🪞 Self-Reflection Journal Pack — 30 Prompts for Honest Life Review

Your Self-Reflection Session — Q1 Review, VP-Role Restlessness

What I'm Noticing

You're 6 months into a role that was supposed to be arrival, and you're restless. That's diagnostically significant. 'Settling in' and 'this isn't it' feel identical at 6 months — both produce restlessness, both produce second-guessing. The difference is what the restlessness is POINTING AT. Today's job is to clarify the pointing, not the decision.

Secondary signal: you have teens. That life-season matters for career reflection. Parents of teens often experience career ambivalence because the window for different fatherhood/motherhood is closing — kids will be out of house in 4-6 years. The restlessness may be less about the VP role and more about what the VP role is COSTING you in the teen years.

Third signal: 18 years at same company. Identity may be fused with organizational role in ways that make role-change feel like identity-collapse. That's normal AND worth examining.

Format I'm Suggesting

Quarterly Review format, extended to address the specific career-identity question. 4-hour window lets us do 3 prompts with real depth. Not trying to decide career move today — trying to clarify WHAT the restlessness is pointing at.

Your Prompts for This Session

Prompt 1: The Two-Values Audit — Last 90 Days (75 min)

Brené Brown's rule: two core values max. Before doing this session: from a list of 50-100 values (search 'Brené Brown values list' if you don't have one), pick 10 that resonate. Then narrow to 2. These are your operational values right now, not aspirational values.

Then, for the last 90 days specifically:

• Write 500 words examining: in what specific moments did I HONOR these two values? (not 'I generally try to be X' — specific moments)
• Write 500 words examining: in what specific moments did I VIOLATE these two values? (again, specific moments — not 'I sometimes failed at Y')
• For each violation moment, answer: why did I violate? What competing pressure won?

Framework: Brown's values operationalization + ACT's directions-vs-goals distinction. What you actually HONOR vs. what you claim reveals the real value hierarchy. The competing pressures that won reveal your unconscious priorities.

Time box: 75 minutes. 45 minutes writing, 30 minutes review/edit for specificity.

Constraints:

• Must be 2 values, not 3-10
• Specific moments required (time, place, who was there, what happened)
• No self-flagellation — this is diagnostic, not punitive
• Do not write 'I should do better at X' — we're surfacing, not prescribing

Prompt 2: The VP-Role Tuesday Test (60 min)

Imagine a typical Tuesday 2 years from now, 2.5 years into the VP role. Not a glamorous launch day, not a crisis day — an ordinary Tuesday.

Describe it in specific detail, 400-500 words:

• What time do you wake up?
• What is the first work-related thing you do?
• How do you feel physically by 11am?
• What are your three main interactions that Tuesday? (specific people, specific conversations)
• When do you leave work? What are you doing at 8pm?
• Did you see your teens today? How? For how long?

Then answer: Is this Tuesday ACCEPTABLE to me?

Not 'exciting.' Not 'my dream life.' Acceptable — meaning, could I live this Tuesday every week for 2 years without eroding?

Framework: Cal Newport's deep-work-calendar thinking + Tim Ferriss's 'Tuesday test' + Ken Wilber's life-phase integration. Ordinary days reveal real preference. Glamorous-day fantasies reveal performed aspiration.

Time box: 60 minutes. 40 writing, 20 review.

Constraints:

• Specific, ordinary Tuesday — NOT launch day, presentation day, promotion day
• Must include teen-parent interaction (or its absence)
• Physical-state details required (sleep, energy, body)
• Must answer the 'acceptable' question with yes or no, not 'it depends'

Prompt 3: The Restlessness-Pointing Inquiry (45 min)

Given what surfaced in Prompts 1 and 2, answer these questions:

a) Is the restlessness pointing at the ROLE?

Evidence for: specific parts of the VP work that feel misaligned with your values. Specific interactions that drain rather than energize. Specific things you thought VP would give you that it hasn't.

b) Is the restlessness pointing at the COMPANY?

