Being Disappointed in People

Hi everyone,

This was originally meant as paid content for Sunday’s newsletter, but I decided the tone was more suitable for a general audience, so Sunday subscribers got Returning to the World instead, a piece about my experiences of depression and its lifting, and you get a piece about the practice of philosophy and the nature of disappointment.

I’m just disappointed

Michael: Are you mad at me?

Eleanor: I’m not mad. I’m just disappointed.

Michael: Oh come on. Everyone knows that’s worse.

- The Good Place

One of the things that I’ve been coming to terms with over the last couple of years is that so called “negative” emotions are generally important and healthy parts of normal functioning, and when we treat them as inherently bad and unmanageable we end up the worse for it rather than the paragons of virtue we pretend we would be if we never had those emotions. Last week, this came out as anger. Apparently today we’re doing disappointment.

Over the course of my life so far I’ve gone from being extremely judgemental of other people, to being extremely non-judgemental, and now I’m back to somewhere in the middle and think to a large degree judging people is good actually, most people are just really bad at it.1

Being good at it requires being disappointed in people, and we’re not very good at that either, because it tends to be treated as a much harsher judgement than it needs to be. Today I’d like to talk a little bit about how to do it well.

Philosophers’ Lives

In my inaugural paid newsletter issue, I concluded that to my great regret I should probably read some Existentialists.

I’ve now read “Existentialism: A Very Short Introduction”, so I now understand everything about Existentialism and am prepared to write a long newsletter issue about it.

Umm. Obviously that isn’t true, I still don’t understand Existentialism at all. But reading it highlighted a problem I often have with reading other people’s life advice: I’m here, reading about the existentialists, and their philosophy on how to live a good life and how to make your own choices while respecting others, and navigating the inherent tension between person and community, and all I can think of is “OK, but, looking at the actual facts… you’re not very good at it, are you?”

The lives of the existentialists are a tire fire, filled with broken friendships, petty drama, and overly dramatic feuds. I thought existential comics was exaggerating when they portrayed the existentialists but now I’m starting to suspect they were toning it down.

Granted that there was a war on, and granted that they were mostly very French, but these are the people whose philosophy of the good life I’m supposed to learn from?

I have a similar problem with Alasdair MacIntyre:2 I would be much more interested in his advice on ethics and how to treat people if he was less of a disagreeable person.3

I’m also much less interested in Josef Pieper’s thoughts on courage and personal integrity since I learned that he basically rolled over and collaborated with the Nazis.

Eric Schwitzgebel has done a lot of interesting work on the limitations of of philosophy of ethics in terms of actually making people into better human beings. The short version is that it doesn’t. Contra the Good Place,4 ethicists mostly behave exactly like everyone else. He treats this as an interesting puzzle to explore, and never goes as far as to suggest that maybe this is just a damning indictment of the entire discipline and the individuals who practice it. I understand that he probably doesn’t want to rock the boat even if this is what he thinks but I am, if I’m honest, a little disappointed in him for this.

Life of the Author

I’ve previously been very sceptical of the tendency of philosophy to centre the philosopher rather than the philosophy. I’m used to mathematicians’ approach where we endlessly re-arrange and re-abstract things to come up with better ways to look at the problem, only lightly referencing its history, but I think perhaps I was wrong and if anything the problem is that philosophy does not go far enough in this.

One can certainly read philosophy with a “death of the author” mindset, separating the philosophy from the philosopher, but I don’t think it’s a good idea.

To be clear, this is not an opinion that you should not consume philosophy from bad people. Everyone is a bad person to some degree, and I am never going to suggest that you should purity test every piece of media you consume. I’m sure I consume works from much worse people than Sartre.

There’s especially no point in avoiding philosophy when it’s unrelated to their failings. Reading Wittgenstein on language, no problem. Reading Wittgenstein on the philosophy of threatening Karl Popper with a fireplace poker, well you at least have to take into account that it’s philosophy coming from someone who thinks that’s a valid thing for him to be doing.5

Even when their lives and their philosophy interact, it can still be worth reading works by philosophers who have failed to live up to their philosophical ideals, because often the reason why they wrote those works at all was because they were struggling with these exact issues. It’s often worth reading material from people with interesting and important problems, even if they fail to solve that problems.

But it’s important to bear in mind when consuming philosophy that necessarily some combination of the following is true:

  1. The life the philosopher lived is a life that their philosophy helped to create.

  2. This philosophy came from someone who didn’t live it, and thus has not seen how it plays out in practice.

Philosophy, along with a wide variety of other literature, is often painted as not being a particularly empirical subject, but perhaps we were looking in the wrong place, and the authors are the data points more than the data gatherers.

Anti-Role Models

I acquired my first anti-role model who I remember when I was in my teens (no, I’m not going to say who it was). I don’t know if this is normal, it certainly seems not to be a thing people talk about that much, but it has been significantly life improving for me to have a steady stream of these people throughout my life.

An anti-role model is literally what it sounds like: Where a role model is someone who you aspire to be more like, an anti-role model is someone you aspire to be less like.

An anti-role model is not just someone you dislike. Donald Trump would make a terrible anti-role model for me, not because I want to be more like Donald Trump, but because there is literally no risk of me being like Donald Trump. “Don’t do what Trump would do” offers no useful guidance to me because yeah duh.

Instead, an anti-role model is someone who you can look upon with a certain degree of love. In your heart you are able to think “I see you, I respect you, I believe I understand you, I recognise that which is common in us. I am glad that you exist. I value you as a human being. Your choice are your own, and I acknowledge your right to make them, and I expect no dominion over you or your life. And, with all of this in mind, and with love in my heart and determination in my soul, I will dedicate my very existence to ensuring that I never under any circumstances become you.”

