The financial weirdness of health insurance in 2018

I’d like to start by admitting that I’m not nearly qualified for anything I’m writing here to count as “definitive”. So take it with a huge grain of salt, do your own supplemental research, and don’t hold me accountable for any health, financial, or legal trouble you might get yourself into.

This is a strange post, and one that mostly targets the intersection between health insurance, financial strategy, and general risk/reward. It’s probably most useful to people who are pursuing financial independence / early retirement (FIRE), working on starting their own businesses, taking time off to travel and live on savings, or doing something else delightfully unusual.

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Own yourself, not stuff

Yesterday I finished reading ‘Goodbye, Things‘, which I found to be a quick and enjoyable read on minimalism. I’m happy to find another book on the subject, since I find it useful to read (or reread) one every six months or so. It’s like a fresh blast of inspiration to declutter, clean, and optimize my life.

But I think the true power of minimalism is in the mindset shift that follows. Because once you start to appreciate the power of less – the idea can start to spread, benefitting parts of your life far beyond physical objects.

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Finding happiness through reduction

Let me preface this by saying that happiness, like many words, is kinda bullshit.

So this post is actually about finding passion(s), a general sense of contentment, or perhaps a mild but stable sense of enjoyment in life. Things that I think are real and attainable – rather than some inflated notion of ‘happiness’ that tries to promise us an unbounded state of ecstasy.


Happiness is a myth . . . It was invented to make us buy things.

– Gregory David Roberts, Shantaram


Something I once heard that stuck with me is that happiness is the difference between expectations and reality… So maybe it’s having an unrealistic expectation for ‘happiness’ that sets us up for failure in the first place.

Anyway…

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India, and taking on the Rickshaw Run

Last month my buddy Lars and I made it back from India, in one piece thankfully, from a thoroughly ridiculous event known as The Rickshaw Run

It’s an absurd concept – where your fine self and a pile of other madwomen and madmen start at the top of India and race alllll the way to the bottom… In an auto-rickshaw. A silly three-wheeled lawnmower of a vehicle with a top speed of roughly ~30mph downhill on the highway.

They are notorious for breaking down, tipping over, falling apart, and of course – being the most fun way of possibly seeing the Indian subcontinent.

Our noble lawnmower, atop some mountain somewhere in India
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What I packed for 7 weeks in Southeast Asia

The milky way above a mountain pass in northern Thailand

I knew I was going to be overseas for seven weeks, staying mostly in hostels, and that I wanted to pack as light as possible while dabbling in some fairly serious photography.

This article wanders a bit, but I’ll try to cover the packing philosophy I used, the key decisions I made, and provide a list of everything I carried.

In the end it felt like I had everything needed, and my total packed weight wound up being just under 20 pounds; including the clothes on my back and the shoes on my feet.

This kit worked great for my needs in Singapore, Bali, Thailand, Cambodia, and Vietnam.

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