Based on a tutorial by Tiago Forte
Have you ever wondered if AI could provide the same deep, personal insights as a human life coach? If you’re like most people, you’ve probably considered hiring a coach but hesitated due to the cost or time commitment involved in building that crucial context.
I’m summarizing this fascinating experiment where Tiago Forte loaded 150,000 words of his most personal documents into Notebook LM to test whether AI can truly understand us at a coaching level. The results are both impressive and revealing about where AI coaching succeeds—and where it still falls short.
Quick Navigation
- The Experimental Setup (00:00-05:30)
- Three Categories of Personal Sources (05:31-08:45)
- Loading Sources into Notebook LM (08:46-12:15)
- Testing Basic Understanding (12:16-17:30)
- Uncovering Contradictions & Blind Spots (17:31-25:20)
- Rediscovering Moments of True Happiness (25:21-28:45)
- Future-Focused Coaching Questions (28:46-32:10)
- The Most Revealing Question (32:11-36:30)
- Final Evaluation: AI vs Human Coaching (36:31-end)
The Experimental Setup
Tiago begins with a bold premise: good coaching requires extensive context about your life, goals, strengths, and weaknesses. Traditional coaching takes years to build this understanding, but AI tools like Notebook LM have essentially unlimited context windows.
His experiment involved uploading 40 separate documents containing almost 150,000 words of personal material—everything from private coaching notes to annual reviews spanning five years.
Key Points:
- Context is crucial for effective coaching
- AI can process massive amounts of personal data instantly
- This experiment tests whether quantity of context can replace human intuition
- Uses Notebook LM Plus ($20/month) for enhanced capabilities
My Take:
This is exactly the kind of experiment I’ve been curious about. While most of us won’t have 150,000 words of personal documentation, even a fraction of this material could provide valuable insights when processed by AI.
Three Categories of Personal Sources
Tiago organizes his uploaded materials into three distinct categories, each serving a different purpose in building comprehensive context.
Category 1: Private Notes
- Coaching session notes from several years
- Mind maps with life goals (updated annually)
- Big Five personality traits and time perspective assessments
- Customer testimonials highlighting strengths
- Annual gratitude lists
- Myers-Briggs profile (INFJ)
Category 2: Public Writing
- Course takeaways and book summaries
- Personal experiences (like Burning Man)
- Autobiographical writing
- Favorite open questions
Category 3: Year-End Reviews
- Five years of December reviews
- High points, low points, and lessons learned
- Goal setting and progress tracking
My Take:
The genius here is combining three different types of self-reflection: honest private thoughts, public articulation of ideas, and structured annual reviews. This creates a 360-degree view that even we might not have of ourselves.
Loading Sources into Notebook LM
The loading process took approximately 17 minutes for all 40 documents. While this might seem tedious, Tiago emphasizes the sci-fi nature of what’s happening—decades of context building compressed into minutes.
Technical Details:
- 40 separate documents uploaded individually
- Total of 150,000+ words processed
- Notebook LM Plus required for this volume
- Process is manual but straightforward
My Take:
Seventeen minutes to upload what would take a human coach years to absorb and understand—that’s the real power here. The time investment is minimal compared to the potential insights gained.
Testing Basic Understanding
Tiago starts with fundamental questions to verify the AI’s comprehension before moving to more complex coaching inquiries.
AI-Identified Strengths:
- Deep knowledge and understanding
- Visionary and futuristic thinking
- Creativity and innovation
- Insightful perspective
AI-Identified Weaknesses:
- Self-criticism and perfectionism (typical of INFJ personality)
- Sensitivity to criticism and conflict
- Tendency toward idealism
- Overlooking details
- Social skills as perceived challenge
- Emotional vulnerability
- Resistance to emotional processing
- Fear of being ordinary
- Overthinking and analysis paralysis
My Take:
What’s remarkable is how the AI connects personality type characteristics (INFJ) with observed patterns in the personal writing. This shows genuine synthesis rather than just summarization.
