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Career Path Mapper

Most career advice is either a platitude ('follow your passion') or a job-search tactic. Neither helps when you're a Senior X trying to figure out how to become a VP of Y in five years. The Career Path Mapper builds the actual sequence — stepping stones, gap analysis, quarter-by-quarter actions — to get from where you are to where you want to be.

What this skill does

The default career narrative is a ladder — junior, mid, senior, manager, director. Modern careers don't work that way. They look more like climbing walls, where a lateral move into product unlocks a vertical move into the C-suite, and the shortest line between two roles is rarely straight. Mapping the path properly means treating each role as a strategic position that builds the credentials for the next one, not as a destination in itself.

This skill starts by sharpening the destination. "I want to be in leadership" is not a target — it's a wish. People management, strategic leadership, and thought leadership are three different jobs requiring three different paths. Same for "Director" — at a startup that's three reports, at an enterprise that's three hundred. The skill pushes for the specific version: role, level, company stage, industry, timeline. If the answer is vague, the plan will be too.

Then it runs gap analysis across four dimensions, not just skills. Skills gaps are the obvious ones. Experience gaps are sneakier — agency work rarely qualifies you for product leadership no matter how senior you got. Credential gaps catch people who assumed an MBA wasn't relevant until they tried to make the jump. Network gaps are the most under-counted of all: if you don't know anyone in the target role, the path is longer by default. Each gap gets named, then sequenced by leverage — biggest first.

The output is a phased plan with stepping stones, not a single leap. For each stone the skill answers: why this role is necessary, how long to stay, what to achieve in it, how to position for the next move while you're still in it. Then a quarterly action plan — specific courses, communities, stretch assignments, target company criteria. Plus a feasibility rating that's honest: if the timeline is unrealistic for the gap size, the skill says so and offers the slower path rather than promising the fast one. Careers aren't built on optimism. They're built on sequencing.

When this triggers

  • ·You know roughly where you want to end up but not how to get there
  • ·You've been in the same role two years and the next move isn't obvious
  • ·You want to change industry or function and 'just apply' isn't working
  • ·Your manager wants a development plan and 'learn more about leadership' won't cut it
  • ·You're choosing between two roles and need to see which one sets you up better

Example

Trigger

User: 'Senior developer at an agency, 6 years in. Want to be VP Engineering at a growth-stage company within 5 years. No people management experience yet.'

Output

Destination (sharpened): VP Engineering at a 100-500 person B2B SaaS, Series B/C, within 5 years. Gap analysis: · Skills: people management, hiring, eng-org design · Experience: agency work doesn't count as product experience · Network: zero senior eng leaders in your current circle Stepping stones: Year 0-1: Senior Dev at a product company (not agency) Year 1-2: Tech Lead (3-5 reports, architectural ownership) Year 2-4: Engineering Manager (team of 8-12) Year 4-5: VP Engineering at growth-stage company Q1 actions: · Apply to 5 product companies (target list provided) · Start one-on-ones with junior devs at current job · Join [community] — 2 events/month minimum Feasibility: Yellow. Tight but possible. The agency → product jump is the highest-risk move — do it first, not last.

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What you get

  • 206-line SKILL.md, ready to drop into ~/.claude/skills/
  • Tested through 3 Karpathy-loop iterations (versions v1.0.0 → v1.3.0)
  • Triggers automatically when relevant — no command to remember
  • Lifetime updates as the skill is refined further

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