Evidence for: 18 years of identity fusion making any role at this company feel confining. Systemic things you've been tolerating that have now accumulated to intolerable. Specific external opportunities you notice pulling attention.

c) Is the restlessness pointing at the LIFE CHAPTER?

Evidence for: teen-parent awareness of closing windows. Health markers that demand life-rhythm change. Financial arrivals that now permit different questions. Relationship dynamics that need more attention than the current setup allows.

d) Is it three different restlessnesses braided together?

If yes: separate them. Each may have a different response.

Framework: Peter Koestenbaum's existential leadership work — restlessness is always pointing at something specific. The job is diagnosis, not resolution.

Time box: 45 minutes. This is the clarifying prompt — take time with it.

Constraints:

• Name evidence for each possibility, not just gut feel
• Do NOT try to decide between a/b/c today
• If multiple possibilities, note which feels MOST right — but trust that today's feeling may shift with distance
• End with a single sentence: 'The restlessness is primarily pointing at [X], and secondarily at [Y].'

Session Close

Before closing, answer this: What concrete commitment do I have for the next 90 days that honors what surfaced today?

NOT a career decision. A commitment.

Examples:

• 'Over the next 90 days, I will have 3 specific conversations with senior leaders outside my current company — not for job search, but for external-perspective calibration.'
• 'Over the next 90 days, I will do one concrete thing to reduce VP-role hours by 20% — not quit, experiment.'
• 'Over the next 90 days, I will plan a specific 4-day trip with my teens — before-kids-leave-house material.'

The 90-day commitment is how quarterly reflection becomes integration. Without it, reflection is just journaling.

Write the commitment. Print it. Put it where you'll see it weekly.

The Full 30-Prompt Library (Copy Ready)

CATEGORY 1: Values Audit (Brown, ACT)

1.1 — The Two-Values Operational Audit

Pick 2 core values (not 10). For the last 90 days, examine specific moments you honored AND specific moments you violated each value. What competing pressures won when you violated?

1.2 — The Values-Behavior Gap

For each of your 2 chosen values, write: (a) what would someone observing my last 90 days conclude I value, based on behavior alone? (b) Where is the gap between claimed values and observed values? (c) What would closing the gap require?

1.3 — Values in Money

Your bank/credit-card statements for the last 90 days are a values record. What do the specific line items say you value? Not 'I value experiences' — what line items? What's missing that you claim to value but didn't spend on?

1.4 — Values in Time

Audit your calendar for the last 30 days. What percentage of time honored each of your 2 values? What percentage violated? What does the calendar say you actually prioritize?

1.5 — The Partner's-Eye Audit

If your partner, closest friend, or trusted colleague were writing YOUR values audit for the last 90 days, what would they write? What would they say you honor vs. violate? (You can ask them if useful.)

CATEGORY 2: Quarterly Review (90-day rhythm)

2.1 — The Three Things That Went Right

Three specific things from the last 90 days that went BETTER than you expected. For each: what worked? What systems/people/conditions contributed? Can you replicate deliberately?

2.2 — The Three Things That Went Wrong

Three specific things that went WORSE than expected. For each: what failed? Where was the leading indicator you missed? What would you do differently?

2.3 — Energy Pattern Map

When did you have most energy in the last 90 days? Least? Map the pattern — time of day, week, month; particular people/activities/situations. What would structure more of the high-energy patterns into the next 90 days?

2.4 — The Identity Commitments You Kept

What did you SAY you would do 90 days ago that you actually DID? What did you say you would do that you didn't? The kept/not-kept ratio is a leading indicator of trust in yourself.

2.5 — The Next 90-Day Intentions

3 specific commitments for the next 90 days. NOT goals ('I will hit $X revenue') but commitments ('I will have the hard conversation with my business partner by April 15'). Commitments are action-verbs with deadlines.

CATEGORY 3: Identity Inquiry (Wilber, Koestenbaum)

3.1 — The Identity You're Performing

What identity are you currently performing — professionally, relationally, socially? Specifically (the VP, the caretaker, the 'strong one,' the peacemaker). What does this performance cost you? What does it protect?

