The Executor Dilemma
A Boy Scout’s Guide to Late-life Logistics
In my previous essay, I found myself reflecting on the subject of time. Writing it left me thinking much more seriously about how much of it I may have left. At my age — I’m now in my 79th year — existential angst is to be expected. Many friends and colleagues are now gone, while those of us still here seem increasingly occupied with managing one physical malady or another.
Ah yes, the maladies. They arrive in clusters at this stage of life, don’t they? For example, my walking regimen, once integral to both my physical and mental health, has become disturbingly limited. Chronic nerve pain from spinal stenosis now restricts my mobility, and more recently I have added compression stockings to my wardrobe to deal with peripheral edema. It really is no secret that a senior-citizen’s body is a full-time maintenance project.
Now, as it happens, I was a Boy Scout in my youth, and the motto drilled into every Scout was simple: Be Prepared.
Robert Baden-Powell, the founder of Scouting, did not mean that only in the sense of carrying the right gear on a camping trip. He meant it as a way of approaching life itself. Think ahead. Get things in order before the moment arrives.
So. Let’s get real. It definitely is time for me to get serious about preparing for my Final Exit.
The pandemic, of course, had previously served to sharpen this realization. In 2020 I was well into the category of people considered highly vulnerable to COVID. Although we did not know the precise statistics at the time, we now know that people over 65 accounted for the vast majority of deaths from the disease. I behaved cautiously and, for whatever reason, never contracted the virus.
However, during that unsettling time, I did make a few modest strides toward “getting my affairs in order.” Ever since then, a white 9×12 envelope labeled “Important Stuff” has been attached to my refrigerator door, quietly waiting to be needed. Inside it are my Advance Directive, which I prepared back in 2014 (upon retirement), along with some basic information about my finances and where funds should be directed upon my death.
Of course, one rather obvious detail remained unresolved. Who exactly would carry out these wishes? I never actually completed a Will.
Not that I didn’t try. I went to the FreeWill website and started working through the prompts. Everything went smoothly until I reached the section asking me to name an Executor. Who would that be? I do not have a spouse or significant other, and most of my relatives live far away. Asking friends to take on the administrative burden of settling someone’s affairs felt like a rather large favor to request.
So the process stalled.
But I have just recently discovered that there are professionals who can perform this role. Licensed Professional Fiduciaries can serve as a Personal Representative, handling the various financial, legal, and logistical details that follow a person’s death. In cases like mine, where the estate is modest, the process may even be handled through a Simple Estate Affidavit rather than a lengthy probate proceeding.
I am still learning about how all of this works, of course, but I have already contacted a local firm that provides fiduciary services and requested an initial consultation.
None of this is especially dramatic; it is simply the quiet work of tidying up important details. It’s the kind of effort that is easy to postpone because the moment requiring it always seems far away. Yet eventually the time arrives. Deep down, we all know that.
And so I find myself returning to bits of advice first learned long ago in the Boy Scout Handbook. The lessons were about life. And now death.
Be prepared.
Soundtrack Suggestion
I’m not scared of dying
And I don't really care
If it’s peace you find in dying
Well, then let the time be near
If it’s peace you find in dying
And if dying time is near
Just bundle up my coffin cause
It’s cold way down there
I hear that's it’s cold way down there
Yeah, crazy cold way down there
(“And When I Die”— Laura Nyro; Blood, Sweat & Tears)
Meditations on Time
Here I am, at age 78, seemingly surrounded by stories about time. These stories naturally have a way of turning my thoughts toward how short my own time may be.
I just reread a novel in which every adult on the planet receives a box containing a string that reveals exactly how long they will live. And I’m recalling the television comedy about a moral accounting system that tracks a person’s life here on Earth. Finally, there’s the recent film that imagines we get to choose the precise form our eternity will take.
I did not set out to braid these snippets of our popular culture together. They braided themselves. At this age, time insists on being the subject.
The reminders are constant. Obituary columns, for one. My personal calendar, for another, which now includes far more medical appointments than it once did. Routine blood work. MRI, CT and DEXA scans. Follow-ups, with each visit carrying the distinct possibility that this will be the one where the doctor pauses too long before speaking. Most of the time the news is ordinary. “See you in six months.” But the suspense never quite disappears.
