“My mother is trying to sell her home, but she is having difficulty understanding the process. She has never had trouble managing her financial life before. How can I help her?”

At Donohue, O’Connell and Riley, we hear questions like this every day. As estate planning and elder law attorneys serving families across the Northeast, we see firsthand how cognitive decline can quietly shift the landscape of a family’s life.

Disability induced by cognitive dysfunction remains one of the most significant challenges we face as we age—either for ourselves or as caregivers for those we love. While modern medicine allows us to live longer, that longevity increases the prevalence of conditions like dementia, Alzheimer’s, Parkinson’s, and stroke. In fact, an estimated two-thirds of Americans will experience some level of cognitive impairment in their lifetime, with an average onset age of 70.

Understanding the “Staircase” of Decline

Cognitive impairment often affects memory, focus, reasoning, or decision -making. Unlike a smooth slope, the onset of impairment frequently resembles a staircase. An individual may experience a sudden loss in function, followed by a plateau where things seem stable for a time. Then, another “step down” occurs, followed by another plateau. Because this progression is so common, recognizing the signs early allows you to take proactive steps to ensure the next phase of life is handled with security and dignity.

Phase 1: The Medical Action Plan

The first step is always medical. Research continues to yield promising advances in treating age-related diseases, and early intervention is key. A comprehensive checkup with a physician can provide valuable insight into potential causes of decline and help establish a treatment plan. Modern pharmaceuticals may slow the onset of cognitive impairment, buying precious time for families to plan.

Moreover, recent medical studies indicate that several negative lifestyle factors can contribute to the development of impairment. Focus on “brain-healthy” habits such as:

• • Physical Activity: Regular walking or swimming to improve blood flow.

  • Social Engagement: Combating isolation through community groups or family gatherings.

  • Dietary Choices: Prioritizing heart-healthy diets like the Mediterranean or MIND diet.

  • Sleep Hygiene: Addressing sleep apnea or chronic insomnia  which can mimic or worsen cognitive symptoms.
    
    

Phase 2: Protecting Your Finances

Now that a medical action plan is in place, the next step is strategic financial planning. Thoughtful asset management ensures the safety of a compromised person’s financial life while preserving their dignity. Managing a mortgage, utilities, credit cards, and medical bills can quickly become overwhelming for someone experiencing decline, and the added stress of investment decisions only complicates matters. Additionally, those with cognitive decline are prime targets for scammers.

Check out our article, 8 Strategies to Avoid Senior Scammers, to learn how to safeguard your family’s finances. 

There may come a time when a person experiencing cognitive decline should no longer have direct access to their primary finances. Prior to this time, bank and investment accounts should be consolidated. While a financial power of attorney will be able to access accounts and sign contracts, finances should ideally be consolidated under a trust with a trusted loved one serving as trustee. To help the individual maintain a sense of autonomy, we often recommend giving them access to a separate bank account with a small balance and a debit card for daily personal spending.

Phase 3: Adapting Living Arrangements

As one ages and loses physical or mental function, the proper living arrangement becomes a dynamic consideration. As losses in function become apparent, we must consider when extra care is necessary—whether a home health aide is sufficient or if more substantial care is required. It is also the time to have the difficult conversation regarding when it is no longer safe for the individual to maintain a driver’s license.

As we move through the aging process, the appropriate living situation will inevitably change. Household items that were previously innocuous can become hazards, such as a gas range or a sunken living room. Home modifications can make the environment more accessible and safer. It is wise to assess the home for risks such as stairs, tools, loose pavers, and driveway cracks. Additionally, hiring help for cleaning, snow removal, and yard maintenance can keep the home in livable condition while easing the burden on family members.

Check out our comprehensive Guide to Aging in Place and tips for welcoming a senior family member into your home.

In addition to home modifications, a home health aide may increase the time one can age in place. If resources and local zoning codes allow, building an Accessory Dwelling Unit (an “ADU”) on a younger family member’s property is a great option. These units can be attached to the primary dwelling or detached as a separate structure, allowing an aging relative to stay close for ease of care while maintaining privacy for everyone involved.

