Monkey-Bar Careers
Leave the second you can no longer learn more or earn more, and swing to the next position of higher power.
- Difficulty
- Easy
- Time to result
- ~months to results
- Steps
- 4
- Confidence
- 92%
Sanchez stayed at most jobs eighteen months to two years, and the exit trigger was mechanical rather than emotional: the second she was told she could not progress further, or the second she could no longer learn exponentially, she left. She frames it as monkey-barring both variables at once — how much you earn and what you can learn — swinging to the next position of higher power. The exception proves the rule. She stayed five years at First Trust because she had ownership in the business, skin in the game and control of her outcome, which is exactly the condition under which the two variables keep moving. Her structural conclusion is that the young generation is right that you should not stay at a job for twenty years, unless that job continues to let you earn more and learn more. The final move on the ladder is not a resignation but a fundraise: leave amicably and try to get your boss to write your first cheque.
Origin
Bartlett asked what Sanchez would do after getting cosy with someone rich and powerful. She looked back at her own resume: eighteen months to two years at most jobs, five years at First Trust because she had equity. When she left First Trust, the first person who wanted to give her a cheque was her CEO — the same man who did not want her running the business her way.
Core principles
- 01Two exit triggers: no more progression, or no more exponential learning.
- 02Ownership is the only thing that legitimately makes a long tenure rational.
- 03Move to positions of higher power, not just higher pay.
- 04Learn on somebody else's dime before risking your own.
- 05Leave amicably; your former boss is your best first investor.
How to run it
- 1
Define the two exit triggers up front
Sanchez leaves the second she is told she cannot progress any further, or the second she does not feel she can learn exponentially. Both are observable events, not moods, so the decision does not require a crisis.
Pro tip Stating both triggers before you join makes the eventual exit unemotional.
Watch out Waiting for dissatisfaction rather than watching the triggers costs you the eighteen months you would have swung.
- 2
Ask for ownership before you swing
Ask your boss directly: if I am consistently a top performer and make myself materially important to this business, can I get ownership in this or anything else we do — and I am willing to earn it or invest in it. Ownership is what converts a job into a reason to stay.
Pro tip Sanchez copied the private-equity model where managers can invest in the best deals; US rules allow employees to invest even when not accredited.
Watch out The answer may be no, as it is for her own media company where she wants to own her name forever. That is still information.
- 3
Swing to higher power, not just higher pay
Each move should leapfrog you into a position of greater authority and steeper learning. Sanchez explicitly frames the endpoint of the ladder as eventually becoming an entrepreneur, after five to seven years working for entrepreneurs.
Pro tip You can learn on somebody else's dime instead of losing your own money without enough knowledge to do the job.
Watch out A lateral move that only raises pay does not advance the ladder.
- 4
Convert the exit into your first cheque
Sanchez left First Trust on good terms and her CEO — who did not want her running the business her way — asked to be her first investment when she went looking for investors. She argues employees should actively strive for this and that great employees make their bosses happy to fund them.
Pro tip In finance the convention is to play with a departing person; she thinks more industries should adopt it.
Watch out A scorched exit destroys the single most informed source of first capital you will ever have.
In the wild
Sanchez's only long tenure was First Trust, where she had ownership in the business. She describes having skin in the game and control of her outcome, which is why the eighteen-month pattern did not apply.
→ She also learned the partnership mechanic there from Jim Bowen — you had to pay into the partnership to become a partner, and the offer was celebrated as an event.
Sanchez's CEO told her he did not want her running the business her way. They parted amicably and he told her he wanted to be her first investment when she raised.
→ The first person who wanted to write her a cheque was the man who had just declined to let her run things her way.
Common mistakes
Starting entrepreneurship too early
Sanchez says too many people go out and do the brutal, awful thing that can put them ten years behind, because they lose all their money and do not yet have enough knowledge to do the job. Work for entrepreneurs for five to seven years first.
Staying twenty years without ownership
A long tenure is only rational while earning and learning keep rising. Without equity, both eventually flatten and the tenure becomes a slow loss.
Never asking about equity
The ownership question has to be asked explicitly, including the willingness to earn or invest in it. Most employees never ask and therefore never find out that the door existed.
Is it for you?
Best for
Employees deciding whether to stay or move, and pre-founders working out how long to apprentice before starting something.
Not ideal for
People in a role where the learning curve is still steep and equity is genuinely on the table — the rule tells them to stay.
From the transcript
“the second that they told me I couldn't progress anymore or I couldn't have an option to make more money I left”
“you're kind of monkey barring both how much you earn and what you can learn to your next position”
“try to get your boss to give you your first capital”
From the episode
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