The questioning philosopher
A good philosopher should question everything. Even the answers he got through the process of questioning. I recall a fragment of a recent dream in which I had the realization that most of my beliefs and the facts I know about the world are most probably wrong – even after all these years of learning, critical thinking, and the collection of empirical evidence. This seems intuitively true to me. My views of the world have developed, evolved, oscillated. I used to hold strong and extreme views. Now I seem to converge towards boring balanced centrism, even if that kind of centrism is on a higher level.
Uncertainty
From time to time people tell me that I should be more confident, more certain about my skills, abilities, and beliefs. That sounds like good advice, if you want to convince others of something. But what if you question whether that something is really the best, as a good philosopher should? I don’t want to pretend that I have the best answers to any question. I know more than most other people that good answers are easily invalidated by better answers, or even whole new way of thinking – in which those good answers suddenly become bad answers. Perhaps my personal lack of confidence is actually a strength in disguise, rather than a weakness. It allows me to question more deeply, and develop my own thinking faster, avoiding dead ends more efficiently than others. Of course, I could be wrong about that, too… I don’t want to become a bland post-modernist anyway.
Can philosophers be leaders?
People look for leaders who can provide direction. For that, they need to convey an aura of conviction, certainty, and self-confidence. Thus, true philosophers can’t seem to be good leaders when they express their doubts about being actually right. Are philosopher kings impossible for that reason? At least that’s a very plausible claim which isn’t easily empirically invalidated by pointing to a large number of actual philosopher kings. 
A philosopher would need to become untruthful to himself to actually become an effective leader. Effective leaders are consistent and don’t change their views often. Of course, a good philosopher doesn’t change his views easily either, but when he does, he should have a really good reason to. Even if a philosopher can build up a following, he will lose most of them when he evolves further and becomes disloyal to his previous views. Interestingly, when this happens his previous following will stay loyal to the previous views of the philosopher, rather than the philosopher and his updated views.
Oscillating uncertainty
Sometimes I feel that thinking about stuff decreases my uncertainty. At other times, I feel like it increases it. If some kind of big philosophical convergence lies ahead, at which there is great and certain wisdom, I am sure that it lies very far away. Probably it lies beyond the cognitive horizon of any human. And that’s either a good reason to resign and surrender, or to strive beyond our current human limitations and go the transhumanist way. The latter seems to make more sense. I don’t see much value in surrendering, but perhaps I will change my view about that, too – who knows (I don’t)?
What is good?
I have a deep desire to improve the world, but how can I do that, if I don’t even know what’s good? It seems we humans are forced to stumble around blindly. Trying out new things to see whether they make our overall situation better or worse. We don’t seem to have good way for figuring out in advance whether any alternative approach will make things better or worse. Empirical results can and do break the neck of any theory. The best thing we might be able to do is stumble around in the dark methodically. Don’t try things that have proven not to work in the past – unless the situation has actually changed on a fundamental level. It’s frustrating how difficult it is to learn from the past.
We learn by making mistakes
So, why shouldn’t we embrace making mistakes regardless? We can’t avoid making mistakes at all. We don’t know what’s right and what’s wrong in advance. We can only try to do things better than in the past. We might fail catastrophically, but such mistakes will be remembered for a long time and guide our progress towards higher levels of knowledge and wisdom. Perhaps the best we should hope for is to fail in more interesting and insightful ways.
Personal conclusions – first attempt
I hoped these thoughts would help me to gain more clarity about what to do with my life, how to define my plans, and how to proceed with my plans. Previously I thought that having a clear goal would help me to find clarity, strength, determination, and certainty. However, more recently I found that even with a clear goal, there are still countless routes towards that goal, and it’s just as hard to choose the “best” route as to choose the “best” goal. Clear principles are welcome guides, because they eliminate routes that are in contradiction to those principles. Yet, if principles are subject to being questioned, too, they lose their clear and definite value. Everything becomes fuzzy, even the rules you set for yourself.
Once I had the hope that a deeper mathematical understanding of the world would help me to make better decisions. After having studied mathematics I have become less convinced that this is a promising approach – for humans. I still have hopes that posthumans will be able to understand the world in a deep mathematical and holistic way that allows them to achieve levels of deep wisdom at which uncertainty actually becomes manageable relatively easily – or even disappears eventually.
Personal conclusions – second attempt
I am having an experience of dissolution. Certainties dissolve and I am left with few things that guide me. What I am left with is hope that we will be able to become wiser and reach higher levels at which things start to make more sense, again. Problems will get solved, progress will be made, post-traumatic growth will happen. As long as we manage to increase our wisdom, we are on the right track.
Foundations
I cannot evade the insight that on a deep level I am a philosopher more than anything else. Even if my insights as thinker and philosopher compel me to become a leader for a certain cause, I cannot stay perfectly loyal to that cause. After all, I might find out that I was following a flawed path. And I don’t want to lead humanity on a wrong path, even if that path is less wrong than previous paths. Instead, I want a path that is even less wrong than less wrong – if I cannot even reasonable hope for a true path. For every path I take, I am highly likely to become disloyal to that path once I’ve found a better path. This philosophical integrity to always choose the best currently visible path will be seen as indecision, as lack of determination, as lack of principles, as lack of vision, as opportunism, as betrayal, or as weakness (or worse) by those who don’t understand my reasons for progressing beyond my previous horizon.
Acceptance as solution?
So what? What if I simply accept this to be true and decide to go ahead anyway? After all, I need to work with reality as it is, in order to change reality. Even if others will condemn me, and get stuck in routes that I have long since deserted, I still have no better choice than to stick to what I see as best possible way forward. I can’t make things better by standing still, or deciding not to act decisively.
Can this rant become even more abstract?
Of course I could point to the challenges and decision I am faced with in my current situation, but some things become clearer when described in the abstract. The concrete has its way of muddying clear thinking with accidental particularities. That’s why I won’t bother in this opening post to mention the decisions and options that stand in front of me.
Perhaps I will look back to this text in the future and see it as profound triviality, or deep nonsense, or basis of the development I will have been going through the next years. I wouldn’t be surprised at all about any of that.