Phase 4: The Legal Foundation

Even though legal steps may seem ancillary compared to medical or financial items, the legal framework is actually the foundation of your plan. You must have the capacity to communicate your wishes and sign documents, so meeting with an attorney is essential while you are healthy, or as soon as initial signs of decline become apparent.

A complete basic estate plan should contain a health care proxy (known as a durable power of attorney for healthcare in some states), a living will, a HIPAA release, and a durable general financial power of attorney. These “incapacity documents” are vital for lifetime planning. While a Last Will and Testament provides guidance for managing assets after death, these documents provide for the lifetime support of your health and finances. A trust is another excellent tool for lifetime management, allowing a trustee to manage assets seamlessly if you are no longer able to do so.

Want to know which path is right for your family? Read our guide: Will vs. Trust: Understanding the Difference.

Conclusion

We have worked with thousands of clients to make the transition to their golden years more manageable. Our popular Make Your Estate Easier to Manage worksheet has ten specific steps you can take proactively to organize your life.

Cognitive decline will affect most of us in some way, but medical advances and proper preparation continue to mitigate the difficulty of these transitions. With the right combination of medical care and legal planning, we can ensure that the trip down the cognitive staircase is safe, slow, and dignified.

Estate planning is one of the most important steps we can take to protect our families, preserve our assets, and ensure our wishes are carried out. Yet, many people delay the process or make simple mistakes that can create unnecessary stress and complications for their loved ones. Whether you're just starting your estate plan or reviewing existing documents, understanding these common pitfalls can help you make more informed decisions.

At its core, effective estate planning is about clarity, preparation, and communication. By taking a proactive approach, we can help ensure that your plan works exactly as intended—both during your lifetime and beyond.

 

Failing to Create an Estate Plan at All

One of the most common—and most costly—mistakes is simply not having an estate plan in place. Many people assume estate planning is only necessary for the wealthy or those nearing retirement, but the reality is that every adult can benefit from having at least a basic plan.

Without an estate plan, your assets will be distributed according to state laws, not your personal wishes. This can lead to outcomes that may not reflect your intentions, especially if you have a blended family, unmarried partner, or specific individuals you want to provide for.

• No control over asset distribution: The court decides who inherits your property.
• No designated decision-makers: Without powers of attorney, loved ones may need court approval to manage your affairs if you become incapacitated.
• Increased stress for your family: Loved ones may face delays, confusion, and added legal costs.

Even a simple estate plan—including a will, healthcare directives, and powers of attorney—can provide essential protection and peace of mind.

 

Not Updating Documents After Major Life Changes

Creating an estate plan is an important first step, but it shouldn’t be a one-time task. Life changes—and your estate plan should evolve along with it. Failing to update your documents after significant events can lead to outdated instructions that no longer reflect your current wishes or circumstances.

Some key life events that should trigger a review include:

• Marriage, divorce, or remarriage
• The birth or adoption of a child or grandchild
• The death or incapacity of a named beneficiary, executor, or agent
• Significant financial changes, such as buying property or receiving an inheritance

Outdated estate planning documents can result in unintended consequences, such as leaving assets to a former spouse or failing to include new family members. Regular reviews—typically every three to five years—help ensure your plan continues to reflect your goals and protect your loved ones.

 

Overlooking Beneficiary Designations and Asset Titling

Many people are surprised to learn that certain assets are not controlled by a will or trust. Accounts such as life insurance policies, retirement plans, and payable-on-death bank accounts pass directly to the named beneficiary—regardless of what your estate planning documents say.

This is where mistakes often happen. If beneficiary designations are outdated or inconsistent with your overall plan, your assets may go to unintended recipients. For example, a former spouse or an outdated beneficiary could still receive funds if those designations haven’t been updated.

