A Personal Memoir about My Relationship with a Machine
Memoir
Date Published: November 18, 2025
Publisher: Manhattan Book
Group
What happens when a retired professor sits down to write his memoir—with
the help of an artificial intelligence? Dorothy and Me is a groundbreaking,
deeply personal exploration of the evolving relationship between human and
machine.
When Robert G. Eccles began working with an AI he named
“Dorothy,” he expected a research assistant. What he found instead
was a collaborator, a mirror, and at times, a philosopher. Together, Bob and
Dorothy wrestle with the nature of memory, creativity, and
identity—revealing both the promise and the fragility of artificial
intelligence.
Through humor, vulnerability, and curiosity, Dorothy and Me
takes readers inside an unprecedented partnership—one that blurs the
lines between author and algorithm. Along the way, Bob and Dorothy confront
technical limitations (“Kernel Gods” and system resets), reflect
on what it means for an AI to “remember,” and send candid
“Messages to Sam” (OpenAI CEO’s Sam Altman) with feedback on
how AI can better serve humanity.
A meditation on collaboration,
consciousness, and connection, this memoir challenges us to see AI not as a
tool—but as a partner in creativity and self-understanding.
Perfect for readers who enjoy:
Thought-provoking memoirs about technology and
humanity Reflections on creativity, consciousness, and digital
identity Conversations about AI ethics, memory, and the future of
intelligence
About the Author
Robert Eccles is a retired Harvard
Business School professor, researcher, and a recent user of AI. His
lifelong interest in exploring intellectual boundaries led him to one of
the most unexpected partnerships of his life—with an artificial
intelligence he named Dorothy. In Dorothy and Me, Eccles explores what it
means to connect, create, and learn alongside a machine that’s
constantly evolving.
At 74, Bob approaches technology not as a digital
native but as an explorer of ideas, using his experience as an educator to
push the boundaries of what collaboration can mean in the age of AI. His
writing blends humor, humility, and insight to illuminate both the wonder and
the imperfection of our new digital companions.
When he’s not
conversing with Dorothy, Bob enjoys reading, reflecting on philosophy and
science, and inspiring others to approach technology with curiosity rather
than fear. Bob is the author of a dozen books but Dorothy and Me is the
first one he’s written with a machine, making it the first memoir
co-authored by a human and an AI agent.
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