As the new year begins, Howard S. Krooks shares insights into one of the most challenging issues many families face: navigating the complexities of family caregiving and end-of-life financial planning. His perspective is informed by his personal experience managing the finances and long-term care needs of his mother, his professional background as an elder law and special needs planning attorney, and a series of interviews with Beth Pinsker, CFP, a financial planning columnist at MarketWatch.

Those interviews were conducted for Pinsker’s book, My Mother’s Money: A Guide to Financial Caregiving, published Nov. 4, 2025, by Crown Publishing Group. Krooks is featured in the book (click here to see the Cozen O’Connor news item with direct quotes), addressing the needs of older adults and the management of assets during life and after death.

Drawing on these experiences, Krooks developed a practical checklist designed to help families care for elderly loved ones. The checklist serves as a brief introduction to the most common obstacles that arise when a family member steps in to manage another’s financial affairs.

Lack of clarity and access

The first thing that becomes apparent when an elderly individual is no longer able to manage his/her own financial affairs, especially at the beginning, is the lack of clarity regarding the aging person’s finances and lack of access to the information needed to manage their finances and bill pay. There is no list of accounts, no passwords for digital accounts, and no clear delineation of bills that need to be paid (or when). There is little to no paperwork, or the paperwork is scattered, disorganized, or outdated. Online accounts with two-factor authentication tied to the loved one’s phone/email can prove difficult, if not impossible, to access. This becomes such a huge challenge for people because you’re expected to act responsibly before you actually have the information or authority to do so.

Solution – Sit down with your parent or loved one and let them know of your concerns. Offer to assist them in completing a Financial Planning Organizer document that lists all accounts, account numbers, where assets are held, physical branch locations, information regarding the financial advisor, accountant, and estate planning attorney, etc. Include password for digital accounts and assets. Of course, some of you will face resistance from the family member in revealing this otherwise confidential information – but it will make your job much easier if you can get past this.

Here are some ready-to-use scripts you can use or adapt to your preference/loved one, depending on the specific kind of resistance or tension you’re facing. These are designed to preserve dignity, reduce defensiveness, and keep the focus on support—not control.

Opening the Conversation (Before There’s a Crisis)

“Mom/Dad - I want to talk about something that’s been on my mind—not because anything is wrong right now, but because things are going well and I’ve seen how stressful it can be for families when no one knows where things are or what someone wants when it comes to financial management. I’d really like to understand how you’ve been handling things, so I can support you if you ever want or need help.”

When They Say “I don’t need help”

“I know you’ve handled your finances for a long time, and you’ve done a really good job. I’m not trying to take anything over. I’m asking so that if there’s ever a time when you don’t feel like dealing with something, I already know how things work.”

When They Say “I don’t trust banks/lawyers /the system”

“I get why you feel that way—there are a lot of confusing rules, and it’s not always clear who’s actually looking out for you. What I’m hoping is that we can put something simple in place now, so neither of us has to deal with the system in a rush later.”

Asking for Transparency (Accounts, Bills, Passwords)

“I’m not asking to log in or make changes. I just want to know what exists—what accounts you have, what bills come in, and what gets paid automatically—so if something unexpected happens, I’m not scrambling or guessing.”

You would add, if this would be helpful:

“We can even write it down and seal it in an envelope. This is about preparedness, not access.”

Introducing Power of Attorney (Without Triggering Alarm)

“A power of attorney doesn’t take away your control. It just means that if you ever want me to help—or if you’re temporarily unable to—it allows me to step in without court involvement. You’d still be in charge, and you can revoke it anytime.”

When They Feel You’re Taking Over

“I’m sorry if this feels like I’m stepping on your toes—that’s not what I want. You’re still the decision-maker. What I’m trying to do is handle the mechanics so you don’t have to spend your energy on paperwork and phone calls.”

Discussing Spending or Budget Concerns

“I’m not worried about any single purchase. I’m thinking longer-term—making sure your money supports the life you want, and that we don’t get forced into choices later because we didn’t plan ahead.”

