Practical Wisdom

Practical Wisdom

Practical Wisdom is allowing someone to evolve, rather than follow a ruleset.

3 Points:

  • Rules are short term good, long term bad.
  • It's easier to use incentives than to influence someone to care, but is less long term effective.
  • Mastery is trial and error; a testing mindset.


Favourite Quotes:

The army is creating cooks, says Wong, leaders who are "quite adept at carrying out a recipe," rather than chefs who can "look at the ingredients available to them and create a meal. [Pg. 159 & same analogy as Tim Urban in
Top 4 Podcast Episodes
Incentives may get you what you pay for, but they often will not get you what you want... [Pg. 180]
Teaching writing is like teaching a kid how to tie a shoelace. First you describe it. Then you show it. You 'scaffold' it; I'll make this loop, you make the next one. [Pg. 253]
You give them models. Then you tweak the model and have them apply it in new situations. It's like training wheels on a bike. And it's safe for them. -Joey Hawkins [Pg. 254]
The more people's behavior at work is controlled by rules and incentives, and the less opportunity they have to exercise - and develop - practical wisdom, the worse their work will be.

Would I re-read this?

Yes. Given the large ruleset my organization uses, I want to keep this concept of 'incentives/rules can backfire' front of mind. It's also a long-form reminder of my principle of


The stories within it were hard for me to digest, but the topic is unique enough to warrant extra reading time.

One of my favorites, older minds decline. 'Brain cells die, memory gets worse.' But, "The mature mind and brain can make good decisions with less effort than the inexperienced mind..." This proves to me the power of reading and application. If I can learn dozens of heuristics per year, I'm effectively giving myself the advantage of an older brain without waiting for the biological downsides that come later in life.

What did I implement?

  • A search for incentives in my life:
    • Where are there incentives that are backfiring? Is my dentist incentivised to fix my teeth long term, or to get me to return every 6 months.
  • We damage ability to learn by prohibiting mistakes
    • Like the old saying "Once bitten, twice shy", we damage ability to learn with restrictions and rules. If someone can fail with a reversible decision, it's better training to let them fail.
      Reversible & Irreversible Decisions
    • Allowing someone to fail allows them to build their own scaffolding of wisdom, rather than relying on static rulesets/role knowledge.
  • Performance vs. Mastery People:
  • Mastery Oriented
    • Goal is to improve ability, trial and error, continuous loops.
    • Prefer hard tasks.
    • Motivated by feedback on the skill.
    • Failure = Opportunity to Learn

  • Performance Oriented
    • A form of status signaling. ("I proved I was smart by getting into Yale")
    • Prefer easier tasks.
    • Motivated by gold star stickers.
    • Failure = The End

In Summary...Stop giving gold stars and making rules. Start encouraging learning by failure.