Session 1 · Guide and forms

Retirement Readiness Assessment

A Self-Evaluation for Men Approaching or In Retirement — organized by the Ten Domains of Life

“The purposes of a person’s heart are deep waters, but one who has insight draws them out.” — Proverbs 20:5

Purpose of This Assessment

This assessment serves two purposes:

To help you honestly evaluate your readiness for this season of life — not just financially, but emotionally, relationally, and spiritually.

To open your eyes to dimensions of retirement you may not have considered — areas where intentional preparation can make the difference between thriving and merely surviving.

There are no ‘right’ answers. Low scores aren’t failures — they’re invitations to growth. This assessment is organized by the same Ten Domains of Life that frame your Harvest Charter, so what you discover here points directly to where the work begins.

Optional: If you share this completed assessment with the WhyzMen facilitator, we can better tailor discussion topics, connect you with relevant resources, and if appropriate, suggest conversations with men who’ve navigated similar challenges.

Section A — Basic Information

Name:
Date:
Age:
Marital Status:	○ Married ○ Widowed ○ Divorced ○ Single
Years Married:

Retirement Status:

○ Not yet retired — planning to retire within _____ years

○ Recently retired (within the past 2 years)

○ Retired 2–5 years

○ Retired 5–10 years

○ Retired more than 10 years

○ Semi-retired / working part-time

Primary Career / Profession:

How did you hear about WhyzMen?

For each statement in the ten domains below, rate yourself: 1 = Strongly Disagree · 2 = Disagree · 3 = Neutral · 4 = Agree · 5 = Strongly Agree

1. Faith & Spiritual Life

The anchor for everything else

Statement	1	2	3	4	5
1. I have a consistent personal devotional or prayer life.	○	○	○	○	○
2. I am actively engaged in a church community.	○	○	○	○	○
3. I sense God’s leading for this season of my life.	○	○	○	○	○
4. I have processed questions about suffering, mortality, and legacy with faith.	○	○	○	○	○
5. I am growing spiritually, not just maintaining.	○	○	○	○	○
6. I have mentors or spiritual friends who encourage my faith.	○	○	○	○	○
7. I see retirement as an opportunity for deeper spiritual investment.	○	○	○	○	○
8. I am at peace with God regardless of circumstances.	○	○	○	○	○

Domain 1 Subtotal: _______ / 40

2. Marriage & Family

The closest people who journey with you

If married, rate each statement. If not married, skip to Domain 3.

Statement	1	2	3	4	5
1. My wife and I have discussed our expectations for retirement.	○	○	○	○	○
2. We have a shared vision (or compatible individual visions) for this season.	○	○	○	○	○
3. We communicate openly about fears, hopes, and concerns.	○	○	○	○	○
4. I feel emotionally connected to my wife — not just cohabiting.	○	○	○	○	○
5. We have navigated the ‘more time together’ transition well (or have a plan to).	○	○	○	○	○
6. I do not need my wife’s approval to pursue my sense of calling.	○	○	○	○	○
7. We have addressed any significant unresolved conflicts or wounds.	○	○	○	○	○
8. Our marriage is a source of support, not stress, as I consider my next chapter.	○	○	○	○	○

Domain 2 Subtotal: _______ / 40

3. Friendships & Community

The brotherhood and belonging that sustain a life

Statement	1	2	3	4	5
1. I have at least 2–3 close male friends I can confide in honestly.	○	○	○	○	○
2. I have friendships that don’t depend on work or professional connections.	○	○	○	○	○
3. I have people who will hold me accountable and ask hard questions.	○	○	○	○	○
4. I am comfortable being emotionally vulnerable with other men.	○	○	○	○	○
5. I have relationships with people of different generations.	○	○	○	○	○
6. My friendships are not dependent on my wife to initiate or maintain.	○	○	○	○	○

