10 honest questions that will show you exactly where you stand — and what to think about next.
⏱ About 3 minutes
📋 10 questions
🔒 Completely private
Question 1 of 10
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Welcome
This quiz isn't a test — there are no wrong answers.
It's a quick way to get clear on where you actually stand across five areas: finances, health, your home, lifestyle, and legal planning. Most people find that some areas are further along than they thought — and a couple need more attention.
Answer honestly. You'll get a personalized score and some practical next steps at the end.
💰 Finances
Question 1 of 10
Do you have a clear picture of what your monthly income will look like in retirement?
Think Social Security, any pension, investment withdrawals, rental income, or part-time work. The goal isn't perfection — it's knowing roughly what's coming in.
Yes — I know my numbers and feel confident about them
Mostly — I have a rough idea but haven't nailed down the details
Not really — I know I should figure this out but haven't yet
No — this is the part that worries me most
💰 Finances
Question 2 of 10
Are you on track to be debt-free — or close to it — when you make this move?
High-interest debt like credit cards can put real pressure on a fixed income. A paid-off or nearly paid-off mortgage going into retirement is one of the best financial positions you can be in.
Yes — I'm debt-free or will be very close to it
Mostly — manageable debt with a clear payoff plan
Working on it — it's more than I'd like but I'm making progress
Not yet — debt is a real concern for me right now
❤️ Health & Wellness
Question 3 of 10
Do you have health insurance coverage figured out for retirement?
For most people, this means Medicare starting at 65 — possibly with a supplement plan. If you're retiring before 65, the gap between your employer coverage ending and Medicare beginning needs a plan. Healthcare is often the biggest surprise expense in retirement.
Yes — Medicare and/or supplements are sorted out
Mostly — I understand my options and have a general plan
Somewhat — I know I need to deal with this but haven't yet
Not yet — this is a gap I need to address
❤️ Health & Wellness
Question 4 of 10
Have you thought about what you'd need if your mobility or independence changed down the road?
This one's easy to skip because nobody likes thinking about it. But the couples who navigate this best are the ones who had the conversation before they needed to — about care preferences, who's involved, and what "aging well" looks like for them.
Yes — we've talked about it and have a general plan
Somewhat — we've touched on it but haven't gone deep
Not really — it's on the list but we keep putting it off
No — we haven't gone there yet
🏠 Your Current Home
Question 5 of 10
Is your current home realistically set up for the next 10-20 years of your life?
Think about stairs, maintenance demands, how many rooms you actually use, and what happens if one of you has a health issue. A lot of people love their home but quietly know it's not the forever answer.
Yes — it works well and I can see us here long-term
Mostly — with some modifications it could work
Not really — it's starting to feel like more than we need or can manage
No — we know this house isn't the right long-term fit
🏠 Your Current Home
Question 6 of 10
Have you thought seriously about where you'd want to live next?
Not necessarily a specific address — but a direction. Closer to family? A 55+ community? A smaller town? A different state? People who've given this real thought tend to make much better moves than those who decide in a hurry.
Yes — I have a clear idea of what I want and where
Somewhat — I have a general direction but haven't gotten specific
Not really — I know what I don't want more than what I do
No — I haven't gotten that far in my thinking yet
🌟 Lifestyle & Purpose
Question 7 of 10
Do you have a clear sense of what you're moving toward — not just what you're leaving behind?
This is the question most people skip. The best moves happen when people have a vision of what the next chapter looks like — hobbies, travel, volunteering, family time, community. When you're just "getting out," it's easy to land somewhere that doesn't really fit either.
Yes — I have a genuine vision for what I want this next chapter to look like
Somewhat — I have ideas but haven't gotten really clear on it
Not yet — I mostly know what I want less of, not more of
No — I'm still figuring out what retirement even looks like for me
🌟 Lifestyle & Purpose
Question 8 of 10
Are your close relationships — family, friends, community — set up to support this transition?
People often underestimate how much the social side of retirement matters. Work provides structure, identity, and connection. When that goes away, what fills it? And are the people in your corner aligned with your plan?
Yes — I have strong connections and people who support this direction
Mostly — good relationships but could be stronger in some areas
Somewhat — I have some concerns about isolation or family alignment
Not really — this is an area I need to work on
📄 Legal & Planning
Question 9 of 10
Do you have the basic legal documents in place — will, power of attorney, healthcare directive?
These aren't fun to think about but they're genuinely important. Without them, your family is left making difficult decisions without guidance — often under stress and time pressure. Getting these done is one of the best gifts you can give to the people you love.
Yes — everything is up to date and current
Mostly — some documents in place but need updating
Partially — I have a will but the other pieces are missing
No — this is on the to-do list but hasn't happened yet
📄 Legal & Planning
Question 10 of 10
Have you had an honest conversation with your spouse, partner, or family about your plans and timeline?
You'd be surprised how many people are planning a move that their partner hasn't fully agreed to — or vice versa. Getting aligned on the "what, where, and when" before you start looking at houses makes everything easier.
Yes — we're fully aligned and on the same page
Mostly — we've talked but there are still some things to work through
Not really — we've mentioned it but haven't had a real conversation
No — this is just my thinking so far
🎉
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