A Heavy Joy, or, Planning, Decluttering, and Dementia (2Q25 Wealthwise by WEIL)

June 15, 2025

Tyler Hewes, CFP®

My heart is heavy, and mine age grows on;

For sorrow ends not when it seemeth done. — Richard II

I’ll let you in on a secret: today is Mother’s Day, and writing this newsletter is making me profoundly sad, but I have hope that the end result will, ultimately, be of benefit to others. Let me give you some context as to how the personal and professional have collided in a way that has left me pensive. 

Earlier this spring, I traveled to Connecticut for an extended visit with my parents. Typically, my parents come to San Diego at least annually to visit me, but more importantly, to spend time with their grandchildren. This year, though, it was far easier for me to head east, in part to assist my father following cataract surgery, and to spend time with my mother, hopefully while she still knew who I was. My mother has been swiftly declining due to an accelerated dementia and aphasia.

My mother has been, or maybe I should say was, a classical choral musician, contractor, and conductor in New York City for the past five decades. She was instrumental, pun intended, in building choirs that brought the great works of Mozart, Bach, Beethoven, Glass, and countless other composers to vivid life; she built choirs like a painter: using the hues and shades of each voice blended in harmony and counterpoint, unity and diversity to give the music life. She had that most rare of musical gifts, perfect pitch, and would describe sound in the most fascinating ways (when a tone or phrase was just right, she would call it “sexy”...much to her teenage son’s horror). She performed all over the world, fought for the rights of artists by negotiating contracts for the American Guild of Musical Artists, and was the person people called when they needed a choir pulled together at the drop of a hat, including organizing musicians to perform at Yankee Stadium just days after the September 11th attacks. She voiced a villager (the redheaded woman who asks the butcher, “How is your wife?”), Spoons, Knives, Forks, and various flatware in Disney’s Beauty and the Beast, put together and sang in a choir that marked the entrance of The Undertaker in the WWE, and was one of the most rabid fans of her alma mater, the University of Michigan, you ever did see. My mother believed that speed limits were more suggestions than hard-and-fast rules, and it is my firm belief that she missed her real calling in life as a Formula 1 driver (she could make it from our home to midtown Manhattan in a shockingly short amount of time).

My mother, who could sight-read the most complex music ever set down, now struggles to answer the simplest of questions: Are you thirsty? Do you want to eat? The woman who once brought audiences to tears with her voice can no longer reliably speak. And yet—

When I arrived home and entered the family room, she looked up at me with shock, surprise, and, miraculously, recognition. She squeezed my hand so tightly, conveying her love and fierce affection even though the words weren’t there. At that moment, it didn’t matter that she did not recall my name; she knew she loved me and was joyful that I was there. The look of overwhelming delight on her face is etched in my memory; a talisman I can clutch in moments of grief. It is, as a friend recently called it, a heavy joy.

Dementia is not a cliff but a slope — slow, uneven, treacherous. One day it's a forgotten word, another it's repeating a story, confusion about a year, names, faces, timelines. It can manifest as an erosion of impulse control, outbursts of anger or sadness, obstinacy or affability hiding a lack of comprehension. By the time there's a diagnosis (in my mother’s case, it started as a type of aphasia and a diminishment of impulse control), much ground has already been lost.

Dementia is primarily an age-related condition, and its prevalence increases sharply with age. Roughly 7 million Americans over the age of 65 are currently living with Alzheimer’s disease, the most common form of dementia. That number is projected to rise to nearly 13 million by 2050. A recent study in Nature Medicine estimated that the lifetime risk of developing some form of dementia after age 55 is a sobering 42%. As of 2021, Alzheimer's was the fifth-leading cause of death among individuals aged 65 and older. Notably, research suggests that women and Black Americans face a disproportionately higher risk of developing dementia. These statistics paint a clear picture of the escalating risk of dementia with advancing age, and that it will touch nearly every family.

