Or, Proactive Planned Paranoia: An ounce of prevention is worth a pound of cure when it comes to tail risk. Related: preventative medicine
Building on: What Doesn’t Happen
It’s a good idea to set aside a fixed amount of time each week for Proactive Prevention and Planning (PPP). This means proactively looking for possible threats that you aren’t currently aware of (unknown unknowns) in addition to researching already known threats (known unknowns). As you come across and learn more about these threats, you can start creating plans for how to avoid these unwanted scenarios.
It’s hard to see that payoff for this kind of work because the reward is having something not happen to you, which doesn’t register in the same way as getting something. So, psychologically, you have to treat this time as overhead or a necessary write-off, like how you would treat paying your insurance premiums. In a way, this is a form of insurance.
Sex ed is a good example of Proactive Prevention and Planning (PPP). The purpose of sex ed is to teach kids about sex, STDs and pregnancy and inform them on ways to avoid contracting STDS or getting an unwanted pregnancy (basically, wear a condom). By educating kids about this sort of stuff before they start having sex, you have the potential to avoid a ton of unwanted situations in the future.
If you want to apply this idea, you could set aside an hour each week to look for and research threats in various domains, including but limited to: Diseases, Finances, Violent Confrontations, War, Political Upheaval, etc. In addition to planning for these scenarios with large downside, you should also plan for scenarios with large upside. Downside risk is obvious, but there is also risk associated with upside that people often ignore (see: Upside Risk). The classic example of some upside scenarios that you’d probably want to plan for include increases in money, power, status, sexual desirability, etc.
Related: Negative Decision Making