When You Need to Say “No” (or “Not Right Now”)

“I hear that this is important to you, and I’m not dismissing that. Right now, though, this would put pressure on other things we’ve said matter—like staying at home/having help/peace of mind. Let’s talk about whether there’s another way to handle it.”

If They Get Emotional or Accuse You of Motives

“I’m not doing this for myself, and I’m not thinking about inheritance. I’m doing this because I care about you and I want to make sure you’re protected and comfortable. If this conversation feels like too much right now, we can pause and come back to it.”

Closing the Conversation (So It Ends Safely)

“Thank you for talking about this with me. I know it’s not easy. We don’t have to solve everything today. Even just starting the conversation helps, and we can take this one small step at a time.”

Legal authority gaps

As if the lack of clarity and access to information wasn’t enough of a hurdle, each individual approaches his/her elder law and estate planning very differently, and on his/her own timeline! This means you could be faced with having to make sense of another person’s finances, however disorganized they may be, with no Power of Attorney (POA), or one which is outdated or too limited. Without a broadly drafted POA (and preferably one drafted by an elder law/special needs planning attorney and not just a general estate planning attorney), you may find that financial institutions are refusing to speak with you. Even with a properly drafted POA, some financial institutions will refuse to speak with the agent under a POA. This forces you to do the work without proper legal standing, which slows everything down and creates risk that your loved one’s finances are not being properly managed.

And, although the focus of this article is on financial decision making for another, you will want to make sure that health care advance directives, such as a health care proxy, living will and HIPAA Authorization are similarly in place. In addition, if there is a need to manage a loved one’s Social Security benefits, then you may want to consider becoming a Representative Payee for your loved one’s retirement or disability benefits paid by the Social Security Administration.

Solution – Go to the bank (or send the POA to each and every financial institution where assets are held) with your loved one introducing you as their agent, and requesting the POA be kept on file should the need arise. Doing this while your loved one is healthy or even if of diminished capacity before s/he loses capacity will save many hours of frustration and delay.

Emotional and relational strain

When a loved one begins to lose independence, the responsibility of managing their finances often falls to a family caregiver, creating a complex emotional and relational strain. The caregiver may feel a heavy burden of responsibility, balancing the need to safeguard financial stability with a deep desire to honor the loved one’s autonomy. This can lead to feelings of guilt, stress, and even conflict within the family. Meanwhile, the loved one may experience frustration, fear, or resentment as financial decisions become a symbol of lost control. These emotions can erode trust and communication, making an already challenging situation even more difficult. Navigating this delicate balance requires empathy, transparency, and ongoing dialogue to preserve both financial security and family harmony.

Another component of the relational strain is created when you are caregiving and providing financial management assistance to a parent. When caregiving and managing a parent’s finances, the relationship often shifts into an unexpected role reversal. The adult child assumes responsibilities traditionally held by the parent, which can feel unsettling for both parties. For the caregiver, stepping into a position of authority may bring discomfort or guilt, while the parent may struggle with feelings of diminished autonomy and identity. This reversal can amplify emotional strain, as long-standing family roles and boundaries are redefined under the weight of necessity.

Guilt often surfaces when making decisions that limit a parent’s autonomy, even if those choices are necessary for safety or stability. Caregivers may question whether they are overstepping boundaries or failing to honor long-standing family values.

On the other side, resentment can build—both for the caregiver, who may feel burdened by constant responsibility, and for the parent, who may perceive the shift as a loss of control or independence.

Perhaps most pervasive is the fear of “getting it wrong.” Caregivers worry about making mistakes that could jeopardize financial security or family harmony. This fear can lead to decision paralysis, second-guessing, and heightened stress, especially when siblings or other relatives are involved. The pressure to “do the right thing” in an unfamiliar role often amplifies feelings of isolation and anxiety for the family caregiver.

All of this leads to one inescapable conclusion: money decisions are rarely just financial—they’re deeply tied to dignity, trust, and identity.

