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Health Insurance Planning
Updated 2026Dental Care in Retirement
Where dental care comes from in retirement: what Medicare pays for, insurance versus discount plans, lower-cost clinics in Arizona and Las Vegas, and how to use your plan's dental benefit.
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GuideThe IRMAA Trap
Why your Medicare premium just doubled. 2026 surcharge brackets, the 2-year lookback, how to appeal, and 6 strategies to plan ahead.
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Updated 2026Health Care Sharing Ministries
Faith-based health sharing before Medicare: what ministries are, how they compare with a Marketplace plan, other ways to bridge to 65, and why sharing doesn't replace Medicare.
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Updated 2026Leaving Your Employer's Plan
Working past 65? How to move from job-based coverage to Medicare on time: when you can wait on Part B, the 8-month window, late-enrollment penalties, the HSA rule and the forms Social Security takes online.
View GuideRetirement Income Planning
Fiscal FootnotesWhy Social Security Is Taxed
They taxed it to build it, then taxed it again. David Schaeffer walks through why your benefit was tax-free for almost fifty years, the 1983 and 1993 laws that changed it, the income lines that never moved, the honest double-tax answer, and what the 2025 law really did.
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Fiscal FootnotesRequired Minimum Distributions (RMDs)
The rule that taxes your retirement, explained. David Schaeffer walks through where the RMD came from, the age ladder (72, 73, 75), how the amount is calculated, the penalty for missing one, and the traps nobody warns you about.
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Fiscal FootnotesWhat Changed About Retirement
The system changed. Nobody sent a memo. David Schaeffer walks through how we went from pensions to 401(k)s, what inflation quietly doubled, and why retirement taxes feel different now.
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Free GuideNot All Annuities Are Created Equal
The four main types of annuities explained in plain language: fixed, variable, fixed indexed, and hybrid. Know what you are looking at before you commit to anything.
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Free GuideI Retired... Now What?
Your first 90 days checklist. Covers finances, health insurance, the emotional transition, taxes, and finding purpose. Printable checklist included.
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Updated 2026Tax Facts 2026
Current year tax brackets, standard deductions, contribution limits, and all the key numbers you need for retirement tax planning.
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Free GuideIs Your Social Security Right?
The $50,000 mistake hiding in your earnings record. How to check your record, fix errors, understand the benefit formula, and decide when to claim.
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Free GuideThe Roth Conversion Playbook
How retirees are turning taxable IRAs into tax-free retirement income. 2026 tax brackets, IRMAA interaction, gap years strategy, smaller RMDs, and legacy planning.
Download Free GuideLong-Term Care Planning
Updated 2026The Long-Term Care Planning Guide
What Medicare doesn't cover, and what you can do about it. Arizona, Nevada and national costs, hybrid vs traditional insurance, Medicaid planning, tax benefits, and caregiver impact. 15 pages.
View GuideLife and Legacy Planning
New GuideThe Loopholes That Aren't
Selling a business, starting one in retirement, or setting up a trust? Learn which tax and trust rules are real, which "loopholes" are traps, and what to ask your tax professional.
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Fiscal FootnotesYour Home, Your Legacy
When to sell, when to hold, and how to hand it down. David Schaeffer and Kyle Jacobs walk through the capital gains math, the Medicare IRMAA surprise, and the step-up in basis your family will live with.
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Free GuideBucket List Planning
How to plan and fund the experiences that matter most to you in retirement, from travel to hobbies to giving back, without jeopardizing your financial security.
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Most RequestedBefore Death Do Us Part
Our most-requested guidepost. A comprehensive checklist of everything you need to have in order for your family, from accounts and passwords to legal documents and final wishes.
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New GuideLegacy Contacts
Choose who can look after your Apple, Google, and Facebook accounts after you pass. Two pages, step by step. Part of The Beneficiary Box Program.
View GuideQuick one-page overviews
The big picture on each way we help, one page at a time.
One-Page OverviewRetirement Income Planning
Will my money last? A one-page look at how Yellow, Green and Red money work together to give you a paycheck that keeps coming.
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One-Page OverviewGenerational Wealth Strategies
How much will actually arrive? Simple ways to protect what you built, pass it on, and give with purpose, for parents and their grown kids.
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One-Page OverviewThe BeneficiaryBox™ Program
What if your family never had to wonder? Four guided sessions with David Schaeffer put your accounts, papers and wishes in one place, ending with a family meeting.
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One-Page OverviewLong-Term Care Planning
Medicare does not pay for long-term care. What care costs, how families pay for it, and the two triggers every policy should include.
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One-Page OverviewLife Insurance
When did you last look at your policy? How the main kinds of life insurance work, with room to note what you already have before a review.
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One-Page OverviewYour Trust Is Just the First Step
A trust only controls what it owns. How to fund it, line up every beneficiary form, and keep it current, working alongside your attorney.
View OverviewWorkshops
Watch our educational workshops at your own pace. No registration required. Just press play and learn.
Retirement Readiness Workshop
The Three Types of Money framework, market volatility, sequence of returns risk, and how to build a retirement income plan that lasts.
Inheritance Planning Workshop
Prepare, Protect, Preserve. Estate attorney Sean Greengard joins to cover trusts, probate avoidance, power of attorney, and the steps most families miss.
Series
Longer-form article and podcast series from Retirement Insights. Read online, or listen to the podcast episode for each part.
Series · 7 PartsBoth Ends of the Table
A high net worth family's real conversation about inheritance, from both sides of the table.
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Series · 7 PartsMore Than a Death Benefit
Life insurance as a living tool for income and legacy, not just a payout.
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Series · 4 PartsThe Gap Years
The low-tax window between retiring and RMDs, where the biggest income decisions get made.
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Series · 3 PartsPassing It On
A personal series on wills, hard family conversations, and inheriting well.
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Series · 3 PartsThe Fourth Color
David’s Three Colors of Money just got a fourth: Purple, for real estate. Your home, its taxes, and passing it on.
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SeriesThe Widow's Penalty
The rules that change when you lose a spouse, at 55, in your 60s, and at 75, plus the first-90-days playbook.
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SeriesWhen the Kids Inherit
What your kids will actually face when it all passes to them, and how to plan the handoff from their side of the table.
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SeriesThe Promise They Called Socialism
How Medicare was actually won, what it quietly changed, and the gap at 65 that still catches families.
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SeriesThe Evolution of a Promise
Where life insurance came from, how it became fair, and what the modern version actually does for a family.
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SeriesSeven Ways In
How seven very different people actually chose their Medicare coverage, and the one detail that decided each case.
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SeriesThe Whole Chart
The financial products nobody checks against each other, and what a full review catches before it costs your family.
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SeriesThe Fridge List
Five long-avoided estate tasks (the call, the trust, the talk, the box, the first meeting) and how each one gets finished in a single afternoon.
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SeriesHealthcare in Retirement
The tricky corners of Medicare, one real situation at a time, and what a planner does about each.
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SeriesTake-Home Notes
Our Medicare workshop in print: every section of the live show, one article and one podcast each.
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SeriesWhat the Letter Leaves Out
Five things your plan's Annual Notice of Change does not tell you, and where to find each answer.
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