Open Thinkering


Tag: philosophy

That silent disappointment face, the one that I can’t bear

Parents talking to child

Perhaps one of the most powerful tools in the toolbox for parents, educators, coaches is disappointment. Whether real or feigned, once a relationship of respect is established between child or student and the person with “pedagogical authority”, then expressing disappointment can be amazingly effective.

In the film Coach Carter, which I watched again with my son at the weekend, the coach in question establishes a culture of respect in a basketball team. He does this initially through discipline. Once this discipline is established, however, he maintains team performance by conveying disappointment when its members contravene the established rules.

Conveying disappointment can be done in at least three ways. Depending on the skills of the pedagogical authority, this can be done in more or less precise ways. In my experience, the most common way of expressing disappointment is through body language: facial expressions, sighing, turning the back. The child or student needs to be able to connect that body language to the thing they have just done.

The next level is verbal: pointing out what the child or student has done to disappoint the pedagogical authority. This is more precise as the child or student is left in no doubt as to what it is they have done. The third level, however, takes on a longer temporal element in that it is written. In my experience, expressing disappointment in written form is the most powerful way of conveying it to a child or student. Unlike body language and verbal expressions which are transitory, a written expression of disappointment is something they can read several times.

As such, disappointment as a tool needs to be conveyed as precisely as possible. The temptation is to over-use it, especially body language and verbal expressions. This can lead to either the child or student starting to ignore the disappointment, or to do the opposite: to take it all onboard which leads to a feeling of helplessness, and a culture of negativity.

Disappointment as a tool between pedagogical authority and child or student is a form of interpersonal relationship. Another form of interpersonal disappointment happens between friends, lovers, and colleagues. In other words, whereas the previous type involved a hierarchical relationship, this type of disappointment happens between peers.

The same three types of expression (body language, verbal, and written) are the forms taken by this disappointment, in my experience. However, because the power relationship is different, the results also differ. In my experience, expressions of disappointment are much less likely to be precisely articulated and instead conveyed via body language. Sometimes (often?) this is involuntary.

As the connection between what the other person has done and the (involuntary) body language is not clear, the feedback loop is often incomplete. This can lead to confusion and problematic relations between the two people, as the cause of the problem has not been identified precisely. There is a feeling of tension, which contribute to what Alex Komoroske calls ‘coordination headwinds’.

The best thing to do in this situation is for one person to verbalise their disappointment in ways that focus on their emotions. For example, there are techniques in both sociocracy and counselling that include sentence templates such as, “When you do… I feel… because…”

The third type of disappointment is intrapersonal. That is to say, it involves disappointment with oneself. In my experience, this kind of disappointment is often felt rather than expressed in a form that involves words. It is a form of internal body language.

One strategy to explore with disappointment with oneself is to externalise the feelings. This is explored in the book How To Think Like a Roman Emperor by the philosopher and psychotherapist Donald Robertson, who has a special interest in Stoicism and Cognitive Behavioural Therapy (CBT).

Carrying on with the above theme, then, there are two ways to do this: to verbalise the disappointment and to write it down. CBT is an extremely effective way to verbalise disappointment in oneself, as a trained therapist and guide is there to help you stop spiralling downwards.

Journaling, or maintaining a diary, is a good way to write down the disappointment. Once it’s there on the page in front of you, it either has the power to change your actions going forward, or it looks less of a big deal than it felt in your head. Either way, you can do something about it.

As you may have gathered, I have been both on the receiving end of disappointment and the person conveying it to others recently. This is not a “philosophy of disappointment” as such, although I purposely avoided searching for the term until I’d written the preceding. Perhaps to develop it further I need to read this article in The Independent, watch this 2010 talk by Simon Critchley, and perhaps examine this analysis of the philosophy of Schopenhauer and Nietzsche…

Image based on an original by Monstera. Quotation-as-title via Arctic Monkeys.

40 things I’ve learned in 40 years.

Signpost showing the number 40

I turn forty years old today. Some people will be surprised at this, as my hair has been turning grey for the last 15 years!

A decade ago, I wrote a post entitled 30 things I’ve learned in 30 years. While I still agree with most of that, on reflection it just doesn’t seem particularly… deep? So, here, in no particular order are 40 things I’ve learned in 40 years:

