“You want your life to be where, if it was your last year, you’d happy with how your life turned out.” Letters from a Stoic is one of Neil’s and Nat’s favorite works of philosophy, and has taken the world by storm in a massive resurgence over the last 10 years. Unlike most philosophy works, it’s extremely readable and endlessly applicable, and you’ll stumble upon useful bits of wisdom on every page. We’ve both read it and re-read it multiple times, and knew it had to be one of the first books and collections of wisdom that we shared with you. We covered a ton of topics from the book, including:

Focusing on developing deep friendships.
Reading more timeless books and rereading books.
Practicing negative scenarios to better prepare yourself for them.
Being grateful for what you currently have.
Being content your life now, for there may not be a tomorrow.
Removing the unpragmatic fear of death.
Facing difficult obstacles head on, instead of avoiding them.

Enjoy! If you want more on Letters from a Stoic, be sure to check out Nat’s notes on the book and pick up a copy yourself. And let Neil and Nat know on Twitter what you thought of this episode!

If you enjoyed this episode, be sure to check out our other launch episode on Antifragile by Nassim Taleb, on how to turn chaos to your advantage!

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1:26 - Intro to the book discussion. Some background on Seneca and stoicism.

5:25 - The issue of not settling in one place or focusing on one thing at a time, costing you strong personal relationships and richer knowledge on one subject.

8:00 - Speaking of the Lindy rule of books, paying more attention to older books that are still popular today.

9:59 - Rereading books every so often to gain new insights and learning more from them.

12:40 - Doing things to strengthen yourself from poverty each day, learning the limits of wealth, and being content with what you have.

17:40 - Using excuses to abstain from discipline and your personal plans. Also, speaking on the nature of fasting.

22:33 - Setting aside a number of days in which you do away with indulgences and pleasures to increase your resilience and gratitude for these things.

25:47 - During times of safety, build yourself up to possible negative events to prepare yourself beforehand.

28:45 - Despite growing physically old, you can maintain your spirit, your willpower, and how you respond to negative events.

30:52 - Enjoying what you’re doing now and making sure that you’re happy with your life if it was your last year. Also, speaking on proving your words with actions and explaining Seneca’s suicide.

35:19 - Escaping deep inner issues with travel and new experiences is faulty. “The same thing that drove you away, you carry with you.”. Advice and perspective on traveling with these issues.

42:00 - Investing in religious items will not increase your chances of what you want to happen, it’s more going to come from you and what you’re doing. Also, abstaining from your pride in things that aren’t your own or that can be taken away.

46:21 - Internalizing the idea of death and making the most of your life while alive. Behaving well because it’s the right thing to do, instead of behaving well for a reward at the end of your life.

49:18 - Becoming comfortable with your death and recognizing that death is nothingness, as it was before you were born. Also, Nat on a good way to introduce others to stoicism.

51:43 - Doing away with all of those who complain or who worry about things outside of their control. Labeling unpragmatic emotions as useless and asking yourself whether it is necessary.

56:50 - Facing difficult obstacles and your struggles, instead of running away from them in order to lessen the burden.

59:22 - Being happier with less, you can appreciate having more, that much more. A few real world examples of this and some advice for being more appreciative and grateful.

1:04:22 - The issue of the constant comparison game we face today and the constant want of having more, which creates problems.

1:08:45 - Doing the things that scare you and being suspicious of the things that seem easy. Some thoughts on the timeless nature of the book and on its wide application to improve our daily lives.

1:11:20 - Wrap up and some last thoughts.

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“It is precisely in times of immunity from care that the soul should toughen itself beforehand for occasions of greater stress, and it is while Fortune is kind that it should fortify itself against her violence.”

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