Exploration-Exploitation Hill Climbing
Keep climbing, but regularly test whether a larger hill lies elsewhere.
- Difficulty
- Moderate
- Time to result
- ~ongoing to results
- Steps
- 5
- Confidence
- 100%
Exploration-Exploitation Hill Climbing applies an optimization problem to careers. Exploitation means continuing up the current hill by collecting the next promotion, bonus, or credential. Exploration means testing other parts of the terrain so that local progress does not conceal a much higher or better-fitting peak. Dixon argues that ambitious people are especially vulnerable because every nearby upward step feels productive, even when it deepens commitment to the wrong path. The remedy is not literal randomness but protected curiosity: try different work, meet people on other frontiers, and occasionally accept an apparent step backward. Once a clearly better hill is found, move rather than allowing the next small reward on the current hill to dictate the decision.
Origin
Chris Dixon translated hill-climbing algorithms, simulated annealing, and machine learning's exploration-versus-exploitation tradeoff into a career decision model in his essay Climbing the Wrong Hill.
Core principles
- 01Local progress can hide a much larger opportunity elsewhere.
- 02Nearby rewards are systematically easier to overvalue.
- 03Exploration protects against becoming excellent at the wrong game.
- 04Temporary backward steps can move a person onto a higher hill.
How to run it
- 1
Map the current hill
Name the path, its next rewards, and the best plausible destination if you continue climbing.
Pro tip Describe the destination in life terms, not only job titles.
Watch out Do not confuse a visible promotion ladder with a desirable peak.
- 2
Protect exploration
Keep enough time and flexibility to follow intellectual curiosity into genuinely different terrain.
Pro tip Use small projects, conversations, or temporary roles to sample a field.
Watch out A completely full schedule quietly eliminates exploration.
- 3
Drop into new terrain
Try opportunities far enough from the current path to reveal hills that incremental planning cannot see.
Watch out Changing employers without changing the underlying game may be only lateral exploitation.
- 4
Compare peaks
Assess the potential height, personal fit, learning, and long-term direction of each sampled hill.
Pro tip Include evidence from people already farther up each path.
Watch out Do not compare a polished current path with only the awkward first step of a new one.
- 5
Switch decisively
When a better hill is credible, accept a short-term loss of status or income and begin climbing it.
Watch out The next nearby reward will always provide a reason to delay.
In the wild
Dixon describes a young person at McKinsey or Google who can always see a promotion or bonus six months away. Joining a startup may look like a backward step, but it can place the person on a much larger hill.
→ Deliberate exploration prevents repeated local optimization from becoming an unhappy long-term career.
Dixon uses restaurant choices as a small illustration: sometimes return to a favorite and sometimes try a new restaurant. The first exploits known value; the second gathers information about alternatives.
→ A recurring exploration allocation keeps the decision set from freezing around the first acceptable option.
Common mistakes
Optimizing only the next step
A promotion can be locally rational while making a poor long-term destination more likely.
Treating exploration as aimlessness
The model calls for deliberate sampling and comparison, not endless random movement.
Is it for you?
Best for
It is best for people early in a career or at a point where curiosity suggests a materially different path.
Not ideal for
It is not ideal when immediate financial, health, or family obligations leave no safe capacity for experimentation.
From the transcript
“the mistake i saw a lot of young people making was they're at mckinsey or google or something and they see kind of the next…”
“the lesson i take from the computer science is to add some randomness to some exploration”
“when you find the highest hill don't waste any more time on the current hill no matter how much better the next step might appear”
From the episode
#542: Chris Dixon and Naval Ravikant — The Wonders of Web3, How to Pick the Right Hill to Climb, Finding the Right Amount of Crypto Regulation, Friends with Benefits, and the Untapped Potential of NFTs
Chris Dixon