The Long View Podcast
Episode: Harry Margolis: How to Confront Aging Challenges Head-On
Air Date: April 14, 2026
Hosts: Christine Benz, Amy C. Arnott (Morningstar)
Guest: Harry Margolis, Elder Law Attorney and Author
Episode Overview
In this rich and practical episode, elder law attorney Harry Margolis joins Christine Benz and Amy Arnott to discuss the unique legal, financial, and lifestyle challenges faced by aging individuals and their families. Margolis draws from decades of experience working with seniors and those with special needs, offering nuanced guidance on estate planning, the complexities of aging in place, long-term care funding, family dynamics, special needs planning, and much more. The conversation emphasizes the importance of realistic, proactive planning and candid family communication to ensure security and dignity as life's later stages approach.
Key Discussion Points and Insights
Harry Margolis' Path to Elder Law
[02:04 – 03:35]
- Margolis entered elder law “very much by chance” during a pro bono stint at Greater Boston Elderly Legal Services, drawn by the opportunity to help real, middle-class people, as opposed to “larger law firm” clients.
“It seemed more like why I went to law school than working again for a larger law firm...” – Harry Margolis [02:43]
- His career has been notably entrepreneurial, launching publications, websites, and now spending more time writing and podcasting about the coming elder care crisis.
Unique Aspects of Estate Planning for Aging Clients
[04:42 – 05:56]
- Older clients’ planning is more focused on incapacity and long-term care needs, in addition to traditional estate planning.
“All these become more pressing the older you get...” – Harry Margolis [04:57]
- Discussion of Medicaid planning and the unpredictability of long-term care expenses.
The Advisor's Role: Conversations Many Clients Avoid
[05:56 – 07:12]
- Advisors should raise the possibility of incapacity, who will manage affairs, and contingency plans for long-term care costs.
- The need for “contingency plans,” as many are financially stable "as long as they don’t have a crisis."
“...if all of a sudden they’re having to pay for round the clock care, this financial plan that was working doesn’t work anymore.” – Harry Margolis [06:52]
Realistically Planning for Long-Term Care
[07:12 – 08:56]
- Need for care is “somewhat random” on an individual level. Factors like family history, living situation, geography, and available support play a role.
- Margolis urges reconsidering whether aging in place is realistic; sometimes alternative housing can mean greater safety and cost effectiveness.
Complexities of Aging in Place
[08:56 – 10:40]
- People often underestimate non-financial complexities (e.g., home upkeep, hiring/managing caregivers).
- Hiring help is complicated by minimum shift requirements, tax issues, and liability.
“Houses, I think, are beginning to fall apart as soon as they’re built.” – Harry Margolis [09:32]
- Oversight often falls on adult children, adding stress.
Continuing Care Retirement Communities (CCRCs)
[10:40 – 12:13]
- CCRCs can offer tremendous value—good service, community, peace of mind for families—but require thorough due diligence.
“You really need to kick the tires and make sure it’s a community that’s been around for a while...” – Harry Margolis [11:32]
The Importance of Midlife Planning
[12:13 – 13:39]
- Greatest regret is delaying relocation. Age 75 is optimal for reassessing living situations and planning for the future.
“You’re also probably still healthy. So you’re able to make a move...” – Harry Margolis [12:45]
- Moving proactively offers more choices and less disruption later.
Navigating Family Disagreement About Aging in Place
[13:39 – 15:02]
- Ultimately, the individual’s choice prevails.
- Need for “clear-eyed” contingency planning—unexpected events may abruptly limit options.
- Some facilities (e.g., CCRCs) require admission while still healthy.
Misconceptions About Medicare & Long-Term Care
[15:02 – 16:12]
- Major misconception: Medicare will cover long-term care.
“Medicare is really a health insurance program... But beyond that, you’re on your own.” – Harry Margolis [15:34]
Estate Planning Documents: Gaps and Maintenance
[16:12 – 18:00]
- Durable Power of Attorney (POA) is often missing or outdated; financial institutions may not accept “stale” documents.
“I think every five years or so review and renew your durable power of attorney...” – Harry Margolis [17:16]
- Each institution may require their own POA form.
Review Schedule for Estate Documents
[18:34 – 19:59]
- Frequency increases with age/life changes (e.g., marriage, divorce, grandchildren).
- Younger individuals: every 10–20 years may suffice; more frequently after significant life events or beyond age 60.
DIY Estate Planning: Pros and Cons
[19:59 – 21:51]
- Quality of online forms is high, but most people don’t complete them due to stuck points (e.g., naming executors or guardians, tricky questions).
“People find it hard to get the answers that they want that can help move them forward. And that’s the issue where you probably need a lawyer to really make it happen....” – Harry Margolis [21:18]
- DIY can work for straightforward, lower-wealth situations—but better than having nothing.
Mistakes in Naming Powers of Attorney and Healthcare Proxies
[22:20 – 23:09]
- Don’t name multiple people who may disagree.
“If you do name two, which…is fine. Make sure they get along and can work together, because if they don’t, then you may as well not have appointed anybody…” – Harry Margolis [22:51]
- Some states (like Massachusetts) allow only one healthcare proxy for this reason.
