The Power of a Question: Unlocking Happiness in Retirement

One of my favorite questions to ask clients — especially those transitioning into retirement — is this:

“What is your happiest time of the day? The week? The month? The year? Your life?”

When I ask this, most people pause. Very few can answer immediately. And that’s the point — it’s a question meant for reflection, not quick replies.

One of the most effective tools a coach can use is the powerful question. These aren’t your everyday inquiries — they’re designed to stop you in your tracks, make you think deeply, and often leave you feeling just uncomfortable enough to spark real insight. A well-timed, powerful question can shift your perspective, open a new mental doorway, or create the space for a fresh possibility to emerge.

Most of the time, these questions arise naturally when a coach is fully present and deeply listening to their client. But occasionally, a thoughtfully curated question, delivered at just the right moment, can have a profound and lasting impact.

I often assign the questions above as homework, encouraging clients to observe and note when and where happiness shows up in their lives. The insights that follow can be incredibly powerful. They help illuminate patterns, themes, and values that matter most — ultimately giving clients a blueprint for cultivating happiness in retirement and making it a daily habit.

I’d love to hear your answers. But first, I’ll share mine:

• Happiest time of the day? Around two o’clock in the morning. It’s so quiet and peaceful — the perfect time for reflection. I often do my best writing at this hour. While I strive for an earlier bedtime, I have to admit, this nighttime solitude brings me genuine happiness.

• Happiest time of the week? Sunday evenings, when our adult children come home for dinner. There’s nothing like the comfort of shared meals, laughter, and conversation around the table.

• Happiest time of the month? When my magazine subscriptions arrive! I’m a self-proclaimed magazine junkie — from Harper’s Bazaar to Veranda, I love flipping through pages filled with fashion, design, and inspiration.

• Happiest time of the year? When my azaleas bloom. The front of my house turns a vibrant, joyful pink. It’s breathtaking.

• Happiest time of my life? That’s harder to pin down — happiness has come in many forms. As a child, it was visiting a family friend with a swimming pool and lots of dogs. As an adult, graduating with my master’s in counseling was a moment of deep pride. Getting married and honeymooning in England was filled with joy. And starting my own business — training coaches for 18 years — has brought incredible fulfillment. Seeing those coaches now spread knowledge and support across the globe fills my heart.

• Yet, perhaps the happiest time of our lives isn't tucked away in the past—it's happening right now. As I reflect on the years behind me, I realize that this moment, with all its richness, may be the most fulfilling yet. I’m still achieving, still creating, still discovering new passions and connections—while cherishing and nurturing the relationships and memories that shaped me. There’s a quiet confidence in knowing who I am and a deeper appreciation for the simple joys I once overlooked. In many ways, this season of life—rich with purpose, presence, and peace—is the happiest time of all.

As you can see, happiness is deeply personal. No two people will have the same answers. And yet, exploring these questions can help you uncover what truly matters to you — especially as you redefine your life in retirement.

So, I’ll ask again:What is your happiest time of day? Week? Month? Year? Life?