☝️ Upwarding #11: Triumph or Hope?, Do your thing, $10 sleep hack, Rebalancing

Welcome to this week's Upwarding newsletter. Issue #11


Shackleton’s Endurance is one of my favorite stories. In short, a trip to the Antarctic takes a bitter turn leaving the men stranded for almost two years before a triumphant return. When trip photographer Frank Hurley gave presentations after the voyage, he showed this picture at the end, still titled by the Royal Geographic Society as “Cheering The Relief Boat”. , supposedly showing the men’s rescue.

But..it’s not their rescue. They’re actually waving to Shackelton as he leaves them for an insane 800-mile journey through massive ice cold waves to find help. It’s not celebration, it’s hope beyond all odds. Which version do you like better?


“When you feel judged, it’s because you’re judging yourself”. Lots of interesting quotes in this piece, appropriately titled “Research Confirms No One Is Really Thinking About You”. Philosophically linked to my grandmother’s favorite quote: “To Thine Own Self Be True” (though we might be interpreting this quote incorrectly). Also linked to the greatest regret of the dying: “I wish I’d had the courage to live a life true to myself, not the life others expected of me”.


The single best thing I’ve done to improve my sleep is to block out blue light using these $10 orange glasses. Wearing them a couple of hours before bed will do wonders for your ZZZs. It will not do wonders for your sex life.


A bunch of people have contacted me recently about investing. In most cases, they either newly decided to invest in the stock market, or want to invest more this year. This is clearly related to how well stocks performed in 2019.

Our primitive brain thinks: we made money in the stock market last year, why not do more this year? This works in most of life, but not in investing.

A sane way to deal with this: 1) divide your money into buckets, with different jobs (emergency fund, retirement, etc); 2) have a predetermined and consistent allocation for that bucket (e.g. 60% stocks). 3) rebalance at regular intervals (e.g. once per year). The result: this year’s rebalance makes you sell US stocks in favor of international ones and non-stock investments.

Random Thought

I pretty much never buy in bulk, whether it’s grocery items or 10-packs of fitness classes. It seems to move my decisions away from what is natural in the moment. This article discusses bulk buying for the home.

I think the best system for home goods is a simple reorder point/reorder quantity. E.g. Always buy 10 razor blades when you have three left. We do this for everything from milk to supplements and it works very well without stress.


“There are two ways of spreading light: to be the candle or the mirror that reflects it.” -
Edith Wharton, novelist (24 Jan 1861-1937)

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