Just found the piece on Reading and Rabbit Holes by Tyler Cowan (hat tip: Farnam Street – one of the best resources on learning, wisdom, mental models and more).
The money quote for me from the piece:
Follow the questions, not the books per se. Don’t focus on which books to read, focus on which questions to ask. Then the books, and other sources, will follow almost automatically.
Think about it. Asking “what book on real estate investing should I read?” is a one-way ticket to inefficient learning. There are a multitude of followup questions necessary to help hone into a recommendation. How experienced are you? What strategies do you have /goals you are trying to achieve? Do you know what real estate investing is?
But asking the right question – a better question – is a force multiplier. When you ask what book you should read, what you’re really asking is “how can I learn X?” And learning X starts with asking the right question(s).
The right question is the most specific version of what you’re most curious about and most need right now.
Instead of “what book on real estate investing should I read?”, one example might be “what are the strategies new real estate investors are using to build up their pool of available capital?” or “what are some reliable ways to reduce the amount of capital I need to invest into each real estate deal?”
Then try your question on Google, on Quora and Twitter for feedback and discussion, on relevant message forums. Follow the rabbit hole of learning: articles & posts, book recommendations, podcasts, and people to connect with.
Do the work, follow the trail of your question, then hone and ask your next question – a better question.
