In times of comfort, we usually enjoy the ride for as long as possible. Instead, we should prepare for when things sour. By experiencing the worst-case scenario, you realise you can get through it. This knowledge, reminiscent of stoicism, will soothe your anxieties.
It’s similar to how athletes train: For example, tennis champion Roger Federer knew he would play in high humidity in Beijing, so he deliberately trained in Dubai, which has even higher humidity, to prep for his match. Author Ryan Holiday wrote about stoic philosopher Seneca in an article:
Seneca, who enjoyed great wealth as the adviser of Nero, suggested that we ought to set aside a certain number of days each month to practice poverty. Take a little food, wear your worst clothes, get away from the comfort of your home and bed. Put yourself face to face with want, he said, you’ll ask yourself “Is this what I used to dread?”
It’s important to remember that this is an exercise and not a rhetorical device. He doesn’t mean “think about” misfortune, he means live it. Comfort is the worst kind of slavery because you’re always afraid that something or someone will take it away. But if you can not just anticipate but practice misfortune, then chance loses its ability to disrupt your life.
The advice might sound extreme, and we’re certainly not telling you to live like you were homeless. In practice, this could look different for everyone. If you know there are inevitable all-nighters coming up, don’t cherish your sleep. Instead, once every couple of weeks, brace yourself by sleeping just a few hours. If you’re a freelancer, live a couple of days on a lower budget even when you’re feasting. (As a student, Elon Musk lived on a dollar a day.)
Stoicism 101: A Practical Guide for Entrepreneurs [The Blog of Tim Ferriss]