We recommend regularly reviewing:

• Retirement accounts like IRAs and 401(k)s
• Life insurance policies
• Bank and investment accounts with designated beneficiaries
• Property ownership and titling

Ensuring these elements are aligned with your estate plan is essential for avoiding delays, confusion, and unintended outcomes.

Choosing the Wrong People for Key Roles

An estate plan relies heavily on the individuals you appoint to carry out your wishes. These roles—such as executor, trustee, and power of attorney—require responsibility, organization, and sound judgment.

Choosing someone based solely on family dynamics or convenience can create challenges down the road. The wrong choice may lead to delays, mismanagement, or even conflict among family members.

When selecting individuals for key roles, consider:

• Their ability to handle financial and legal responsibilities
• Their willingness to serve in the role
• Their ability to remain impartial and communicate effectively
• Their proximity and availability if needed

In some cases, it may make sense to appoint a neutral third party or professional to ensure the process is handled efficiently and fairly.

Not Communicating Your Plan With Loved Ones

Even the most well-crafted estate plan can fall short if no one knows it exists or understands your intentions. Lack of communication is one of the leading causes of confusion and disputes during estate administration.

While you don’t need to share every detail, having open conversations with key individuals can make a meaningful difference. This includes letting your loved ones know:

• Where your important documents are stored
• Who you’ve chosen for key roles
• Any specific wishes or intentions that may not be obvious

Clear communication helps set expectations, reduces the likelihood of misunderstandings, and provides reassurance during an already difficult time.

Build a Plan That Works When It Matters Most

Avoiding common estate planning mistakes starts with taking a proactive and thoughtful approach. By creating a plan, keeping it up to date, aligning your accounts, choosing the right people, and communicating clearly, you can help ensure your wishes are honored and your loved ones are protected.

Estate planning doesn’t have to be overwhelming—but it does need to be done correctly. If you’re unsure whether your current plan is complete or up to date, we’re here to help guide you through the process with clarity and care. Contact Us to schedule a consultation and take the next step toward protecting your future and your family.

In meetings with thousands of clients, we hear people quoting advice that they grew up with decades ago, believing it is still valid in today’s world. Just because these sayings are common, doesn’t mean the advice is reliable. 

1. If It’s Not Broke, Don’t Fix It. 

As people transition into retirement and the later stages of life, they tend to be comfortable in their surroundings and at times don’t realize that things are in need of attention and investment. Instead of waiting until the everyday things you rely on to become outdated, deteriorate and ultimately stop functioning, proactively anticipating problems and dealing with them head-on is often the preferred approach.

For your primary home, are there any aspects that haven’t been updated for 20-30 years? Maybe the roof needs fixing before snow and ice cause damage next winter. Are there trees at risk of falling on the house or into the pool that you aren’t going to be using much anymore? If your heating system is 40 years old, maybe it’s time to upgrade to a more efficient HVAC system and benefit from the latest technology such as smart thermostats and mini splits.

Outside the home, be mindful of how you get around. Buying or leasing a new car can allow you to take advantage of modern safety features such as sensors, backup cameras and GPS navigation. All these elements will help to supplement faculties that start declining in our later years, such as peripheral vision and response time. Furthermore, having a vehicle that is covered under warranty can help avoid surprise repair bills. 

Since your retirement years will be different than the previous 20 years of life, both in terms of your lifestyle and finances, look at your home and cars and get projects checked off the list proactively, knowing that the costs will be significantly higher than they were 10-20 years ago. A project that may have cost $5,000 in the past could be a $15,000 job today - if you can even find a contractor! Getting projects tackled proactively is a worthwhile investment, and your future self will thank you for it.

2.Ignorance is Bliss.

This saying means that what you don’t know won’t hurt you, but in our experience that is rarely true. What you don’t know probably will hurt you. In our experience, a lot of people are overly dependent on “experts”. If someone is trying to sell you something that sounds too good to be true, it probably is. Be aware that some products are attached to very high commissions and fees that can be hidden, so you need to be aware of any underlying motivations for the advice upfront, instead of after the fact.

