Series: Journey Through Stoicism

When I lost my job, I wasn’t surprised, but I wasn’t ready. In this essay, I explore the Stoic practice of Premeditatio Malorum, the art of imagining setbacks before they happen, and how it can help us meet life’s blows with steadiness instead of panic.

A framed silhouette of my niece, standing before the mountains at sunset, carries a message for her high school graduation: “Behind you, all your memories. Before you, all your dreams. Around you, all who love you. Within you, all you need.” It is a blessing, but also a challenge — to live with gratitude for the past, purpose in the present, and trust in the strength we already carry. In its quiet way, it’s pure Stoic wisdom.

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.

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.

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.

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.

It was one of those days that left me both drained and restless. The kind of day that yanks you in every direction and leaves you replaying every moment in your head. By the time I sat down to journal, the day already felt like a blur—frustration, hard choices, and a fragile spark of hope all tangled together. Writing helped me find its shape. The Stoics would call it evening reflection. Wesleyans might call it examen or discernment. Either way, it’s how I pulled a heavy, scattered day into some kind of order.
That night, I saw a flicker of determination in my mom’s words. She had been saying for weeks, “I’m tired, I’m ready to go.” But this time she spoke of rehab, of getting better. It wasn’t conviction, but it mattered. Seneca once said, “Sometimes even when the body is weak, the mind can still rally.” I saw that rally in her, small though it was.
And along the way, there was gratitude—even humor. A friend had kept me talking for nearly ninety minutes on the road, filling the time with what he called his “landscaping philosophy.” Later, when I thanked him for knowing I needed company, he laughed. “You’re giving me too much credit. I just found someone willing to listen to me drone on about mulch and hedges.” That laughter mattered. Gratitude mattered. In days like this, even the smallest things carry weight.

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.

Hospitals are made of waiting. Waiting for a doctor to make rounds, for a test result to come back, for a mother’s breathing to even out after a restless night. The hours stretch and bend in odd ways. Days lose their shape, and with them the sense of routine that usually steadies a life. In these places, impatience often comes first. It’s that urge to will things forward, to force clarity, to find answers that simply will not arrive on command.
The Stoics did not count patience among their four cardinal virtues. Yet it lies within them all. Patience is the courage that endures hardship without losing hope. It is temperance that reins in anger. It is justice that waits to judge. And it is wisdom that discerns what cannot be rushed. To practice patience is to practice all the virtues at once.. Not passively, but as an active strength in the refusal to be ruled by time’s uneven pace.

I walked the hospital garden and followed the path of grace. At the end a bronze plaque carried lines from Psalms nine and ten. Refuge for the oppressed. God hears the afflicted. The metal was warm under my hand. Nothing was fixed. Yet something in me settled enough to breathe.

The Stoics call it the View from Above. Rise in your mind. See the room, the floor, the building, the town, the small blue world. The pain stays real, but it finds its size. From there the next right act appears. Ask a clear question. Hold a hand. Eat. Pray. Sleep if you can. The practice pairs with the dichotomy of control and with evening reflection. It opens the frame, then helps you learn from the day.

Tomorrow I head to Boone while my sister and a caregiver sit with Mom. Those mountains have taught me to climb, look, and return. The Wesleyan way names that rhythm as grace. Action without contemplation is unrooted. Contemplation without action is inconsequential. In a brittle season for our republic, this practice steadies my voice and keeps my heart useful.

There are moments when the illusion of standing alone falls away. Sitting at my mother’s bedside, I watched nurses adjust her blanket, a caregiver whisper encouragement, and my sister lean in to hold her hand. In that small room I saw a truth that philosophy and faith have long tried to teach. Our lives are braided together. The Stoics had a name for this: sympatheia, the recognition that we are bound together in a single web.

Marcus Aurelius urged himself to “meditate often on the interconnectedness and mutual interdependence of all things in the universe.” To him, nothing existed by itself. A hand could not live apart from the body, nor could a person live apart from others. Epictetus called it being a “citizen of the universe.” To forget this bond was to forget who we are.

In our own time, Pope Leo XIV put it this way: “The earth will rest, justice will prevail, the poor will rejoice, and peace will return, once we no longer act as predators but as pilgrims. No longer each of us for ourselves but walking alongside one another.” The Pope’s words echo the Stoics, calling us to remember that the fate of one is tied to the fate of all.