 family

Four things deserve more than ten minutes.

The HSA is not a checking account. If you are in a high deductible plan, this is the only account in the tax code that is deductible going in, grows tax free, and comes out tax free for qualified medical expenses. The IRS does not hand out three tax breaks on the same dollar anywhere else. Funding it and leaving it invested is one of the best moves available to you. Using it to cover this year’s dentist visit is like raiding your 401(k) to buy a toaster.

The FSA has a clock on it. Anything above the carryover amount is forfeited at year end, which is why December is high season for buying sunscreen you do not need in bulk.

Your disability coverage replaces less than you think. Group plans typically cover around 60% of base pay, often excluding bonus and commission, and when your employer pays the premium the benefit shows up taxable. For plenty of households the actual replacement rate is closer to 40%.

Your life election may be doing almost nothing. One or two times salary sounds like coverage. Set against a mortgage and the cost of getting two kids through college, it is closer to a nice gesture.

What they have in common

Neither decision can be undone mid-year without a qualifying life event. Both default to the status quo. And both are priced on next year’s terms, not last year’s.

Fifteen minutes now, or twelve months of finding out.

If you would like a second set of eyes on either one, send us what you are looking at. We don’t sell insurance and have nothing riding on what you pick, which makes this the rare decision where asking for help costs you nothing but the email.

What's New?

Social Security raises benefits 3.6%. Announced in mid-October, the cost of living adjustment works out to roughly $75 a month on a $2,000 benefit. Worth noting that Medicare Part B premiums are deducted before the check arrives, so the net raise will be smaller than the headline.

The annual gift exclusion rises to $20,000. Up from $19,000, and a clean number to plan around. A married couple can now move $40,000 to each child, grandchild, or anyone else in 2027 without touching the lifetime exemption or filing a gift tax return.

The estate exemption climbs to $15.48 million per person. Up from $15 million. For couples, that is just under $31 million before federal estate tax applies. Most families are comfortably below it, but state-level thresholds are a different conversation and North Carolina residents with property in other states should keep that in mind.

The standard deduction reaches $33,200 for couples. Up $1,000, with $16,600 for single filers. The practical effect is that the bar for itemizing keeps rising, which is why bunching deductions into alternating years is worth a look for anyone sitting near the line.

What Caught Our Eye

A couple of charts and graphics we found insightful this month.

The Index Is Not the Companies.

More than a quarter of the S&P 500 is sitting 40% or more below its all-time high. Names in this chart include Nike, Adobe, Disney, Netflix, Oracle and UnitedHealth, companies most people would have described as safe at some point in the last five years. The index itself has held up because a small number of very large companies have carried it. That gap between how the index feels and how its average member has actually done is the entire argument for owning all of them rather than picking a few.

The Retirement Wave That Didn’t Reverse

Economists expected the surge in early retirements after 2020 to unwind once conditions normalized. It largely didn’t. Several million people left the workforce ahead of schedule and stayed out. For anyone within a decade of retiring, the practical takeaway is that the exit often arrives sooner and less gradually than planned, which is an argument for knowing your number well before you think you need it.

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