If financial concepts such as budgeting, cash flow projections, the sequence of returns and market volatility are new to you, it can be a steep learning curve to develop these skills later in life, but they are important for self-reliance. Taxes will likewise have a significant effect on your income and investments in retirement. Having a liquid source of funds will be essential, so you’re not forced to sell equity investments in an economic downturn.

In addition, the force of inflation is also quite real. We hear people complaining all the time that things have become more expensive, but on average, inflation runs about 2-3% per year, and you need to be planning for that. Something as simple as a 3% inflation rate cuts your spending power in half in about 20 years, so if you think you will be spending the same amount in 20 years as you do today, think again.

Investing in a broad-based portfolio that reflects the performance of the overall stock market, coupled with some conservative elements that can be relied upon during a downturn, means your portfolio can keep pace with the force of inflation over time.

3. Don’t Put All Your Eggs In One Basket.

In an attempt to follow this old adage and benefit from diversification, we often see clients open up multiple accounts with multiple institutions, but they are not quite sure how these accounts fit into an overall plan. Rather than being truly diversified, at times we find their investments are quite heavily concentrated in certain asset classes
and that clients may not understand what risks they are running.

Thus we recommend: 

• One checking account;

• One pre-tax retirement account (or add a Roth IRA if you can); and

• One post-tax investment account.

That’s it. Pool your savings with your after-tax investments. If you want to buy CDs at multiple banks, you can buy them through a broker, without opening 10 accounts at 10 banks across town. Having multiple accounts can also create a tax compliance nightmare for your beneficiaries as they try to gather 1099s from multiple accounts.

By simply multiplying accounts, you don’t make your life better or less risky. In fact, you make it more complicated and possibly more costly to administer your estate after you pass, or for someone else to pick up if something happens to you, so try to keep it simple and to understand what diversification really is.

No one has a crystal ball to predict where the stock market is going or what the best stock is going to be in the next year or 10 years from now, but we do know that the US stock market tends to return about 10% a year, and in an inflationary environment, that means you can spend about 5-6% a year without dipping in to your principal.

4. A Penny Saved Is A Penny Earned.

While no one can deny the benefits of frugality, sometimes you need to spend money to make money.

We often see clients chase coupons and believe saving is done through spending on sale items. They see a discount offer and feel proud of themselves for buying something to “get the deal”, but many times the purchase is something that they don’t need at all.

Other times, clients buy something in bulk, but the volume becomes a burden because they aren’t consuming at the rate they used to. This is especially true when people buy too much perishable food, which ends up spoiling in the fridge. Don’t chase these low dollar savings. 

Instead, think about quality over quantity and buying things that will last. Rather than buying something online that takes up space, such as another kitchen gadget that will only be used once or twice, or another duck decoy that just gathers dust, have a sense of mindfulness and intentionality about the cost, purpose and value of the item. Each time you purchase something, you also need to have a budget to maintain it, and a place to store it. These hidden costs are not advertised in sale fliers. Instead, consider purchasing an experience that creates lasting memories. You can keep the digital pictures as a visual reminder of a wonderful occasion or vacation with family and friends.

5. I Paid Cash For That.

Sometimes paying cash is great if you can afford to do so, but often times, it makes sense to take advantage of a low interest rate if your investments offer a higher rate of return.

Many people realize a higher rate of return on their investment portfolio than they would save by buying a car for cash. Some people avoid leasing a car, but that can be a wonderful option for an older person who doesn’t put a lot of miles on their car and doesn’t want to have the hassle of owning a car that suddenly goes out of warranty and needs a costly repair.

Instead of owning a vacation home, it may be cheaper to sell the property and use the earnings on the proceeds for short-term rental stays. This choice gives you flexibility and you don’t have to worry about the constant costs for maintenance, repairs, insurance and property taxes.