3.2 — The Identity You're Becoming

Separate from current performance: who are you becoming over the next 5 years, based on actual trajectory (not wishful thinking)? What does the trajectory suggest? Are you okay with it?

3.3 — The Identity You Refuse To Claim

What version of yourself do you keep at the edge of possibility but not actually live into? The writer, the activist, the parent who prioritizes that differently, the quitter? What would claiming cost? What would not claiming cost?

3.4 — The Identity You're Growing Out Of

Who have you been that you no longer are? Who are you no longer willing to be? Where is this transition showing up in specific behaviors? What support does this ending need?

3.5 — The Integrated Self

Wilber's integral approach: interior-individual (thoughts, feelings), exterior-individual (body, behavior), interior-collective (culture, values), exterior-collective (systems, institutions). In which quadrant are you most integrated? Least? What does that suggest?

CATEGORY 4: Relationship Map

4.1 — The Five-Closest Audit

List your 5 closest people (time spent, emotional intimacy — not social-media-closest). For each: are they becoming who you want to become? Are you becoming who you want to become through them? What does the aggregate suggest?

4.2 — The Upcoming Conversations

What are the 3 hardest conversations you need to have in the next 90 days? Who, what about, what's at stake. Do you know what to say? What's stopping you?

4.3 — The Relationships You're Maintaining vs. Feeding

Which of your 10 closest relationships are you MAINTAINING (minimal contact, keeping alive) vs. FEEDING (actively investing in, growing)? Is the balance right? What shifts would serve you over next 90 days?

4.4 — The Grief of Ended Relationships

What relationships have ended in the last year (by choice, by drift, by circumstance)? What did you lose? Have you acknowledged the loss or moved past without grieving? What completion would serve?

4.5 — The Relationships You're Avoiding Starting

Who do you know you should meet, reach out to, build relationship with — and haven't? What's the avoidance? What would initiating cost? What would it produce?

CATEGORY 5: Five-Year Vision (Tuesday Test)

5.1 — The Ordinary Tuesday, Five Years Out

Describe a specific ordinary Tuesday 5 years from now. Not glamorous day. Tuesday. Wake time, eating, work, interactions, 8pm, 10pm. Is this Tuesday acceptable?

5.2 — The Work You Want To Be Doing In Five Years

Specifically. Not 'more senior' — what type of problems do you want to be solving? Who do you want to be working with? What does the daily texture of the work look like? Is it 80% of your current work or 20%?

5.3 — The Relationships You Want In Five Years

Your 5 closest — are they the same people as today, or different? What relationships do you want to have developed? What relationships might need to be released? Is anyone missing who you want included?

5.4 — The Body You Want In Five Years

How does your body FEEL daily? What can it do that your current body can't? What chronic conditions, if any, have you addressed? Is the body path you're on aligned with the body you want?

5.5 — The Five-Year Resource Question

How much money do you want, and to what end? Not 'more' — specific. What capacity does the money unlock? What does the exercise of figuring out your specific number reveal about what you actually want?

CATEGORY 6: Life-Season Check

6.1 — The Chapter Audit

What chapter of your life are you in? Not calendar-year, chapter. Name it. What defines this chapter? What chapter came before? What ended that made this chapter possible? (Requires courage.)

6.2 — The Window That's Closing

What window is closing in your life right now? Teen-parent years? Parents' good-health years? Career peak? Fertility? Particular creative window? Be specific. What would regret look like 10 years from now if you didn't act on this window?

6.3 — The Window That's Opening

What window is OPENING? Empty-nest creativity? Post-retirement freedom? Mid-career authority? Health-investment compounding? Identify specifically. What would leaning into this window require?

6.4 — Tim Urban's Life Calendar

Draw 90 rows × 52 weeks. Color your age in weeks. How many weeks of being a parent of YOUNG children do you have left? Of having your parents alive? Of being able-bodied? The visual is the lesson.