Solutions - Some practical strategies to help reduce emotional and relational strain when managing a loved one’s finances during a loss of independence requires paying attention to a variety of factors, including: 1) engaging in open and honest communication, 2) setting clear boundaries and rules, 3) involving neutral parties/professionals when necessary, 4) prioritizing autonomy where possible, and 5) planning ahead. I know – this is easier said than done. Here are several suggestions as to how you can achieve this:

• Schedule regular conversations about financial decisions with your loved one and family members (even if they’re difficult).
• Use empathetic language that acknowledges the loved one’s feelings of vulnerability and loss of control.
• Frame decisions as collaborative whenever possible, so your loved one and family members feel included rather than sidelined, even if you retain legal authority.
• Define who is responsible for which financial tasks to avoid confusion or conflict among family members.
• Document agreements in writing to prevent misunderstandings and maintain transparency.
• Consider engaging a financial advisor, elder law attorney, or care manager to provide objective guidance.
• Professional input can reduce tension and reassure the loved one that decisions are based on best practices, not personal bias.
• Allow the loved one to make smaller, non-critical financial choices to preserve dignity and independence.
• Use tools like joint accounts or spending limits to balance safety with autonomy.
• Discuss and document financial wishes early, before cognitive or physical decline accelerates.
• Create durable powers of attorney and advance directives to minimize future disputes.

Family conflict and suspicion

Managing a parent’s finances rarely happens in isolation. Even when one family member takes the lead, siblings or other relatives often have opinions—and sometimes strong objections—about how money is handled. This dynamic can introduce a new layer of tension, as financial decisions become a focal point for long-standing family dynamics, differing values, and even unresolved conflicts.

Caregivers may feel scrutinized or second-guessed, which can amplify stress and the fear of making mistakes. Relatives might question spending choices, investment strategies, or the fairness of resource allocation, especially if inheritance concerns linger in the background. These disputes can quickly shift from practical disagreements to emotional battles, fueled by perceptions of favoritism or mistrust.

Without clear communication and transparency, these situations risk fracturing family relationships at a time when unity is most needed. The caregiver may feel isolated and defensive, while others feel excluded or powerless, creating a cycle of resentment that overshadows the shared goal of supporting the parent. Even well-intentioned actions can be misinterpreted when money and caregiving overlap.

Solution – When multiple family members are involved in a parent’s care, financial decisions can quickly become a source of tension. Differing opinions, emotional attachments, and concerns about fairness often lead to conflict. To preserve family harmony and keep the focus on supporting your loved one, proactive strategies are essential.

Setting clear expectations early is crucial to success. Schedule a family meeting to outline the parent’s financial situation, caregiving needs, and your role in managing these responsibilities. Invite input on major decisions and establish shared goals—such as ensuring comfort and security—to keep everyone aligned.

Engage neutral professionals when needed. If disagreements escalate, consider bringing in an elder law attorney, financial advisor, or professional mediator. These experts provide objective guidance and help reduce emotional bias, reassuring relatives that decisions are based on best practices rather than personal preferences.

Document agreements in writing. Create a clear record of responsibilities and decision-making processes, including who manages day-to-day finances, how major expenses will be approved, and how transparency will be maintained. Written agreements prevent misunderstandings and serve as a reference point during disputes.

Maintain transparency throughout the process. Share regular updates with siblings and relatives, even if they’re not directly involved in daily management. Tools like shared spreadsheets or secure family portals can make communication easier and build trust.

Finally, anchor every discussion in the parent’s wishes. Refer to advance directives or previously expressed preferences to guide decisions. Keeping the parent’s values at the center helps reduce subjective conflict and reminds every one of the ultimate goal: preserving dignity and the quality of life of your loved one.

Complexity of the financial picture

Managing a parent’s finances often means stepping into a world of intricate financial matters and requires interaction with third parties. It’s rarely as simple as paying bills. Instead, you may find yourself juggling multiple income sources—such as Social Security, pensions, annuities, and IRA distributions—each with its own rules and timelines. Add to that the complexity of dealing with health and other insurance policies (life or disability), Medicare and Medicaid regulations, which require that you navigate a maze of eligibility requirements and coverage details, and long term care insurance, which requires understanding coverage terms and submitting an application to activate coverage at the appropriate time. Credit card management issues present additional concerns and responsibilities. Investment accounts will require establishing a relationship with your loved one’s financial advisor and monitoring of such accounts. Then there are tax issues and tax liability payment obligations and estate planning/legal documents, all of which demand careful attention to avoid costly mistakes. Beneficiary designations bring another set of concerns due to the spending of funds from such accounts that may ruffle the feathers of the named beneficiaries on such accounts.