In Nikki Erlick’s 2022 novel The Measure, a mid-life character suggests that a string long enough to reach age eighty would count as good news. When I read that passage, I felt a small jolt. Eighty no longer feels like a distant horizon. It is a number that is uncomfortably close.
If I opened my box today, I would automatically have a long string. The real question would be: how much longer? A year? Five years? Ten? More? Though If I died today, surely no one would lament that I was gone before my time.
All of which leads to other concerns. How many more years would I want if they are shadowed by increasing pain — or other physical or mental decline? Longevity, at this stage, is not automatically the goal. There are conditions.
The Good Place, the four-season television series originally airing on NBC (and now available on Peacock), begins with a moral scoring system; every human action or interaction earns positive or negative points. An endless array of cosmic accountants supposedly keeps track of these tallies someplace up there in the sky, and when you die your final count decides your destiny. It is morality, and judgment day, rendered as a dispassionate spreadsheet.
At 78, that premise feels less like satire and more like a quiet audit. I find myself reviewing my own ledger. Have I been good? Not necessarily accomplished. Nor productive. But good?
My entries must be mixed. I have lived and loved imperfectly. I have hurt people I did not intend to hurt. There are relationships that did not endure. Some ended gently. Others did not. Even now there is sadness attached to those chapters, a sense that certain conversations might have gone differently if I had been wiser, braver or simply more skilled.
I sometimes wonder whether those endings count against me, or whether they merely show that I kept trying to connect and sometimes failed.
The show ultimately dismantles its point system, though. Life, it suggests, is far too entangled for simple math. Growth matters more than totals; it matters more than being flawless.
What lingers for me now is the series’ ending. Even paradise becomes hollow if it stretches on forever. In the final season, the characters are offered an exit. They step through one last door when they feel complete. Eternity with no ending, the show suggests, flattens meaning.
So, I wonder: How, ultimately, will I measure my existence? Will there ever be a time when will I feel complete?
Those questions followed me into the 2025 film Eternity, now on Apple TV, where humanity is invited to choose the form one’s forever will take. The idea sounds appealing at first. Pick your paradise. A tropical beach, for example. Perfect weather. Endless calm.
But what would that mean after a thousand years? Ten thousand? How could any single scene, no matter how beautiful, sustain significance without limit? Without scarcity?
Part of what makes a late-life conversation more vivid is precisely that it may not be repeated endlessly. Scarcity is what gives weight to life’s ordinary moments.
If I knew the precise length of my string, maybe I would live differently. I might rush to repair what remains frayed. Or I might grow cautious, conserving energy. Uncertainty leaves me in between. Aware of the limit, but not of its measure. Isn’t it that uncertainty that keeps life from becoming either frantic or complacent?
If there is a ledger somewhere, I hope it records effort. That it shows I kept revising myself. That I tried to mend what I could. That I did not stop growing simply because the horizon drew closer.
I am not eager to open the box. And I am not certain I want a tropical eternity with no horizon. I only know that the ticking is audible now. Doctor visits. Quiet evenings. Old relationships to ponder. Meditations on time.
Age 78. Still adding to the ledger.
Poetry Selection: The Summer Day
Who made the world?
Who made the swan, and the black bear?
Who made the grasshopper?
This grasshopper, I mean —
the one who has flung herself out of the grass,
the one who is eating sugar out of my hand,
who is moving her jaws back and forth instead of up and down —
who is gazing around with her enormous and complicated eyes.
Now she lifts her pale forearms and thoroughly washes her face.
Now she snaps her wings open, and floats away.
I don't know exactly what a prayer is.
I do know how to pay attention, how to fall down
into the grass, how to kneel down in the grass,
how to be idle and blessed, how to stroll through the fields,
which is what I have been doing all day.
Tell me, what else should I have done?
Doesn't everything die at last, and too soon?
Tell me, what is it you plan to do
with your one wild and precious life?
-Mary Oliver
Sardines in the Back Bar: My High School Reunion
I graduated from high school in 1965, right in the middle of that turbulent, unforgettable decade. Last month, I made the cross-country trek from Eugene, Oregon to Rice Lake, Wisconsin for my 60-year reunion.
