21 Lessons from 999 Episodes - Naval Ravikant, Roger Federer & Vincent van Gogh - #999 artwork

21 Lessons from 999 Episodes - Naval Ravikant, Roger Federer & Vincent van Gogh - #999

Modern Wisdom

September 27, 2025

To celebrate 999, almost 1000, episodes of Modern Wisdom, I broke down some of my favourite lessons, insights and quotes from the last hundred episodes.
Speakers: Chris Williamson

Topics: Society & Culture, Health & Fitness

**Chris Williamson** (0:04)
999 episodes.
Don't know what to say, really. It's a lot, and I wouldn't have thought that it was even half that number if it hadn't been for the fact that they were all recorded and numbered. And on Monday, episode 1000 goes live with Matthew McConaughey on the biggest video wall in Texas with a real life Airstream reversed onto the set. And I'm about to go on tour, so it kind of all feels, there's a lot of chaos happening at the moment, it's very exciting. But it's been interesting getting to do this, preparing for this episode and sort of reflecting on seven and a half years of not really knowing what I'm doing, and hoping that something good and useful comes out of it. And we just crossed a billion plays, which is also very flattering. But it's felt like a period of reflection. And today, I'm going to take you through some of the best lessons that I think I've ever learned. And it's from the last 100 episodes only, or since February time. Stuff from the newsletter, things that I've read, ideas that I've taken from the podcast. But I've worked really hard. So if this, if 999 is a flop, we'll just throw this one in the bin, chalk it up that I fucked it. And McConaughey is phenomenal on Monday. So you just, but I think this one is really special. I hope it's going to be. I did mention I'm going on tour. A lot of those shows are sold out. So Toronto sold out, Los Angeles is sold out, Austin, no, Nashville sold out, and Vancouver all sold out. But there are still tickets available. If you want to go and see me on tour, chriswilliamson.live, I'm doing New York on Thursday, October 23rd at the Town Hall. I am doing tour that sold out. All of those are sold out. Boston at the Wilbur, Thursday, November 13th. Chicago at the Vic, Friday, November 14th. Austin at the Paramount, the adopted hometown show on Thursday, November 20th. Salt Lake City at the Complex, Thursday, December 4th. Denver at the Paramount Theater, Friday, December 5th. And that's it, because Vancouver sold out. All of those are available now at chriswilliamson.live. So you can go and get those tickets. It's a huge show. It's sold out in London. It's sold out in Australia. It's an hour and a half long of just me. Zach Talander is warming up playing music. There's a Q&A at the end. There's meet and greet. It's all happening. So go and get your tickets now. Also, I wanted to give you a gift in true British fashion. Try and give back after giving 999 episodes. I have made a playlist of music. This has been something that's been requested for quite a while. I've made the Modern Wisdom Bangers playlist, which is all of the stuff that I listen to, a lot of tracks that you'll have heard me speak about on the show, use in vlogs that Max, the videographer will have used in those, plus just stuff that inspires me generally. There is a lot of metal, emo stuff, alternative music, grime, drum bass. It's everything. You can go and get the brand new Modern Wisdom Bangers playlist at chriswillx.com/bangers.
You can go and save that playlist. I hope it's cool. I really enjoyed putting it together and thinking about music taste. But before we even get started, thank you to everyone who supported the show. Those of you that have been here from the early hundreds episodes, think about this. If you started listening to the show on episode 499, you were in the first 50 percent, 499 episodes and you're in the first 50 percent of listeners arriving, which is crazy. Up to that point, we'd already had Peterson on, I think, maybe twice. James Clear had been on, Robert Greene had been on, Rory Sutherland had been on a ton of times. We've done 30 Lifehacks episodes, just about moved countries. Very strange, but feeling the love at the moment and I'm super fired up. The next few months have got the biggest episodes that we've ever done. The run that we recorded in London is out of this world, so I very much appreciate you all. Enough waffle and retrospective whimsy from me. Let's get into some lessons. All right, first one. I've been thinking about the shame of simple pleasures. There's a quote from Visekan Verasamy that says, I have not yet grown wise enough to deeply enjoy simple things. We are all terrible accountants of our own joy. Most of us only accept deposits when the transaction is sufficiently large. The day we get married, the night that we played the main stage at Glastonbury, the moment that the business sells for $100 million, anything less, and the entry doesn't even make the ledger. We treat small pleasures like counterfeit currency. And you think, oh, that little thing made your day, that small moment made your week, how feeble, how desperate, how limited your life must be to be thrilled by something so unimpressive. You must not have a lot going on. We roll our eyes at the tiny events that others get excited at, as though joy must be proportionate to scale. And yet, life is made up of little things exactly like this. Not once in a while, always. Your life is entirely constructed out of moments so small, they wouldn't even register as events on someone's calendar. So, why can't something small be something great? Well, I realized sometimes I feel things more deeply than I should do, including the shame at feeling things more deeply than I should do, and also including the shame of being delighted by little things more than I think I should. And I felt like it was as if taking pleasure in something tiny revealed the smallness of my life. But maybe that's exactly backward. Maybe the true richness of a life is how much joy you can harvest from