Yes I have anti-role models right now, no I’m not going to tell you who they are (I don’t think any of them are reading this though).

I think core to the anti-role model is that they are like you, and that you do not think they are a bad person. You’re just disappointed in them, because you can understand at a visceral level the path that would lead to you becoming as they are, and you would be disappointed in yourself if you had chosen to take that path.

You cannot have an anti-role model you don’t learn from. In order to know how not to be them, you need to learn from them - learn how they became themselves. What bits of that path lead to good outcomes, where they failed, and how they ultimately arrived at where they are and where you do not want to be.

Being disappointed in yourself

I often look back at my past self and try to decide how to feel about my actions then, and I conclude that the bad thing I did was actually basically fine because I did not have the ability to do differently at the time. I am not disappointed in myself for these, because I could not have chosen differently. It is, I think, important to only be disappointed in people when they could not have done otherwise.

This is complicated of course. There are definitely cases where someone acts in such a way and it’s still right to be disappointed in them because they could have chosen differently earlier. If someone takes on a task that they are not competent to do, and harms others through their incompetence, I am not disappointed in them for failing in the task (they could not have done otherwise), but I am disappointed in them for getting into that situation in the first place.

Similarly I am not disappointed in bad people for doing bad things, because I think often they are not the sort of person who could choose to do otherwise, but I am disappointed in them for having chosen to become a bad person in the first place.6

But looking back at my life: Yeah, there are some things I am disappointed in myself for. It would have been hard for me to do some of the better, but even the hard ones I was definitely capable of doing better.

That’s OK. I’ll do better next time.

Disappointment, Guilt, Shame

There is a distinction I like that guilt is when you feel you’ve done a bad thing, while shame is when you feel you are a bad person. This isn’t a definition and it doesn’t completely capture the subjective difference between the two, but it’s a good rule of thumb.

Bearing this distinction in mind: When you are disappointed in yourself, do you feel guilt or shame?

Based on my observation of a lot of friends, I think for a lot of people the phrase “I’m disappointed in myself. That’s OK. I’ll do better next time.” might as well have come from a different planet it’s so alien to their experience.

It’s hard for me to say for sure because I’ve changed so much in the last few years, but I think five years ago I’d have been right on their side. This way is healthier, sorry.

I think the basic problem here is that people are bad at feeling guilt (yes, I know you want to respond with “On the contrary I’m great at feeling guilt”): They lack a productive response to it, and as a result the guilt spirals out of control, turning into shame. The internal logic is probably something like “I did a bad thing. A good person would not have done a bad thing in these circumstances. Therefore I am a bad person.”

Don’t do that. It’s dumb. Good people do bad things all the time. The only way to avoid doing bad things is to never do anything at all. When you do a bad thing, you repair what damage you can, and resolve to do better the next time. That’s what guilt is for.

I could probably write a whole other essay on these dynamics, and likely will at some point, but I’m not going to right now. I just thought it was worth highlighting.

Being Disappointed in Philosophy

Philosophy is a very interesting discipline that I draw on to a reasonably large degree. I applaud its strengths, I am a huge fan of many of the people working in it, and also the more I learn about it the more I think it has utterly failed on its own terms, and I am deeply disappointed in it.

If I were to put my disappointment in words, it goes something like this: How do you take a discipline that starts from questions like “What is the good life?” and “How do I be a good person?” and end up in a situation where you have failed so completely that some guy comes along, concludes that literally none of the things this discipline is doing to try to help people be a good person do anything at all, and then goes “Huh. Weird. Anyway here’s another interesting problem for me to think about unrelated to this.”

The book I mentioned at the start of this, the Very Short Introduction to Existentialism, starts by talking about philosophy as a way of life. It quotes Socrates: “If I do not reveal my views on justice in words, I do so by my conduct.”

Socrates has a point.

Anyway, I still intend to read more of the Existentialists. I am very interested in many of the problems they are interested in, and some of their thoughts on the subject do sound relevant to my interests, but as I read them I am going to bear this one very important mantra in mind: I am reading your works because I recognise the part of me that is like you, and I want to understand how you become who you are, so I can dedicate my life to ensuring that under no circumstances do I become you.

Coaching Auction

Every week right now I’m auctioning off a one-off coaching session based around the theme of the week’s newsletter. If you’d like a coaching session around the theme of disappointment, or anything else reasonably related to what I’ve touched on today, I encourage you to bid on it, which you can do by filling out this Google form.

The auction is done using a mechanism called a Vickrey auction, so you should bid however much you’d want to pay for it, and will usually end up paying less than that (and never pay more). You’re welcome and indeed actively encouraged to enter a £0 bid if you’d like to talk about this but don’t want to or can’t afford to pay to do so. The winning bid last time was £50, but there weren’t that many bids so I expect prices to be highly variable and there’s every chance of a £0 bid winning.


Yes, I do judge them a little for being bad at it, why do you ask?


Sorry, Mikael. I will eventually read After Virtue, I promise.


Possibly I’m doing him a disservice here, as this is based on hearsay from people who knew or know him, but it does seem to be a reasonably consistent picture of him, particularly of him when he was younger.


The Good Place actually perfectly demonstrates the true and accurate way in which we come better people: We learn to be better people from and for each other. The Philosophy of Ethics bit is just window dressing, they probably could have used any other mechanism for demonstrating their commitment to goodness and it would have worked out for them just as well. It wouldn’t have made as good TV though.


TBF I might make an exception to my general philosophical principles against threatening people with pokers for Karl Popper.


Yes, I think this is a choice. Choosing to be a good person can be made harder by circumstances, but it is almost never impossible, and by pretending that bad people are bad only because their environment made them bad you are doing a grave injustice to some amazing people who came out of those same environments. We should fix systemic issues, but we cannot ethically ignore the role of choice even in the presence of those issues.