Free workbook · From Purposeful Living

The Ready-to-Retire Checklist & Workbook

Five sections — money, Mondays, connection, health, and meaning — turned into simple worksheets so you can walk into retirement with a plan on paper, not just in your head.

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This workbook turns the five questions from our article 5 Questions to Answer Before You Retire into fill-in pages. Work through them with a pen, a partner if you have one, and no rush. The goal is clarity on paper — not perfection.

This workbook is general guidance, not financial, tax, legal, or medical advice. Before making irreversible decisions about pensions, benefits, investments, or healthcare coverage, speak with a qualified professional who knows your situation.

How to use this workbook

  1. Print it or copy the tables into a notebook.
  2. Complete Sections 1–5 in order if you can; money first often lowers anxiety for the rest.
  3. Mark one action at the end of each section you can finish in the next 14 days.
  4. Revisit every 6–12 months, or whenever your plans change.

Section 1 · Money: Do I have enough — and for how long?

List expected yearly spending and yearly income. Round numbers are fine; honesty beats precision.

1A · Annual spending estimate

Write a yearly amount (or monthly × 12) for each category.

  • Housing (mortgage/rent, tax, insurance, HOA): $ _______________ / year
  • Utilities & communications: $ _______________ / year
  • Food & household: $ _______________ / year
  • Transport: $ _______________ / year
  • Healthcare (premiums, out-of-pocket, dental, vision, meds): $ _______________ / year
  • Insurance (life, long-term care, home, auto): $ _______________ / year
  • Travel & hobbies: $ _______________ / year
  • Gifts, family support, charity: $ _______________ / year
  • Debt payments: $ _______________ / year
  • Other / buffer (10–15% is wise): $ _______________ / year
  • Total estimated spending: $ _______________ / year

1B · Annual income in retirement

  • Social Security / state pension (estimate at planned claim age): $ _______________ / year
  • Workplace pensions / annuities: $ _______________ / year
  • Part-time or online work: $ _______________ / year
  • Rental or other passive income: $ _______________ / year
  • Planned draw from savings/investments: $ _______________ / year
  • Total estimated income: $ _______________ / year

1C · The gap check

  • Income − spending = $ _______________ (surplus or shortfall)
  • Years I want this plan to cover (e.g. to age 90+): _______________
  • Have I allowed for inflation? ☐ Yes ☐ Not yet
  • Have I listed large one-off costs (car, roof, move, care)? ☐ Yes ☐ Not yet

If there is a shortfall, which levers will I explore? (work longer, delay benefits, downsize, cut large costs, adjust draw rate, side income)

14-day action:

Section 2 · Mondays: What will I do with my days?

Work quietly provides structure, purpose, social contact, and identity. Plan what replaces them.

2A · Picture an ordinary Wednesday six months in

Wake time, morning, afternoon, evening — who you see, what you work toward:

2B · Build the non-financial plan now

  • One class, club, or hobby I will start or restart: _______________
  • One project I want to finish this year: _______________
  • One standing social appointment (coffee, walk, group): _______________
  • One way I will keep a weekly rhythm (see also our Purpose Playbook): _______________

14-day action:

Section 3 · Connection: How will I stay with people?

3A · My community map

  • Friends I will actively tend (list 3–5): _______________
  • Family presence I want more of: _______________
  • Activity-based group to join before I retire: _______________
  • Faith, volunteer, or interest community: _______________

Where will low-effort daily contact come from once colleagues are gone?

14-day action:

Section 4 · Health: Is my health plan as solid as my money plan?

4A · Habits

  • Movement plan (walk / morning routine / strength): _______________
  • Sleep target: _______________
  • Eating pattern I can sustain: _______________
  • Next check-up / screening dates: _______________

4B · Coverage & costs

  • Healthcare coverage the day after I stop working: _______________
  • Any gap before Medicare / other benefits? ☐ No ☐ Yes — plan: _______________
  • Estimated annual out-of-pocket healthcare: $ _______________
  • Medications list reviewed with doctor this year? ☐ Yes ☐ Not yet
  • Long-term care conversation started with family? ☐ Yes ☐ Not yet

14-day action:

Section 5 · Meaning: A good day and a good decade

5A · Direction, not a grand mission

What do I want these years to mean? Skills to pass on, places, causes, family presence, things to learn or make:

5B · One-page retirement vision

In 5–8 sentences, describe a well-lived ordinary week in your third act:

Optional: complete the free guided journal and purpose playbook for deeper work.

Master checklist · Ready to retire?

  • ☐ Spending and income lists drafted
  • ☐ Gap (if any) has at least one planned lever
  • ☐ Inflation and longevity considered
  • ☐ Ordinary-day plan written
  • ☐ At least one social/community anchor in place or scheduled
  • ☐ Healthcare coverage path understood
  • ☐ Movement habit started (even 10 minutes)
  • ☐ Meaning / direction statement written
  • ☐ Partner/family conversation held (if applicable)
  • ☐ Professional advice booked where money decisions are irreversible

Target retirement window (flexible is fine): _______________

My next three actions, with dates:

The date on the calendar matters far less than the clarity you bring to it.