Vertical Mentor Portfolio
Choose different mentors for different parts of life and work
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 98%
The Vertical Mentor Portfolio divides development into specific domains and selects mentors separately for each one. Start by naming the verticals that matter, such as leadership, marriage, parenting, or entrepreneurship. For each vertical, identify people whose demonstrated behaviour you want to understand, then ask them focused questions rather than adopting their entire worldview. Combine useful lessons into your own approach and revisit the portfolio as your stage changes. Finkelstein notes that a mentor who helped him think about education and skill stacking was not therefore the right marriage mentor. He also describes changing parenting guidance as his children grew. The mechanism is selective evidence: narrow the domain, learn from demonstrated strength, synthesize, and update.
Origin
Finkelstein says he formed the framework while preparing for marriage and realizing that no one person modelled every part of life he wanted to improve.
Core principles
- 01No single mentor should be copied wholesale
- 02Expertise in one life vertical does not imply expertise in another
- 03Combine advice into your own approach
- 04Change mentors as the problem or stage changes
How to run it
- 1
Define the verticals
Separate the areas in which you want guidance instead of combining them into a vague search for one mentor. Make each area narrow enough to evaluate.
Pro tip Leadership, parenting, and partnership can require different reference people.
- 2
Select demonstrated strengths
Find people whose conduct in one vertical appears worth learning from. Do not require them to be exemplary in unrelated areas.
Watch out Admiration for one achievement can create false authority in another domain.
- 3
Ask narrow questions
Discuss the habits, decisions, and trade-offs behind the specific strength you selected. Gather perspectives from more than one person when useful.
- 4
Synthesize your version
Adapt the relevant lessons rather than copying a mentor wholesale. Keep what fits your values and circumstances.
- 5
Refresh by stage
Reassess whether the mentor still fits the current problem or life stage. Retain long-term mentors where useful and change others when their relevance ends.
Pro tip A mentor useful for newborn parenting may not fit later childhood.
In the wild
Finkelstein values Philip Reimer's guidance on law school and skill development but notes that Reimer's relationship history did not make him the model Finkelstein wanted for marriage. He instead approached someone whose relationship with his wife he particularly admired.
→ Advice was selected by relevant vertical rather than the mentor's overall status.
Common mistakes
Searching for one perfect mentor
One person is unlikely to model every role or capability you want to develop.
Keeping stage-specific advice forever
Guidance can lose relevance as the problem, business, or family stage changes.
Is it for you?
Best for
People developing across several distinct roles such as leadership, partnership, parenting, and entrepreneurship.
Not ideal for
Situations requiring licensed professional advice rather than informal mentorship.
From the transcript
“I don't think any one particular mentor is going to be you should wholesale take everything they say”
“find these different people for different aspects of your life”
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