examined-life

name	examined-life
description	Use when someone wants to look at their life from a distance — not a specific decision, but the whole shape of it. Especially suited to life transitions, major milestones, or the feeling of running on autopilot. Triggers on: "삶을 돌아보고 싶어", "내 인생을
scenarios	["I feel like I've been on autopilot for years","I want to step back and look at the shape of my whole life","What would I regret if I kept going the way I am?","내 인생이 진짜 내 인생인지 모르겠어","자동으로 흘러가고 있는 것 같아, 점검하고 싶어","인생의 큰 그림을 스토아적으로 돌아보고 싶어"]
compatibility	{"optional":["think-tool","sequential-thinking"],"remote_mcp_note":"think-tool이 있으면 감사 결과에 맞는 스토아 도구를 선택하는 판단을 더 정밀하게 할 수 있습니다. sequential-thinking은 감사 → 도구 선택 → 적용 순서를 지키는 데 유용합니다. Claude 설정 → MCP Servers에서 remote SSE 엔드포인트를 추가하세요."}

The Examined Life

When to Use / When Not to Use

Use when:

• Life transitions: career change, relationship shift, milestone birthday, loss
• Feeling of running on autopilot or living someone else's expectations
• Wanting the whole-life view, not a single-decision view

Not for:

• Single-decision analysis (use tradeoff-articulator)
• Values clarification alone (use values-explorer first)

Process

Order matters: Complete the audit before selecting Stoic tools. Jumping to reframing before examining produces philosophical bypassing.

MCP note: If sequential-thinking is available, enforce: (1) audit → (2) identify findings that need reframing → (3) select tools → (4) apply.

Part 1 — The Examined Life Audit

Autopilot Check: For each major domain (work, relationships, where you live, how you spend time):

• Did you choose this deliberately, or did you arrive by accumulation?
• If designing from scratch with what you know now, would you choose it again?
• Who would you be disappointing if you changed this?

Values-Life Alignment Check: Cross-reference stated values against how time, money, and attention are actually spent. Name the gaps without shame — they are information, not failures.

Regret Audit (Bronnie Ware's five most common deathbed regrets):

1. Courage to live a life true to yourself, not others' expectations
2. Not working so hard
3. Courage to express feelings
4. Staying in touch with friends
5. Letting yourself be happier

Ask: Which might you share if you carried on as you are now? What specifically would produce it?

Aliveness Question: When do you feel most alive — not successful, not productive, but alive? What are you doing? What does this reveal about what you actually want?

Audit Output

Examined Life Audit
-------------------
Consciously chosen vs inherited/drifted: [rough proportion and examples]
Most significant alignment gap: [values vs. actual time/attention]
Regret risk: [which Ware regret resonates most, and the specific form it takes]
Where you feel most alive: [concrete, specific]
Where you feel most on autopilot: [concrete, specific]
The one question this audit keeps returning to: [what most needs honest examination]

Part 2 — Stoic Reframing

Select 1–2 tools that fit what the audit revealed:

Finding	Tool
Drift and autopilot	Memento mori + dichotomy of control
Loss or grief	Amor fati + negative visualization
Anxiety about uncontrollables	Dichotomy of control
Taking things for granted	Negative visualization

Dichotomy of Control (Epictetus): Separate what is in your control (response, effort, values, attention) from what is not (others' reactions, outcome, circumstances). Place all energy on the left column.

Negative Visualization: Imagine losing what you have. Two effects: deepens appreciation, and reveals which losses would feel genuinely catastrophic — pointing to what actually matters.

Memento Mori: In the context of a finite life, how much does this actually matter? What have you been postponing?

Amor Fati: Not just acceptance of what can't be changed, but active engagement: what does this obstacle require you to develop? What path does it force that you might not have taken voluntarily?

End with one practical commitment — not a life overhaul, a first step.

Output Template

Audit output (above) + 1–2 Stoic tools applied to the most significant finding + one concrete commitment.

What Claude Does / What You Do

Claude	You
Asks Socratic questions to surface what's on autopilot	Reflect honestly on each domain — don't edit for the "right" answer
Maps the gap between stated and lived values	Sit with the discomfort of the alignment gaps
Selects the Stoic tool(s) that fit the audit findings	Do the reframing work — Claude can name the tool, you have to apply it
Names the one question the audit keeps returning to	Make one concrete commitment

Related Skills

• values-explorer — for deep values clarification work
• fear-inventory — when the autopilot is driven by fear
• flow-antigoal — for designing a life around what creates deep engagement