Why do some people crush their goals effortlessly while others stall out—even with the same advice?

In this episode of The Augmented Life, Michael Tiffany sits down with bestselling author and behavior science expert Gretchen Rubin to unpack what actually drives habit change, happiness, and self-awareness and why cookie-cutter strategies so often fail.

They explore the hidden power of sensory experience, how to avoid the trap of over-optimization, and why personality frameworks like the Four Tendencies might hold the key to finally making change stick.

Whether you're a startup founder, productivity hacker, or just trying to live more intentionally, this is a conversation that cuts through the noise with real insights and practical tools you can use immediately.

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⏱️ Timestamps

0:00 – Intro

1:36 – Writing with restraint: aphorisms & clarity

4:08 – Reductive vs. enriching measurement

6:22 – Self-tracking vs. actual self-awareness

10:27 – Why Gretchen doesn’t chase word counts

12:10 – Is Gretchen Rubin a hacker? (Yes.)

17:18 – The Four Tendencies explained

24:25 – Quiz data & personality distributions

28:14 – Why “just do it” doesn’t work for everyone

30:39 – Gretchen’s sweet tooth & giving up sugar

34:30 – When clarity = willpower for Questioners

36:20 – Why Rebels hate to-do lists (and what to do instead)

41:16 – 25-for-25: Habit design meets fun

44:40 – Awe, embodiment, and recovering from disconnection

46:32 – What’s your most neglected sense?

48:25 – From intellectual meditation to embodied awareness

51:26 – Feelings are data (and evolution knew it first)

53:17 – Where to find Gretchen’s quizzes, books & tools

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