Identifying expenses presents additional challenges along with establishing a systematic way of paying those expenses, which may include household expenses (mortgage payments, homeowner’s insurance, rent, property taxes, and utilities), caregiving expenses, and medical expenses (premiums, deductibles, and other out-of-pocket costs). Caregiving/aide expenses, and an often overlooked item, subscriptions. Finally, there is the matter of burial/funeral expenses that must be attended to.

Digital assets, accounts, and website access requirements will require special attention and may prove very challenging if your loved one does not already have this aspect of his/her financial life well-organized.

Why is this so hard? Because these obligations historically were being handled by your loved one in conjunction with financial and legal professionals, and not by you, the family caregiver. Suddenly, you’re expected to master assets owned, terminology, deadlines, and compliance/timeliness issues that can feel overwhelming, all while managing the emotional weight of caregiving. Oh, and by the way, you also need to keep all of the balls in the air regarding your own life, financial and otherwise!

Solution – Begin the process of organizing documents early. Create a centralized system for income statements, insurance policies, tax returns, and legal paperwork. Whether you use labeled folders or secure digital storage, accessibility is key. Maintain a checklist of recurring deadlines—such as tax filings and RMD dates—to avoid costly oversights.

Leverage professional help

Financial advisors and elder law attorneys can provide clarity on trusts, Medicaid eligibility, and tax planning. Their expertise not only prevents mistakes but also reduces stress by handling specialized tasks.

Use technology to your advantage

Financial management apps and secure online portals can simplify tracking accounts and automate bill payments. Shared digital tools allow multiple family members to stay informed without endless phone calls or emails.

Create a clear action plan

Break tasks into manageable steps. Start with income sources, then insurance, then taxes—and document who is responsible for each if others are involved. Finally, stay ahead of deadlines by setting reminders for key dates like tax filings and Medicare enrollment periods. Early action reduces last-minute stress and ensures compliance.

By combining organization, professional guidance, and technology, caregivers can transform a daunting financial landscape into a structured, manageable process—freeing up time and energy for what matters most: caring for their loved one. And, while you will want to get everything in order as soon as practicable, give yourself the time and space needed to accomplish everything required to feel on top of all these issues. Consider the incremental approach of moving the ball forward and develop a timeline for accomplishing each task required to put everything in good working order.

Time and bandwidth overload

Managing a loved one’s finances isn’t just about numbers—it’s about time. Caregivers often find themselves buried under a mountain of tasks: paying bills, tracking expenses, and handling endless paperwork. Add to that the frustration of long phone calls and hold times with banks, insurance companies, and government agencies, and the hours quickly disappear.

The real challenge? These responsibilities rarely exist in isolation. They pile on top of caregiving duties, work obligations, and family life, creating a relentless cycle of demands. What starts as a helpful role can easily become a second—or even third—unpaid job with no off-switch. The constant juggling leaves caregivers exhausted, stressed, and struggling to find balance.

Solution – Set up scheduled and automated payments and deposits to reduce manual tasks, such as bill pay and incoming funds. You can also delegate responsibilities among family members to share the load. Another time saver would be to group tasks for efficiency by scheduling dedicated time blocks for calls and paperwork, freeing yourself up to enjoy other aspects of your life. You can and should hire professional support for complex tasks, such as taxes or trust management. Finally, you will want to set boundaries to protect your time and, most of all, your mental health.

By combining automation, delegation, and professional help, caregivers can reclaim time and reduce stress—making it easier to focus on what truly matters: caring for their loved one and maintaining their own well-being.

Fear of personal liability

For many family caregivers, managing a loved one’s finances comes with an added layer of stress: the fear of personal liability. Every decision brings with it a component of “am I doing the right thing here?” and feels like higher stakes than managing one’s own money. There’s the constant worry about making a mistake, whether it’s mismanaging funds or overlooking a critical deadline. Anxiety often creeps in around mixing personal and parental funds or reimbursing yourself incorrectly—actions that could raise questions later. And then there’s the uncertainty about what’s allowed versus prohibited, especially when handling accounts, trusts, or government benefits.