Addressing Family Conflicts Around Estate Roles
[23:09 – 23:57]
- Transparency is key to minimize family suspicion and resentment.
“If you explain it, and it’s clearly your choice, people may grumble...but they have to accept it.” – Harry Margolis [23:39]
Living Wills and Dementia/Alzheimer’s Provisions
[23:57 – 25:17]
- Margolis’ practice focuses on medical care in living wills; broader directives may address dementia care.
- Special instructions about spending and care often included in trusts for clients without children.
Aging Solo: The Professional Helper Dilemma
[25:17 – 27:39]
- Growing group of “solo agers” without family to name as agents.
- Hardest role is healthcare proxy, as professionals are usually unwilling to take on; organizing mutual support (friendship circles) or using nonprofit resources may help.
Talking to Parents About Care and Finances
[27:59 – 29:27]
- These conversations are difficult—Margolis suggests age 75 as a reasonable benchmark for initiating them.
- Sometimes parents simply don’t want to be a burden and may welcome the discussion.
Warning Signs for Elder Financial Incapacity
[29:27 – 30:12]
- Warning signs: missed bills, double payments, falling for scams, confusion with online tasks, or changes in financial behavior.
Dividing Caregiving Among Siblings
[30:12 – 32:03]
- Responsibilities often fall on the closest or oldest daughter.
- Communication and organization are essential; remote siblings can assist financially, with taxes, or provide respite care.
- Avoid silent overburdening—discuss roles openly.
Mistakes Adult Children Make Assisting Parents
[32:03 – 32:45]
- Failing to get a “full picture” of parents’ finances and future costs.
- Importance of holistic planning and involving financial professionals.
New Approaches in Senior Housing
[32:45 – 35:01]
- Naturally Occurring Retirement Communities (NORCs), middle-market co-housing (e.g., Opus in Newton, MA), and community volunteer models are emerging.
- In-building health agencies offer flexible help and cost savings.
Special Needs Planning
[35:01 – 41:17]
- Key issue is housing and transition planning for adult children with special needs as parents age.
- Special needs trusts: protect eligibility for government benefits and provide for ongoing needs.
- If parent-funded (third-party), no Medicaid payback required.
- If funded by the individual (self-settled), Medicaid payback applies.
- Margolis notes importance of life insurance as trust funding for younger families.
- Siblings may overcommit to caregiving out of affection but struggle later; outside facilitators can help families discuss realistic roles.
- Proactive housing placement relieves much burden from siblings.
Notable Quotes & Memorable Moments
- “I think everyone wants to age in place and stay home. But...as they get older, have to really consider whether that’s the best plan.” – Harry Margolis [07:49]
- “Houses are beginning to fall apart as soon as they’re built.” – Harry Margolis [09:32]
- “Probably the biggest [misconception] is that Medicare will take care of everything...Medicare is really a health insurance program... beyond that, you’re on your own.” – Harry Margolis [15:15]
- “Every five years or so review and renew your durable power of attorney—just make sure it's fresh and not stale.” – Harry Margolis [17:17]
- “If you do name two [POAs], which I think in most cases is fine. Make sure they get along and can work together, because if they don’t...it won’t work.” – Harry Margolis [22:51]
- “Transparency is key...if you explain it, and it’s clearly your choice, people may grumble...but they have to accept it.” – Harry Margolis [23:39]
- “We should kind of key in on 75 as the time to do it...” (for family conversations and transitions) – Harry Margolis [28:23]
- “[With special needs siblings,] people love their sibling and they want to take care of them...but it's a challenge and lives are very busy...they're not required to step in like that...” – Harry Margolis [39:12]
Timestamps for Critical Segments
- Harry Margolis’ Backstory & Mission: [02:04 – 03:35]
- Estate Planning for Older Adults vs. Younger: [04:42 – 05:56]
- Advisor Roles & Difficult Conversations: [05:56 – 07:12]
- Planning for Long-Term Care Needs: [07:12 – 10:40]
- Aging in Place vs. Moving: [08:56 – 13:39]
- Misconceptions About Medicare: [15:02 – 16:12]
- POA 'Staleness', When to Review Docs: [16:12 – 19:59]
- DIY vs. Professional Estate Planning: [19:59 – 21:51]
- Naming Agents and Avoiding Family Conflict: [22:20 – 23:57]
- Living Wills & Alzheimer's Provisions: [23:57 – 25:17]
- Solo Aging and Professional Agents: [25:17 – 27:39]
- When and How to Talk to Parents: [27:59 – 29:27]
- Financial Warning Signs in Older Adults: [29:27 – 30:12]
- Sibling Roles in Caregiving: [30:12 – 32:03]
- Mistakes Adult Children Make: [32:03 – 32:45]
- Innovative Housing Options: [32:45 – 35:01]
- Special Needs Planning & Trusts: [35:01 – 41:17]
Conclusion
Harry Margolis offers invaluable insights into the practical and emotional complexities of aging, emphasizing early, realistic planning and open communication as the keys to managing elder care crises, estate planning, family harmony, and quality of life. The episode provides both professionals and families with actionable ideas and compassionate perspective—making it an essential listen for anyone facing the challenges and opportunities of aging.