The 8 Most Important Questions to Ask About Retirement (at Any Age)

If you’re in your 30s, 40s, or 50s and starting to think ahead — or you’re just a few years from retirement — here’s a reality check: most people spend more time planning their next vacation than they do planning the next 30+ years of their life.

Retirement isn’t just a finish line. It’s a whole new chapter. And whether you plan to retire early, work forever, or just want the freedom to choose, asking the right questions now can completely reshape your future.

These eight questions will help you build a retirement plan that’s driven by purpose — not guesswork.

1. What does retirement look like to you?

Everyone’s vision is different. For some, it’s reading and gardening. For others, it’s travel, adventure, or leaving a legacy.

There’s no one right way to retire — but there is your way. And that vision is the first step in designing a financial strategy that actually supports it.

2. If money were no object, how would you live?

This is one of my favorite questions to ask clients. Why? Because it gets us dreaming again.

If you could design your perfect retirement day, week, or year — what would that look like?

Now, you may not have an unlimited budget, but we can begin reverse-engineering the income you’ll need to support what matters most to you.

3. When do you want to retire — and when can you?

Some people never want to stop working. Others want to retire yesterday.

Whatever your dream, it’s important to ask: Have I built the income floor I need to step away from work confidently?

Whether it’s Social Security, annuities, whole life insurance, or other predictable income streams, knowing your numbers — and your timeline — is key.

4. What are you retiring to — not just from?

This is your “why.”

What’s the purpose behind your retirement? What legacy do you want to leave? What experiences do you want to have while your health and energy are still strong?

I often remind clients about the phases of retirement:

• Go-go years

• Slow-go years

• No-go years

Let’s front-load your financial freedom so you can make the most of that early phase.

5. How long does your money need to last?

This is your longevity question.

If you live to 95 or even 100 (and many people will), will your money last that long?

If you're retiring at 50, your income might need to stretch for 40 or 50 years. That's why guaranteed income — like annuities — becomes so powerful. It takes the guesswork and anxiety out of the equation.

Bonus tip: Try the quiz at Livingto100.com for a personalized longevity estimate.

6. What risks keep you up at night?

Inflation? Market crashes? Long-term care?

Whatever your concerns are, we need to name them so we can plan around them.

You deserve a plan that lets you sleep at night — and that’s what safe money strategies are designed for.

7. Who will you need to rely on — and who’s relying on you?

Family dynamics matter more than most people realize. Spouses, kids, aging parents — all of this affects your financial decisions.

We’ll also look at strategies like survivor benefits, tax-efficient wealth transfer, and long-term care planning to ensure no one is burdened — and everyone is supported.

8. Who will you trust to guide you through it all?

This is the question that ties it all together. Because building a solid retirement plan isn’t just about spreadsheets — it’s about strategy.

And honestly? Most people don’t have a money problem — they have a planning problem.

That’s what I’m here for. I love helping clients take the stress and confusion out of retirement planning and create a strategy that brings peace of mind.

Ready to Retire Financially Relaxed?

My goal is to help you eliminate the fear of running out of money, avoid costly mistakes, and retire with confidence and security. When you have safe, predictable income in place, you’re free to actually enjoy retirement — not just worry your way through it.

• Learn more at the Retirement Income School™

• Want to talk? Schedule a Retirement Income Q&A Call — I’d love to support you.

This is your chance to learn what you wish school had taught you — and discover how to keep your money safe and make it last, so you can enjoy retirement!