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Ancient Greeks hired philosophers to help their sons develop various skills, such as rhetoric and politics. I might not have that same kind of tutor now, but through books, conversations, and contemplation, maybe I can teach myself a little. It's like having an imaginary board of advisors with different perspectives that I can draw on, a technique that Napoleon Hill describes in depth in "Think and Grow Rich".
It might help to ask myself; What are the life skills I want to learn, and which philosophers might be able to help me along those journeys? Let me take a look at some of the things I've already learned so that I can sketch out the next steps in that trajectory.
Equanimity: From Epictetus, I learned to focus only on what I can control: not what happens to me, but how I perceive and respond to that. I've also been learning about detachment from things I don't control. Why fear death? And if one doesn't fear death, why should one fear anything lesser? I'd already found it easy to take responsibility for my own happiness and outlook, but learning from Epictetus gave me a clearer way to see all those little decisions I make about how I see the world.
Self-improvement: From Aristotle, I'm learning to allow myself to use my leisure time to improve as a person. I occasionally worry that I should be spending this time building businesses and developing marketable skills, but I'm willing to experiment with Aristotle's assertion that philosophy is a worthwhile use of leisure time. I'm also learning that virtue is a muscle that you can exercise. As you get better at finding good activities that you enjoy more than activities that get in the way of your long-term happiness, and as you get better at wanting what's good for you instead of what's bad for you, virtue will become more natural. For example, I'm working on enjoying exercise and hanging out, and I'll work on appreciating art someday.
What else would I like to learn?
Getting along with people: I like this quote I came across in Bertrand Russell's The Conquest of Happiness:
"Fundamental happiness depends more than anything else upon what may be called a friendly interest in persons and things. … The kind that makes for happiness is the kind that likes to observe people and finds pleasure in their individual traits, that wishes to afford scope for the interests and pleasures of those with whom it is brought into contact without desiring to acquire power over them or to secure their enthusiastic admiration. The person whose attitude towards others is genuinely of this kind will be a source of happiness and a recipient of reciprocal kindness. … To like many people spontaneously and without effort is perhaps the greatest of all sources of personal happiness.
… The secret of happiness is this: let your interests be as wide as possible, and let your reactions to the things and persons that interest you be as far as possible friendly rather than hostile."
I like a few people spontaneously, and others with some effort. If I can identify the things that are getting in the way of my appreciation of other people, use Epictetus' teachings to detach myself from those hidden fears and anxieties, and use Aristotle's exercises to eventually prefer things that are good for me, I think I'll be able to appreciate people more. =)
Developing a better appreciation of people is probably a good next step to focus on. It seems kinda weird to think of it as a skill to improve, but we take all sorts of things for granted (and our corresponding mediocrity as a given) when they're really skills one can learn.