The progression of cognitive decline associated with dementia not only impacts the emotional well-being of a family, but can also create substantial obstacles for managing financial and legal affairs. As memory loss, impaired judgment, and difficulties in decision-making become more pronounced, individuals may struggle to handle even basic financial tasks, necessitating a need for others to “take the wheel.” This need to hand off the management of financial matters can be made all the more complex should the family’s “financial manager” have a reduced capacity to understand and approve the actions to be taken on their behalf. Legal documents, including essential estate documents, powers of attorney, and medical directives, require an understanding of the nature and consequences of the decisions being made. This is one of the reasons we, as advisors, preach the importance of taking action early on estate planning and building a culture of financial transparency within the family unit. Documenting your wishes, arranging durable powers of attorney, advanced healthcare directives, and taking action to consolidate your finances are prudent moves to take before the unknown arrives. I say this as both a financial advisor and a son: you do not want to be caught unprepared should the insidiousness of dementia sneak into your life.

If you haven’t yet had these important conversations about your wishes, your documents, the location of your passwords and paperwork, start now. Not tomorrow. Not when the diagnosis comes. Now.

Adding to the complexities of addressing dementia is the often overwhelming task of managing the accumulated possessions of prior generations (including Greatest, Silent, and Baby Boomer generations). These generations frequently amassed lifetimes’ worth of belongings, including books, paperwork, keepsakes, and furniture spanning decades (or even centuries). The sheer volume of possessions can create a significant hurdle for their heirs, to whom falls the responsibility of decluttering and disposing of the accumulated effluvia of lifetimes. My own family is an example: after the passing of my grandparents, a great many of their possessions, including books, papers, and knick-knacks, were inherited by my parents. Despite both having passed almost 30 years ago, many of the possessions of my Greatest Generation grandparents still reside in my parents’ furnished basement. At some point in the (hopefully far) future, my sister, Cecily, and I will need to sort through and dispose of the amassed possessions of not just my Baby Boomer parents, but their parents as well. The process of sorting through over a century’s worth of accumulated, for lack of a better word, “stuff” is a daunting prospect.

With the specter of this decluttering in mind, I decided to assist Future-Tyler and Future-Cecily by acting in the here and now. In anticipation of my visit, my father rearranged my mother’s desk in the family room so I would have a place from which to work. (I am incredibly grateful to my WEIL-family for both pushing me to visit and making it possible for me to work from Connecticut for a time. The 2024 San Diego Business Journal win for Best Small Business to Work in San Diego was well earned.) It all began with a search for a pen; I opened the center drawer on her desk and saw dozens of pens. After attempting to use nine or ten pens in a row, finding each to be a dried-out husk, I decided that my planned purge would start with the desk. I tested each pen, marker, and pencil I found; any that still worked were set aside, along with unused notebooks, for my brother-in-law to take to work (he teaches at Bronx Science High School, where there are plenty of students who will make good use of the supplies). Following the Great Writing Tool Test of 2025, I began to declutter in earnest. Sitting at my mother’s desk—a repository of a professional life fully lived—I sorted decades of paper for disposal. Contracts for concerts long since passed. Birthday, Mother’s Day, Anniversary, and Christmas cards dating back half a century. Reviews. An incident report from 1974, when her purse was stolen, and the New York Public Library issued a new card. Details on union negotiations with the American Guild of Musical Artists. Handwritten notes about which singers to contract for Basically Bach at Lincoln Center. Old bank statements. Outdated headshots that were both glamorous and funny. I considered keeping some treasures, but only for a moment. I took a photo, then let them go.

I heard the clarion voice of Laura Sword, our Chief Compliance Officer, admonishing me to destroy anything with sensitive information on it, including all those contracts. I sat at my father’s shredder and was equally aghast and amused by my mother’s lack of data security. It was dusty, emotional work. But it was necessary.

I debated keeping one item in particular: the spiral-bound notebook she used for contracting. It had phone numbers, notes on the color of singers' voices, and seating arrangements for choirs based on the needs of various compositions. She’d written it all by hand in the early 1980s, and I remembered it so clearly from childhood, watching her dial numbers on a rotary phone, speaking with warmth and authority to singer after singer, putting together a choir for Handel’s Messiah or Mozart’s Requiem. That notebook, and all the ones that came after, were her Grail Diary, Rosetta Stone, and magnum opus all rolled into one. I was halfway towards putting it in my suitcase when I had a vision of my children opening a drawer in the future while cleaning out my desk and finding it sitting there. To them, it will be just another thing to sort and toss, lacking the context of meaning it had to me. So, I let it go, too. I will keep the memory.

