I was interesting in philosophy from my late teens; and then in my mid-twenties became gripped by some philosophical problems to the point that they seemed of vital importance to sort-out, in some way.
These rather abstract problems - such as about how we could know something, and be sure ("certain") that we knew, what did knowing mean? etc - seemed also very relevant to my then personal happiness, and my ability to make life-choices, and to lead a satisfying life in my future.
I had a general hunch that if I questioned and questioned, rigorously and honestly, I would reach a bedrock of solid truth that would satisfy me, and upon which I could build my life.
Being then young and gregarious; I thought of philosophy as a group activity; and I wanted above all to be able to discuss it - A Lot - until I got to the bottom of these things. It hurt to put off this discussing, yet of course there was nobody in my circle that wanted to talk (and talk!) about the things that seemed important to me.
Nonetheless, I though that maybe I could find a situation in which I might be guided to the right sources, and find such conversation. I went to a couple of evening classes, but I presumably did not find them to be what I wanted, because I quickly dropped out of the courses.
The problem was, at root, I was being taught about the stuff on the course - whereas I wanted to work on what seemed important to me: here, now. I did not want to put-off my life until later.
So I thought maybe I could go back to university and do a philosophy bachelors degree. I realized that this would still have the problem of being taught other stuff; but I thought that I would there be able to spend a lot of consecutive time on working at the problems that really interested me, I hoped I would find the conversation I wanted; and at the end of it get credentials by which people would 'take me seriously' when I reached my own conclusions.
There was a mixture of wanting to make a life-commitment - to show to myself (perhaps) that I was serious about this stuff, and of expediency.
Since I had found Wittgenstein's On Certainty to be discussing almost exactly what concerned me - I went so far as to arrange to study philosophy at his college (Trinity) in Cambridge but in two years instead of three (shortened because I already had a degree); my recollection is that I was to begin the degree in autumn 1986.
But I did not proceed with this plan, partly because I had seriously underestimated the extra cost of college fees (on top of university fees), and partly because my experience of meeting and talking with three philosophy academics at Cambridge (including Wittgenstein's pupil Elizabeth Anscombe) was disappointing.
You see; reading about the best old philosophers - and I had been especially reading about some of the more ancient and more 'existential' ones (and in this respect Wittgenstein was a throwback); you get the impression of people whose lives were dedicated to the 'love of wisdom' - but meeting modern philosophers, you meet professional academics whose specialty is philosophy (although some of them can act the part of the old-style type - whether in person or in print).
This was, of course, my own stupid fault. It was a case of wanting something exact but incoherent that could not be had, and then being disappointed when I could not get it!
Instead of a bachelors in philosophy, I ended by doing a masters in english literature; but spending about half that year reading philosophy, and informally attending philosophy seminars, and talking to a few philosophers - albeit rather superficially because our interests were so different.
Over the following years; I gradually realized that philosophy was really important to me (e.g. I continued attending seminars while I was on the faculty at Glasgow University), but that it was something I would mostly need to do by myself - navigating my way to the relevant authors and ideas, and working my way through the ideas.
For a few years I did have a lot of genuine philosophical conversations with a colleague (Peter Andras) about Niklaus Luhmann's Systems Theory - so I did end up having that experience.
I mean really working ('doing' philosophy, as Wittgenstein called it - but in his case it sound like a kind of monologue to disciples, rather than genuinely dyadic); in real time, sticking to the detail of specific and mutually fascinating ideas.
Talking on and past the surfaces that are usual in social chit chat so that personality falls away - being led by the ideas rather than politeness, or trying to be interesting; the conventions and considerations of sociability and the other limitations that constrains normal discourse to be little more than amusing or arguing for dominance.
Philosophical conversation turned out to be very helpful in grasping the (already defined) theory, and at developing applications and implications.
But - since two people are always somewhat different in the content and direction of their lives and destinies - conversation also can have a constraining effect on development and learning. And therefore it became necessary to return to working (essentially) on my own at philosophy.
My impression was that serious conversation about philosophy is only sometimes and temporarily possible, when the interests of two (maybe more) people happen to converge and run together for a while; but that this has a natural lifespan of value, after which it would become routinized, professionalized, or merely sociable.
In other words, and despite the allure of Platonic Dialogues - which are, after all, a kind of fiction; and also seem like expositions of ready-made philosophy, rather than depicting a process of genuine discovery - I have come to believe that philosophy is in its essence a solitary activity.
If we don't do it ourselves; there is nobody that can do it for us.
Indeed, given all the constraints and difficulties, it is nearly always easier and more philosophically helpful to engage deeply with a book than with a person. And even better to debate 'with oneself'; in the sense that we ought to become our own best critics.
And the whole business of following set curricula, performing exercises and examinations, developing professional expertise, or being guided by a canon of required authors; that stuff constitutes an activity which is something-else other than real philosophy.