SPOS #994 – Vicki Tan On Life's Big And Little Decisions

Jul 27, 2025

Vicki Tan, author of Ask This Book A Question and product designer for giants like Google and Spotify, dives into the intricacies of decision-making. She discusses how cognitive biases shape our choices and the importance of storytelling in helping us navigate life's complexity. Vicki emphasizes that reframing questions can unlock clarity over simply seeking answers. The conversation also touches on cultural attitudes towards risk and the intersection of design with personal growth, providing a refreshing perspective on the art of decision-making.

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ANECDOTE

Vicki Tan's Career Journey

Vicki Tan shared her career journey from behavioral science to tech design without a formal design background.
She became a product designer by leveraging curiosity and learning on the job at Google.

INSIGHT

Rethinking Luck

Luck requires both effort and being aware to spot opportunities.
Luck is like seeing dollar bills on the floor; you must pay attention to benefit from it.

INSIGHT

Tech’s Impact on Decision Making

Personalization algorithms create narrow content consumption, risking echo chambers.
Designers must consider long-term impact and the full timeline of user decisions.

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Welcome to episode #994 of Six Pixels of Separation - The ThinkersOne Podcast.

Vicki Tan has designed experiences for some of the most influential companies in the world (Pinterest, Airbnb, Headspace, Lyft, Google) and her work has always focused on helping people make better choices in complex environments. Her new book, Ask This Book A Question, continues that mission in a radically creative form. This isn’t your typical self-help guide. It’s an interactive journey through the beautiful mess of human decision-making, shaped by the science of cognitive bias, the power of storytelling and the playfulness of visual design. Vicki explores how our mental shortcuts shape everything - from whether we leave our job to how we fall in love - and how reframing our questions can unlock more clarity than any answer ever could. She talks about the tension between intuition and logic, the real-world costs of not understanding our own biases and the way interface design and behavior design intersect in both delightful and dangerous ways. In this epsiode, she also digs into the deeper story behind the book: How she collaborated with artists to visualize psychological concepts and why she believes our decisions deserve more compassion than critique. This episode is for anyone who’s ever overthought a text message… or stood paralyzed in a grocery aisle… or wondered why being human feels so confusing sometimes. Which is to say: it’s for all of us. Enjoy the conversation…

Running time: 54:55.
Hello from beautiful Montreal.
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Here is my conversation with Vicki Tan.
Ask This Book A Question.
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Chapters:

(00:00) - Introduction to Vicki Tan and Her Journey. (02:57) - Balancing Work and Writing. (05:55) - Understanding Product Design. (08:56) - The Role of Luck in Career Success. (12:00) - The Importance of Asking Questions. (15:01) - The Process of Writing a Book. (17:49) - Cognitive Biases and Decision Making. (20:52) - Cultural Perspectives on Risk. (24:10) - Engaging with the Book and Its Purpose. (28:23) - The Polarization of Society and Technology's Role. (29:16) - The Evolution of Music Consumption and Its Implications. (32:16) - Designing for the Future: The Role of Creators. (37:25) - Risk Tolerance and the Art of Quitting. (41:41) - Navigating Decision Fatigue in a Complex World. (46:08) - The Impact of AI on Decision Making. (52:20) - Understanding Time and Decision Making in a Vortex of Choices.