Answering your Questions


Hey friends,

This week, I did a 600,000 subscribers Q&A video on YouTube where I answered ~20 questions sent in via Twitter. In this email, I’ll post some quick notes to some of the more interesting answers in case you don’t have the time to sit through 26 minutes of video (don’t worry, I don’t blame you).

How did you figure out what you wanted to do on YouTube?

Tried a lot of things, some of them stuck, others didn’t. Pursued the ones that (a) I enjoyed making, and (b) seemed to resonate with people.

What is something that 99% of your followers don’t know?

I’ve had a stutter since the age of ~5. It’s quite annoying.

Advice on starting a YouTube channel?

Focus on quantity. The quality will follow. Related post: The Parable of the Pottery Class.

Most important principle in your life?

These days, to maximise randomness and optionality. Ie: to keep my options open because the future is so unpredictable.

5 Habits that have brought the most value?

  1. Reading a lot
  2. Listening to lots of podcasts (I’m a 2x speed kinda guy)
  3. The Capture Habit
  4. Understanding the Trichotomy of Control
  5. Brushing my teeth

Most Valuable Micro-Efficiency to save time in the long term?

Alfred – an incredible Mac app that lets you navigate the computer with keyboard shortcuts. Here’s a blog post I wrote about it years ago.

One thing you’d put on a billboard?

It won’t make you happy.

Advice for starting a blog?

Consistency and patience. At the start it’ll feel like you’re shouting into the void. Keep at it.

AirPods or Apple Watch?

The AirPods are life-changing. The Apple Watch is meh kinda nice to have.

If you could go back 5 years what would you change?

I’d take 100x as many notes on the stuff I was reading, watching and listening to. I’d write book reviews for every book I’d read. And I’d post all of it publicly on my blog.

Hope some of that was helpful. If you fancy checking the video out, there are time stamps in its video description and in the pinned comment so you don’t have to watch all of it if you’re just interested in specifics 🙂

Have a great week!


This Week On Not Overthinking

Not Overthinking is the weekly podcast hosted by me and my brother. If you enjoy these emails, you’ll hopefully like that too. You can listen on Apple PodcastsSpotifyGoogle PodcastsStitcherCastro (my favourite podcast app) or any other podcast app – just search for ‘Not Overthinking’.

Vision, Leadership and Winning the Lottery – An open-ended discussion | Not Overthinking

In this episode we take a ramble through a number of topics from statistics to value propositions to what we’d do if we won the lottery to Animal Crossing. Enjoy!

My Favourite Things This Week

1 – Article – Signaling as a Service – This was an article recommended by Nat Eliason which looks at the roles that status and signalling have in our lives. I’d like to think that my own behaviour isn’t motivated by signalling, but reading articles like this always makes you reconsider and think about all your actions and how we’re all involved, in one way or another, in some form of signalling.

2 – YouTube Video – Once again, Tom Scott has produced a wonderful video entitled Abso-b████y-lutely: Expletive Infixation which looks at a particular quirk of the English language – amusing and interesting.

3 – Book – I devoured Michael Hyatt’s Your World-Class Assistant in one sitting after someone recommended it on Twitter following this tweet:

Quote of the Week

Just write a song. Make it as stupid and silly as you can. Finish it. Allow it to be a little strange, weird and rough around the edges. In fact, go especially out of your way to try and write the worst song ever. Then try and top that with something even worse, if possible. It’s hard to find good ideas when you’re looking for good ideas, but you can sometimes find them just next door when you’re looking for bad ideas.

When you’ve written a hundred songs, you’ll look back and realize that you’ve learnt things that you couldn’t possibly have anticipated when you were starting out. I haven’t written a hundred songs, but this is my experience with writing blogposts, and I imagine songs are no different. Quantity has a quality all of its own.

From Letter To A Young Songwriter by @visakanv. Resurfaced with Readwise.

This Week’s Videos

Support the Newsletter

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Alternatively, I’d love it if you would forward the newsletter to a friend or two who might find it helpful.

Thank you!

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