3 Questions to Ask Before You Retire (Most People Never Ask #3!)

Executive Summary

Most retirement planning focuses on numbers: savings, investments, and withdrawal strategies. But the truth is, retirement satisfaction depends on much more than finances. If you don’t ask the right questions about your lifestyle and identity, you may end up with disappointment instead of fulfillment. 

Discover three questions most people never ask, but should, before they retire.

Want to watch an in-depth exploration of this topic?
Check out this video on my YouTube channel, @SavvySteward: 3 Questions to Ask Before You Retire (Most People Never Ask #3!)

Take the free “How Much Do I Need To Retire” Quiz here:
https://secure.kingsview.com/keith-savvy-steward-quiz-youtube#q1

3 Questions to Ask Before You Retire (Most People Never Ask #3!)

After thousands of planning conversations, one theme stands out: the happiest retirees don’t just prepare financially. They prepare for real life. They look past the glossy picture of golf and travel and take the time to shape an everyday rhythm that works for them.

These three questions are designed to help you reality-test your assumptions and define not just how you’ll afford retirement, but how you’ll live it.

Why isn’t retirement just a “permanent vacation”?

When you imagine retirement, you might picture travel, leisure, or long mornings over coffee. But retirement isn’t a 20-year holiday—it’s life, with all its ordinary routines. You’ll still have bills, grocery lists, insurance decisions, and quiet afternoons.

The danger is expecting constant excitement and then feeling let down when most days look more ordinary. To avoid that trap, focus on:

• Mapping out what a typical week looks like, not just the highlights
• Considering whether you prefer structure or flexibility
• Building around your true energy patterns, not an idealized version of yourself

A fulfilling retirement doesn’t come from chasing highlights. It comes from building a rhythm you enjoy.

How can you test your retirement plans before making big decisions?

Too many retirement visions collapse under untested assumptions. A couple may dream of RV travel, only to discover after a trial run that they dislike small spaces. Without testing, that misstep could become a six-figure mistake.

Here are ways to reality-check your plans:

• Relocation: Rent in your desired area for an extended stay, in different seasons, and live like a local before committing
• Housing: Experiment with smaller homes, condos, or apartments before downsizing permanently
• Togetherness: If you’re married, test extended time together. Retirement changes the dynamic from part-time to full-time companionship

Testing reveals trade-offs you can’t see on paper and helps you adjust before locking in costly decisions.

Why does identity matter so much when transitioning into retirement?

Retirement is more than a financial milestone: it’s an identity shift. For decades, your work shaped your schedule, goals, and even your sense of self. Without it, you need to decide who you want to become.

This stage is an opportunity, not a void. Retirement gives you freedom to grow into qualities you admire in others: things like curiosity, generosity, confidence, or creativity. The key is to ask now:

• Who do you want to be when work no longer defines you?
• What qualities do you want to cultivate?
• How will you use your time to grow in ways that weren’t possible before?

As Stephen Covey put it, “Begin with the end in mind.” When you know what you want from your retirement, you’re better able to prepare for the result you want.

Real wealth starts with real life. Don’t just plan the numbers. Plan the life.

Contact Information

Keith Demetriades, CFP®, CKA®, believes real wealth starts with real life. He created the 4D Client Experience to help guide decision-making and ensure your money works as a tool to support your life. If you’re ready for a financial plan that reflects how you live and what you’re building toward, contact Keith at (806) 223-1105 or visit Kingsview Partners.

Disclaimer: The information provided in this blog is for educational purposes only and should not be considered financial advice. Please consult a qualified financial advisor to discuss your specific situation and needs. Past performance does not indicate future results, and all investments carry risks, including potential loss of principal. Any financial product or strategy references are purely illustrative and should not be construed as endorsements or recommendations.