liqiongyu/lenny_skills_plus/career-transitions

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 already have a target role at your current company and want to build a promotion case — use building-a-promotion-case
• You have a concrete job offer and need negotiation tactics — use negotiating-offers
• You want to build a mentor/sponsor network (not plan a transition) — use finding-mentors-sponsors
• You want to validate a startup idea, not plan a career move — use startup-ideation
• 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.
• 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 Expanded guidance: references/WORKFLOW.md

Workflow (8 steps)

1) Intake + current state snapshot

• Inputs: user context; 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 and score with 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 and 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.

Anti-patterns

1. ”Grass is greener” planning — Generating target archetypes based only on what you dislike about your current role without validating what the new path actually requires. Every archetype needs both “fit signals” and “reality-check” evidence from real conversations.
2. Analysis paralysis scorecard — Building a 20-criterion weighted scorecard that delays action. Keep criteria to 5-7 and pair the scorecard with a time-bound decision rule (“decide by date X with evidence Y”).
3. Network-free pipeline — Creating an outreach plan with zero warm paths. If fewer than 30% of targets have a plausible warm intro, invest first in community engagement and 2nd-degree mapping before outreach.
4. Skipping the experiment — Committing to a full transition (quitting, enrolling, relocating) without running a low-cost test. The experiment plan exists to de-risk the leap, not to delay it indefinitely.