Family caregivers find this challenging because the rules aren’t always clear, and the consequences can feel personal and severe. A simple error can lead to family conflict, financial penalties, or even legal complications. This fear can paralyze decision-making and add emotional strain to an already overwhelming role.

Solution – For many caregivers, these practical steps can help you to protect yourself and gain peace of mind.

Keeping detailed records of every transaction, from bill payments to reimbursements, and saving receipts, is a good start. A simple spreadsheet or ledger can make everything transparent and easier to share with family members. Whenever possible, use separate accounts for caregiving expenses to avoid confusion and prevent accidental commingling. If you need to reimburse yourself, do it through clear, documented transfers rather than informal withdrawals.

Make sure you have the right legal authority before making financial decisions. Documents like a Power of Attorney or guardianship papers not only protect you legally but also clarify your role for others. When in doubt, consult professionals—elder law attorneys and financial advisors can help you navigate complex rules around trusts, benefits, and reimbursements, reducing the chance of costly mistakes.

Transparency is key. Share financial summaries regularly with siblings or other stakeholders, and consider using secure online tools that allow family members to view transactions without giving them control. Finally, take time to learn the rules that apply to Social Security, Medicare or Medicaid, and trust management. Many states offer caregiver resources and legal guides that can help.

By combining clear documentation, legal safeguards, and professional support, you can manage finances confidently and focus on what truly matters: caring for your loved one without the constant fear of “getting it wrong.”

Changing capacity over time

One of the most challenging aspects of financial caregiving is the reality that a loved one’s capacity doesn’t change all at once—it shifts gradually, and sometimes unpredictably. Abilities may fluctuate from day to day or decline over time, making it difficult to know when to intervene more fully. Plans that once seemed solid can suddenly fall apart, forcing caregivers to revisit decisions they thought were settled. Each adjustment brings hard conversations about autonomy, safety, and trust—conversations no one wants to have, but everyone knows are necessary.

What makes this so difficult is the lack of clear indicators. There’s no definitive moment when the responsibility transfers; instead, you’re constantly recalibrating—financially and emotionally—while trying to honor your loved one’s dignity. It’s a delicate balancing act, requiring flexibility, empathy, and the courage to step in when circumstances demand it. What has worked until now may have to be pared back or require more assertiveness, and the new benchmark may work on some days and not others. Knowing when to pare back or become more assertive becomes as important as recognizing that you must.

Solution – How can caregivers navigate these transitions more smoothly? Begin by establishing clear triggers for intervention. These might include missed bill payments, confusion about account balances, or signs of cognitive decline. Agreeing on these markers early—ideally while your loved one can participate—helps reduce uncertainty and conflict later.

Open communication is essential. Revisit financial plans regularly and frame conversations around shared goals, such as safety and peace of mind, rather than control. Involve professionals when needed; elder law attorneys, financial advisors, and care managers can provide objective guidance and help mediate difficult decisions. Finally, document changes as they occur. Written records of changes, decline or inability to manage as well as agreements and delegation of responsibilities not only provide clarity but also protect relationships during emotionally charged moments.

By combining foresight, transparency, and professional support, caregivers can manage shifting capacity with confidence—preserving dignity while ensuring financial security through every stage of change.

Ethical dilemmas

Few aspects of financial caregiving are as fraught as the ethical dilemmas that arise along the way. These decisions rarely come with clear answers—only trade-offs that weigh heavily on both the caregiver and the family. One of the most common challenges is balancing your loved one’s quality of life against the need to preserve assets. Should funds be used to enhance comfort and experiences now, or conserved to ensure long-term security? Each choice carries emotional heaviness and financial consequences.

Then there’s the question of when to say “no” to spending requests. Declining a loved one’s wishes—whether for a discretionary purchase or a costly service—can feel harsh, even when it’s necessary to protect their future. Add to this the complexity of managing gifts, financial support to other family members, or charitable giving. These decisions often touch on deeply held values and family traditions, making them even more sensitive. Try telling a family member who has relied on economic support for years to live that this support can no longer be provided – it doesn’t bode well.