the smallest possible patch of soil. And here's the payoff. When you lower the threshold for joy, you don't just get more of it, you get it now. Like, who is truly the more impressive person? The one who requires a grand cathedral of bullshit, fanfare and galactic accomplishment in order to get the slightest flicker of pleasure, like some masochist at a sex party demanding car batteries get clamped onto his nipples before he can even get started. Or the person who can do it with a good coffee and a fresh breeze. This feels like a test of emotional robustness. If the only experiences you allow to bring you joy are big, impressive and rare, then your happiness is brittle. You've made it dependent on external circumstances lining up in just the right way. You have taken your joy hostage until the ransom note of life offers you something sufficiently worth it. We are already primed to be easy to trigger. Just not in the right direction. Think about this. We already let the tiniest inconveniences ruin our mood. A slow barista, the Wi-Fi buffering, a traffic jam that adds seven minutes to our commute. So our threshold for irritation is comically low, but our threshold for joy is absurdly high. A stranger's smile doesn't count. A great song coming on shuffle is not enough. Throwing a towel into the washing basket from across the room, that's lame. If something as insignificant as a red light can make you snap, why can't a good coffee make you glow? We are already easily tipped into frustration. So you have to work equally hard to be as easy to tip into delight. So Joe Hudson says enjoyment is efficiency. The less grandiosity that you need to feel good, the more happiness coins that you get to pick up across your day. So a good challenge is how little of a thing could happen to make your day. That's a great question to ask. How little of a thing could happen to make your day? How much excitement could you squeeze out of clean bedsheets, or the smell of rain on hot pavement, or a cool breeze when you step outside? Small winds might seem feeble, but refusing to take joy from mundane victories simply because they're insufficiently grand is the same as refusing a free ride to the airport just because you're getting on a plane when you arrive there. So ask yourself this, what if something small could be something great? Most people already have a high threshold for joy. Do not make it worse by feeling shame when little things break through your defenses and make you smile. I adore this idea because it speaks to, you know, sort of frankly, this odd sense of shame that I have had about taking pleasure in small things being a comment on not being impressive enough. That there is this kind of embarrassment that, you know, seeing a cute golden retriever on your morning walk is enough to make your morning. Because how small does your life have to be that that's the thing that breaks through. But it just seems to me that if you hold your happiness hostage, you have got the entire idea of how happiness is supposed to work upside down. And even if you have the most grand, extravagant life, you're going from private jet to Michelin star restaurant to rock concert, to art exhibition, to LSD, whatever it is. Like even in between those things, there are opportunities for you to have your day made by something small. And since thinking about that idea more, it has made a huge impact on me. So what if something small could be something great? Similarly to that, I talked about this idea from Joe Hudson, that operator guy to idea guy, which is you need to think about where productivity comes from a little bit more carefully. And I also realized that there is surprisingly an analogy between gastric band surgery and being busy. So the gastric band surgery of being busy is after ongoing gastric band surgery, people's risk of suicide tends to go up. And that's perhaps unsurprising because gastric band surgery is a big deal and can sometimes have complications, infections, painful outcomes. You're literally like putting a belt around your stomach to make it smaller so that you can't eat as much. It's like the old school version of a Zempik. You're physically getting in there and having to limit the space. But one of the unseen reasons for this increased suicide risk is actually due to the surgery going right, not it going wrong. So you understand gastric band surgery, lots of complications, infections, painful outcomes, but it going right can have as bad of an impact on people as it going wrong. Many patients used food as a way to deal with issues in their lives, emotional challenges, loneliness, anxiety, and after having their stomach shrunk, the ability to use food as a comforting crutch has been taken away. But the emotional challenges that they were using food to deal with still remain. So the coping mechanism has been taken away and it forces patients now to face their issues without a release valve. And I think that there is an equivalent dynamic happening when you try to elevate your life to take your sense of self-worth from things other than your work and your level of busyness. So let's say that in the past you used busyness and chaos as a way to distract yourself from feeling unwanted emotions. It meant that you didn't need to reflect on your decisions or sit in discomfort, that you're moving so quickly that you never fully connect with the things that are happening in your life. Lost relationships, disconnected friends, poor decisions, accumulated negative character traits, they're all swept away so quickly that you don't even have time to consider them by manic work rate. So eventually you realize that chaotic business is not your highest calling in life and maybe you value different things now or maybe you've outgrown that phase of your life or maybe you realize that busyness for busyness' sake is detaching you from connecting to your existence. So the question here is what happens when this coping mechanism gets taken away?

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