Wild Problems: A Guide to the Decisions That Define Us

Wild problems are the sorts of problems that Pro vs Con lists don't quite help with. They're problems where the unknowns surpass the knowns, such as whether to have kids, whether and who to marry, where to live, where to work, etc. The core issue is that evaluating options requires already being there. No one knows what marriage, particularly to a specific person, is like until they are married to them.

Roberts writes clearly and has many great insights, particularly about how to think about these problems. However, don't expect a simple plan that gives you the solution; he can't tell you whether you should marry a specific person, but does offer several guides and tips about making good decisions and minimizing regret. Overall, a nice read.