288: Testing When You Can Stop Working

This is the Monday Medley, a newsletter that goes out, you guessed it, every Monday. I republish it here for sharing and referencing, but if you'd like to sign up you can do so right here:

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Happy Monday!

First off, this is a very exciting week. You have the opportunity to own part of the US Constitution! Packy did a good writeup about it here. I've joined in, can't really pass up an opportunity to be a part of something like this.

Second, I published a post on Friday about "Yield DAOs," exploring how we can use the high returns of DeFi and organization power of DAOs to enhance our real-world lives. I'm actually talking to someone about the Cow one... stay tuned.

I also published two sets of book notes last week, one on "Mastering the Market Cycle" and one on "Die With Zero," which I'm going to riff on this week.

Dying with Zero and the Hedonic Treadmill

Die with Zero is worth picking up and reading. The core idea is quite powerful and worth ruminating on for any Type-A work driven high performer type.

If you have any money left when you die, you worked too much. Having to throw out rotten produce at the end of the week means you bought too much food, and having to redistribute tons of assets in your will means you accumulated too much money.

Why is this the case? Because any time you put towards work is time you're not putting towards fun and especially memories. Even for someone who truly loves what they do, it's unlikely they would choose to work as hard or on the same things if they didn't feel the need to accumulate more resources.

Memories are an important callout here too vs. just fun. Our perception of time and the speed at which time is passing is largely dictated by how many events and memories we can peg recent periods of time to. A party with four distinct chunks will be more memorable and remembered as more fun than a party where everyone just mingles and talks to each other (more on this in Moonwalking with Einstein).

Therefore if you want your life to feel more fun and meaningful over time, it's worthwhile to think about how you can make it more memorable. Photos and videos are an easy way to do this, so long as you make an effort to organize them into an easily digestible format for this later. I rather like Google Photos for this too, since they automatically organize photos by people, locations, and surface photos from the same date over past years.

Back to dying with zero though. Why is it worthwhile to think about trying to die with zero, vs. dying with a huge amount of wealth? As I said, any time you're putting towards work is time you're not putting towards the more meaningful things. I love what I do. But would I rather write code & words all day, or hang out with my daughter and cook with my friends? Obviously the latter. Maybe 1-2 hours of writing a day and the rest socializing. I suspect most people would end up with a similar breakdown, with some creative outlet that may or may not be profitable and then most of their time on social or exciting activities.

We usually don't do this of course because money is still a consideration and it's very hard to not get sucked into the hedonic treadmill. You get used to better and better lifestyles very quickly, and it's easy to fall into the trap of thinking you need to keep increasing your income both so you can afford the lifestyle you want, and so you can comfortably retire later.

But I think given the option, we'd prefer a comfortable, and at times lavish life with less work, than a maximally extravagant life with twice the work hours. And we'd prefer to have the option to retire when we're 40 than to have to wait till we're 65.

Die With Zero introduces a useful framework for thinking about how to achieve that. Instead of assuming your wealth should go up somewhat exponentially till some later age, then level off or decline, think about more of a gentle slope up, leveling, then a gentle slope back to zero.

It's helpful because it makes you rethink two things:

  • What kind of lifestyle would I enjoy if the need to work were removed from the equation?
  • How much do I actually need to get it?

I've recommended other books on this topic in the past, like "Money Master the Game" and "Early Retirement Extreme" but I haven't seen this concept explained quite like this before.

And I think one important aspect Perkins leaves out is testing retirement. Essentially, once you hit the ability to sustain certain lifestyle levels, try them out, and see if it's actually enough to be comfortable living on.

The 4-Hour Workweek introduced this idea as "mini retirements." Taking breaks from work for months at a time to spread out your enjoyment of non-work life throughout your life, instead of waiting for some big endless vacation later. Now I think they're not only helpful for sanity and drive, but also probably for figuring out when to stop trying to accumulate more money.

The first time I tried this was a year after I graduated, and I moved to Argentina try the passive income life for a little bit, living rather comfortably on around $3,000 a month.

It didn't make me that happy, and I realized it's not worth saving money to live somewhere without a strong community of likeminded people. So when Cosette and I moved to New York, it was worth earning more to have a more comfortable life there. That's partially what led to starting Growth Machine.

Last year, I stepped out of Growth Machine and decided to try out a few different new work paths to see what stuck. I ended up flying down the programming and crypto rabbit hole, and it went quite a bit better than I could have expected.

So now, in the spirit of working in seasons, I'm back into "not working" mode. And one question I have from reading Die With Zero is: is this enough? Does any part of my life feel lacking living at the income level I can currently live at? And if it does, does it make sense to give up some more life time in pursuit of elevating my lifestyle to that new threshold?

If not, then it doesn't make sense to work much at all for the near future. But if it does, then at least I know what new target I'm aiming at, so I can scale back down when I get there.

Have a great week,

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