Traveling to rural northern Wisconsin isn’t easy. These days, I take two days just to get there. This time I flew to Minneapolis via Seattle, rented a car, and drove to a nearby hotel in the dark. Car rentals, of course, come with their own set of challenges. I drive a 2020 Subaru Crosstrek at home, so when I found myself behind the wheel of a 2025 Nissan Rogue, I had to pause in the airport lot, dig out the 600-page manual, and acquaint myself with the vehicle’s basics. Eventually, I made it to the airport Holiday Inn Express, tired but in one piece.
Day two was the drive to Rice Lake. I stopped in Menomonie to see my friend “BA,” a classmate I’ve known since I was 12. We’ve been in steady contact — often over Zoom during and since the pandemic — so our conversation flowed easily, even if it wasn’t about anything in particular. Politics and religion are off-limits between us, so our chatter resembled a Seinfeld-style “conversation about nothing.” Still, it was grounding to reconnect before the busy weekend ahead.
On day three, I had breakfast with another classmate, “CJ.” We first reconnected at our 40th reunion and in recent times have grown a bit closer through regular Zoom calls. Our conversations are different from most — personal, probing, unafraid of difficult topics like family dynamics, belonging, and the choices that shaped our lives. Sitting across from her in person gave those exchanges a richness I rarely find elsewhere.
That evening was the first group gathering at a local pizza place. I had gone in with low expectations, and still, the chaotic setup surprised me: thirty or so people crammed into the back corner of a bar with no clear plan for how to mingle or sit together. Consequently, BA and I retreated to a booth for dinner before cautiously rejoining the group once the crowd thinned. To my relief, I found a few familiar faces and even received a warm hug from a female classmate who had been reading my writings over the years. Those small moments of recognition helped balance out the initial frustration.
The next morning, BA and I met again for breakfast, this time joined by “WJ.” Our conversation took a surprising turn when, at one point, he asked, “Do you believe in vaccines?” The question startled me, but to my relief, all three of us agreed. Still, it was a reminder of the cultural divide I often feel when I return to Rice Lake — a blue-leaning visitor navigating a visit to a deeply red part of the country.
Saturday night was the main event at Lehman’s Supper Club, the classic Rice Lake venue for special occasions. Drinks started at five, but I stuck with ginger ale while classmates sipped their cocktails. I chatted briefly with a few people, but the connections felt fleeting. Dinner was buffet-style, serviceable but unremarkable, and I found myself at a table where conversation was scarce. By 7:30, much of the room had emptied out.
There was no program to speak of, aside from WJ’s attempt to spark discussion about future reunions. He floated the idea of meeting every year at Lehman’s. To me, that seemed unrealistic, for how many of us in our late seventies are going to make an annual pilgrimage back to Rice Lake? Still, he made an effort to keep something alive.
The highlight of the night was another chance to talk with CJ, this time in the middle of the busy dining room. While classmates milled about, we found ourselves absorbed in yet another meaningful exchange, the kind that lingers long after the event ends.
Looking back, I left the weekend with mixed feelings. Unlike past reunions where unexpected conversations left me energized, this one felt quieter, thinner, as if the spark had dimmed. Most classmates seemed eager to head home early, and true reconnections were rare. Was it me? Or was it simply the reality of our age, our numbers dwindling, and our capacity for long evenings fading? I honestly don’t know.
One regret lingers: I could have picked up my phone and taken photos. As an old event photographer, I had the skills and opportunity to document the gathering and share it on our class Facebook page. Instead, I sat passively, missing a chance to contribute. That realization stings.
And yet, in the end, the reunion gave me what I’ve come to value most in these years — small moments of closeness with a few old friends. A booth dinner with BA. A searching breakfast with CJ. Even an awkward question from WJ that revealed common ground. Perhaps that’s what reunions are really about: not the big group photos, or the banquet meals, but the quiet exchanges that tend to remind us who we were, and who we’ve now become.
