The Learning Hub
Plain answers to the money questions nobody explains.
36 guides, answers, and tools on Medicare, Social Security, taxes, and insurance. Organized by where you are, written the way I’d explain it at your kitchen table. No sales pitch. No email wall.
New here? Start with one of these.
GuideTurning 65: when to sign up for MedicareToolDoes your Medicare plan still fit?Turning 65
Your enrollment window, what to sign up for, and what to do first.
- GuideTurning 65: when to sign up for MedicareYour seven-month window, coverage through work, and what to do first.
- ChecklistYour turning-65 checklistEight steps to take before your 65th birthday, in order.
- GuideMedicare Advantage or a Medigap plan?How the two paths differ on doctors, costs, and travel.
- GuideSpecial Enrollment PeriodsWhen you can sign up or change plans outside the usual windows.
- Answer · 3 min readAre Medicare Supplement plans the same no matter the company?The letter tells you what is covered. The company decides the price and the extras.
- Answer · 3 min readTurning 65 in North Carolina: your Medicare checklistYour enrollment window, how to sign up, and what to do at 3 months out, 1 month out, and after.
Already on Medicare
Reviewing your plan each fall, changing plans, and keeping your doctors.
- ToolDoes your Medicare plan still fit?Seven questions, about 90 seconds, and an honest read on whether to look again.
- GuideReviewing your plan each fallWhat changes every year and what to check before December 7.
- ChecklistAnnual Enrollment 2026 checklistA step-by-step review list for this fall.
- GuideGot your Annual Notice of Change letter?How to read it, and the lines that matter most.
- GuideCan I keep my doctors?What to check for Triad doctors and hospitals before you choose.
- GuideTriad doctor networks and Medicare AdvantageHow networks work here, and how to check yours.
- Answer · 3 min readShould I stay on Original Medicare or switch to Medicare Advantage?What each path covers, what it leaves to you, and the three things to check before you change anything.
- Answer · 3 min readDoes Medicare Advantage cover dental?Original Medicare does not cover routine dental. Many Advantage plans add some. Here is what the benefit usually includes, and where people get surprised.
- Answer · 4 min readWhat is the difference between HMO and PPO Medicare Advantage plans?HMOs keep costs tight with a network and referrals. PPOs give you more freedom, and you pay for it. Here is how to think about the tradeoff.
- Answer · 4 min readWhat should I check before switching Medicare Advantage plans?October 15 to December 7 is your yearly window to switch. Six checks, in order, so January never surprises you.
Medicare costs
Premiums, deductibles, penalties, and what higher income does to them.
- GuideEvery 2026 Medicare cost, with its sourcePremiums, deductibles, and income brackets on one page.
- GuideWhat does Medicare cost?A plain walk-through of what you pay and when.
- ToolThe Part B late penalty, worked outFind out whether a penalty applies to you and what it adds.
- ToolPart B and IRMAA premium estimateSee what your income could mean for your Medicare premiums.
- GuideAppealing a high Medicare premiumWhen a life change means you can ask Social Security to look again.
- Answer · 4 min readWill Medicare cost me more because of my income?Your 2024 tax return sets your 2026 Medicare premiums. Here is how the income surcharge works, and what to do if your income has dropped since.
Taxes in retirement
Social Security taxes, RMDs, Roth conversions, in plain English.
- ToolYour Roth conversion windowHow many lower-income years you might have before RMDs start.
- ToolConversion and Medicare timing plannerLine up conversions with the years Medicare looks at your income.
- Explainer · 3 min readDo I have to pay taxes on my Social Security?Maybe some of it. Here's the test the IRS uses, the numbers that matter, and what North Carolina does.
- Explainer · 3 min readWhat are required minimum distributions, and when do they start?The IRS let your retirement savings grow without tax for years. RMDs are when it starts asking for its share.
- Explainer · 3 min readWhat is a Roth conversion, and who looks at one?Pay tax now so you don't pay it later. Sometimes that's smart, sometimes it isn't. Here's how it works.
Retirement income
When to take Social Security and how to turn savings into a paycheck.
Insurance explained
Life insurance, long-term care, and critical illness coverage.
- GuideLife insurance, in plain EnglishWhat it's for, and how to review the coverage you already have.
- GuideLong-term care insuranceWhat it pays for, what it costs, and the alternatives.
- GuideShort-term care insuranceCoverage for recovery stays that Medicare doesn't fully pay.
- GuideCritical illness insuranceA lump sum if you're diagnosed with a covered illness.
Helping a parent
For the adult kids sorting this out alongside Mom or Dad.
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