The Optimisation Paradox


Hey friends,

Quick thing before we start: My team and I are fleshing out new productivity software ideas. We’re looking for an awesome product designer to join us. If you’re interested, let me know in this form & we’ll be in touch if we think there’s a fit.

Anyway, I was watching some videos about video games this week (as one does), and I came across a great quote from a game designer: “Left unchecked, players will optimise the fun out of the game they’re playing”. It refers to the natural tendency of a certain type of video game player to do whatever it takes to ‘optimise’ their character, even at the expense of actually having fun.

I found myself thinking about this quote in the context of my own life and business. In particular, my podcast: Deep Dive. It’s been running for around 2.5y, it’s grown to around 450k subscribers on YouTube, and we’ve done over 100 episodes across 8 seasons. The podcast started as a source of fun for me. It was supposed to be a fun, chill way to have interesting conversations with interesting people, and share those conversations with the audience. And it worked – I was able to connect with incredible people, have some wonderful conversations, and publish those to the internet (in audio and video format over the last 2+ years) to hopefully add some value to viewers and listeners.

But somewhere down the line, the scale tipped. What started as a passion project slowly morphed into something less… fun. It’s a strange phenomenon, really. Much like video gamers, I found myself wanting to optimise every aspect of Deep Dive and encouraging my team to approach it in this way. From planning titles and thumbnails ahead of time, to batch filming 15 episodes in “filming weeks”, to structuring the conversation in a way that would add the most value to the audience, rather than based on my own curiosity. Over time, the focus shifted from the joy of conversation to the strategy of audience engagement, retention and growth. The podcast that was once a source of fun and learning began to feel like a job — another platform to consistently post content on for the sake of algorithms and audiences, for growth and monetisation.

Don’t get me wrong – there’s nothing wrong with optimising something for growth, and “treating it like a business”. But it comes with the trade-off that usually, the thing becomes a little less fun.

This is the danger with overly monetising any hobby. It’s really fun, for example, to make money from doing close-up magic. In my university days, I used to get paid £100 per hour to walk around balls and parties and offer to show guests magic tricks. That was really cool. But having spoken to plenty of professional magicians, when magic shifts from being a fun hobby that earns pocket money, and becomes a major source of income, it loses some of the magic and joy it once had.

That’s where I’ve come to with the podcast. I’ve optimised the fun out of it. And a few weeks ago, I decided after some long journaling sessions, to “de-optimise” the podcast, to bring the fun back into it.

I’ve made a video covering this in more detail, but in a nutshell, it involves:

  • Not being wedded to an upload schedule
  • Not seeking to batch-film multiple episodes at a time
  • Recording conversations with guests I’m interested in talking to if the opportunity arises
  • Having the conversation that I want to have, rather than the conversation I think the audience wants to hear

This absolutely isn’t the recipe for podcast growth. But that’s the point. The focus of our podcast is shifting away from “growth and monetisation” and back towards “being a fun thing that Ali enjoys”.

This has been a hard decision to make because, by all accounts, the podcast is doing really well. We’ve been breaking internal viewer records each month, our sponsorship rates keep increasing, and we keep getting amazing comments on the YouTube channel from people getting enormous value from the episodes. Because things are going well, it’s felt harder than it would’ve otherwise to take my foot off the proverbial gas pedal. But after some soul searching, I came to the conclusion that it has to be done.

So moving forwards, Deep Dive will continue as a podcast, but it’ll be less “optimised”. For example, I often have super interesting Zoom calls and coaching sessions about growing the business, which I often think: “man this would make for such a good podcast episode” but we never publish them because they’re too niche, or not high-quality enough, or not relatable to the majority of our audience. The plan moving forwards, is to publish more of these sorts of episodes, knowing they won’t get massive views, but might add a lot of value to the right person at the right time.

So I’ll leave you with this question: in your own work and life, are there any areas where you’re at risk of optimising the fun out of them? Do hit reply and let me know if so.

Have a great week!

Ali xx

💻 WeWork

Being able to work remotely is pretty game changing. You don’t have to spend time and money commuting, and often you can work from anywhere in the world. But it has its downsides too – it can get pretty lonely working from home, and if you’re off travelling it can be really hard to find somewhere to sit down and work.

That’s where WeWork comes in. WeWork is a co-working space with offices all over the world. They have everything you need – fast WiFi, free tea and coffee, and loads of desk space and meeting rooms, so that you always have somewhere to get your work done, whether that’s alone or with friends and co-workers.

And, with a WeWork All Access monthly membership, you can book one co-working space or private office a day, and you can book meeting rooms by the hour at locations around the world with credits on your WeWork All Access account. Check out this link,, and enter the code ALIWORKS20 for 20% off a WeWork All Access monthly membership, and transform the way you work.

Thanks to WeWork for sponsoring this issue of Sunday Snippets 🙏

❤️ My Favourite Things this Week

  1. Podcast – I really enjoyed Tim Ferriss’ latest conversation with Greg McKeown (author of Essentialism). They shared some good ideas around how to find your purpose, and the importance of investing in important relationships without regret. This is the sort of stuff I’ve been thinking about a lot recently, so the conversation really hit home.
  2. YouTube Channel – In my recent quest to level-up my relationships game, I’ve discovered the YouTube channel Jimmy on Relationships and been binging literally dozens of his videos each day. They’re incredible.
  3. Blog Post – I absolutely loved this blog post (and its sequel) from Jay Acunzo titled The Idea Impact Matrix: How to Craft Higher-Impact Content. Some really practical, useful advice around how to stand out in this online creator business game lots of us are playing.
  4. Video – This was a really cool live coaching session where Nathan Barry (founder of ConvertKit, the platform I’m using to send this email) coaches Tiago Forte on how to grow his business to $10m/y. If you’re an entrepreneur (or an aspiring one) there’s a lot to be gained from the way Nathan thinks about business strategy in this easy-to-follow video.

PS: My friend and YouTuber Nathaniel Drew is launching his video editing & animation course, Frame by Frame, for its final live cohort. My editing team has taken the course, and it’s amazing. If you’re interested in learning how to edit, animate, or shoot great videos (or level up your existing skills), you should definitely jump in while it’s still available. Use this link + Coupon Code ALIFRAME3 to get 20% off the course when you join.

🎬 My New Videos

🗻 How to Figure Out What You Really Want in Life – Hey friends, this is the second in a series of videos about how to figure out what to do with your life. In this video, I’ll be going through a bunch of different techniques and journalling prompts to help you understand your life up to this point, which will hopefully help you make decisions about the future.

⏳How to Change your Life in a Year – Hey friends, this is the third in a series of videos about how to figure out what to do with your life. In this video, I’ll be going through a how to go figure out what you might want from the next 10 years of your life, down to how to change your life this year. Enjoy x

Also, check out my Wheel of Life Quiz! It will help you figure out your satisfaction in life right now, so that you can make positive changes to improve your happiness and wellbeing.

✍️ Quote of the Week

“Wanting well, like thinking clearly, is not an ability we’re born with. It’s a freedom we have to earn. Due to one powerful yet little-known feature of human desire, that freedom is hard-won.”

From Wanting by Luke Burgis. Resurfaced using Readwise.

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