In summary, it is important to have a simple and rational approach to life in retirement. By following these five tips, you can spend more time enjoying your golden years and less time chasing paper and maintaining  an overly complex lifestyle that does not align with your long-term goals.

If you are struggling in one of more of these areas, one of our attorneys will be happy to bring you up to speed with our time-tested, streamlined approach. Here’s to a great New Year!

 

 

 

 

 

In our work with families, we often see a common theme: a vacation home that gradually becomes something more complex. What was once a simple retreat evolves into a shared responsibility—one that carries financial, legal, and emotional weight across generations.

That shift doesn’t happen all at once, and it’s rarely planned for as early as it should be. Families hold onto the idea that goodwill and shared history will be enough to carry things forward. Sometimes it is—but more often, without structure, even the most meaningful places can become sources of tension rather than connection.

To help guide these conversations, we’ve created our newest workbook: Strategic Stewardship of the Family Vacation Home.

This resource is designed to walk families through the realities of multi-generational ownership—from understanding the true cost of keeping a second home, to exploring legal structures like trusts and LLCs, to establishing clear governance around usage, expenses, and decision-making. It also addresses the less obvious, but equally important considerations: how to plan for conflict before it arises, how to create fair exit strategies, and how to preserve not just the property, but the relationships tied to it.

You can access the full workbook on our website or download it directly using the link below. Whether you are just beginning to think about the future of a family property or are already navigating shared ownership, this guide is meant to serve as a practical starting point for more informed, productive conversations.

In the end, successful stewardship isn’t about holding onto a home at all costs; but rather about making intentional, informed decisions that align with your family’s values—so that the place you’ve built together continues to bring people closer, not pull them apart.

DOWNLOAD WORKBOOK

In meetings with thousands of clients, we hear people quoting advice that they grew up with decades ago, believing it is still valid in today’s world. Just because these sayings are common, doesn’t mean the advice is reliable. 

1. If It’s Not Broke, Don’t Fix It. 

As people transition into retirement and the later stages of life, they tend to be comfortable in their surroundings and at times don’t realize that things are in need of attention and investment. Instead of waiting until the everyday things you rely on to become outdated, deteriorate and ultimately stop functioning, proactively anticipating problems and dealing with them head-on is often the preferred approach.

For your primary home, are there any aspects that haven’t been updated for 20-30 years? Maybe the roof needs fixing before snow and ice cause damage next winter. Are there trees at risk of falling on the house or into the pool that you aren’t going to be using much anymore? If your heating system is 40 years old, maybe it’s time to upgrade to a more efficient HVAC system and benefit from the latest technology such as smart thermostats and mini splits.

Outside the home, be mindful of how you get around. Buying or leasing a new car can allow you to take advantage of modern safety features such as sensors, backup cameras and GPS navigation. All these elements will help to supplement faculties that start declining in our later years, such as peripheral vision and response time. Furthermore, having a vehicle that is covered under warranty can help avoid surprise repair bills. 

Since your retirement years will be different than the previous 20 years of life, both in terms of your lifestyle and finances, look at your home and cars and get projects checked off the list proactively, knowing that the costs will be significantly higher than they were 10-20 years ago. A project that may have cost $5,000 in the past could be a $15,000 job today - if you can even find a contractor! Getting projects tackled proactively is a worthwhile investment, and your future self will thank you for it.

2.Ignorance is Bliss.

This saying means that what you don’t know won’t hurt you, but in our experience that is rarely true. What you don’t know probably will hurt you. In our experience, a lot of people are overly dependent on “experts”. If someone is trying to sell you something that sounds too good to be true, it probably is. Be aware that some products are attached to very high commissions and fees that can be hidden, so you need to be aware of any underlying motivations for the advice upfront, instead of after the fact.

If financial concepts such as budgeting, cash flow projections, the sequence of returns and market volatility are new to you, it can be a steep learning curve to develop these skills later in life, but they are important for self-reliance. Taxes will likewise have a significant effect on your income and investments in retirement. Having a liquid source of funds will be essential, so you’re not forced to sell equity investments in an economic downturn.

