A Decade Watching the Craziest Game

Investing is the craziest game I’ve ever seen. It mixes high stakes with strong emotions, intelligence with luck, and long-term innovation with short-term trading.

I started writing about investing 10 years ago this week. A few things I’ve learned …

I’ve learned that having your views confirmed is a powerful and addictive drug.

I’ve learned that most investors have a hard time distinguishing between what happened and what they think should have happened.

I’ve learned that not caring about temporary things, and obsessing over permanent things, is underrated.

I’ve learned that most risks are overblown, except the ones no one’s talking about.

I’ve learned there are two red flags: Beliefs that haven’t changed in 20 years, and beliefs that changed overnight.

I’ve learned that good marketing wins in the short run, good products win in the long run.

I’ve learned that telling the difference between patience and stubbornness is incredibly hard.

I’ve learned that the numbers of words is negatively correlated with the amount of insight.

I’ve learned that people can be led to believe and defend anything with the right incentives.

I’ve learned that the ability to absorb manageable damage is the key to success for businesses, careers, and investments.

I’ve learned that every investor should go to investment conferences, if only to meet 400 other people who look like you, think like you, speak like you, work like you, went to the same as school you, and look at the same data as you, all of whom claim to have an edge over everyone else in the room.

I’ve learned great things happen slow, and bad things happen fast, so a narrative of pessimism often accompanies a backdrop of progress.

I’ve learned that the need to earn a paycheck can override the desire for intellectual honesty.

I’ve learned that cash earns the lowest return but offers the most options, and options can provide the highest long-term returns.

I’ve learned that you can increase your reading productivity 100x by asking, “Will I still care about this a year from now?”

I’ve learned that dealing with difficult people is an increasingly important skill, as digital communication means we miss nuance that body language used to convey.

I’ve learned that doing what everyone else is doing feels like the safest thing to do, but it’s the most competitive, which makes it the riskiest.

I’ve learned that student loans can’t be discharged in bankruptcy, gambling losses are tax deductible, and people seem mostly OK with that.

I’ve learned there are popular things we will laugh at in a few years, including grocery stores, gas stations, and the expectation of privacy.


Read next
All posts