Think Day
Create protected space to challenge assumptions and remove life’s drag
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 6
- Confidence
- 99%
A Think Day is a protected block for wrestling with consequential questions that ordinary schedules suppress. Inspired by Bill Gates’s week-long reading retreats, Bloom compresses the practice into a few hours once a month, though quarterly or annual versions can work. The user changes setting, reduces incoming stimulus, and examines a small set of bigger-picture questions. Two core prompts drive the method: “What do I assume is true that may not be?” and “What are the boat anchors creating drag on my progress?” The first tests whether a chosen path rests on a false certainty; the second identifies people, habits, actions, or mindsets that prevent full movement. The output is not merely insight: the session should produce at least one practical change to direction or environment.
Origin
Bloom adapted Bill Gates’s week-long cabin retreats into a realistic monthly session lasting a few hours at an Airbnb or coffee shop.
Core principles
- 01Daily stimulus crowds out deliberate choice
- 02Protected thinking time reveals wrong assumptions
- 03Progress can require removing drag rather than adding effort
- 04A few hours of reflection is more practical than waiting for a free week
How to run it
- 1
Protect the space
Schedule a few uninterrupted hours monthly or quarterly and treat them as a real commitment.
Pro tip A coffee shop or Airbnb can create useful distance from normal cues.
- 2
Reduce stimulus
Step away from routine messages, tasks, and immediate responses so there is room to choose rather than react.
Watch out A Think Day filled with normal inbox work is not protected thinking time.
- 3
Challenge certainty
Ask what you automatically assume is correct about your life or approach that may not be true.
Pro tip Test assumptions tied to your current definition of success and the path you are marching on.
- 4
Find the boat anchors
List the people, actions, habits, and mindsets creating drag on the life or work you want to build.
Pro tip Include subtle sources of realism, ridicule, or routine friction, not only obvious crises.
Watch out Do not label a person an anchor solely because they offer uncomfortable but valid feedback.
- 5
Translate insight into change
Choose at least one assumption to test or one source of drag to reduce before the next session.
Pro tip Prefer a small observable experiment over a sweeping declaration.
- 6
Review the course
On the next Think Day, assess what changed and whether your direction now fits what matters.
Watch out Reflection without follow-through becomes another form of information consumption.
In the wild
Bloom once assumed that making more money would make him feel happy and successful. Examining that certainty against his deteriorating health and relationships revealed that the path itself was wrong, not merely that he needed to progress faster.
→ He redefined what a wealthy life meant and changed his work and location around that broader scoreboard.
A builder uses a Think Day to list recurring drag: a habit of checking messages before creative work, a peer who mocks every early experiment, and an assumption that a prestigious role is the only safe path. They choose to protect the first hour of each day and test an independent project for one month.
→ Abstract dissatisfaction becomes a bounded experiment that reduces two sources of drag.
Common mistakes
Waiting for a free week
The adapted method exists because a full retreat is often unrealistic. A protected few hours is enough to begin.
Thinking without acting
Insight must lead to an assumption test or a reduction in drag before the next session.
Using only comfortable prompts
The value comes from questioning apparent certainties and current direction, not merely affirming existing plans.
Is it for you?
Best for
People who are busy executing but rarely examine their assumptions, priorities, or sources of drag.
Not ideal for
Urgent operational decisions that need immediate facts or collaborative input rather than solitary reflection.
From the transcript
“the idea of pausing to just think about bigger picture questions in your work in your life and the things that you're doing is really…”
“what do I automatically assume is correct in my life and in my approach to life that may not be what am I marching on…”
“what are the boat anchors in my life and a boat anchor is something that is creating a drag on your progress”
From the episode
Episode 421: Sahil Bloom: How Boring and Basic Routines Can Build 5 Types of True Wealth
Sahil Bloom