Annual Planning Retreat

Day 1: Reflection, Vision & Life Planning

A Pocket Guide for Couples

How to Use This Guide

This guide walks you through your annual planning retreat, step by step.

For each section:

  • Read the prompt together

  • Reflect individually (where noted)

  • Share and discuss

  • Capture your decisions

Time estimate: Full day (10am-5pm with lunch break)

What you'll need:

  • This guide

  • Pens

  • Your phones (to browse through photos and relive the year)

  • Open hearts

Note: Skip or adapt any sections that don't apply to your situation.

Morning Block

Opening & Intention Setting

15 minutes

Before diving in, ground yourselves. This isn't just planning — it's an investment in your relationship, family, and future.

❋

Opening Questions

Discuss together:

  1. What do we want to get out of today?

  2. How do we want to show up for each other?

  3. Any ground rules?

    • No phones (except for photos)?

    • Assume good intent?

    • Take breaks when needed?

Year in Review

30 minutes

Look back before looking forward.

Format: Write separately for 10 minutes, then share for 20 minutes.

Tip: Before answering, scroll through your photo gallery together or separately. Let the images remind you of moments you may have forgotten. Your camera roll is a time capsule — use it.

Year in Review — Questions

  1. What were the 3-5 key moments of this year?

  2. What did we do that I loved?

  3. What was my favorite trip / experience and why?

  4. What surprised me this year (good or bad)?

  5. What am I most proud of from this year?

Year in Review — Partner's Answers

Listen to your partner share, then capture:

  • What stood out to me from their answers:

  • What surprised me:

  • What I want to remember:

Wheel of Life

30 minutes

Rate each area of your life 1-10, then compare.

Format: Rate independently for 10 minutes, then discuss for 20 minutes.

Mission Family Friends Romance Mind Soul Body Growth Money Joy 1 2 3 4 5 6 7 8 9 10 1 2 3 4 5 6 7 8 9 10 1 2 3 4 5 6 7 8 9 10 1 2 3 4 5 6 7 8 9 10 1 2 3 4 5 6 7 8 9 10 1 2 3 4 5 6 7 8 9 10 1 2 3 4 5 6 7 8 9 10 1 2 3 4 5 6 7 8 9 10 1 2 3 4 5 6 7 8 9 10 1 2 3 4 5 6 7 8 9 10
Mission Purpose, direction, meaningful contribution
Family Family relationships (however you define family)
Friends Friendships, social life, community
Romance Your relationship as a couple, intimacy, connection
Mind Mental health, clarity, intellectual stimulation
Soul Spirituality, inner peace, connection to something larger
Body Physical health, fitness, energy, sleep
Growth Personal development, learning, becoming
Money Financial health, security, abundance
Joy Are you actually enjoying life? Fun, play, pleasure

How to Score the Wheel of Life

Important: The scores measure how aligned your actions are with each category — not how you feel about the category or how much you want it.

If you're going to the gym every week, you're taking action on Body — that deserves a higher score, even if you're not where you want to be yet.

Ask yourself: "Am I actively doing something about this area of my life?"

  • 1-3: I'm not taking any action in this area

  • 4-6: I'm taking some action, but inconsistently

  • 7-8: I'm taking regular, consistent action

  • 9-10: This area is thriving and I'm fully engaged

Wheel of Life — Discussion

Important: The Wheel of Life is NOT a compatibility test. It's a tool to track and measure your actions toward self-improvement.

You're comparing current you to last year you — not comparing yourself to your partner.

Different scores between partners are normal and healthy. You're two different people on two different journeys.

Wheel of Life — What to Improve

Question: Which 2-3 areas feel most urgent to address next year? And why?

For each area you want to improve, write:

  1. What you want to improve

  2. Why it matters to you

  3. How you'll measure success

  4. End with "...while having fun"

Important: Only the unhinged attempt to improve all areas in the same year. You’ve been warned.

Partnership Check-in

45 minutes

Time for honest conversation about how you're operating as a team.

Format: Write separately for 10 minutes, then share for 35 minutes.

Partnership — Division of Labor

Think about all the responsibilities in your shared life — household, finances, planning, emotional labor, family logistics, etc.

Answer these questions:

  1. What feels balanced and fair?

  2. What feels unbalanced or heavy for me?

  3. What does my partner do that I'm grateful for?

Partnership — Energy

  1. What in our daily/weekly life drains my energy?

  2. What gives me energy?

  3. What do I wish we did more of together?

  4. What do I wish we did less of?

Partnership — Pride

  1. What am I proud of us for as a couple this year?

  2. What am I proud of my partner for individually?

Partnership — Discussion Guide

Tips for this conversation:

  • Lead with gratitude before discussing imbalances

  • Focus on understanding, not defending

  • Listen without interrupting

  • This is vulnerable — be gentle with each other

Vision for Next Year

45 minutes

Now look forward. What kind of year do you want to create?

Format: Write separately for 10 minutes, share for 20 minutes, agree on theme for 15 minutes.

Vision — Questions

  1. If next year had a theme or word, what would it be?

  2. What do I want the overall vibe of next year to feel like?

  3. What would make next year a great year for me personally?

  4. What would make it a great year for us as a couple?

  5. What would make it a great year for our household/family?

  6. What do I NOT want to repeat from this year?

Vision — Our Theme

After sharing, find common threads.

