In ancient Rome, there was an entrepreneur-turned-statesman named Lucius Seneca. He was a philosopher who counted himself among the Roman Stoics. Seneca started from humble beginnings and rose to become one of the wealthiest and most powerful men in the world at the time. Some people say he was like a modern day investment banker, but he was a bit more difficult to classify than that. He was an entrepreneur who built up a fortune, lost most of it, and faced exile for years before eventually returning to Rome. Slowly, Seneca rebuilt his fortune. Towards the peak of his power, he was a bit like a venture capitalist or entrepreneur-in-residence for the Roman State. Seneca tutored the Roman Emperor, Nero, and was regarded by many as one of the wisest men in Rome.
Seneca’s success and popularity had turned him into an enemy of the state, and towards the end of his life, he was faced with death for the crime of being too good. The corrupt emperor, Nero, who sentenced Seneca to death, didn’t realize that Seneca was a master of long-term thinking. Seneca strategized as to how his teachings would survive and grow after he was gone. He knew the state would confiscate and destroy nearly everything he owned, so he needed a way to make his teachings antifragile. He compiled many of his teachings and philosophies into letters, which he strategically mailed to his friend, Lucilius. Those letters which Seneca wrote to Lucilius became a book called Letters from a Stoic, or sometimes called Seneca’s Epistles.
In letter IX of Seneca’s Epistles, he writes to Lucilius and relays with admiration the story of Stilbo, a practicing Roman Stoic. Being a practicing stoic meant that he would occasionally go through the mental practice of writing things off, or preparing in advance for the loss of certain things. We’ve seen earlier that reflecting on our own mortality is an endless well for our motivational thirst. The practice of considering losing what, and who, we love is no different. This practice forces us to face the present moment with gratitude. It forces us into engagement and ensures that we properly value those we love today, while we still have them.