Ryan Holiday

speaker
1,843 appearances 1 recordings 1 series first heard Jul 2026 last heard 13 Jul

Ryan Holiday’s voice in public audio — every appearance, attributed to the second.

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recordings per month · last 12 months
1 · Jul OctJan 26AprJulnow

Recordings per month over the last 12 months — 1 in all, peaking in Jul 2026 with 1.

Appearances

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I don't have these tools in my toolkit, but I do have this thing, right?
And so humility to me is a key element in matching what every battle, figurative and literal, is about, which is about matching strength against weakness.
Like, strength against strength is stupid.
It...
usually creates two losers, even if there's one winner, right?
Like what a great general does, what a great athlete does, what a great entrepreneur does,
is match strength against weakness.
Like, and by the way, also protects, hides your own weakness, right?
Because that's where you don't want their strength to go against yours.
So to me, this humility is really important.
Like knowing what you're not that good at, what you need to get better at is, yeah, it's like a big part of it.
How do you keep yourself humble?
You know, the kids help, spouse helps.
Trying to do hard shit helps.
Like if you are only doing what you're really comfortable with and you're never in situations that you're outmatched, that you're out of your depth in,
you lose that feeling of like, oh shit, I gotta figure this out.
And so like when I take on projects, one of the things I think about is like, is this something I've done before?
And if it's something I've done before, like it's not that interesting to me.
And if it's something where I'm like, oh, I'm gonna have to figure out a lot of different skills to be able to do this.
And this can be in, I don't mean like you're reinventing the wheel every time.
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