I cannot recommend Alain de Botton‘s The School of Life enough. I know of no other thinkers who approach and understand the wide range of pains of the modern world as profoundly, yet keeping a sober optimism about the future.
This is a fine example of their work, a short video essay on the dark side of meritocracy: https://www.youtube.com/watch?v=bTDGdKaMDhQ
YouTube Channel: https://www.youtube.com/channel/UC7IcJI8PUf5Z3zKxnZvTBog
Text essays: http://www.thebookoflife.org