In addition, the force of inflation is also quite real. We hear people complaining all the time that things have become more expensive, but on average, inflation runs about 2-3% per year, and you need to be planning for that. Something as simple as a 3% inflation rate cuts your spending power in half in about 20 years, so if you think you will be spending the same amount in 20 years as you do today, think again.

Investing in a broad-based portfolio that reflects the performance of the overall stock market, coupled with some conservative elements that can be relied upon during a downturn, means your portfolio can keep pace with the force of inflation over time.

3. Don’t Put All Your Eggs In One Basket.

In an attempt to follow this old adage and benefit from diversification, we often see clients open up multiple accounts with multiple institutions, but they are not quite sure how these accounts fit into an overall plan. Rather than being truly diversified, at times we find their investments are quite heavily concentrated in certain asset classes
and that clients may not understand what risks they are running.

Thus we recommend: 

• One checking account;

• One pre-tax retirement account (or add a Roth IRA if you can); and

• One post-tax investment account.

That’s it. Pool your savings with your after-tax investments. If you want to buy CDs at multiple banks, you can buy them through a broker, without opening 10 accounts at 10 banks across town. Having multiple accounts can also create a tax compliance nightmare for your beneficiaries as they try to gather 1099s from multiple accounts.

By simply multiplying accounts, you don’t make your life better or less risky. In fact, you make it more complicated and possibly more costly to administer your estate after you pass, or for someone else to pick up if something happens to you, so try to keep it simple and to understand what diversification really is.

No one has a crystal ball to predict where the stock market is going or what the best stock is going to be in the next year or 10 years from now, but we do know that the US stock market tends to return about 10% a year, and in an inflationary environment, that means you can spend about 5-6% a year without dipping in to your principal.

4. A Penny Saved Is A Penny Earned.

While no one can deny the benefits of frugality, sometimes you need to spend money to make money.

We often see clients chase coupons and believe saving is done through spending on sale items. They see a discount offer and feel proud of themselves for buying something to “get the deal”, but many times the purchase is something that they don’t need at all.

Other times, clients buy something in bulk, but the volume becomes a burden because they aren’t consuming at the rate they used to. This is especially true when people buy too much perishable food, which ends up spoiling in the fridge. Don’t chase these low dollar savings. 

Instead, think about quality over quantity and buying things that will last. Rather than buying something online that takes up space, such as another kitchen gadget that will only be used once or twice, or another duck decoy that just gathers dust, have a sense of mindfulness and intentionality about the cost, purpose and value of the item. Each time you purchase something, you also need to have a budget to maintain it, and a place to store it. These hidden costs are not advertised in sale fliers. Instead, consider purchasing an experience that creates lasting memories. You can keep the digital pictures as a visual reminder of a wonderful occasion or vacation with family and friends.

5. I Paid Cash For That.

Sometimes paying cash is great if you can afford to do so, but often times, it makes sense to take advantage of a low interest rate if your investments offer a higher rate of return.

Many people realize a higher rate of return on their investment portfolio than they would save by buying a car for cash. Some people avoid leasing a car, but that can be a wonderful option for an older person who doesn’t put a lot of miles on their car and doesn’t want to have the hassle of owning a car that suddenly goes out of warranty and needs a costly repair.

Instead of owning a vacation home, it may be cheaper to sell the property and use the earnings on the proceeds for short-term rental stays. This choice gives you flexibility and you don’t have to worry about the constant costs for maintenance, repairs, insurance and property taxes.

In summary, it is important to have a simple and rational approach to life in retirement. By following these five tips, you can spend more time enjoying your golden years and less time chasing paper and maintaining  an overly complex lifestyle that does not align with your long-term goals.

If you are struggling in one of more of these areas, one of our attorneys will be happy to bring you up to speed with our time-tested, streamlined approach. Here’s to a great New Year!