I won’t bore you with the minutia of the rest of my decluttering journey, suffice it to say there is still a lot more to go. My father does yeoman's work taking care of my mom, but doesn’t have the time or energy needed to do it all by himself. I am grateful to my sister and brother-in-law, as they continue the work of letting go of lifetimes of stuff. I have come to realize that decluttering is an act of mercy, relieving the next generation of the burden of choice.

My father is a veteran of the Air Force (having served at Strategic Air Command, flying ready-alert supersonic nuclear bombers) and is a retired pilot for United Airlines; he knows what it is like to perform under pressure. Yet if you asked him what the most stressful thing he’s ever taken on, I think, if he were being honest, he would say it is watching the love of his life deteriorate while doing his best to take care of her. They started dating as 16-year-old kids attending Battle Creek Central High School. They called each other LOML (Love of my Life). He loved to hear her sing. She loved to watch him laugh, to see behind the mask of the debate team captain turned Air Force officer.

The guiding principle for the Wealthwise by WEIL newsletters is to provide actionable advice and recommendations. I fear that I may have “lost the plot” a little with this one, but know that it comes from a place of genuine care. I love my parents very much; it breaks my heart to see both my mother’s decline and the toll it exacts on my father. I say this as a son as much as an advisor: take action now to reduce the potential burden to both yourself and the next generation. Begin small, work collaboratively, and, if you can, start now.

Emptying the desk, clearing out boxes from the basement, and shredding documents was not about tidying up. It was, I hope, an act of love. A mitzvah. Since the goal is to provide you with actionable steps in your own mitzvah, here are some decluttering and downsizing recommendations: 

1.      Envision: Before you do anything, picture what you want to achieve. Let one question guide you through your work: Do I want my children/heirs to have to deal with this? If the answer is no, you have your decision. Having a clear end-goal will keep you motivated and give you parameters within which to work.

2.     Inventory: Walk through each room, closet, and storage area. Look at what is there (what is really there, even the things to which you have become blind as they blend into the background) and make a note of what is where.

3.     Prioritize: Decide which areas to address first. It may be the room you use the most, or the entryway closet that always makes you sigh. Starting with the high-visibility spots provides a sense of accomplishment and momentum.

4.     Gather Supplies: Get your boxes, trash bags, labels, and a good marker ready (I can recommend a highly effective Writing Implement testing method if you need one). Having everything at hand means you won’t have to stop and search, interrupting your momentum.

5.     One Space at a Time: Don’t try to do everything at once; it can be both overwhelming and paralyzing. Focus on one shelf, one drawer, one room at a time. Each small victory will compound over time.

6.     Paper: Sort through important documents, old paperwork, and anything that you have deemed valuable enough to file away. Shred anything you no longer need (especially anything with personal info) and digitize the rest.

7.     Wardrobe: Go through your clothes and be realistic about what you actually wear and what you enjoy. If you have some clothing that predates the Millennium, consider donating it and slimming down your closet.

8.     Digital Preservation: Do you have stacks of old photos, celluloid or VHS family movies, and/or slides in your Kodak Carousel? Scan them or have digital copies made. It will save space and allow you to easily share both the images and the stories behind them with your family.

9.     Sentimental Treasures: This can be the toughest part, but also the most rewarding. Consider gifting the treasures you’ve accumulated to your family and friends so you can watch them enjoy them in the here and now.

10.   Ask for Help: Make the process a participatory activity, involving your family/heirs. This will help avoid any surprises after you pass and allow you to share the stories of why the items in your life have had meaning. 

This process can be difficult but also rewarding. Take your time and do what feels right for you. You do not need to wait for a diagnosis or some external crisis to begin the work. I won’t lie, I did not particularly enjoy writing this newsletter, but it was needed. Too many carry the emotional weight of dementia alone and in silence.

If anything I have said resonates with you, please reach out to the WEIL team to chat. We are here not just to discuss the markets, IRAs, and Roth conversions, but also about love, legacy, and what we owe to each other and the generations that come after. We are here for you. We are here for your family.

Sincerely,

Tyler Hewes, CFP®

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