Am I A Stoic? AI Says…meh

This entry is part 29 of 60 in the series Journey Through Stoicism

I get some “Prompt-A-Day” emails. One asked for a 10-question Enneagram quiz. I’m fascinated by these personality tests, though I dislike taking them. This time, instead of answering it myself, I fed the prompt into Claude, an AI system, and answered the quiz it created. What followed was more interesting than I expected.

The analysis suggested I’m an Enneagram Type 7, “The Enthusiast.” Energetic, future-focused, quick to act, and sometimes scattered under stress. It also noted I may lean on a Type 6 wing, which adds loyalty and a concern about what others think. Claude then connected this to Stoicism and told me I had some Stoic tendencies—but also some traits that make the Stoic life harder.
That led to a deeper exchange about the practices I’ve been turning to during hard times. When asked which practice mattered most, I answered quickly: memento mori. For me, remembering death isn’t just philosophy. I grew up in the funeral industry, worked in it during the early days of the AIDS epidemic, and cared for friends in their final days. Those experiences taught me more about life than death—and made Stoic practice feel like coming home.

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Expecting Trouble-Premeditatio Malorum

This entry is part 27 of 60 in the series Journey Through Stoicism

Trouble will come. That is not a threat. It is the world as it is. Premeditatio malorum is simple training for a steady heart. Picture what could go wrong. Picture your first response. Keep it short. Keep it concrete. You cannot script life. You can be ready to meet it. Then even hard days make room for small good things. A call from a friend. Light on the trees at dusk. Thanks for what remains.

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Embracing the Unforeseen

This entry is part 26 of 60 in the series Journey Through Stoicism

So I’ll drive north. I’ll carry with me a fortune cookie scrap of paper that turned out wiser than I expected. And I’ll try to remember that philosophy is not about lofty words on a page. It’s about how you hold yourself when the phone rings at 3 a.m., how you respond when plans dissolve, how you see both the bitter and the sweet.

Marcus and Seneca remind us: surprises are not intruders. They are part of the order of things. To embrace them is to live in step with nature itself.

And maybe that is the real fortune. Not that life will protect us from pain, but that it will give us endless chances to practice courage, patience, and love.

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Memento Mori: A Practice for the Living

This entry is part 25 of 60 in the series Journey Through Stoicism
This entry is part 16 of 18 in the series Stoicism Practices

We don’t know how much gas is left in the tank. That truth, far from morbid, can be a guide to living with gratitude, courage, and clarity.

Memento Mori is the Stoic reminder that life is finite. For me, it has meant fewer grudges, more calls to friends, and a better sense of when to set work aside. It has reminded me that my “last great days” may already have happened, or they may still be ahead—but I will only recognize them if I am paying attention.

This is not about fearing death. It is about remembering life. When we keep the end in view, even quietly, the days we have become more precious and more alive.

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Stoic Practices: The Dichotomy of Control

This entry is part 17 of 18 in the series Stoicism Practices
This entry is part 24 of 60 in the series Journey Through Stoicism

The Dichotomy of Control teaches that some things are up to us and some are not. My own health journey and a job loss taught me that lesson in very different ways. Both proved the same point: act fully where you can, and accept what you cannot change.

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Rising from the Defeat That Wasn’t

This entry is part 19 of 60 in the series Journey Through Stoicism

Sometimes the worst defeats are the ones you didn’t cause but still feel responsible for. A job ends. A friendship slips away. You tell yourself it wasn’t your fault, but that doesn’t stop the questions. Maya Angelou once wrote that defeat might be necessary—not because we deserve it, but because it reveals who we really are. This essay reflects on regret and unexpected renewal through the lens of Stoic thought and lived experience. What you rise from, it turns out, may be the truest part of you.

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Boone, Facebook, and Marcus Aurelius…Oh My

This entry is part 18 of 60 in the series Journey Through Stoicism

I came across a meme that read, “There are two places you need to go often: The place that heals you. The place that inspires you.” It struck me deeply, because for me, one of those places is Boone, North Carolina, where I went to college. But as I reflected on that idea through the lens of Stoic philosophy, I realized the Stoics might offer a very different kind of guidance: to go inward. This essay explores the contrast, and surprising harmony, between modern healing and ancient inner retreat.

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A Way Out of No Way: John Lewis and the Moral Will

This entry is part 17 of 60 in the series Journey Through Stoicism

“Lewis did not need a theory of justice. He lived one.”
Five years after the death of Congressman John Lewis, his words and witness still call us to the hard, necessary work of moral courage. Drawing from Christian theology, the Black church, and the discipline of nonviolence, Lewis embodied a philosophy of action that mirrors the core of Stoic thought—and resonates just as deeply with the teachings of Judaism, Islam, and Buddhism. He did not merely protest injustice. He met it with clarity, hope, and a soul unshaken by cruelty. His legacy extends beyond American history. It is human wisdom.

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Amor Fati: Love What Happens

This entry is part 15 of 60 in the series Journey Through Stoicism

In a time of political unrest, personal uncertainty, and social fracture, the ancient Stoic idea of Amor Fati — to love one’s fate — offers a powerful challenge. Not to surrender to injustice, but to meet it with clarity, courage, and compassion. This essay reflects on the tension between acceptance and action, drawing on Marcus Aurelius, the Serenity Prayer, and a timely conversation with Rev. Justin LaRosa to explore how we can live fully and faithfully in the world we have, not just the one we wish for.

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The Silence Between Us

This entry is part 14 of 60 in the series Journey Through Stoicism

This piece began with a line from Carl Jung I read, which surfaced something I hadn’t yet put into words: “Loneliness does not come from having no people around you, but from being unable to communicate the things that seem important to you.”  Based on my reading in Stoicism, it seemed to fit with the thoughts of some of the Stoics. I’ve been thinking about what it means to remain engaged, to keep doing meaningful work, and still feel a growing distance from close friendships. This is a quiet reflection on that kind of loneliness, not isolation exactly, but a thinning of connection. A longing for the kind of relationships where nothing important has to be explained.

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Willing or Dragged: Cleanthes, Fate, and the Way of Alignment

This entry is part 12 of 60 in the series Journey Through Stoicism

What if freedom isn’t about control, but about cooperation with the deeper order of things? Inspired by Cleanthes’ timeless Stoic insight, this essay explores how fate doesn’t force us—it invites us. Whether guided or dragged, the choice is ours.

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