  1. There are things you can control and things you cannot. There is no point in worrying about the latter.
  2. Inspire other people to be inspired yourself.
  3. Most people care less than you think about almost everything that you deem important.
  4. Get some therapy, even if you don’t think you need it. Especially if you don’t think you need it.
  5. Keep your options open.
  6. Sometimes it’s OK to burn your bridges and to do so in a way that other people notice.
  7. Resist the urge to suppress randomness.
  8. Nobody knows what goes on inside your head until you say it or write it down.
  9. Happiness is not something that you can find, but rather is something that you discover when you stop looking for it.
  10. Organisations are groups of people that can have a positive or negative effect on the world. Do not work with or for the latter.
  11. Money can only buy choices, not happiness, time, or anything which constitutes human flourishing.
  12. Life is too short to deal with adults who display little in the way of emotional intelligence.
  13. Listen to what people actually say.
  14. Read inspirational things often, especially quotations and proverbs. Dwell upon them.
  15. Education is not the same as learning. Nor are qualifications the same as real-world knowledge, skills, and experience.
  16. Focus on routines and rituals. Nail these and you’re (mostly) sorted.
  17. Practice eloquence. People like listening to those who have a way with words.
  18. At the end of it all, the only person who stops you doing something is yourself. Confidence is a preference.
  19. Stand for something bigger.
  20. Find somewhere that is completely quiet and you can be undisturbed. Visit it often.
  21. Ask. People can only say no.
  22. You are a human, not a machine. You don’t need to sound grown up, or professional, or ‘respectable’.
  23. Money is important only in the way that it flows (both in society, and at family/individual level).
  24. 90% of ‘success’ (as other people define it) is being in the right place at the right time, the other 10% is extremely hard work.
  25. Perfect is the enemy of done.
  26. How you do something is as important as what you say or what you do.
  27. Transparency is the best policy.
  28. Exercise more than you think you need to. When you’re young you think your body will be in peak condition forever. It won’t.
  29. Endeavour to be the least knowledgeable person in the room at any given time.
  30. There is no final authority. Seniority is a mindset.
  31. Try and explain complex things to other people as often as you can. It’s a valuable process for both parties.
  32. Travel, both literally and metaphorically. Go on journeys and adventures by yourself and with others.
  33. Let other people boast and do your PR (but don’t believe everything you see/read/hear)
  34. Writing is a form of thinking
  35. Know what you like, but don’t get stale; mix things up sometimes.
  36. Habits can make or break you, so create positive ones.
  37. Avoidance is rarely the correct option.
  38. Technology can free people or it can enslave them, so work to give as many people as much freedom as possible.
  39. Removing ego from the equation gets things done.
  40. We all will die and don’t know when, so act today in a way whereby people will remember you well.

Much of these come through my daily(ish) reading of Stoic philosophers but also come via therapy sessions, Nassim Nicholas Taleb’s rules for living an antifragile life, Buster Benson’s Live like a hydra, and Dancing Fox’s Inappropriate Guidelines for Unacceptable Behaviour.

Image CC BY-NC-ND Jeronimo G+E

Free Software and two forms of liberty

Somehow, I missed a BBC Radio 4 series on A History of Ideas, both when it originally aired (2014-15) and then when it was repeated a couple of years ago. The ‘history of ideas’ is, of course, another name for the study of Philosophy, the subject of my first degree, and something which remains a lifelong interest of mine.

Starting with the beginning of the BBC series, I’ve begun listening to a philosopher, neuropsychologist, theologian, and lawyer debate what it means to be ‘free’.

There are fundamentally two types of freedom, as defined by great thinkers: freedom from and freedom to. Some people frame this as ‘negative’ liberty (i.e. freedom from) and ‘positive’ liberty (i.e. freedom to).

In general, I would say that it’s negative liberty that most of us mean when we talk about freedom. That’s the freedom from coercion, so that you can do what you like with your time, your body, or your possessions. This is different to positive liberty, which can be thought of as the freedom to participate in society on your own terms.

The question of technology is an interesting one to consider here, as I’ve always understood negative liberty to be the main driver behind the Free Software movement:

Free software (or libre software) is computer software distributed under terms that allow users to run the software for any purpose as well as to study, change, and distribute it and any adapted versions. Free software is a matter of liberty, not price: all users are legally free to do what they want with their copies of a free software (including profiting from them) regardless of how much is paid to obtain the program. Computer programs are deemed “free” if they give end-users (not just the developer) ultimate control over the software and, subsequently, over their devices.


Interestingly, although the Four Freedoms talk about ‘freedom to‘ they’re actually, to my mind at least, all couched in terms of negative liberty. For example, the first of these is “The freedom to run the program as you wish, for any purpose”. This could perhaps be more accurately be rendered: “The freedom from being prevented from running the program as you wish, for any purpose.”

In short, we in the Free Software community often miss the importance of positive liberty. While negative liberty frees us from the constraints of others, positive liberty allows us to act upon our free will, something that’s (sadly) often still a lot easier with well-designed proprietary services.

Ben Werdmuller, who has spent his career trying to push forward easy-to-use Free Software, said recently:

The only real way to avoid tracking and surveillance is to host things yourself, but that’s not an option because hosting things yourself is still too hard for most people and it’s easy to compromise on security. We need the iPhone of self-hosting.


In other words, when it comes to technology, most people have the freedom to do things but not the freedom from some of consequences of using proprietary services. For example, it’s easy to express a controversial political opinion using Facebook, but not to avoid being tracked and surveilled on that platform.

I think we’re at a bit of an inflection point. There are those of us who have enough technical skills to be able to self-host and spin up a VPS to run Free Software. We can experiment and express ourselves however we wish. And then, sadly, there’s everyone else.

We Free Software enthusiasts value our negative liberty and use it to promote our positive liberty. Less technical people have only the amount of positive liberty allowed by proprietary services under capitalism. I believe we need to focus on enabling that positive liberty with Free Software under socialism, even if that means compromising a bit of negative liberty.

This post is Day 77 of my #100DaysToOffload challenge. Want to get involved? Find out more at