The Odyssey Plan Revisited


Hey friends,

Short(ish) email today – it’s currently 2:30am and I’ve just arrived back in London from a surfing camp in Morocco. While I was out there, I had a lot of time to think during the endless paddling to get to the waves, while of course being buffeted backwards by the oncoming waves.

One of the main things I’ve been thinking about is “what do I actually want to do with my life?”

It’s a question I’ve been asking myself a lot more since I left Medicine. A traditional career path gives an easy(ish) answer to the question – “I don’t need to think about it too hard because I’ve got a path laid out in front of me and I can just follow that path”. But as I’ve learned from speaking to dozens of other entrepreneurs, creators, authors and friends who have left ‘traditional’ career paths to carve out their own way in the world, the question of “what the hell am I doing?” comes up quite a lot.

One tool that helped me answer the question a couple of years ago is called The Odyssey Plan. It’s an exercise taught by professors at the Stanford Life Design Lab (which is apparently a thing). If you’ve followed my stuff for a while, you might’ve heard me mention it a few times.

The idea is that you answer the following 3 prompts –

  1. Write out, in detail, what your life would look like 5 years from now if you continued down your current path.
  2. Write out, in detail, what your life would look like 5 years from now if you took a completely different path.
  3. Write out, in detail, what your life would look like 5 years from now if money, social obligations, and what people would think, were irrelevant.

If you’re interested, here’s what I wrote in this newsletter in December 2019 when first thinking about this question.

But now that I feel like I’m always asking the question of “what shall I do with my life?” I think it’s time to repeat the exercise.

So, in my usual vein of using this newsletter as a source of public accountability, here’s the commitment – I’m going to map out my Odyssey Plan this week, and share the results in next week’s newsletter.

Have a great week!

Ali xx

♥️ My Favourite Things

📖 Shortform Summary – So You’ve Been Publicly Shamed by Jon Ronson. Interesting look at social media pile-ons, cancel culture, and how “shame is used as a punishment and control mechanism”.

🎙️Podcast – Deep Dive with Lauren Razavi In this episode Lauren and I talk about being a digital nomad (something I’ve been considering for a while now). We also discussed the history of borderless work, and what it means to build an internet country.

📝 Article – If money doesn’t make you happy, you probably aren’t spending it right by Elizabeth W. Dunn et al. Academic paper about the ‘weak link’ between happiness and money. Some recommendations:

  1. Buy more experiences and fewer material goods
  2. Use your money to benefit others instead of yourself
  3. Buy many small pleasures rather than fewer large ones
  4. Don’t buy extended warranties and other forms of overpriced insurance
  5. Delay consumption

📱 App – Readwise. I recently got alpha access to Readwise’s new read-it-later app (a bit like Instapaper), and it’s perfect. I can read articles in the app, and the highlights go straight to my Roam database. I might switch from Roam to Obsidian soon – shoutout to Danny Hatcher for giving me a tutorial.

✍️ Quote of the Week

Do not spoil what you have by desiring what you have not; remember that what you now have was once among the things you only hoped for.

From The Art of Happiness by Epicurus. Resurfaced using Readwise.

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