Our Theme for Next Year:

This becomes your filter for decisions throughout the year.

Lunch Break

1 hour

Step away. Don't talk about planning. Rest your brains.

Afternoon Block

Milestone Celebrations

30 minutes — Optional

Are there any significant birthdays, anniversaries, or milestones coming up next year?

Skip this section if nothing major is on the horizon.

Milestones — Questions

  1. What milestones are we celebrating next year? (Birthdays, anniversaries, achievements, retirements, etc.)

  2. How significant does this milestone feel to each of you? (1-10)

  3. Do you want to celebrate together, separately, or both?

  4. What kind of celebration feels right?

    • Big party vs intimate gathering

    • Trip vs local

    • Surprise elements or fully planned

  5. Budget range you're comfortable with?

  6. Any bucket list items to tie to this milestone?

Vacations, Holidays & Getaways

60 minutes

Plan your adventures for the year ahead.

Vacations — Questions

  1. How many big trips do we want to take next year?

  2. What destinations are we drawn to?

  3. What kind of trips? (Adventure, relaxation, cultural, exploring new places)

  4. Any trips tied to milestones or special occasions?

  5. Budget per trip?

  6. What needs to be booked early?

Holidays — Questions

  1. Where are we spending major holidays?

  2. Any family obligations or traditions to honor?

  3. What do we want to do differently this year?

Weekend Getaways — Questions

  1. How often do we want to get away? (Monthly, quarterly?)

  2. Just the two of us, or including others?

  3. Regular destinations or variety?

Travel Optimization — Questions

  1. How do we maximize platforms like Home Exchange, Airbnb, or Booking.com?

  2. Are there benefits to starting new accounts on any platform?

  3. Would consolidating to a single platform give us better rewards or status?

  4. What about credit card or debit card air miles? Are we maximizing points?

  5. Any travel memberships, loyalty programs, or hacks we should explore?

Individual Growth

30 minutes

Personal goals you'll each pursue next year.

Format: Write separately for 5 minutes, share for 25 minutes.

Individual Growth — Questions

  1. What do I want to learn or develop next year?

  2. What personal goal matters most to me?

  3. What do I need to do on my own to grow?

  4. What do I need my partner's help or support with?

  5. What might get in my way, and how can we protect against that?

Individual Growth — Partner's Answers & My Reaction

Their goals:

How I can support them:

Any conflicts I see (time, money, priorities):

How we'll check in on this:

Family & Household

30-45 minutes — Customize to Your Situation

This section covers household operations and, if applicable, children.

Choose the sections that apply to you:

  • Household operations (everyone)

  • Children (if you have kids)

Meal Planning & Food

15 minutes — Optional

If food waste, meal planning, or grocery shopping is a pain point, discuss it here.

Skip if this isn't an issue for you.

Meal Planning — Questions

  1. Is food waste or meal chaos a problem for us?

  2. Do we want to meal plan? If so, how often?

  3. Who owns this? Or do we share it?

  4. Do we want an app or system?

  5. Grocery shopping rhythm — who, when, how?

Personal Acquisitions

10 minutes

Things you each want to buy for yourselves next year.

Make something resembling Santa’s List, but you have to pay for them.

Children Section

Optional — Skip if not applicable

The following slides are for couples with children.

If you don't have children, skip ahead to "Quarterly Rhythm."

Parenting Check-in

15 minutes

How are things going with your kid(s)?

Parenting — Questions

  1. What's going well with our kid(s) right now?

  2. What's challenging?

  3. Are we getting enough quality time with them?

  4. Any parenting decisions we need to align on?

  5. Any activities, schools, or commitments to plan for next year?

Children & Money

15 minutes — Optional

Some families choose to teach children about money through allowances or other systems. This is entirely optional and depends on your values and your child's readiness.

Skip if this isn't something you want to implement.

Children & Money — Questions to Consider

  1. Do we want to introduce any money concepts to our child(ren)? If so, what feels age-appropriate?

  2. Allowance: Is this something we want to do?

    • If yes: How much? How often?

    • Tied to responsibilities, or unconditional?

  3. Savings: Do we want to introduce saving concepts?

    • Spend / Save / Give jars?

    • Saving toward a goal?

  4. What money values, if any, do we want to model or teach?

  5. What's our comfort level with these conversations?

Quarterly Rhythm

15 minutes

Set up your check-in system for the year.

Quarterly Reviews — Questions

  1. When will we do quarterly check-ins? (Pick specific weekends)

  2. Where will we do them? (Home, a getaway, coffee shop)

  3. How long should they be?

Quarterly Review — What to Cover

Personal & Relationship

  • Wheel of Life quick check

  • Partnership health

  • Individual growth progress

Household & Family

  • Any systems we implemented — working?

  • Household friction points?

  • Kids (if applicable) — how's it going?

Calendar

  • Last quarter's trips — lessons?

  • Next quarter — what's booked?

Finances

  • Budget check

  • Acquisitions progress

  • Net worth snapshot (optional)

Theme Check

  • Are we living our theme?

Day 1 Closing

Closing Reflection

What am I most excited about from today?

What is my partner most excited about?

What Feels Unresolved?

Anything we need to revisit or discuss more?

Day 1 Complete

Congratulations!

You've done important work together today.

Take time to celebrate, rest and prepare for Day 2 - (Business & Finances)