Four months earlier he was living on a Californian ranch working in exchange for rent, supporting his mother, and both of them living off credit cards until every card was full. That is where the main series starts, and the honesty of the opening is what makes the rest readable.
Jess and Philo write about deciding to stop waiting for life to work out, and they treat it as a decision with a date on it rather than as a gradual change of heart.
Their strongest idea concerns struggle as a habit. They argue that people become attached to difficulty and then define themselves by it, and that changing the world starts with noticing exactly that in yourself.
One post is purely technical, explaining how to stop a mail provider filing messages you asked for somewhere you never look.
Read the first part of the life change series if you are somewhere you cannot yet see a way out of.