home / skills / oldwinter / skills / career-transitions
npx playbooks add skill oldwinter/skills --skill career-transitionsReview the files below or copy the command above to add this skill to your agents.
---
name: "career-transitions"
description: "Plan and execute a career transition and produce a Career Transition Pack (progress metric + push/pull map, target archetypes, option scorecard, opportunity pipeline + outreach scripts, skills plan, 4–12 week experiment plan). Use for career change, career pivot, career transition, switching roles. Category: Career."
---
# Career Transitions
## Scope
**Covers**
- Clarifying what “progress” means to you (beyond compensation) and using it as a decision rule
- Mapping your current situation into **pushes** (frictions) and **pulls** (attractions)
- Defining a motivating “genie goal” (what you’d do if success were guaranteed) and backcasting into near-term moves
- Turning vague ideas into 2–4 concrete **target archetypes** (roles/companies/paths) with clear fit filters
- Building an opportunity pipeline (network map + weekly outreach plan) and ready-to-send outreach scripts
- Creating a realistic 4–12 week experiment plan to de-risk the transition
**When to use**
- “I want to change careers / pivot roles but I’m not sure to what.”
- “Help me evaluate two career paths and pick one.”
- “I feel stuck; help me figure out what I actually want next and how to get there.”
- “I want a structured plan for a career transition, including networking/outreach scripts.”
**When NOT to use**
- You need clinical mental health support for burnout/anxiety/depression (seek professional support; this skill can complement, not replace it).
- You need legal advice (employment law, immigration/visa, contracts) or financial/tax planning.
- You only want a resume/LinkedIn rewrite with no decision/process work (use a resume-specific workflow instead).
- You are in an urgent workplace investigation/HR escalation where legal/process guidance is required.
## Inputs
**Minimum required**
- Your current role/situation (title, scope, industry) and what’s prompting change
- Your constraints (location/remote, time, money/runway, family, visa, schedule)
- Your timeline (when you need a decision; when you could start something new)
- What you’re optimizing for (learning, autonomy, mission, stability, leadership, compensation, flexibility)
- 2–6 candidate directions you’re considering (even if vague) OR what you explicitly want to avoid
- Your current “assets” (skills, strengths, portfolio/work examples, network access)
**Missing-info strategy**
- Ask **3–5 questions at a time** from [references/INTAKE.md](references/INTAKE.md).
- If the user is unsure of targets, propose 2–3 plausible archetypes and label assumptions for the user to correct.
- If numbers are missing (runway/comp), proceed with ranges and decision thresholds.
- Never request confidential employer information; use redacted details.
## Outputs (deliverables)
Produce a **Career Transition Pack** (Markdown in chat; or as files if requested) in this order:
1) **Current State + Constraints Snapshot** (what’s true now; must-haves; timeline)
2) **Progress Metric + Push/Pull Map** (what “progress” means; why now)
3) **Genie Goal + 10-Year Backcast** (vision; 3-year waypoint; next 12 weeks)
4) **Target Archetypes + Fit Filters** (2–4 options with “fit signals” and dealbreakers)
5) **Option Scorecard + Decision Rule** (how you’ll choose; what evidence you need)
6) **Opportunity Pipeline Plan** (network map, weekly outreach cadence, tracking)
7) **Skills & Proof Plan** (gaps, learning sprints, portfolio/proof artifacts)
8) **Experiment Plan (4–12 weeks)** (tests to run; sequencing; sabbatical/bridge option if relevant)
9) **Risks / Open questions / Next steps** (always)
Templates: [references/TEMPLATES.md](references/TEMPLATES.md)
Expanded guidance: [references/WORKFLOW.md](references/WORKFLOW.md)
## Workflow (8 steps)
### 1) Intake + current state snapshot
- **Inputs:** user context; [references/INTAKE.md](references/INTAKE.md).
- **Actions:** Capture the current role, what’s driving the change, constraints, and decision timeline. Identify what must remain true (e.g., location, comp floor, hours, mission).
- **Outputs:** **Current State + Constraints Snapshot** + assumptions/unknowns list.
- **Checks:** Constraints are explicit; timeline has dates; unknowns are listed.
### 2) Define progress metric + push/pull map
- **Inputs:** frustrations and attractions; desired learning; values.
