Reconsider Victory Conditions


Hey friends,

One of my favourite pastimes is to think about the myriad ways in which life is like a game.

In ‘proper’ board games (ie: not terrible ones like Monopoly and Snakes & Ladders) there are often multiple ways to win the game (‘victory conditions’). We might need the highest number of points, or the biggest army, or the most castles, or some combination of those etc.

If we’re new to the game, we’d read the rulebook at the start, find the victory conditions and start following a plan that we think will lead to victory. But one of the most important strategy points in these board games is to continuously reconsider the victory conditions.

Throughout the game, as we discover more information about the game circumstances and what our opponents are doing, we should re-read the victory conditions. If we do, we may well find that the strategy we adopted at the start is no longer serving us, and that there might be a much easier way to win with an alternative strategy suited for a different victory condition.

This strategy of reconsidering victory conditions applies to life as well. Our original strategy might be ‘I need to make $250k per year to be happy’. We might spend our whole lives climbing the corporate ladder to try and get to that point. But if we were to reconsider the victory conditions, we might ask ‘do I really need all that money to be happy? Can’t I just… move somewhere less expensive?’

Or maybe we wanted to be a neurosurgeon since we were young. And so we study hard at school to get into a good university, and then at university we spend all our free time in the library to boost our grades to get a good junior doctor rotation, and then when we start working we spend all our free time doing audits and trawling for publications to boost our CV so that we can maximise our chances of getting that competitive neurosurgery training post.

Somewhere along this path, we might reconsider the victory conditions. We might wonder if there are alternative paths to happiness and meaning. True, we might well decide that we actually love the journey to becoming a neurosurgeon, and don’t mind the extra work it takes because we enjoy it. That’s great. But maybe we’d realise that we’d been so focused on our original strategy that we forgot about the bigger picture, the other ways to play and win the game.

As the year draws to a close, this is something I’m thinking a lot about. What am I really optimising for? What does ‘winning the game’ of life look like? Have the rules of the game changed since I last considered them? Are there alternative paths to victory that might now be more suited to the cards in my hand and the state of the board?

Have a great week, and thanks for a wonderful year.


This week’s podcast episode

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’.

2019: The Not Overthinking Review | Not Overthinking

In (by far) our longest episode yet, we look back on 2019. First, we go through the Not Overthinking catalogue — we talk about the episodes that stood out to us (both good and bad!) and our key takeaways from each. Then, we reflect on how 2019 went for us personally — we each dig into 3 areas of personal growth that we had this year.

My Favourite Things this week

1 – Podcast – This email was inspired by this episode of the James Altucher show. He interviews Jonathan Kay, who literally wrote a book about the life lessons we can learn from games. Can’t wait to read it.

2 – Article – Mimetic Traps – This is an excellent article about a similar theme – Why does this matter? Especially relevant for students, but it would appeal to anyone who’s wondered whether they might be pursuing something ultimately pointless or not-enjoyable.

Kindle Highlight of the Week

Most of us, of course, have never taken such vows—but we choose to live like monks anyway, rooting ourselves to a home or a career and using the future as a kind of phony ritual that justifies the present. In this way, we end up spending (as Thoreau put it) “the best part of one’s life earning money in order to enjoy a questionable liberty during the least valuable part of it.”

From Vagabonding by Rolf Potts. Resurfaced with Readwise.

This week’s videos

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