The Question That Stopped Me Cold
A colleague asked me this at a team offsite in Mahajanga, Madagascar, somewhere between the fish and Zebu skewers and coconut water. She was Malagasy of Mahafaly ethnicity and sharp, the kind of person who asks questions that feel casual but land like a scalpel.
“If you could have dinner with any philosopher, who would it be?”
I laughed. Bought time. Said something forgettable about Aristotle.
But on the drive back — twelve hours of open countryside, lush green vegetation, and vastness around me, the kind of emptiness you only really understand if you grew up on a small island where the sky at night is genuinely completely black — I kept turning the question over and over. Who would I choose? And more honestly: what would I actually want to talk about?
The answer I kept arriving at surprised me. Not Aristotle. It was not Kant, Nietzsche, or any of the heavy-hitters I had encountered in university. I’d choose Epictetus. A man who was born a slave, walked with a permanent limp from abuse his master inflicted, and still somehow built one of the most durable philosophies of human freedom ever written.
Why a Former Slave Has the Most Useful Advice for Professionals
Epictetus never wrote a single word himself. Everything we know about him comes through his student Arrian, who took notes and published them as the Discourses and the shorter Enchiridion — a word that simply means “handbook”. That framing matters. This wasn’t philosophy as performance. It was philosophy as a tool.
His central idea is disarmingly simple: divide your life into what is “up to you” and what is not. Your opinions, your impulses, your desires, your decisions — those are yours. Everything else — other people’s opinions, your job title, economic conditions, whether your pitch lands, whether your manager appreciates you — does not matter. Trying to control the second category while neglecting the first is, in his view, the root of almost all human suffering.
I’ve worked across three continents. I’ve watched talented people in Mumbai burn out chasing promotions that never came. I’ve seen colleagues in London paralysed by organisational restructuring they had no power to influence. I’ve sat in meetings in New York where the entire energy of a room was consumed by anxiety about things nobody in the room could actually change. Epictetus would have recognised all of it immediately. He’d seen the same patterns in Rome two thousand years ago.
What I’d Actually Ask Him Over Dinner
I’d want to order something unpretentious. Bread, olives, grilled fish — something close to what he might have eaten himself. And then I’d push him on the parts of his philosophy that still feel unresolved to me.
First, I’d ask about ambition.
His philosophy can sound, if you read it quickly, like an argument for passivity. Don’t want what you can’t control. Accept your circumstances. This reading bothers me. I grew up on an island so small that “going somewhere” was almost a literal requirement — the economy, the geography, and the sense of possibility all pointed outward. Ambition wasn’t a luxury. It was practical.
I’d want to know, is striving compatible with equanimity? Can you work hard toward a goal while also genuinely not minding if you fail?
I suspect he’d say yes – that the confusion is between effort and attachment. You can throw yourself completely into your work without making your identity hostage to the outcome. In fact, that’s the only way to work well. I’ve seen enough competent leaders operate this way to believe him. The ones who do their best work usually care deeply but aren’t destroyed by setbacks. The ones who tie too much of their self-worth to a specific result tend to be the ones most derailed by failure.
Second, I’d push him on other people.
Epictetus lived in a world with slaves and emperors. The power differentials were extreme and largely fixed. My world has terrible bosses, unfair performance reviews, office politics, and colleagues who take credit for your work. These aren’t the same as slavery — obviously — but they’re still external constraints that affect real lives.
I’d want to know where he draws the line between acceptance and action. There’s a meaningful difference between “This thing bothers me unnecessarily” and “This thing is genuinely unjust and should be changed.” His framework can blur that line if you’re not careful, and I’ve watched people use Stoic philosophy as a reason not to advocate for themselves when they absolutely should have.
He’d have a more nuanced answer than his popular reputation suggests. He wasn’t passive in his life. He ran a school. He argued. He disagreed openly with powerful people. Acceptance of what you can’t change differs from acceptance of everything, including things you can change.
What Growing Up on an Island Taught Me About Control
There’s something about island life that makes Stoic ideas feel physically real rather than abstract.
When a cyclone warning goes up in the Indian Ocean between November and April, there is nothing to do but prepare well and let go. You secure what can be secured. You gather people you care about. And then you wait, because the ocean doesn’t negotiate.
I think that early education in the limits of control made me more receptive to Epictetus than I would have been otherwise. The Mediterranean world he lived in had similar rhythms – the sea, the seasons, the unpredictability of empire. His philosophy wasn’t developed in an air-conditioned office building. It was built for a world with genuine, non-negotiable uncertainty.
That feels relevant now, in workplaces reshaped by AI, remote work, and global economic volatility. The uncertainty isn’t going away. The question is whether you have a framework that allows you to live inside it without being undone by it.
The Dinner I’d Want to Have
Toward the end of the meal, I think I’d want to stop asking smart questions and just listen.
Epictetus apparently had a gift for plain speech — he didn’t lecture, he talked. He used examples from daily life: how you react when someone cuts in front of you, what you do when a cup you love breaks, and how you feel when a colleague is promoted over you. Small moments. But he treated them with complete seriousness because he understood that how we handle small moments is exactly who we are.
I’d want to hear him talk about a specific day. What it felt like. What he noticed. What he was still working on.
Because that, in the end, is what I’d actually want from any philosopher worth their dinner: not a system, but evidence that living thoughtfully is possible — and what it truly looks like when someone tries.
L J Padayachy 
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