Hey Jaime, great questions! I don’t think there’s anything I could say that would help you know the answers immediate, but I can tell you what to do.
For me, I learn the most when I’m shipping a lot. So, try shipping a lot. Also, as I said in my book, How to Write a Book, don’t be afraid to repeat yourself.
So, if you have an idea you want to express, write about it in every format: Write it as tweets; write it as 100-word, 250-word, and 500-word blog posts; do a Facebook Live about it; talk about it on your podcast, or just at dinner with friends.
Each time, think about the constraints of the medium: What barriers are there to getting someone to engage with what you’re saying, and how can you overcome those barriers.
And pay attention to feedback: Did one tweet go crazy, when nobody read your blog post? Why? Did the stranger at the cocktail party start looking around the room while you were telling your story?
Do this over and over again, every day, and it will start to become clear what works for what medium.
The most important thing is to not treat your writing like it’s drops of liquid gold that must be salvaged. You have to think There’s always more where that came from.
Even just replying to you on this comment is a learning experience for me. It’s giving me an opportunity to write about things I’ve already written about, but in a different way, because I’m responding to a real person with a real question.
Packaging a book is a similar exercise. In my book about writing books, I encourage a Kindle-sample-reading habit. Sometimes, I’ll make a night out of reading a bunch of Kindle samples. I’m asking myself why I would want to write this book, I’m looking at the Amazon page, I’m reading the reviews to find out what people loved and hated.
Finally, I’m reading the sample and trying to really feel whether or not I want to buy the book after reading that sample. Why or why not? That all goes into my global understanding of books.
I will say that book titles are very important, and sometimes it’s counterintuitive what works (not that I can begin to claim to know everything about book titles!). Over here, I wrote a whole post about book titles.
You might also enjoy my podcast interview with Tucker Max, where we get really deep into book-buying psychology.