Writing: A short history of lessons learned

Background: This post began as my side of an email conversation with a friend who is also a professional illustrator/author. I did warn them it would become a blog post! They had had rigorous artistic training with solid mentors, but their writing education was more diffuse, focussed on the sentence level, and usually in service to illustration rather than pursued as an independent craft (they are very good, though! also this is de-identified but it describes a lot of illustrator-authors I know, in one direction or another, including myself). This made me sit down and think about how I have learned the bits about writing that I do know, resulting in the following very high-level summary.

Caveats: I’m still learning. This is less advice than description, and therefore partly cautionary — to the extent it is advice, it is advice to a particular person.

Short answer: The most important thing for me — and from what you’ve said, possibly also for you — is to actually finish an (ugly and incoherent) Thing of roughly the size and type you want to write (ignoring ALL the sentence-level stuff) and then learn on that as you try to breathe life into it. It gives you something to put the bigger craft lessons to work on, and also very viscerally teaches you what not to do. And it might turn into something great (parts of Flyaway started as very larval drafts a long time ago) but it will CERTAINLY make everything you do next make more sense and be easier. This does not seem efficient. But it is. 
If I were you, I would foolishly and gleefully do NaNoWriMo and damn the torpedoes. And then possibly do it again. But I treat it as the world’s largest parlour game, so your mileage may vary.

Long answer: I was trying to work out how best to organise my thoughts, and thought it might be simplest to just list the order in which I think I learned things, and how it happened. Then you can ask me for more information on any of them!

1. I always wrote: It sounds like this is you, too! Just that constant background hum of thinking in words, doing exercises, reading books — sort of doing scales on a mental piano. I accidentally became an illustrator due to the events in Step 6.
2. I entered poetry and writing competitions early and relatively often: That was one of the first experiences of deadlines and an external standard to try and meet — and the high you get when things are well-received.
3. A genre writing group: (Vision Writers in Brisbane — and I still have many friends from those days.) This came with a degree of expectation that I would write. It taught me to take and give critique. It also taught me to navigate people’s tastes and come to terms with them. It also gave that sense that we were all running together in the same direction.
   Also when I started we had to bring printouts of our story and then sit there while people quietly read through them, and few things really feel stressful after that.
4. Rereading and deep reading of books: I’m not naturally a structural thinker. Rereading and talking about and thinking through books gave me a deep familiarity with books and stories I like that can stand in for structure. It also gave me a library/arsenal of techniques and tricks. It’s also become a source of things to reimagine. Also my dad’s favourite book is Pride & Prejudice, which I like but getting through many, many, manymany readings and viewings of it (since he can’t read for himself any more) has been educational!
5. Conventions: Again, that sense of possibility and running together. Enthusiasm and ideas. Friendships that later make projects happen. “Benchmarking” in the sense of realising these people do what you do. You know all this!
6. Writing regularly: This looks different at different times. At the most significant point, I was doing 100 words (of anything) every day — very brief. This is like doing scales: I stay in practice and if I need to/decide to write anything serious, I’m not starting cold. Also eventually it frustrated me and I wanted to write more. Also it meant I couldn’t get to the end of a year and say I hadn’t written anything. And little bits add up — the cumulative power of it is impressive. The reason for the 100 words/day was that I was working until 1 in the morning, often, as a young lawyer, and doing too many other things, so I picked the ones I wanted to, could do, and would do every day — I lived in a wooden sharehouse and so had to quit the bagpipes, but I could write 100 words and draw a smiley face before I fell into bed. 
7. Ad hoc mentorship: My relationship with Angela Slatter progressed from my being the terrified (but grateful) recipient of rigorous critiques (“flensing“) to a friend and mentor. Consistent and rigorous feedback is incredibly educational, once you work out and apply the lessons! This helped me to acquire a voice-in-the-back-of-my-mind which could stand in for instinct on some things (the rule of threes, not waffling, remembering to put page numbers in…). I was also able to sort of sit on her shoulder and watch her navigating the industry. Someone to scold you and vouch for you and help you send your stories to the right places is very useful.
8. NaNoWriMo: Some people loathe NaNoWriMo. I adore it. Basically, you race to write 50,000 consecutive words of fiction in November. I learn slowly, so over a series of years it taught me: the fun of spreadsheets; to write; to write fast; to write and not even think about editing until the draft is down; when and how to start shaping a story towards an end; how to finish a story; how a story feels as it takes shape; how much easier things are with a plan; how to write fast to a plan. 
9. FINISHING A THING: Probably the most important thing. Not enough on its own but I couldn’t have done anything else without it. There are things I couldn’t have understood without getting to that stage. It comes with a sense of desperation, the vital lessons of plastering cracks and skating over thin ice, patch fixes and so on. But you also learn what the shape of a whole thing feels like, even if it is weirdly boneless and strangely formed and far too large. It’s a remarkable high having done it. Even — and maybe especially — if you’re exhausted and it’s ugly. And after that so much writing advice I “knew” actually started to make sense. (For example: I always secretly thought people who talked about writing 15 drafts were being inefficient, but it’s incredible to get to the end of a first draft and look at it and tell yourself: it’s okay. I have 14 more tries to get this right.)
10. Kim Wilkin’s Bootcamp: I did a structural workshop run by Kim Wilkins (later my MPhil and current PhD advisor). She has a very pragmatic and quite flexible approach to structure, and it helped me a lot with later plans. A big lesson somewhere in all of this, though, was that for me and the sort of writing I want to do (possibly similar to you), narrative structure and the theories about it are fun and inspiring and FAR more useful as a diagnostic tool than as an actual guide to writing. (Also I’ve discovered I plan at different stages depending on the genre.)
11. Doing the MPhil (sort of a half-size PhD — I wrote Flyaway during it): This gave me space, money, expectation, deadline, and obligation. It gave me an external purpose and structure. It also gave me the impetus to really analyse other people’s work, as part of the research, which turned out to be a valuable skill (who knew?). This helped me learn to write as a writer, not as a reader.  
12. Analysis: I did this with the MPhil, and the Observation Journal activities I’ve been blogging about help a lot. But I learned the importance of it when I decided to analyse things that weren’t in my genre. I was too close to fantasy to read it critically — at some point it would sweep me away. So I chose a genre close to one I like — I like Georgette Heyer, but I hadn’t read a lot of modern Regency romance. I decided to read them seriously and find out how they worked, and what the authors were doing, and why they were doing it (the one that finally made it all click to me was a very consciously and delightfully ridiculous Tessa Dare Regency that was also kind of about Star Wars fandom). Then I planned a couple and wrote two (currently circulating behind the scenes). Hugely educational, ludicrously entertaining.
13. Various other workshops: These have been great (inspirational, informative) but would have been far less useful without all the lessons above. Kelly Link and Karen Joy Fowler were great (Kelly had a trick for navigating what you want to write), Anne Gracie (the only one I haven’t illustrated for!) had neat ways to trick oneself into planning (while also learning how a book works). I go to illustration workshops looking for writing lessons, too — it’s all narrative.

Main lessons, in the order learned:

• Knowing I wanted to do it.
• Actually doing it.
• Finishing it.
• Getting stylish.
• Running with others.
• Learning structure.