Domain 3 Subtotal: _______ / 30

4. Health & Wellbeing

The foundation that makes everything else possible

Statement	1	2	3	4	5
1. I have a regular exercise routine that I maintain consistently.	○	○	○	○	○
2. I am satisfied with my current physical health and energy level.	○	○	○	○	○
3. I have a plan for maintaining cognitive sharpness (learning, reading, challenges).	○	○	○	○	○
4. I get adequate sleep and manage stress effectively.	○	○	○	○	○
5. I have addressed any mental health concerns (depression, anxiety, etc.).	○	○	○	○	○
6. I have a primary care physician and stay current on preventive care.	○	○	○	○	○
7. I am at a healthy weight or have a realistic plan to get there.	○	○	○	○	○
8. I have accepted the physical limitations that come with aging.	○	○	○	○	○

Domain 4 Subtotal: _______ / 40

5. Identity & Purpose

Moving from ‘What do you do?’ to ‘Who are you?’

Statement	1	2	3	4	5
1. I have a clear sense of who I am apart from my career or job title.	○	○	○	○	○
2. I can articulate my core values and what matters most to me.	○	○	○	○	○
3. I have a sense of purpose or calling for this season of life.	○	○	○	○	○
4. I know what brings me joy and have activities that energize me.	○	○	○	○	○
5. I have processed any grief or loss related to leaving my career.	○	○	○	○	○
6. I feel at peace with my professional accomplishments and legacy.	○	○	○	○	○
7. I have interests and passions outside of work that I’m excited to pursue.	○	○	○	○	○
8. I have a written personal mission statement or life purpose statement.	○	○	○	○	○
9. I wake up with a sense of purpose most days.	○	○	○	○	○

Domain 5 Subtotal: _______ / 45

6. Service & Contribution

From success to significance

Statement	1	2	3	4	5
1. I have identified ways to use my skills and experience to serve others.	○	○	○	○	○
2. I am involved (or plan to be) in meaningful volunteer work or ministry.	○	○	○	○	○
3. I see this season as an opportunity to make an impact, not just relax.	○	○	○	○	○
4. I have considered mentoring or investing in the next generation.	○	○	○	○	○
5. I have a specific cause or group of people I feel called to serve.	○	○	○	○	○
6. I have a way to pass on my experience and wisdom to others.	○	○	○	○	○

Domain 6 Subtotal: _______ / 30

7. Growth & Learning

Staying green and growing, not ripe and rotting

Statement	1	2	3	4	5
1. I am continuing to learn and grow intellectually.	○	○	○	○	○
2. I am actively developing a new skill or area of knowledge.	○	○	○	○	○
3. I read, study, or take on mental challenges regularly.	○	○	○	○	○
4. I welcome feedback and see it as fuel for growth, not criticism.	○	○	○	○	○
5. I am growing in character and wisdom, not only in knowledge.	○	○	○	○	○

Domain 7 Subtotal: _______ / 25

8. Recreation, Adventure & Joy

The God-given gift of delight and rest

Statement	1	2	3	4	5
1. I have hobbies or interests that provide challenge and engagement.	○	○	○	○	○
2. I have a ‘bucket list’ or goals for experiences I want to pursue.	○	○	○	○	○
3. I make regular time for play, fun, or activities that simply bring me joy.	○	○	○	○	○
4. I have new adventures or experiences I am genuinely looking forward to.	○	○	○	○	○
5. I can rest and enjoy leisure without guilt.	○	○	○	○	○

Domain 8 Subtotal: _______ / 25

9. Finances & Stewardship

Money — and time — as tools, not masters

Statement	1	2	3	4	5
1. I have a clear understanding of my retirement income and expenses.	○	○	○	○	○
2. I am confident my finances will sustain my desired lifestyle.	○	○	○	○	○
3. I have discussed financial expectations with my spouse (if applicable).	○	○	○	○	○
4. I have a plan for healthcare costs, including potential long-term care.	○	○	○	○	○
5. I have updated estate planning documents (will, POA, healthcare directive).	○	○	○	○	○
6. I have a giving plan that reflects my values and generosity goals.	○	○	○	○	○
7. I am not anxious about money or fearful of running out.	○	○	○	○	○
8. I view my resources as tools for impact, not just security.	○	○	○	○	○
9. I steward my time as intentionally as I steward my money.	○	○	○	○	○

