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99 Additional Bits of Unsolicited Advice

By Kevin Kelly

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Total length: 4:15
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In one sentence

Good advice is often short, concrete, and behaviorally testable: protect your unusual qualities, reduce avoidable friction, prioritize who you become over what you accomplish, create trust through generosity, and communicate without concealed motives.

Overview

Kelly’s article is mainly a preview rather than a complete essay. It reproduces five pieces from his broader advice project and explains the project’s evolution: an earlier list written for his adult children became popular, leading to additional birthday lists and eventually a 450-item book. The post’s value lies in the memorable rules themselves, not in supporting argument or evidence.

Core ideas

Preserve productive weirdness

A trait that seemed awkward, obsessive, or unusual in childhood may become an adult strength. The practical implication is to distinguish socially inconvenient quirks from genuinely harmful behavior before trying to eliminate them.

Avoid marginal-effort traps

When carrying everything in one trip is uncertain, making two trips is usually cheaper than risking a dropped, damaged, or exhausting load. The broader model is to prevent small gambles from creating disproportionate costs.

Measure success by transformation

Goals are not only endpoints; pursuing them changes abilities, habits, and character. Kelly shifts attention from external accomplishment to the person produced by the process—and to the emotional impression left on others.

Build trust by exceeding expectations

Under-promising and over-delivering creates a favorable reliability gap. Its usefulness depends on making promises realistic; chronic under-promising can instead signal low confidence or reduce ambition.

Remove hidden transactions from speech

An apology weakened by an excuse can sound like self-defense, while a compliment attached to a request can feel like manipulation. The advice favors clean acts of repair and appreciation, without covert bargaining.

Practical takeaways

Caveats and counterpoints

Questions worth revisiting

Return to this when…

Return when you want a compact checklist for judgment, reliability, and communication—or when you are over-optimizing for achievement while neglecting character and relationships.

References

  1. The Technium: 99 Additional Bits of Unsolicited Advice