# Examined Life

> 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".

- Skill: `newkayak12/examined-life` (Agent Skill)
- Install (CLI): `npx skillmds@latest add newkayak12/examined-life`
- Raw SKILL.md: https://api.skillmd.com/api/skills/newkayak12/examined-life/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Coding & Dev Tools
- Author: newkayak12 (https://skillmd.com/u/newkayak12)
- Updated: 2026-09-21
- Page: https://skillmd.com/skills/newkayak12/examined-life

---


# 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