Uncovering Contradictions & Blind Spots
This is where the experiment gets truly interesting. Tiago asks the AI to identify contradictions between his stated intentions and actual behaviors—the kind of insight that requires wisdom, not just information processing.
Major Contradictions Identified:
- Work-Life Balance: Expresses desire for balance but consistently prioritizes work
- Delegation: Wants to delegate but struggles to let go of control
- Financial Habits: Desires prudence but tends toward free spending
- Focus vs. Shiny Objects: Values focus but chases new opportunities
- Family Presence: Wants to be present but remains distracted by work
Surprising Blind Spot:
- Tendency to avoid disappointment, which paradoxically creates more disappointment
- Underestimating team capabilities
- Impact on others from constant self-reinvention
My Take:
The AI’s ability to connect behaviors across different documents and time periods is genuinely impressive. It’s doing pattern recognition that even the person themselves might miss.
Rediscovering Moments of True Happiness
Tiago asks when he’s been happiest, with specific instructions to be truthful, specific, and find surprising moments rather than generic summaries.
Happiness Patterns Identified:
- Day 9 of a meditation retreat (specific physical sensations)
- Psychedelic experiences with ayahuasca
- Beautiful moments with his children as babies
- Consecutive hours of deep reading and writing
- Immersive spaces with fellow entrepreneurs and creators
My Take:
This is coaching gold—the AI isn’t just identifying happy moments but pointing toward actionable patterns. Tiago immediately recognizes he should return to meditation and consider psychedelic-assisted therapy.
Future-Focused Coaching Questions
The conversation shifts toward future-oriented coaching, where the real value of coaching typically lies.
End-of-Life Regret Analysis:
- Primary Fear: “Not fully prioritizing meaningful relationships and balanced life”
- Overemphasizing work and external achievements
- At expense of deeper connections and personal well-being
Comprehensive Life Advice:
- Prioritize self-knowledge and authenticity
- Question personal narratives and stories
- Embrace emotional intelligence and integration
- Strive for integration over compartmentalization
- Value relationships and community
- Define “enough” and prioritize balance
My Take:
The end-of-life regret question hits hard because it crystallizes a core fear many high achievers share. While the advice feels somewhat generic, it’s grounded in specific patterns from Tiago’s own life.
The Most Revealing Question
Tiago asks what question he should have asked that might yield novel insights. The AI’s response leads to the most actionable part of the entire session.
The Suggested Question:
- “What physical sensations and recurring bodily experiences might be offering insights into your current goals, challenges, or unacknowledged desires?”
Somatic Awareness Framework:
- Tension or tightness in specific areas
- Changes in energy levels
- Digestive issues (which Tiago has been experiencing)
- Heart-related sensations
- Changes in breathing patterns
- Temperature changes
- Recurring aches or pains
Practical Application:
- Introduction to “active body awareness” practice
- Specific questions for daily check-ins
- Connection between physical sensations and emotional states
My Take:
This is where AI coaching shows its unique value—connecting disparate information (interest in somatic healing, current physical symptoms, psychological patterns) into actionable insights that might take a human coach months to piece together.
Final Evaluation: AI vs Human Coaching
After this extensive experiment, Tiago provides a balanced assessment of AI coaching capabilities and limitations.
Where AI Coaching Excels:
- Vast context retention (150,000+ words simultaneously)
- Instant pattern recognition across years of data
- Ability to zoom from big picture to specific details
- Objective analysis without emotional interference
- Available 24/7 for ongoing conversations
Where Human Coaching Remains Superior:
- Reading micro-expressions and body language
- Noticing pauses, reactions, and non-verbal cues
- Emotional attunement and empathy
- Intuitive insights based on relational dynamics
- Real-time emotional processing and support
The Complementary Approach:
- AI and human coaching strengthen each other
- Use AI for pattern recognition and context processing
- Use humans for emotional intelligence and relational insights
- Not about choosing one or the other
My Take:
This feels like the most honest assessment I’ve seen of AI’s coaching potential. It’s neither dismissive nor overly optimistic—it recognizes genuine strengths while acknowledging clear limitations.
