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Article notes

103 Bits of Advice I Wish I Had Known

By Kevin Kelly

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Total length: 6:13
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In one sentence

A good life is built less through optimization than through timely action, durable relationships, experimentation, rest, generosity, independent thinking, and the willingness to revise one’s plans. Kelly presents these as portable rules rather than universal laws.

Overview

Kelly’s original article is a short introductory post rather than the complete 103-item list: it explains that the advice was written on his 70th birthday and reproduces the first six items. The full list circulated separately and was later expanded, edited, and combined with earlier advice lists in his book Excellent Advice for Living. The notes below synthesize the recurring ideas in the 103-item set, while treating the article’s six published items as the directly visible source material.

Core ideas

Act before conditions feel perfect

Kelly repeatedly treats delay as a major source of lost opportunity. Most of the time, the appropriate moment is now; being “ready” is often something created by beginning rather than something achieved beforehand.

Choose models, not merely jobs or rewards

Work shapes character through imitation. Select employers, mentors, collaborators, and institutions whose way of living or operating you would willingly adopt—not just those offering status or money.

Invest in a small circle of real affection

A handful of people who genuinely love and know you matter more than a large audience of weak social approval. Friendship, family, and generosity are treated as durable forms of wealth.

Use experimentation as the path to learning

Avoid repeating the same failure, but do not aim to eliminate mistakes. Try new approaches, preserve the ability to persist, and also develop the judgment to quit what is not working. Other people can help distinguish perseverance from stubbornness.

Prefer substance to display

Possessions, credentials, and visible success usually impress their owner more than outsiders. Kelly’s broader implication is to spend less energy signaling and more energy cultivating capability, character, curiosity, and useful relationships.

Protect rest, play, and unstructured time

Efficiency is not the highest good. Vacations, sabbaticals, aimless walks, hobbies, and deliberate idleness can replenish attention and improve work; a strong work ethic requires an equally serious rest ethic.

Stay intellectually independent

Question ideological packages and inherited opinions. If one’s views can be predicted across unrelated subjects, that may indicate conformity rather than thought. Seek the third perspective in disputes and remain willing to update.

Build for the long term while accepting uncertainty

Many valuable outcomes compound slowly and cannot be forecast precisely. Favor learning, reputation, health, trust, and adaptable skills over short-term optimization. Breakthroughs may initially look foolish, implausible, or laughable.

Practical takeaways

Caveats and counterpoints

Questions worth revisiting

Return to this when…

Return to this list when choosing between action and delay, evaluating a job or mentor, recovering from a failed experiment, feeling pressure to signal success, or designing a healthier balance between ambition and rest.

References

  1. kk.org
  2. kk.org
  3. kk.org
  4. daringfireball.net
  5. pointer.io
  6. gigazine.net
  7. alliance4datascience.ai
  8. notes.andymatuschak.org
  9. kk.org
  10. bretpadilla.com
  11. cn-sec.com
  12. lesswrong.com
  13. kk.org