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I have written essays about three previous class reunions, and here they are:
40th reunion: The Class of 65
45th reunion: Social Media & Whatever Happened to the Class of 65
50th reunion: Not As Young As I Once Was
Ten Before Thirty
I just finished reading Ten Before Thirty, the debut novel by Yana Kazan, a work that was recommended to me recently by friends. I was informed that Kazan is the pen name of a former professional colleague and that the novel is autobiographical in nature; of course I was intrigued.
Ten Before Thirty can most appropriately be described as a coming-of-age story. The protagonist is Annie Zechman who we first meet at the age of ten as she mystically encounters her long-dead great-grandmother Flora. Flora warns her that there are ten “really bad” things coming at her and that Annie has the choice of experiencing them early in life - or later. Annie chooses “early,” namely before the age of thirty. Hence the title of the book.
One of the earliest, really bad things to happen is the sudden death of her father at the age of 52. As the narrative unfolds, we learn, in quite some detail, about several of the other traumatic events she encounters; when tallied up they are undoubtedly more than ten in number. We find out, for example, that as a young child, Annie was molested by her grandfather. And early on, Annie’s single-parent mother finds a man, marries, and moves the family to Dallas, Texas. It is the early Sixties and as Annie is finishing high school, President Kennedy is assassinated nearby during her senior year.
We then follow Annie through her undergraduate years at a women’s college in Missouri and to grad school in Wisconsin. And yes, the “really bad” things keep coming. Annie has very few friends during these early years, and her choice of emotionally-unavailable men along the way almost certainly works against her best interest. The list of traumas includes (but is not limited to): the loss of a love; date and stranger rape; being hit by a car; nearly being kidnapped; and being strip-searched in jail. It is an eye-opening account of a somewhat naïve and vulnerable female as she attempts to navigate the rather hostile world of the turbulent Sixties and Seventies.
By the time the book ends, we know that Annie has had a number of therapists to help her along the way, that she has successfully completed her bachelor’s and master’s degrees, and has embarked on the path to a Ph.D. program in educational administration. Of course, life goes on, and nothing protects any of us from the natural and inevitable traumas of being human, but perhaps we can trust that Annie has the tools and life experience to successfully navigate future “really bad” things.
Given the historical references in the text, it is not difficult to discern the actual timeline. The period in which this story takes place corresponds almost precisely with my life. If I’ve calculated correctly, I am one year younger than Annie; I was a junior in high school when JFK was assassinated, for example. To the extent that the story is autobiographical, I now know much more about “Annie’s” early years than she knows of mine. I found the book wonderfully-written, skillfully-edited and highly-compelling. My vote: an enthusiastic thumbs up.
Soundtrack Suggestion
Tin soldiers and Nixon coming
We’re finally on our own
This summer I hear the drumming
Four dead in Ohio
Gotta get down to it, soldiers are cutting us down
Should have been gone long ago
What if you knew her and found her dead on the ground
How can you run when you know?
(“Ohio” – Neil Young – Crosby, Stills, Nash & Young)
Birthday Blackmail
So, here I am, age 70. My birthday was two days ago. As some of you may recall, in my 20s I was skeptical that I would ever live past 30. Ah, well, I have never been so wrong!
This essay is simply a little record about the 24-hour-run-up to my birthday. I really do love it when being alive is so darn fun. (And, yes, we live in very interesting times, but this report has nothing to do with a rich, orange-colored bigot who is bent on destroying our democracy.)
On the morning of August 16, I awoke to a rather unusual junk email. It was addressed to one of my legitimate, widely-known email addresses (in fact, the one associated with this blog). The author purported to be writing from Germany and was issuing a blackmail threat. He (I suppose it’s a “he”) said I had 24 hours to come up with $290 in bitcoin and deposit it in his account (a bitcoin wallet address was given). He claimed that a keystroke-logging program had been deposited on my machine, and that he knew a lot about me. So, if I did not forward the funds, the consequences would be an email message to everyone in my contacts (and everyone I was connected to via social media) containing embarrassing video of me recorded with my MacBook Pro camera. So, two things you should know: (1) my computer’s camera has been completely covered up for at least the last couple years; and (2) if you see a suspicious email from/about me, you might think twice about clicking on whatever link is provided. On the other hand, who knows how interesting it may be! (Yes, you guessed it: I have not paid him.)
