If one liked primary and secondary works by and about Michel de Montaigne (1533–1592; e.g. his essays and biography) where could one turn to next? The Stoics and Nassim Nicholas Taleb come to mind. Who else? Any specific "modern" authors from Asian philosophy perhaps?
If the common thread to Stoics, Montaigne and Taleb is reflexion on living one's life and aphoristic style, who comes to mind first are French moralists, Pascal (especially his Pensées) and La Rochefoucauld being the most famous. "The French Moralists were those writers continuing a tradition in French literature, originating in Michel de Montaigne's Essays, concerned with the description of the moral character of humanity and with providing prescriptive rules, embodied as maxims, to guide living well... perhaps the largest coherent group of writers of aphorisms in the Western literary tradition".
The father of philosophical pessimism, Schopenhauer, wrote a book Parerga and Paralipomena (Appendices and Omissions) with the second part in roughly the same genre. "The subject matter and stylistic arrangement of the paralipomena were significant influences on the work of philosopher and psychologist Paul Ree, and through him most notably the philosopher Friedrich Nietzsche, whose later work explores—following Schopenhauer—the relation of man to himself, the universe, the state, and women through the art of aphorism". This may be particularly fitting since he was significantly influenced by Eastern thought.
Speaking more broadly, some writings by literary existentialists (e.g. Sartre and Camus) may be of interest, Bertrand Russell in his late essays (from 1920s), and some Freudians, starting with Freud's own Civilization and Its Discontents. Fromm's The Art of Loving "recapitulated and complemented the theoretical principles of human nature found in Fromm's Escape from Freedom and Man for Himself...", and Jung was inspired by Eastern philosophy and religion. I suppose Stoics like Seneca, Epictet and Mark Aurelius count too, but if you are looking for edginess there is not much of that there.
Not sure what to make of Taleb, perhaps he is related as in Thatcher's quip:"Economics are the method, but the object is to change the soul." Then this review gives some pointers:"Books like Nicholas Taleb's The Black Swan, Malcolm Gladwell's The Tipping Point and Blink, Gerd Gigerenzer's Gut Feelings, or in the UK Richard Layard's Happiness and Charles Leadbeater's We-Think, are making the same basic proposal. How can I make sense of my personal behaviour as I face the crisis of work, the shocks of globalisation, the pervasiveness of technology, the distractions of consumerism, the churnings of gender and ethnicity?" In the same vein here is Taleb's view of Freakonomics:"I consider Freakonomics one of the few works in empirical economics that is robust to consequential observation errors (i.e., Black Swans). And the results do not come from data mining (unlike, say epidemiology or quantitative finance)".