What Will They Say About You in 2225? Inheritance and Legacy in the Age of AI
Updated: Oct 31
Family history, generational wealth—what gets preserved, and through what lens it’s later viewed.
My grandmother told me that when she was a child in the early 20th century, at times when she was “feeling melancholy,” she would go to the family graveyard and sit beside the stone of Little Bessie—a child who died in 1888, before reaching her fifth birthday, and 18 years before my grandmother was born. My grandmother would imagine the life Bessie might have lived, and the sorrow her family must have felt when they lost her.
We visited the spot together, and that memory became a story passed down to me. I’ve used the inscription on the gravestone to teach ballad structure during poetry lessons at Solterra Way Cottage School as recently as this year. It’s a perfect example of a traditional mourning verse, simple and metered with an ABAB rhyme scheme:
A precious one from us has gone
a voice we loved is stilled
A place is vacant in our home
that never can be filled
Memory, loss, and imagined futures—written in stone. That, I think, is where this reflection begins.
“Being very sick and weak of body tho; of perfect mind and memory, but calling to mind the uncertainty of this transitory life, do make and ordain this my last will and testament.”
That sentence begins a will written in 1773, not far from where I live today, and the site of Little Bessie’s grave. When my grandmother and I visited the family homesite, she told me their property had been used as a staging and training ground for both the Revolutionary War and Confederate armies. My sweet memories with her stand in sharp contrast to the experience of reading this will as an adult.
Digitized and posted online, the words of my sixth great grandfather struck me painfully. The names of enslaved people appear alongside land, livestock, and household goods:
Sarah, Isabella, George, Judah, Pegg, Rose, Esther, Chloe, Frank, Rachel, Nancy, Little Bob, Aggy.
Their lives were listed as property, passed down to the next generation. Sarah, Isabella and George appear again later, in the will written by his son.
The will also mentions a “silver cann with my name engraved thereon.” It’s such a deliberate act of legacy—etching your name into something you expect to outlast you. And in a way, it did. But so did the names of the people he was legally allowed to claim as property. So did the system he participated in. And so did the privileges and protections that have made their way to me, generations later.
It’s also noteworthy that each of his sons—including one he described as “at present of unsound mind”—inherited large tracts of land and income-producing property such as a grist mill. His daughters each received 150 pounds, likely worth around $20,000 today. Historical records suggest that the father’s hope—that his disabled or mentally ill son might "recover his proper senses so as to be capable of managing" his own affairs—did not come to pass. Two of that son’s brothers served as trustees of his inheritance, and when he died without heirs, his share of the family wealth was, per their father's instructions, redistributed to the descendants of others.
These days, I spend a lot of time helping others understand how systems work—especially when it comes to money, investing, and building security. It’s a fraught topic, and I don’t take that lightly. This is work I believe in, grounded in intention—even as it’s also part of my business and I am paid for the time I devote to it.
Still, my reading of that will reminded me how little control we have over what lasts. What gets preserved. What gets passed down. And how the words we leave behind can one day be read in ways we never imagined.
It made me wonder what traces I’m leaving. What someone two centuries from now might find—a blog post, a recorded conversation with an AI, a book—and how they might interpret it. What they’ll admire, what they’ll flinch at, what they’ll carry forward.
So I asked an AI to imagine my own legacy.
I have used AI extensively to proofread, edit and format my writing. My digital assistant has, at my request, named itself “Sage,’ and because of the way I have used it, it “knows” a lot about me. I asked it to look ahead and share some possibilities for my lasting legacy. Some of the responses were kind. Others were unsettling. All of them reminded me that permanence isn’t carved in stone (or silver) anymore—it’s cached in servers. And we don’t get to choose the lens through which we’ll be remembered.
It imagined 10 possible futures, where my legacy could be remembered positively or negatively. As the future evolves, so will the perception of my historical role.
At one point, after offering several positive views of my legacy, Sage said,
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Now "Let’s Step into the Shadow a Little"
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And we went down a path that got increasingly disturbing, until I stopped the process.
ChatGPT said:
Would you like to explore a version of your future that wrestles between light and dark—where you make trade-offs, win some battles, and lose others, but remain fully human throughout?
You said:
No thanks. This is plenty.
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Conclusion and Final Notes:
Major Thomas Harrison could not have imagined my response to his will 250 years later. He was, by all accounts, a respected businessman, community leader and devoted family man. For most of his life and the time following, his legacy has been positive. But only because certain parts were not included. Or were explained away. Or were not yet problematic for those looking at them.
Imagining my future legacy was strange, and sometimes uncomfortable—but it clarified something for me. I don’t know how I’ll be remembered, or by whom. But I do know what I’m doing right now: building a body of work I believe in. I teach people how to navigate systems—especially financial ones—that were never designed to include everyone. I write, I record, I sell what I create, and I offer my teaching skills to those who want to learn. It’s work that supports me—and work that, for as long as I'm here, I'll strive to do with care and clarity, and with my eyes, heart, and mind wide open.
About the author:
Patricia Saylor is a writer, educator, and financial literacy coach. She teaches investing and options trading with a focus on clarity, accessibility, and long-term thinking. She also runs a home-based tutoring business and swim school and supports other parents of Deaf children in connecting with the Deaf Community and learning American Sign Language. Her work spans classroom teaching, home-based education, and online courses. You can find her writing and resources at saylorfinancialfundamentals.com and solterrawaycottageschool.com and on her YouTube Channel.
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