Career Orienteering
Navigate by durable values, move decisively, and periodically recalculate
- Difficulty
- Moderate
- Time to result
- ~ongoing to results
- Steps
- 5
- Confidence
- 98%
Career Orienteering replaces the rigid career map with a repeated navigation cycle. The person defines a destination through durable values rather than a specific title, employer, or route. They then move decisively in the best-known direction, stopping to reassess only when uncertainty becomes significant or at a regular checkpoint. New evidence may change the next leg without invalidating the destination. Over time, roles that appear unrelated can form a coherent story because they express the same underlying values. The method balances commitment with adaptability: constant recalculation creates paralysis, while blindly following an old route ignores changed terrain. Wallaert recommends thinking in roughly two-year chunks, using each checkpoint to ask whether current work still honors the values represented by the destination.
Origin
Extracted from Masters in Business through Matt Wallaert's orienteering metaphor for early-career decisions.
Core principles
- 01Use durable values as the destination
- 02Move while the direction is sufficiently clear
- 03Recalculate when uncertainty becomes material
- 04Judge career coherence by values rather than job titles
- 05Plan in limited chunks instead of pretending to know the whole route
How to run it
- 1
Define point B
Describe the impact and values you want your career to embody. Avoid reducing the destination to one job title.
Pro tip Use statements about who benefits and what kind of change you want to create.
Watch out A prestigious title is not a durable directional value.
- 2
Choose the next bearing
Select the opportunity that moves most directly toward those values using the information currently available.
Pro tip Compare options by alignment and learning, not only by surface similarity to your previous role.
Watch out Waiting for complete certainty can prevent meaningful movement.
- 3
Run in that direction
Commit to the selected path long enough to generate experience and new evidence. Focus on progress rather than continuously reopening the decision.
Pro tip Set a minimum period before reassessment unless important facts change.
Watch out Do not confuse strategic commitment with loyalty to a clearly harmful situation.
- 4
Stop when the bearing is unclear
Pause when you are no longer confident the current path honors your destination. Review the terrain, constraints, and opportunities again.
Pro tip Schedule a formal checkpoint even if no crisis forces one.
Watch out Do not continue from inertia merely because the current path once made sense.
- 5
Recalculate and repeat
Choose the next direction from updated evidence and repeat the movement-and-review cycle. Let the route change while the values maintain coherence.
Pro tip Review the journey every two years and write down how each leg served your values.
Watch out Changing direction without a stable destination can produce random motion rather than adaptation.
In the wild
A behavioral scientist values changing outcomes for large groups but discovers that academic papers do not create the desired practical impact. They move into product development, later shift into ventures, and continue reassessing which environment best expresses the same underlying value.
→ A nonlinear sequence of roles becomes a coherent impact-oriented career.
An early-career product manager wants to expand access for underserved users. They choose a startup for rapid learning, work there for two years, and then reassess whether scale, autonomy, or a different institution now offers the stronger route toward that value.
→ The decision remains flexible without sacrificing long-term direction.
Common mistakes
Planning the entire route upfront
A detailed long-term path assumes knowledge of terrain, opportunities, and personal development that does not yet exist.
Confusing destination with title
Job titles can disappear or cease to fit. Values and intended impact provide a more durable point of orientation.
Reassessing every day
Constantly reopening the decision prevents committed movement and leaves too little time to gather meaningful evidence.
Is it for you?
Best for
People navigating changing industries, nonlinear careers, or several plausible opportunities.
Not ideal for
People who need a fixed credential sequence or cannot yet identify the values that should guide trade-offs.
From the transcript
“I know B is over there. I'm gonna run in that direction until I'm no longer sure I'm going in the right direction, and then…”
“take a point run, take a point run, and actually think careers work best this way.”
“every two years I basically look up and say, am I still honoring those values?”
From the episode
Matt Wallaert Is on a 'Chief Behavioral Officer' Mission
Matt Wallaert