Employment Path Decision Tree
Choose a better job or self-employment from fit, skill, and risk
- Difficulty
- Easy
- Time to result
- ~weeks to results
- Steps
- 6
- Confidence
- 95%
The decision tree starts only after establishing that the current role is a poor fit. The next question is not simply whether to quit, but whether another organization could provide better work. Identify skills in which you outperform peers and interests that produce competence and value. Ask whether those can be used in another company, a small startup, or an adjacent sector. Self-employment becomes the stronger branch when there is a genuine desire to build something that no employer can facilitate, plus the ability to structure one's own work and tolerate months of uncertain income. The hosts reject a universal value judgment: a stable job can be ideal when it supports family, training, or another valued part of life. The correct branch depends on personal preferences and tolerances.
Origin
Chris, Johnny, and Yousef build the decision tree while discussing whether an unhappy employee should change company or work independently.
Core principles
- 01Job dissatisfaction does not automatically imply self-employment
- 02Strong skills and genuine interests can transfer to another employer
- 03Self-employment requires desire, self-direction, and tolerance for uncertain income
- 04A sideways move can preserve useful skills while improving sector fit
- 05Work should support the things the individual actually values
How to run it
- 1
Confirm the mismatch
Separate a sustained problem with the current role from a temporary bad week or ordinary dislike of some tasks.
Pro tip Look for recurring dread, loss of purpose, and reliance on escape behaviors.
Watch out Do not turn one difficult period into a permanent career decision.
- 2
Find transferable strengths
Identify the work you perform much better than peers and the interests that make you feel competent and useful.
Pro tip Search for a role that rewards the strongest part of your current work.
- 3
Test the employment branches
Consider another large organization, a small startup, or an adjacent sector where the same skills can be used differently.
Pro tip A smaller company may offer more upside and broader responsibility without full self-employment risk.
Watch out Do not chase a higher gross salary into the same underlying mismatch.
- 4
Test entrepreneurial fit
Assess whether you genuinely want to build independently and can direct your work without a boss imposing structure.
Pro tip Distinguish wanting autonomy from wanting to operate a business.
Watch out A passion alone does not create the desire or operating profile required for self-employment.
- 5
Stress-test uncertainty
Ask whether you can financially and psychologically tolerate two or three months without income.
Pro tip Treat financial capacity and emotional response as separate tests.
Watch out Income pressure can make independent work unusually stressful.
- 6
Choose by personal values
Select the branch that best supports the work and life you actually value.
Pro tip A secure job that funds family or a serious outside pursuit can be a successful choice.
Watch out Do not adopt the status judgments of either entrepreneurs or employees.
In the wild
The speakers describe a man who deliberately chose cognitively easy administrative work with flexible time and low commitment so he could train and enjoy acrobatics. He did not prioritize upward mobility in the job.
→ Employment successfully facilitated the part of life he cared about most.
Johnny says he could not join another promotion company to run the same club events because those events did not exist. The work he wanted therefore could not be facilitated by an employer.
→ Self-employment was the branch that allowed him to pursue the specific interest.
The group suggests moving from accounting into work that still uses accounting skills but sits in a sector more aligned with the person's interests, including a five- or ten-person startup.
→ The employee can improve fit without immediately assuming all the risk of working alone.
Common mistakes
Equating unhappiness with entrepreneurship
Another company, sector, or startup may solve the mismatch without requiring full self-employment.
Ignoring the need for structure
Independent work is difficult for someone who relies on a boss to organize tasks and time.
Applying someone else's values
A stable role can be a strong fit when it reliably supports family, training, or another priority.
Is it for you?
Best for
It is best for employees choosing among another employer, a smaller company, an adjacent field, and self-employment.
Not ideal for
It is not a substitute for testing whether a proposed business has customers or can support the employee financially.
From the transcript
“the only the option for you is not only to go away for yourself though absolutely you can move to another bureaucratic organization you can…”
“there has to be a desire to want to do that”
“can you deal with potentially going for two months or three months without earning any money”
From the episode
Should I Work For Myself? - Business Principles 102 - #106
Business Principles 102