"Second Visit (367 BCE): When Dionysius I's son took power, Dion convinced Plato to return and educate the young tyrant, hoping he might become the "philosopher-king" Plato described in his writings. Dionysius II showed initial interest but balked when confronted with the discipline philosophical study requires. Raised in luxury and accustomed to flattery, he wasn't willing to do the difficult inner work that genuine transformation demands."
"Third Visit (361 BCE): Despite clear evidence of failure, Plato returned after Dionysius II promised he was now ready to embrace philosophy. In his Letter 7, Plato reflects on this journey, making clear that the failure wasn't his own teaching but rather that Dionysius II had lost whatever small motivation he may have briefly possessed-if he ever truly had it in the first place. The young tyrant proved more interested in appearing philosophical than"
Plato made three journeys to Sicily aiming to influence a ruling family and cultivate philosophical rule. The first visit offended the tyrant but inspired Dion. The second attempt focused on educating Dionysius II, who showed superficial interest yet refused the disciplined inner work required for genuine change. Plato returned a third time, only to find whatever fleeting motivation existed had evaporated and the young ruler prioritized appearance over practice. The historical pattern models modern enabling dynamics: external efforts cannot force deep change, repeated "one more chance" cycles often perpetuate harm, and stepping away guards personal well-being.
Read at Psychology Today
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