Career Path Planning

Overview

Strategic framework for assessing career options, planning transitions, identifying skill gaps, and making intentional career decisions.

Honest inventory of where you are now:

Current role assessment:
- What do you do day-to-day?
- What’s your level/seniority?
- How are you performing?
- What’s your compensation?
- How long have you been in this role?
Satisfaction analysis: Rate 1-10 and explain:
- Work content (do you enjoy the actual tasks?)
- Growth (are you learning and developing?)
- Compensation (fairly paid for your value?)
- Culture (alignment with values, colleagues?)
- Impact (does your work matter?)
- Work-life (sustainable pace, flexibility?)
Trajectory assessment:
- Where does current path lead in 3-5 years?
- Is that where you want to be?
- What’s holding you back (if anything)?

Understand what actually matters to you:

Values clarification: Rank importance (1-5) of:
- Compensation/wealth
- Status/prestige
- Impact/meaning
- Autonomy/freedom
- Learning/growth
- Stability/security
- Work-life balance
- Creative expression
- Leadership/influence
- Relationships/community
Life stage considerations:
- What are your financial obligations?
- Family considerations (current and planned)?
- Geographic preferences or constraints?
- Health considerations?
- Time horizon (years until retirement)?
Identify non-negotiables:
- What would you never sacrifice?
- What must any career path include?
- What are absolute deal-breakers?
The “regret minimization” test:
- At 80, looking back, what would you regret not trying?
- What would you regret spending your life doing?

Catalog what you bring to the table:

Skills inventory: Technical skills:
- What tools, technologies, methods do you know?
- What would you rate yourself on each?
Transferable skills:
- Communication, leadership, analysis
- Project management, negotiation, teaching
- Which are your strongest?
Domain knowledge:
- Industries you know deeply
- Functions you understand
- Networks you have access to
Achievements inventory:
- Biggest accomplishments
- Results you’ve driven
- Problems you’ve solved
- Things you’ve built or shipped
Unique combinations:
- What unusual combination of skills do you have?
- Where do you have rare experience?
- What’s your “unfair advantage”?
Credentials:
- Education and certifications
- Reputation and brand
- Portfolio and evidence of work

Brainstorm possible paths without judgment:

Start with your current path:
- Stay in current role (optimize it)
- Advance in current function (next level)
- Lateral move in current company
- Same role at different company
Explore adjacent moves:
- What functions use your skills?
- What industries value your experience?
- What roles are natural next steps?
Consider transformational moves:
- Complete career change (new function, new industry)
- Entrepreneurship
- Retirement/semi-retirement
- Sabbatical/break
Research options:
- LinkedIn: What paths have similar people taken?
- Informational interviews: How did people get to roles you admire?
- Job postings: What’s the market for various paths?
Generate at least 5-7 distinct options
- Include some “safe” options
- Include some “stretch” options
- Include at least one “wild card”

Assess each option systematically:

For each option, evaluate: Fit:
- Does it align with your values?
- Does it use your strengths?
- Would you enjoy the work?
Feasibility:
- What’s required to pursue this path?
- Do you have or can you get the qualifications?
- Is the market accessible?
Reward:
- What’s the upside if it works?
- What does success look like?
- Does it lead where you want to go?
Risk:
- What could go wrong?
- What’s the worst case?
- Is it recoverable if it fails?
Score each option:
- Create weighted scorecard based on your values
- Compare options on same criteria
- Note intuitive reaction vs analytical score
Reality-test top options:
- Talk to people on that path
- Understand day-to-day reality
- Identify hidden downsides

For your top 1-2 options, determine what’s needed:

Skills gaps:
- What skills do you lack?
- How critical are they vs nice-to-have?
- How long to develop them?
Experience gaps:
- What experience is required?
- How can you get it (current role, side projects, volunteer)?
- What’s the shortest path?
Credential gaps:
- Are specific degrees/certifications required?
- Are they actually required or just common?
- Cost/time to obtain?
Network gaps:
- Who do you need to know?
- How can you build relevant relationships?
- Who can help you transition?
Financial requirements:
- Any income gap during transition?
- Investment needed (education, job search)?
- Runway required?

Build plan to close gaps and execute transition:

Prioritize gap closure:
- Which gaps are blocking?
- Which have highest ROI to close?
- What order to address them?
Create learning plan:
- Specific courses, certifications, or training
- Reading and self-study
- Mentorship and coaching
- Timeline and milestones
Create experience plan:
- Projects to take on (current role or side)
- Volunteer or pro-bono work
- Internal transfers or rotations
- Freelance or consulting
Create network plan:
- Events and communities to join
- People to connect with
- Informational interviews to conduct
- Mentors to cultivate
Create transition timeline:
- When to start making moves
- Key milestones and decision points
- Contingency if timeline slips
Design experiments:
- Low-cost ways to test the path
- Side projects that simulate the work
- Conversations that provide information

Take action and adjust based on learning:

Start immediately:
- What can you do this week?
- First experiment or conversation
- Begin gap closure activities
Regular review cadence:
- Monthly: Am I making progress?
- Quarterly: Is the path still right?
- Annually: Major reassessment
Gather feedback:
- Information from experiments
- Input from mentors and advisors
- Market signals from applications
Adjust as needed:
- Plans will change; that’s normal
- New information may redirect path
- Stay flexible while committed
Know when you’ve arrived:
- Recognize when you’ve achieved a milestone
- Celebrate progress
- Set new goals

Input: $ARGUMENTS

Apply this procedure to the input provided.