What makes these dilemmas so difficult is that there is rarely a single “right” answer. Every option involves compromise, and the stakes feel personal. Caregivers must navigate competing priorities—honoring a loved one’s autonomy, safeguarding resources, and maintaining fairness among family members—while carrying the emotional burden of choices that affect someone else’s life. It’s a delicate balancing act that demands not only financial judgment but empathy, transparency, and, often, the courage to make decisions that others may question.

Solution – How can caregivers approach these ethical dilemmas with confidence? Start by establishing guiding principles early. These might include prioritizing health and safety, preserving dignity, and aligning decisions with your loved one’s values. When possible, involve your loved one in discussions about spending priorities and charitable giving—doing so reinforces autonomy and reduces conflict later.

Transparency is critical. Share your reasoning with siblings or other stakeholders, and document decisions to avoid misunderstandings. For complex or contentious issues, consider consulting professionals such as elder law attorneys or financial advisors. Their objective perspective can help balance competing interests and ensure compliance with legal and fiduciary responsibilities.

Finally, accept that perfection is impossible. Ethical decisions in caregiving are rarely black and white; they require judgment, compassion, and flexibility. By leaning on clear principles, open communication, and expert guidance, caregivers can navigate these dilemmas with integrity—making choices that honor both financial prudence and the humanity that is at the heart of caregiving.

Lack of guidance and validation

One of the most overlooked challenges in financial caregiving is the absence of guidance and validation. Unlike a professional role with clear benchmarks and feedback, this responsibility comes with no roadmap. No one tells you what a “good job” you did or even looks like, and best practices are often vague or hard to find. As a result, caregivers frequently feel isolated, second-guessing every decision and wondering if they’re doing enough—or doing it right.

This lack of support makes an already demanding role even harder. You’re carrying enormous responsibility without reassurance, and navigating complex financial and emotional terrain with little external validation. This uncertainty can erode confidence and amplify stress, leaving caregivers feeling alone in a role that affects both family relationships and a loved one’s well-being. So, how can caregivers find the necessary guidance and support they need?

Solution – Connecting with caregiver networks is a great way to obtain guidance and validation, both online and in person. These communities offer shared experiences, practical advice, and emotional validation that can make the journey feel less isolating. Professional resources are equally important. Elder law attorneys, financial planners, and care managers can provide clarity on best practices and help you feel confident in your decisions.

Setting personal benchmarks can also reduce self-doubt. Define what success looks like for you and your loved one—whether it’s maintaining financial stability, honoring their values, or ensuring transparency with family members, or all of the above. Documenting your decisions and the reasoning behind them not only provides a sense of structure but also serves as a record in case questions arise later.

Finally, give yourself permission to seek reassurance. Caregiving is complex, and perfection is not the goal. By leaning on community, professional guidance, and clear personal standards, you can replace isolation with confidence and navigate this role with integrity and peace of mind.

Conclusion

Financial caregiving for an aging loved one is one of the most complex and emotionally charged responsibilities a family member can undertake. It demands far more than paying bills—it requires navigating shifting capacities, ethical dilemmas, family dynamics, and systems designed for professionals, all while managing your own time and emotional bandwidth. It’s no wonder so many caregivers feel overwhelmed, isolated, and uncertain.

Yet, as I have outlined in this article, these challenges are not insurmountable. By embracing the principles discussed—clear communication, meticulous organization, transparency, and the willingness to seek professional guidance—you can transform a daunting role into a manageable, even meaningful, experience. Setting boundaries, planning ahead, and anchoring decisions in your loved one’s values will help preserve dignity while ensuring financial security. Leaning on technology, community support, and expert advice will lighten the load and reduce risk.

There will never be a single “perfect” answer to every dilemma, but there is a path forward—one built on empathy, structure, and shared understanding. If you follow these strategies, you can navigate the financial and emotional complexities with confidence, protect family harmony, and focus on what truly matters: providing care that honors both your loved one’s well-being and your own peace of mind.