Afterthoughts: Not Overthinking Podcast

Afterthoughts: Anything You Want by Derek Sivers

Afterthoughts: A Force For Good by Daniel Goleman

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Not Overthinking is a podcast hosted by brothers, Taimur and Ali. They chat about happiness, creativity, and the human condition. Having listened to the entirety of their catalogue, I would probably agree with that assessment. 

I have had an on-and-off relationship with podcasts. The first time I learnt of their existence, I happened to stumble across Tim Ferriss’s all the way back in 2013. I listened to a few and marvelled at what a neat concept they were. Here I am learning from people who have done things, it was paradigm-shifting, and contrasted with the mundanity of school. But after a few weeks of listening, I found it a chore to get through. It felt like homework. Not Overthinking is the first (and only) podcast I consistently listen to, week-in and week-out.

What makes it so appealing?

Thanos’ describes how I feel about the podcast.

The selling point of the podcast are the host’s and what they each bring to the conversation. Ali comes across as a classic Type-A personality while Taimur, a Type-B. Alone, this makes the conversations interesting. But when you add that they have differing careers, strong opinions, and generally care-free natures, the blend becomes all the more appealing. The familiarity and comfort that being brothers affords them reduces the lead time into getting into spicy debate. The resulting dynamic of the conversations instantly differentiates the podcast from any other I’ve listened to. 

The Hosts

Ali is a voracious reader while Taimur lives on the internet. It makes for a fabulous balance. Most of the time, Ali will reference books he’s read while Taimur will counter with arguments found on the web. The overlap in where they consume content is minimal. Friction among ideas is inevitable and encourages them to dive into the nuance in the topic. This is fuelled by how distinctive their respective careers are. Ali is a popular YouTuber and full-time Doctor, while Taimur is a working on a technology startup. They have enough diversity between them that falling into groupthink is unlikely. 

They are, for the most parts, open books. Ali, especially. It’s a quality that I admire of him, and so they openly admit when they practice less-than-ideal behaviours or attitudes. I remember on the episode about Status-seeking, Ali talks about a buying a bag due to function (which I suspect it may be a Peak Designs bag). The conversation led down a path where it was clear that he was in-fact status-seeking. Ali then readily submitted to this having this status-seeking behaviour. The man has no shame, and I love it. It allows the conversation to go down more interesting threads and ups the entertainment value considerably. 

A factor that I didn’t consider until writing the draft for this review was the fact that they are PoC. While they don’t market themselves as such, I think that’s a key reason why I’ve remained a fan for as long as I have been. Their perspectives are just novel: the references they make to their childhood and lives are new and interesting (to my ears). It is another point of differentiation across all of the podcasts I’ve ever listened to.

Dynamic between Taimur and Ali

What I love most is that they don’t take themselves seriously. This, combined with their familiarity with one another, breathes space for banter. It adds a light-heartedness which increases the palatability of the ideas at question and overall entertainment value. The other consequence is that they have no issues calling one another out for any perceived leaps in logic. The conversation is, therefore, often adversarial in nature but never antagonising. A issue that plagues popular adversarial systems like in the court of law or in government house among elected officials. At the end of the day, their goal is to improve their thinking on the topic – ego and vanity be damned.

In the episodes where guests feature, the first thing you notice is that this unique dynamic is disrupted and the episode loses its lustre. Having said that, the exception was the episode on Lad Culture. I found that thoroughly entertaining and hilarious that they chose that for a topic to explore.

Podcast Topics

The topics aren’t the most interesting. If you skim through the titles of the episodes, there are plenty that seem skippable like Why you should invest in a good kitchen bin. Generally, the conversations are not show-y. They talk more about things that are high-measure i.e. behaviours or experiences that have little impact on its own, but have a big impact overall because of how frequently they occur. That’s why I found the kitchen bin episode deceptively enlightening, it broke down my thinking on something I never had given a second thought. I think I gravitated to these types of topics because the market for talking about high-impact behaviours or experiences is saturated – there are probably 10 versions of the same conversation from Tim Ferriss and the disciples he has inspired. I’ve listed below a sample of episodes on topics I would have never, otherwise, given much thought to: 

  • Is ambition a virtue?
  • Why do we seek permission?
  • Words that changed our lives
  • Money, stories, and Old people

Overall impression

The listening experience is akin to observing two (smart) friends duke it out for intellectual supremacy! But, importantly, in a manner which prioritises learning and ultimately a growth mindset. My complaint with 99% of all the podcasts I have listened to is that it just feels you are being force-fed information and insight. In contrast, listening to Not Overthinking is a pleasant experience. The unique dynamic between the hosts make Not Overthinking accessible, entertaining, and ultimately good value for your time for anyone remotely interested in happiness, creativity, and the human condition.

Some of my favourite episodes

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