6.5 — The Letter From Your 80-Year-Old Self

500 words from 80-year-old you to current you. What does 80-year-old you want you to know about this season? What to stop worrying about? What to start taking seriously? What regrets are they trying to prevent?

Troubleshooting

If reflection becomes rumination:

Rumination is reflection without time-bounds or action-step. You're ruminating if: (a) you're stuck on the same material for 3+ sessions without new insight, (b) you feel worse after reflection not clearer, (c) no integration intention emerges. Fix: hard-stop time boundaries + mandatory integration-intention close + shift to daily practice (different Pack) if needed.

If you want to decide right now:

DON'T. Decisions made in reflection sessions have ~30% lower stick rate than decisions made with 7+ days of distance. The reflection surfaces clarity; the decision requires integration of clarity with day-to-day life reality. Write the decision candidate. Sleep on it. Week from now, reread. If it still seems right, then decide.

If all your values sound performative:

Common at first. 'Integrity, courage, excellence' = aspiration, not value. Dig deeper. What about Tuesday-ordinary-life is non-negotiable to you? What do you refuse to compromise even when it costs? Those are real values. They are often less impressive than the performed ones ('time with family,' 'not being lied to,' 'creative autonomy on my projects').

If trauma material surfaces:

Stop. This is not the Pack for trauma work. Close the journal. Ground (5-4-3-2-1 sensory). Contact a licensed therapist. Reflection can surface but not process trauma. Do not return to this Pack until cleared with a clinician. US: 988. UK: Samaritans 116 123.

If you're doing this Pack too frequently:

Quarterly max. Daily self-reflection at this depth is destabilizing — too much introspection without integration. If you want daily practice, use the Morning Journaling Pack (different register). If you want exploratory practice, use the Journal Prompts Pack. This Pack is for quarterly or milestone moments.

Variation Playbook

For quarterly (default):

3-4 hour session, Category 1 + 2 + (one other) prompts selected. Execute end of Q1/Q2/Q3/Q4.

For annual year-end:

6-8 hour ritual, Category 1 + 2 + 3 + 6 prompts selected. Between Christmas and New Year. Produces year-ahead intentions (not resolutions — intentions are being-state; resolutions are specific-behavior).

For milestone birthdays:

Category 3 (Identity) + Category 6 (Life-Season) weighted heavily. Use Life Calendar (Prompt 6.4) regardless of context. Decade-level thinking.

For decision-point reflection:

Category 1 (Values) + Category 5 (Five-Year Tuesday Test) + specific-decision analysis. Do NOT decide during session. Use session to clarify, not commit.

For post-loss reflection:

Category 4 (Relationships — 4.4 Grief of Ended) + Category 6 (Life-Season — 6.1 Chapter Audit). Different register than celebration reflection. Pair with grief support (therapist, group). Do not perform 'moving on.'

For couples retreat individual work:

Each partner does individual reflection. Do NOT share during session. Bring clarified values TO the couples conversation afterward. Join facilitation with therapist/counselor if relationship is complex.

For executive coaching homework:

Category 1 + Category 2 + Category 5 weighted. Bring surfaced material to coaching session — especially values-behavior gaps and 90-day commitments. Coach + reflection together produce integration that either alone cannot.

Key Takeaways

• Quarterly rhythm beats daily for identity-level work. Daily journaling = emotional regulation; quarterly reflection = strategic life direction. You need both, not one. This Pack is the quarterly tool.
• Two values max (Brown). Ten-item values lists are performance. The discipline of picking two reveals which values are actually operational vs. aspirational.
• Values are directions, not destinations (ACT). 'Being a loving parent' is a value (direction); 'kids graduating college' is a goal. Reflection on values asks: what direction am I moving in?
• Tuesday test, not weekend test. Real preference shows in ordinary days. Glamorous-day fantasies reveal performed aspiration. Describe the Tuesday; then answer 'is this acceptable?' honestly.
• Reflection surfaces; decisions require distance. 7+ days between clarifying insight and committing to action. Decisions made in-session have lower stick-rate than decisions integrated with daily life over a week.