Domain 9 Subtotal: _______ / 45

10. Practical Readiness

The logistics that support the life you want

Statement	1	2	3	4	5
1. I have a weekly/daily structure that provides rhythm without rigidity.	○	○	○	○	○
2. I have thought about where I want to live long-term.	○	○	○	○	○
3. I have a plan for staying socially connected (not isolated).	○	○	○	○	○
4. I know how I will fill the hours previously spent working.	○	○	○	○	○
5. I have contingency plans for health crises or loss of independence.	○	○	○	○	○
6. I have discussed end-of-life wishes with family.	○	○	○	○	○
7. I have considered what ‘home’ will look like as I age.	○	○	○	○	○
8. I have identified my ‘third places’ — where I’ll regularly engage with others.	○	○	○	○	○
9. I have begun intentionally addressing the accumulation of possessions — deciding what to keep, give to specific people, donate, or release — rather than leaving that burden for others.	○	○	○	○	○
10. (If married) My spouse and I have reached a working peace about possessions — our different tendencies to keep or release are understood and respected, not a source of ongoing conflict.	○	○	○	○	○

Domain 10 Subtotal: _______ / 50 (or _______ / 45 if unmarried)

Scoring Summary

Domain	Your Score	Possible
1. Faith & Spiritual Life		40
2. Marriage & Family		40*
3. Friendships & Community		30
4. Health & Wellbeing		40
5. Identity & Purpose		45
6. Service & Contribution		30
7. Growth & Learning		25
8. Recreation, Adventure & Joy		25
9. Finances & Stewardship		45
10. Practical Readiness		50*
TOTAL		370*

* Domain 2 (Marriage & Family): skip if unmarried. Domain 10: 50 if married, 45 if unmarried. Married total 370; unmarried total 325.

Interpreting Your Scores

Because the domains have different numbers of statements, read each one by percentage of its possible score:

Score	Level	What it means
86–100%	Thriving	A strength. Consider how you might help others here.
67–85%	Strong	You’re in good shape. Maintain and keep growing.
46–66%	Developing	Progress made, room to grow. Intentional effort pays dividends.
≤ 45%	Needs Attention	This area may be limiting your flourishing — a priority for growth.

Your Lowest Two Domains:

1. ________________________________ 2. ________________________________

These are your priority domains for the WhyzMen program — and the first domains you will build in your Harvest Charter.

Reflection Questions

Take a few minutes to reflect. Your honest answers will help you get the most from the WhyzMen experience.

1. What surprised you most about your responses?

2. What domain do you most want to address in the next 6 months?

3. What’s one thing you’ve been avoiding thinking about regarding retirement?

4. If you could achieve one outcome from the WhyzMen program, what would it be?

5. What specific fears or concerns do you have about retirement?

What WhyzMen Can Help You Achieve

Through the WhyzMen program — 15 sessions over two stages — men who engage fully can expect to:

Identity & Purpose

●Develop a clear personal mission statement for this season

●Identify your unique strengths, passions, and calling

●Create a written Harvest Charter documenting your vision and goals

Marriage, Family & Relationships

●Navigate the transition to more time together with your spouse

●Address emotional disconnection and build deeper intimacy

●Build authentic friendships with other men

Health & Wellbeing

●Develop sustainable practices for physical, mental, and emotional health

●Address loneliness and build a support network

Faith & Significance

●Deepen your spiritual life and sense of God’s calling

●Identify opportunities to use your experience for Kingdom impact

●Move from success to significance

Practical Outcomes

●Complete a comprehensive Harvest Charter — a personalized document capturing your purpose, values, goals, and commitments

●Build relationships with a cohort of men navigating similar transitions

●Establish accountability structures that continue beyond the program

Ready to Begin?

Return this assessment to your WhyzMen facilitator. Your answers are confidential and will help us serve you better.

Wise Men Seek, Knowing Their Why’s

WhyzMen · Rewire Retirement · Retirement Readiness Assessment · Aligned to the Ten Domains