Draw Your Life
Map your life and identify the moment that changed your direction
- Difficulty
- Starter
- Time to result
- ~days to results
- Steps
- 4
- Confidence
- 96%
Draw Your Life turns an abstract personal history into a visible timeline. Draw a line that runs from birth to the present, then populate it with the events that shaped you. Review the completed line and identify the crucible moment: the event that shifted you away from the expected groove and changed your direction or story about yourself. The mechanism works by separating socially impressive milestones from causally important choices. Strickler expected starting Kickstarter to be his defining moment, but the map showed that moving to New York after college was the risk that enabled everything that followed. The result is a more accurate account of what shaped your agency and values.
Origin
Strickler uses this exercise in workshops. When he completed it himself, he discovered that moving to New York—not starting Kickstarter—was the moment that most changed his story.
Core principles
- 01Your remembered status milestones may not be your true turning points
- 02A life story becomes clearer when it is made visible
- 03Crucible moments reveal how your self-narrative changed
How to run it
- 1
Create the life line
Draw a line snaking up a page. Label the bottom with your birth and the top with the present.
Pro tip Leave enough space around the line to annotate events.
- 2
Plot the defining dots
Add the meaningful events, decisions, disruptions, and transitions between birth and now.
Pro tip Include difficult and uncertain moments, not only achievements.
Watch out Do not edit the timeline into a polished résumé.
- 3
Find the crucible
Review the full line and identify the moment that most shifted your direction or changed your story about yourself.
Pro tip Ask which later events would not have happened without this one.
Watch out The most prestigious milestone may not be the most causal one.
- 4
Name the change
Describe the old groove, what changed inside you, and the new path the crucible made possible.
In the wild
Strickler assumed that starting Kickstarter would be the proudest and defining point on his life map. Looking at the sequence instead showed that moving to New York after college was the riskiest choice and the event that changed his self-story. Without it, the later milestones would not have happened.
→ He identified the enabling decision beneath the visible achievement.
A manager maps promotions, setbacks, and moves, then notices that volunteering for an unfamiliar project—not the later promotion—first revealed their leadership ability. They treat that earlier experiment as the crucible and use it to guide their next move.
→ The person bases the next decision on a demonstrated source of growth rather than job-title prestige.
Common mistakes
Choosing the flashiest milestone
A famous company, promotion, or award can look defining while an earlier risk actually changed the trajectory.
Mapping achievements only
Leaving out rejection, uncertainty, and difficult transitions removes the moments most likely to have changed your self-narrative.
Is it for you?
Best for
People reflecting on their identity, career path, or next major decision.
Not ideal for
People seeking a predictive assessment or an objective ranking of their achievements.
From the transcript
“there's an exercise i often do called draw your life where you like draw a line snaking up a piece of paper and at the…”
“after you do that you have to identify like what is the crucible moment what is that moment that really shifted your direction in life”
“actually that was the riskiest thing i did that was the thing that most changed my story of myself”
From the episode
Yancey Strickler: Bentoism For a Better World
Yancey Strickler