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Some may think of Chrysippus as an upstanding role model. But did you know he beat his mistresses and was addicted to hallucinogens?
You don’t know if what I just said is true or not, and neither do I, but just to be as clear as possible: I’m not saying it is true, in fact, I made it up completely. I am saying we don’t really know much of anything about Chrysippus — nor of Zeno, Cleanthes, Epictetus, Rufus, or even Marcus. There’s almost no upper-limit to how much we don’t know we don’t know about the Stoic “greats” who we so often look to as nigh-infallible role models of character.
But it’s not just the ancients! Choose any contemporary Stoic you might think of as a role model. How about Kai Whiting? How about me? Donald Robertson? How about John Sellars or Massimo Pigliucci? Are any of these your contemporary role model? If so, I’d like to challenge whether they should be, or whether anyone should be.
The answer, rest assured, will be yes these people should be, and can be your role model! But there’s a lot to consider in making that sort of decision.
“On a Spectrum”
It has not been infrequently that I’ve been asked about why I should be listened to as an authority in any capacity whatsoever — be it as a so-called Stoic, entrepreneur, or marketer. What right do I have to teach others on any of these subjects if I do not know everything about any of them? In fact, what right does anyone have?
My response, for years, has been to ask:
“Did your high school biology teacher know everything about Biology?”
Their answer is always some version of, “no, not everything.” To which I reply,
“But they taught you what you needed to know about biology, didn’t they?”
And of course they did.

Both knowledge and the ability to learn exist on a spectrum
If we imagine this spectrum runs from 1 to 10, with 10 being complete knowledge of a topic and 1 being the least complete knowledge. On this spectrum threes can teach a lot to ones, and eights can teach a lot to fours.
And when it comes to learning instead of teaching: fours can learn from fives and above, ones can learn from two and above, and so on. However, fours would not be able to understand what tens were teaching to nines. Just as ones can’t teach sixes, fours need to learn from fives first. They can then become higher numbers and can go on to learn from higher numbers still, and so on.
The ability to teach does not require perfect or complete knowledge, nor is it ever the case that a student needs to (or should) attain perfect or complete knowledge all in one fell swoop.
You already know this is true because you’ve been through some form of schooling in your life and you surely didn’t start learning quadratic equations in the same grade you learned what numbers even were. Whoever your kindergarten school teacher was, the very likely couldn’t have taught you quadratic equations particularly well; both because you brain wasn’t ready for quadratic equations and that teacher (probably) wasn’t informed enough to teach quadratic equations to you anyway.
What’s that got to do with role models?
When we think about role models, Stoic or otherwise, it’s important, first, to realize that no role model, unless they are a Sage, is capable of having a perfect character and so will, necessarily, fail to be a perfect role model.
Your role models will always be, unavoidably, flawed.
You may find Kai Whiting to be a fantastic role model, but I can tell you with certainty that Kai is classically British and, thus, expertly whingey. We’ve talked about it on the podcast before, right? He once threw a fit because he couldn’t have ice cream. There were other factors involved, none of which need to be recounted here, but the fact of the matter is he threw an absolute fit because he couldn’t have ice cream.
You may think I’m a fantastic role model, but I can tell you with certainty that I am classically American and, thus, place too much importance on money. I throw regular fits about money and frequently remark that it feels required for happiness. There are always other factors involved, like how I feel responsible for the financial security of others, but the fact remains: I get really anxious and worked up about money.
There are other things about Kai and I that, if you caught us in those moments, you’d role your eyes and say “Ugh, these guys are terrible role models”.
But you’d be mistaken in that conclusion. Whether it be about us or any other imperfect role model.

No one you could choose to model yourself after will be as ideal as you imagine them, or hope for them, to be. The only way to keep yourself from running head-first into this disappointing reality is to limit how much you know about your role models.
I mentioned Donald Robertson earlier. I think of Donald as a role model in the sense that I am absolutely blown away by how much he knows about Marcus Aurelius — the guy is like an encyclopedia of knowledge on that topic (and others relating to Classic Greek and Roman studies). I wish I could be as cool and off the cuff with that sort of stuff as Donald.
But, you know what? I bet if I lived with Donald for a month or three, I’d find out things about his character that fell short of the avatar of Donald I have built in my mind having very limited knowledge of him as a complete human being. Maybe he leaves the toilet seat up, maybe he doesn’t pick up after himself, maybe he sneezes without covering his mouth, or maybe he’s rude to waitstaff. Donald isn’t perfect, and the more I would get to know him, the less impressive he would be.
Same with John Sellars and Massimo Pigliucci; with Julia Annas and Margaret Graver as well. Same with anyone and everyone. Everyone is flawed, no one is a Sage. Your role models will always be works in progress.
My point here is that the less we know about our role models, the easier it is to see them as role models because, just like knowledge, quality of character exits on a spectrum and if we blind ourselves to the totality of that spectrum (which we do when we turn people we don’t know intimately into role models), we can’t see the imperfect bits of a person’s character.
But that’s okay, you should still have role models. Necessarily many, in fact
Few humans are Sages. That means few humans are in a position to serve as the example we model the entirety of our lives on. Our expectation that anyone could successfully serve in such a capacity is a reflection of our underdeveloped rational faculties (which, funnily enough, is the same reason so few people are Sages or perfect role models!).
Further, our disappointment when someone we’ve elevated to the position of role model — the faultless and complete sort — borders on audacity and entitlement as we are expecting that all our role models be sages! Imagine how incredibly arrogant is is to suggests we require, and have a right to, role models that are sages — that a role model has failed as a role model if they aren’t a Sage.
How can any of us expect that of another human being?
What we really need in our lives is a sort of “Scope of Work” approach to our role models and mentors. Kai and I are great role models in a few capacities, and so perhaps you could say something like, “Kai is my role model for becoming knowledgeable about the more god-centric aspects of Stoicism” or “Tanner is my role model for turning complex ideas into more practical and easily digested concepts”. You could construct similar statements about the others mentioned in this article.
This approach leaves plenty of room for Kai and I (and everyone else) to be not-sages in all the other areas of our lives without letting you down or expecting perfection of ourselves.
Á la cart your mentors and role models. It’s far more realistic, far more effective, and far more forgiving to everyone involved.