via: http://www.ft.com/cms/s/0/5d5aa24e-23a4-11de-996a-00144feabdc0.html?nclick_check=1

1. What is fragile should break early while it is still small. Nothing should ever become too big to fail.
2. No socialisation of losses and privatisation of gains.
3. People who were driving a school bus blindfolded (and crashed it) should never be given a new bus.
4. Do not let someone making an “incentive” bonus manage a nuclear plant – or your financial risks.
5. Counter-balance complexity with simplicity.
6. Do not give children sticks of dynamite, even if they come with a warning.
7. Only Ponzi schemes should depend on confidence.
8. Do not give an addict more drugs if he has withdrawal pains.
9. Citizens should not depend on financial assets or fallible “expert” advice for their retirement.
10. Make an omelette with the broken eggs.

see also: black swan (and in more detail taleb's rules)

In thinking about system design, it’s important to avoid the temptation to develop detailed top down blueprints for systems. Taleb observes that “if about everything top-down fragilizes and blocks antifragility and growth, everything bottom-up thrives under the right amount of stress and disorder.” Nevertheless, there are certain design principles that emerge from Taleb’s work that can help reduce the fragility of the systems we design. http://edgeperspectives.typepad.com/edge_perspectives/2013/04/getting-stronger-through-stress-making-black-swans-work-for-you.html

1. Stick to simple rules
2. Decentralize
3. Develop layered systems
4. Build in redundancy and overcompensation
5. Resist the urge to suppress randomness
6. Ensure everyone has “skin in the game”
7. Give higher status to practitioners rather than theoreticians

1. Pursue barbell approaches
2. Focus on options
3. Be curious
4. Get out of your comfort zone
5. Focus on the edge
6. Conduct lots of experiments and tinker
7. Don’t get consumed by data
8. Focus on building/accessing tacit knowledge rather than rationality and explicit knowledge
9. Focus on subtractive knowledge
10. Collaborate and trade
11. Respect the old
12. Beware of wealth, debt and reputation

“The Chaos Monkey is here to help you practice switching gears, help you build antifragile responses, help you get stronger and smarter about your life, so that you survive even bigger monkeys in the future.”

https://medium.com/better-humans/c02337782a89