- **Actions:** Translate “I want a change” into: (a) a **progress metric** (what you want more/less of), (b) a push/pull map, and (c) what you refuse to repeat.
- **Outputs:** **Progress Metric + Push/Pull Map**.
- **Checks:** Progress metric is measurable/observable; pushes and pulls are not contradictory.
### 3) Create a motivating north-star (genie goal) + backcast
- **Inputs:** aspiration; risk tolerance; constraints.
- **Actions:** Use the “genie” prompt to surface the most compelling path if success were guaranteed. Backcast to define a 10-year picture, a 3-year waypoint, and the next 12 weeks.
- **Outputs:** **Genie Goal + 10-Year Backcast**.
- **Checks:** Backcast produces concrete near-term moves (not just vision).
### 4) Generate 2–4 target archetypes + fit filters
- **Inputs:** progress metric; backcast; constraints.
- **Actions:** Turn the vision into 2–4 **target archetypes** (role + environment). Define fit filters: culture/people fit, learning, autonomy, trust, pace, stability, mission, comp.
- **Outputs:** **Target Archetypes + Fit Filters**.
- **Checks:** Each archetype has clear “fit signals” and “no-go” signals.
### 5) Build an option scorecard + decision rule
- **Inputs:** archetypes; priorities; constraints.
- **Actions:** Create a lightweight scorecard (weighted criteria) and a decision rule (what evidence is required to choose). Identify the 3–6 biggest unknowns and how to resolve them.
- **Outputs:** **Option Scorecard + Decision Rule**.
- **Checks:** Criteria map to progress metric; weights reflect priorities; unknowns have a plan.
### 6) Build an opportunity pipeline (network + serendipity plan)
- **Inputs:** existing network; target archetypes; time available weekly.
- **Actions:** Build a list of people/communities to engage, a weekly outreach cadence, and a tracking system. Draft outreach scripts (informational interview, referral, follow-up).
- **Outputs:** **Opportunity Pipeline Plan** + outreach scripts.
- **Checks:** Pipeline has weekly targets (e.g., 3 outreach messages/week); next 7 days are scheduled.
### 7) Skills & proof plan (learning sprints + portfolio)
- **Inputs:** target archetypes; current assets; gaps.
- **Actions:** Identify the 3–5 highest-leverage gaps and design learning sprints. Define proof artifacts (project, write-up, demo, case study) that signal capability.
- **Outputs:** **Skills & Proof Plan**.
- **Checks:** Each gap has a concrete proof artifact; plan fits time/runway.
### 8) Quality gate + finalize the 4–12 week experiment plan
- **Inputs:** full draft pack.
- **Actions:** Turn unknowns into a sequenced experiment plan (informational interviews, shadowing, mini-projects, internal transfer, sabbatical/bridge proposal). Run [references/CHECKLISTS.md](references/CHECKLISTS.md) and score with [references/RUBRIC.md](references/RUBRIC.md). Add **Risks / Open questions / Next steps**.
- **Outputs:** Final **Career Transition Pack**.
- **Checks:** The next 2 weeks have scheduled actions; risks and unknowns are explicit; decision rule is clear.
## Quality gate (required)
- Use [references/CHECKLISTS.md](references/CHECKLISTS.md) and [references/RUBRIC.md](references/RUBRIC.md).
- Always include: **Risks**, **Open questions**, **Next steps**.
## Examples
**Example 1 (pivot with constraints):** “I’m a PM considering a move into product marketing or developer relations. I have 10 hours/week and need to stay remote. Use `career-transitions` to create a Career Transition Pack with an option scorecard and a 6-week experiment plan.”
Expected: archetypes + scorecard + outreach/scripts + experiment plan.
**Example 2 (stay vs go):** “I’m feeling stuck at my current company. I’m not sure whether to ask for a 3-month sabbatical, transfer internally, or leave. Use `career-transitions` to help me decide and draft a sabbatical/bridge proposal.”
Expected: push/pull + progress metric + decision rule + sabbatical proposal + next steps.
**Boundary example:** “Tell me whether I should quit tomorrow and move countries on a visa without any plan.”
Response: out of scope for legal/immigration advice; recommend professional support and a safer decision process; offer to help build a plan once constraints are clarified.