Re: A question about organizing thoughts

What follows is an excerpt from a private exchange. I am publishing it with permission, without disclosing the identity of my correspondent.

For a while now I’ve been struggling with an issue I think you might be somewhat qualified to advise me on.

As a philosopher you need to be able to clearly and concisely communicate your ideas across - which I think you succeed in. This is a problem for me though.

I struggle with expressing my thoughts in a meaningful way, one that actually reaches some form of a conclusion. All of my writing feels sloppy, and of low quality. My writings implode on themselves as I inevitably get lost and end up with meaningless word salad, never really leading anywhere. So my question is, how do you manage to keep your train of thought organized, while also expressing yourself clearly so effortlessly?

Personally I think this may be coming from a lack of experience - I am still rather young and studying, I’m also not a native English speaker. I have attempted to organize my thoughts on paper (well, in org-mode). I tried to keep to simpler topics and ideas to somewhat “develop” these skills, but progress seems to be slow.

Do you think this approach can yield good results if I persevere? Have you struggled with something similar?

Note that there is a possibility you are too hard on yourself. Is it really “word salad” or something that is “okay” while it has room for improvement? For example, if I ask you to write to me how you use org-mode for what you mention here, can you provide an answer that is one, two, or three paragraphs long? Can that answer be “okay”? I am just asking for something that is not gibberish. I think you can achieve that given that you already did it with this email, which has a clear intent and communicates it effectively.

I mention “okay” because sometimes the problem is that we operate with an all-or-nothing mindset, where we want stuff to be perfect and discard everything else. We mistake this for ambition, though I think it is closer to insecurity: we use perfectionism as a cover for some deep seated concern we have. We are afraid to make mistakes and end up in a situation where we refrain from acting, from committing to the cause, preferring instead to imagine how we will deal with the potential scenaria. This, in turn, looks like longer-term strategising, though I think it still is a rationalisation of insecurity that actually reinforces our fears, since it embeds them as standard behaviour.

The all-or-nothing approach engenders feelings of worthlessness, as we end up with the “nothing” part of the deal. We develop nihilism vis-à-vis our own works, discounting their utility and dismissing their value. The “nothing” also reminds us how far we are from our ideal standard, invigorating the cycle of negativity.

What I have learnt the hard way is to not be afraid to be imperfect and to make mistakes. Think of the baby that tries to run and falls because it still doesn’t know how to do it properly. The baby has to learn this way. Sure, the fall is painful yet it offers a valuable lesson for life. Intellectual affairs are similar. We err, we feel bad about it for a while, but we retry until we eventually improve ourselves.

The goals we set must be consistent with our actuality. The baby must learn to walk and then run. The teenager can then set a more ambitious target of becoming a sprinter. The young adult can raise the bar and aim for the level of an Olympic athlete. At each stage, there is a different horizon of possibilities that depends on prior work, i.e. lots of trials and errors.

You mention your young age and inexperience. This is encouraging. It shows that you are not expecting too much too quickly. Practice frequently and take setbacks gracefully. No-one starts out as the finished article.

Yes, sticking to realisable objectives will yield results. The key word is “realisable”. You must have a sense of who you are and which targets can be met with your current means. The baby cannot be an Olympic sprinter. By the same token, inexperienced “you” cannot express thoughts with the lucidity of a more experienced thinker. Through continuous practice, you will get better. How good? It does not matter and is not the right question because it prevents you from the here-and-now of acting. Regardless of where your ultimate skill ceiling is, you will not reach it if you are not prepared to admit to your frailties. Make mistakes and learn from them.

Sticking to simpler topics is a helpful method. You need to be comfortable with the basics before expanding any skill set. Don’t worry about developing thoughts too much. State your opinion with honesty: it is a true representation of what you can achieve right now. What matters is that you do not stick with it. Do not have a false sense of duty towards your prior thoughts. Allow yourself the chance to change your mind. This is another way of admitting to your mistakes, taking them as a valuable lesson, and making progress from there.

Which brings me to the part about following a train of thought. If the train is too long, you will face difficulties at this early stage. Keep it to short loops. Instead of “how to organise thoughts” shift your attention to formulating simple ideas, however naive they may seem to be. Do more thinking than organising; more expressing than planning. There is a place for organisational work, though it is not what you need right now. You are at the point where you want to get in the flow of improving yourself through consistent practice.

To your final question, yes I have struggled a lot with notions of perfectionism and the overthinking involved. They almost broke me and I suffered. What I understood was that I was making things too complicated by allowing my insecurities to inhibit my actions. I would remain an outsider to the act and would thus deny myself the chance to improve through trial and error. An outsider cannot have an intimate understanding of the relevant themes and will not develop intuitions for them.

When the standard is too high, you will always find yourself inadequate and you will never do anything that fulfils you. When you are an outsider, you will keep thinking you are too good/bad and live with the accompanying fantasy that is either a cheap imitation of the real experience or an aggrandised fear. Make mistakes and learn to appreciate them. Do what you like without contempt for others and try to be the best version of yourself, one tiny bit of improvement at a time.