A friend sent me a query on facebook about writing, and how to go about it in a way that was personal/non-personal; it was a bit of a confused request but I spent a while answering and thought it might pertain to some stuff here.
Hmm this is a hard question and the simple answer is "you just have to try it and see how you feel about it", which is correct but harder to grasp. I use the sea/see metaphor a lot for writing and it goes something like this: you can only describe the sea to someone who has never seen it so many times, eventually they will have to go and see it for themselves and when they do they will instantly understand what you were trying to say. I like this metaphor a lot because equating the sea to the mystery of the written word seems very accurate; standing on the shore you have no notion of how vast or deep it is, you can enter it and drown or enter it and live but no one is its master and it is capable of beauty and terror, and the sublime moments in-between. So this is my take-things-with-a-grain-of-salt disclaimer moment, as well at the somethings are harder to understand until you take part in them moment.
If you look at writing tutorials there will be a lot of "who/what are you writing for?" arguments, but this is sort of a nonsense question tied into conversations about audiences, style vs story etc, but as a basic question subtracted of that context I encourage you to ask it of yourself. People will give you all sorts of reasons why they write fiction, and why they write what they do but really it all comes down to those personal experiences and emotions that run deep in us and no matter what characters or setting, the frisson of these internal moments is what provides the impetus for what appears on the page--this is the very kernal, the center of what it's all about. What stems from there is all bad poetry, all genius, twilight, heart of darkness etc; this doesn't mean personal narratives about climbing everest are more important than feeding pigeons in the park, it means this is why people do it, and discourses into style vs content, fiction vs non, critique and growth vs a free for all come after here and measure relative cultural or literary worth. What it also means is that writing is a personal task, and like swimming or pole vaulting is an act that ultimately you will have to do alone. This doesn't mean you have to be lonely starving artist to produce anything, rather it means you are engaging in something lots of people do all the time everyday, whether they write it down or not, and to just ignore cultural constructs about 'good/bad', trite and maturity and just do it and see what surfaces.
As to your other questions about looking back at old writing and grimacing, yes I do. Everyone who critiques their own work does (basically anyone with half a brain then). At the same time I don't really care that much anymore, bad writing is a natural first step and you get past it. I am more astounded when I look back and find a good line and am just like "who the fuck wrote this? oh me, lol". Like any task that you seek to become good at, looking back on old work is painful but past, benchmarks on the road to growing up and all that.
From what you've told me it seems like you want to write to both discover, cover, and uncover a connection you've once had with yourself--this is a lot of "covering" and I'd encourage you also to examine your need to do this--you're toeing a line of intimacy with yourself and you're probably afraid of what you'll find beneath. If you want think of writing like inception, falling straight to limbo is terrifying and YOU WILL BECOME AN OLD MAN FILLED WITH REGRET, but there are levels and depending on how you want to approach it you can choose how deep to go. This is also inherently part of the critique aspect of writing, how much you show of yourself, how much is too much etc.
I'm sure you have some inkling that I write fanfic; it's something I do for fun, as part of a community, but I bring it up because it's a very clear example of how people write about characters not themselves but at the same time impart, or cling to characters they have an emotional bond with. The bonds are not always favorable, and have a lot to do with the story of the character, their mannerisms, ways of dress, face etc one of infinite reasons people like/dislike other people. I will also say that my favorite characters of a series, are very much NOT the character that is closest to my personality or personal issues. The few times I did write a character that is very close I found it v. uncomfortable, and found that I lost a necessary distance to critique the work and finish the story arc. To continue with the Inception metaphor, this would be equivalent to the point where Cobb brings Mal in and fucks up the heist, and where a lot of early fiction writing attempts stumble because they want to jump straight to the deep end and dredge up all that stuff and showcase it to you in gory, grandiose statements about love and dreams and other words raped from thesauruses.
This is a lot to take in, but start small and don't jump into limbo. In "Finding Forester" Sean Connery has his pupil do an exercise where he takes a book and has the kid type the paragraph until the kid starts to want to bend and add his own sentences in then just go in from there. Write about the tastes of cheeses, describe oranges, and you will find your subconscious is more tricky then you think. I remember maybe 5 years into doing writing someone asked me to outline my common themes, and I was just like "lololol dudes banging?", but when I sat down and thought about it and asked others they said: nostalgia, cerebral, family issues, inheritance and complications of belonging, which are not things I meant to add but crept in and are v. personal issues for me.
There you have it!
ETA: Continued bomb-ass discussion with
nthcoincident here