Russ Roberts' Wild Problems is a short but interesting book. The central idea is that there are some problems which are "wild", e.g. they don't have a clear way to measure the results or make a decision. A good example is having kids or choosing whom to marry. It's difficult to boil these life-changing decisions down to a simple pro/con list.
One of the central characters in the book is Charles Darwin. We have all of Darwin's notebooks and writings, so we can see him stressing out over some of these same decisions (namely who to marry), written in his own hand.
Darwin basically creates a pro/con list, which is an amusing read. Under pros, he thinks that he'll be healthier and happier (comforted by a woman), and under cons, he lists out all sorts of issues with where he might have to spend time: seeing his in-laws, going to children's obligations, leaving London for the suburbs, etc.
It sums up to: "will spending time having a family take away from becoming the scientist I'm meant to be?"
In some ways this is laughable: Darwin is one of the most famous scientists of all time. He kept thousands of pages of meticulous notes for years on how organisms grow and develop. And yet he was still worried about whether having a family would take away from his scientific pursuits. It's also a good reminder of just how universal these problems are.
Wild problems aren't always evident from the outside
The big issue with wild problems is that the experience being on the other side of them is fundamentally different than the experience of assessing them from the outside! You can make a guess at what it will be like to live in New York City, but you won't truly understand all the ups and downs until you do it.
I'm not sure that Roberts provides a great solution to this problem other than trying to ask the people who have lived it. I think the crux though is that 'living' a certain way consists of thousands of tiny individual experiences that are impossible to really capture.
Wild problems are identity-based
One idea that really gave me a big a-ha was the idea that making a decision in a 'Wild Problem' is primarily a decision of "who you want to be". A colleague who was making the decision to change jobs hard to try on the identify of moving from being a Stanford professor to being a Harvard professor.
There are two saving graces to this idea. 1) If you keep your identity small, you are more likely to fluidly move from one wild problem to the next and not attach any stigma to the choice you make. 2) how happy you'll be is largely defined by your own internal narrative. You are the biggest determinant in how happy you are, and can try on the idea of 'being someone else' ahead of time.
A number of the examples feel 'cherry-picked', and I'm not sure how much directly tactical advice exists in the book. That said, I think it's a reasonable reminder for anyone who is facing a big decision that they control their own narrative. The story you tell yourself is the most important one... and it's one you can change!