Ryan Holiday — Turning the Tables (#410)

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[05:50] How adopting and taking care of a dog has taught me to be better to myself and others (and why this isn’t necessarily the right approach to personal improvement for everyone).

[16:48] Putting us at odds with our evolutionary programming, is the nature of modern life conducive to fostering neuroses and self-absorption to the point where we have to consciously cultivate empathy?

[20:02] Why did I decide to move to Austin, and how do I feel about the decision a few years into it? How does it compare to — and contrast with — other cities where I’ve lived and spent time?

[29:49] Competition is for losers.

[31:03] We’ve covered why I decided to come to Austin, but what really motivated my decision to leave the Bay Area? What historically drives my need to, as Ryan says, “walk away at the top” whether it’s from investing or the fulfillment of a seemingly impossible book deadline?

[38:21] Journaling as a way to think up new ideas rather than merely capturing them (Thanks, Kevin Kelly!), and the perks of remembering that big life choices — like moving to another city or dropping out of college — don’t have to be treated as irrevocable if we want to expand our palette of life experiences and become contenders in our craft(s) of choice.

[45:43] Contrary to popular belief, I’m very risk-averse. So when I weigh good risk vs. bad risk, here’s how I consider what there is to be gained even in the case of “failure.”

[52:10] Fear-setting, premeditatio malorum, and how I cultivate walkaway power with my own projects.

[56:54] Energy management, the value of simplicity, and the question I ask myself now when weighing my potential involvement in any project.

[1:01:12] Why I prefer conducting experiments that promote deliberate lifestyle design and quality of life improvements now to the typical “slave, save, retire” formula so ingrained in the American work ethic.

[1:07:29] Even though it can be challenging to shift gears mid-career, just remember: no one can condemn you to do anything for life just because you’re good at it — except for yourself.

[1:09:05] Costs of inaction, non-morbid ruminations on mortality, and the Stoic reminder of Memento Mori (“Remember you must die”) — that life is not on an indefinite lease.

[1:15:32] Why, even if you keep all your money in a mattress, studying good investors is worth a lot — especially if you’ve ever had a bad math teacher. Remember: anyone who’s alive invests to some capacity, whether it’s capital, time, or energy. Here are some books I recommend that should get you started.

[1:21:19] What are you going to care about if you’re lucky enough to get older than you are right now?

[1:24:23] How exploring the distinction between correlation and causation becomes even more absurd when contributing factors get downplayed or overlooked entirely and lazy media outlets report on extrapolations made from poorly understood abstracts — and the opportunity this spells for those willing to pay attention (whether they’re investors, inventors, designers, or athletes).

[1:30:35] The history of Uber — from a misunderstood concept that was universally mocked by investors to a multi-billion dollar valuation — illustrates this phenomenon and drives home the usefulness of the one percent as a demographic of price-insensitive guinea pigs for prototype testing.

[1:33:44] At any given point, we’re all getting it wrong. So how have I honed the ability to get it right at least some of the time when opportunities hiding in plain sight are ripe for the spotting?

[1:35:10] On learning from the experiences of others, sharing our experiences so others might learn from us, and trying to make sense of those who — for whatever reason — choose not to.

[1:41:46] When life’s so short, how do I decide what gets added to my reading list? What’s my methodology for breaking down books, and where do I get the knowledge that saves me painful (and time-expensive) trial and error?

[1:52:47] Why keeping on top of things is a losing game when you’re more accurately striving to get to the bottom of things.

[1:55:31] Parting thoughts and Stoic farewells.