Curiosity, Lightness and Self-Compassion


Hey friends,

Earlier today, I had the pleasure of doing a live stream with Khe Hy, a blogger (and now YouTuber) who I’ve been following since last year. His blog and email newsletter are wonderful, and I’ve linked several of his pieces in the My Favourite Things section of this newsletter in previous issues.

Anyway, during this 1.5h live stream, we built a Getting Things Done productivity system in Notion, while talking through the principles of GTD. During the stream, Khe very kindly shared his own snippets of wisdom about productivity – here are a three that resonated with me (quotes are paraphrased):

1. Habit change comes before new apps

We all love chasing that next productivity app, hoping it’ll make us productive. But it’s not about the apps, it’s about the habits. The best app in the world won’t help if our habits are sabotaging us. But if we’ve got the right habits, we might not even need the app.

2. Start with a Costco surfboard

Kelly Slater is the best surfer in the world. When we’re starting to learn surfing, we shouldn’t start with Kelly Slater’s board. We should start with the most basic, mattress-sized surfboard from Costco that won’t kill us if it falls on our head. Equally, with productivity apps, if we haven’t yet formed the basic habits of organisation, quick capture and weekly reviews, we shouldn’t lust after an advanced app like OmniFocus. We should focus on forming the habits first, using whatever we’ve got to hand, and only when we’re consistently doing the right things should we think about how to optimise the app that we’re using.

This one hit home for me – I’ve been using Things 3 as my task manager for a few years now (with a brief foray in the world of Todoist), but in that time, I’ve yet to form a proper ‘review’ habit – ie: regularly reviewing my project lists and reflecting on my commitments. Because Khe uses OmniFocus (and because I’ve heard others sing its praises), I was wondering if it would be worth switching to it and how steep the learning curve would be.

Khe however, told me (in a very nice way) that I should probably focus on developing the review habit with the app that I’m using currently (Things 3), and once it’s been developed, then I can consider dabbling with another app. And he was absolutely right – I was falling into the trap of lusting after a new, shiny, complicated app, when actually the bottleneck in my productivity system is the habit formation.

3.Seek approval from your 5-years-older self

Imagine you’ve got a miniature version of yourself standing on your shoulder, but he’s 5 years older. How would that person (5-years-older you) feel about how you’ve spent your time today? Would he be shaking his head? Or nodding in approval?

There are so many things I do each day that feel productive, but that really don’t move the needle. Things like clearing my email inbox, or trying to reply to all my YouTube comments, or optimising videos in a way that really doesn’t matter. Equally, there are plenty of things I don’t do that I really should – taking care of my posture, eating healthily, learning how to cook, exercising regularly. This analogy of the tiny guy on my shoulder nodding or shaking his head really resonated with me, and will (I hope) go some way towards helping me look after my longer term interests.

4. Curiosity, Lightness and Self-Compassion

But when you’re asking yourself whether 5-years-older-you would approve at what you’ve done today, ask the question with curiosity, lightness and self-compassion. Don’t beat yourself up.

I’m quite a beat-myself-up sort of person. Not in a particularly mean way. More in a “you’ve only filmed 2 videos today instead of 10, you’re a wasteman” sort of way. Maybe it’s worth changing that self-talk to something more light and compassionate 🙂

Those were just some of the lessons that I learned from our session (aside from all the Notion-specific ones). I’ll be thinking about them and trying to apply them to my life over the next few weeks. Maybe there’s something in there that can help you too.

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’.

The Principles of Productivity | Not Overthinking

In this episode, we talk about Ali’s favourite thing – productivity – much to Taimur’s joy! Or, more precisely, we talk through the structure and some of the key points from Ali’s upcoming Skillshare class on productivity including Parkinson’s law, the Pareto principle amongst other myths, laws and principles…

My Favourite Things this Week

1 – Podcast – I really enjoyed this episode of the Tim Ferriss show where he interviews Bob Iger, who was CEO of the Walt Disney Company for 15 years. Honestly, the phrase that came to mind as I was listening to it was “wow, this is delightful”.

2 – YouTube Video – Another absolutely delightful (it’s the only word to describe it) video that I watched this week was Tom Scott’s “This video has 6,857,449 views”. I’d highly recommend watching all of it through to the end. I genuinely teared up at the ending.

3 – Podcast – I also enjoyed this episode of the Knowledge Project, an interview with Jeff Hunter about Embracing Confusion. It starts off a bit slow, but had a lot of interesting takeaways about finding meaning and learning from our mistakes.

Quote of the Week

“THE SECRETS TO LIFE ARE HIDDEN BEHIND THE WORD ‘CLICHÉ.’” Shay recalled being on a specific bike ride during his rapid weight-loss period: “I remember exactly where I was. I thought to myself, ‘The secrets to life are hidden behind the word “cliché.”’ So any time you hear something that you think is a cliché, my tip to you is to perk your ears up and listen more carefully.”

From Tools of Titans by Tim Ferriss. Resurfaced with Readwise.

This Week’s Videos

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