In just five years, the oldest of the 65 million baby boomers in the United States will begin reaching their late 80s, the age at which people are more likely to need care. At the same time, most younger baby boomers have already left the workforce, many without enough money to pay for retirement, much less their future care needs. In this podcast, I talk with experts in the fields of aging and elder care about what this will mean for the nation and how we can prepare, both collectively and individually.
More on Harry Margolis: https://margolisbloom.com/harry-s-margolis/ (https://margolisbloom.com/harry-s-margolis/)
Harry’s Substack: https://okayboomer.substack.com/ (https://okayboomer.substack.com/)
How Changing Families Are Reshaping Caregiving with Sarah Elizabeth Patterson
Demographer and sociologist Sarah Elizabeth Patterson explains how demographic change is affecting family caregiving for older adults in the U.S., where paid care remains infrequent and families—broadly including friends and community—still provide most help. She highlights two key shifts: partnership changes (later-life “gray divorce,” remarriage, and stepfamilies) that can reduce spousal caregiving, and adult-child trends such as more stepchildren, greater geographic distance, rising childlessness, and increased discussion of family estrangement. Focus-group findings suggest caregiving decisions are complex even after abuse, with adult children still often willing but setting firmer boundaries; care networks can be resilient, with friends and extended family stepping in. The conversation also covers disparities by race/ethnicity, growing support—especially among under-65s—for government help, strains on the “missing middle,” rising activity limitations and unmet needs among ages 65–74, and recommendations to support caregivers via policies (e.g., tax credits) and to plan medically, financially, and for future care preferences.
Topics
01:37 Why Families Provide Care
02:29 Gray Divorce and Partners
03:31 Adult Children and Distance
04:56 Gender and Social Networks
05:46 Family Estrangement Realities
08:38 Paid Care and the Missing Middle
11:37 Work, Aging, and Sandwich Generation
14:01 Future Trends and Unmet Needs
16:31 Mobility Limits and Modern Jobs
17:53 Race, Kinlessness, and Co-Residence
20:27 Government Support vs Family Duty
24:08 Policy Fixes for Caregivers
25:20 Plan Ahead for Aging
27:07 Closing Thoughts
2 Oct 2026
Ray Madoff on How Tax Policy Lets Wealth Escape Taxation
Harry interviews Boston College law professor Ray Madoff about her book, The Second Estate, arguing the U.S. tax system shifted over the past 40 years to tax wages effectively while letting investment gains and inherited wealth largely escape taxation. She explains how post-1982 stock buybacks increased untaxed appreciation, how gains can be avoided through borrowing and the step-up in basis at death, and how capital gains face lower rates than wages. Madoff says the estate tax functions as political “cover” because loopholes have proliferated since 1990 after a “death tax” campaign, yielding only $28 billion despite $55 trillion held by the richest 1%. She proposes taxing capital gains at transfer or death (as in Canada), ending income-tax exclusions for large inheritances and gifts, and removing tax subsidies for political giving via 501(c)(4)s, while noting wealth taxes face valuation and constitutional issues.
Topics
01:49 How Taxes Were Designed
02:59 Wages vs Wealth Shift
03:57 Stock Buybacks Explained
06:28 Borrowing and Step Up
08:00 Capital Gains Rate Gap
09:02 Estate Tax Quiet Quitting
13:24 Debt and Deficits Pressure
14:22 Dark Money Tax Subsidy
16:21 Fixing Income and Inheritance
20:37 Why Wealth Taxes Struggle
22:51 Valuation and Enforcement
24:42 Traction and Strange Allies
26:28 Public Misconceptions to Watch
28:58 Wrap Up and Book Plug
8 Sept 2026
Nicole Jorwic on Caregiving’s Funding Crisis
Harry interviews Nicole Jorwic, Chief Program Officer at Caring Across Generations, about the challenges facing unpaid family caregivers and the paid direct care workforce. Jorwic explains that unpaid caregivers contribute about $1.1 trillion annually, while the largely female, heavily immigrant direct care workforce faces low wages, limited benefits, and unstable jobs—creating a system where care is both underpaid and unaffordable. She argues Medicaid funds over 70% of direct care wages and warns that the nearly trillion-dollar Medicaid cuts in the One Big Beautiful Bill Act, including work requirements, will increase red tape, strain state systems, reduce provider rates, and worsen waiting lists and caregiver burden. The conversation covers strengthening wages and career pipelines, adding a home care benefit to Medicare (“Medicare at Home”), making Medicaid home- and community-based services mandatory, and exploring payroll-tax models like WA Cares. Jorwic urges families—especially baby boomers—to start planning conversations and highlights CareConversations.com.
Topics
02:00 Who Provides Care
02:43 Caregiver Challenges
04:44 Medicaid Funding Squeeze
06:03 Congress Cuts Fallout
08:45 Work Requirements Red Tape
13:30 Strengthening Care Jobs
15:33 Supporting Family Caregivers
18:29 Paying Family Caregivers
20:15 Credits and Tax Relief
22:07 Future Workforce Crunch
24:15 Fixing the Cost Paradox
26:25 Three Leg Policy Plan
28:37 Public Support and Hope
31:00 Top Policy Priority
32:36 Start Care Conversations
Who has been a guest on Risking Old Age in America
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Catherine Buell
Joe Seldner
Howard Gleckman
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