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Home » CEO Insider » Three Questions Every CEO Should Ask Before the Year Ends
CEO Insider

Three Questions Every CEO Should Ask Before the Year Ends

Gina Maier Vincent

A CEO can tell you precisely how their company performed this year. Revenue. Growth. Margins. Milestones. Ask how much they’ve enjoyed the life those accomplishments made possible, and the answer may take considerably longer.

I’ve always found that fascinating.

Successful executives understand the importance of examining performance. They question assumptions, reassess investments, and recognize when strategies that once delivered extraordinary results deserve reconsideration. Yet many rarely apply that same discernment to their personal lives.

I’ve spent years working with highly capable people who have created remarkable lives. They anticipate problems, manage competing demands, and make difficult circumstances appear effortless. Over time, that ability becomes part of their identity. They’re the person who can handle almost anything.

And that’s precisely where a blind spot can develop.

I call it Underliving™: when life continues to work beautifully on paper, but the experience of living it has quietly gone flat.

Nothing necessarily appears wrong. The business is thriving. Relationships remain intact. Responsibilities are fulfilled. But the experience of living has gradually become less vivid.

The danger is how easily that change goes unnoticed. A life can continue functioning exceptionally well long after we’ve stopped questioning how fully we’re experiencing it.

As another year approaches, three questions deserve consideration.

1. When was the last time you wanted more from life, rather than more to show for it?

Achievement requires knowing what you want and organizing your resources to pursue it. Successful executives become exceptionally practiced at turning ambition into results.

But somewhere between pursuing goals and achieving them, desire itself can become difficult to recognize.

When was the last time something fascinated you without the prospect of a measurable return?

In my book, Exquisitely Aligned, I describe a period when I found myself yearning for “More” from an already beautiful life. I had a wonderful marriage, a beautiful home, and much to be grateful for. Yet I couldn’t explain what I was longing for.

When I confided in a dear friend, she reminded me of everything I had, including a loving husband, a healthy child, and a recent trip to Italy. What more could I possibly want?

Her reaction silenced me. I kept that desire private for years.

I wasn’t seeking another possession or accomplishment. I wanted to experience more of life, although I couldn’t yet articulate what that meant.

I’ve since come to understand something important: gratitude and desire can coexist. Appreciating what you’ve created doesn’t mean you’ve exhausted what life might still have to offer.

2. If you weren’t so good at managing your life, would you still choose it?

Consider how much of your current life was shaped by decisions you made five, ten, or twenty years ago.

Those decisions may have been excellent. They helped build your reputation, establish your relationships, and create opportunities that once seemed unimaginable.

But success has a way of accumulating obligations. Calendars fill. Expectations expand. People become increasingly dependent on your judgment and availability.

And because you’re capable, you adapt.

You can reorganize an entire week around an unexpected business demand, yet the personal experience you’ve talked about for years remains postponed.

Eventually, maintaining what you’ve built can occupy so much attention that reconsidering it rarely occurs to you.

Capability tells us what we can handle. Discernment asks whether it’s still what we want.

This distinction matters because the cost of Underliving™ isn’t necessarily a dramatic breakdown. It’s the gradual surrender of curiosity, desire, and attention while everything continues operating as expected.

What suited the person you were a decade ago may deserve reconsideration today.

Think about how you invest your time, energy, money, attention, and voice. I call these our Divine Resources.

How much of that investment reflects the person you are now?

3. If your calendar were suddenly empty, would your life feel full?

Executives often imagine that greater freedom will arrive when a particular milestone has been reached, a transaction completed, or responsibilities finally ease.

Yet an open calendar doesn’t guarantee a fulfilling experience of time.

I’ve watched accomplished people become so accustomed to anticipating what’s next that even their leisure carries the urgency of their professional lives.

Consider a conversation so captivating you forget to check your phone. Or sunlight crossing a familiar room, suddenly catching your attention as though you’re seeing it for the first time.

These moments remind us that the quality of an experience depends on more than the circumstances surrounding it.

Attention determines how much of our lives we’re actually available to inhabit.

We can acquire extraordinary experiences and still miss much of what makes them extraordinary.

Fascination, to me, is one of life’s great luxuries. It allows us to be moved by what we’ve become accustomed to overlooking.

Before You Plan What’s Next

A successful year deserves recognition. So does the capability that made it possible.

But another year of achievement won’t necessarily answer questions about the quality of the life you’re creating.

Before committing to another ambitious set of objectives, consider whether the life you’ve worked so hard to build still has your full attention.

The familiar deserves examination, too. Particularly the things that continue working so well you’ve stopped questioning them.

Look again.

Where has fine replaced fascination?


Written by Gina Maier Vincent.
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Gina Maier Vincent
Gina Maier Vincent is the Founder of Exquisitely Aligned® and Creator of Underliving™, a modern culture observer exploring the hidden cost of modern achievement and...

Read Gina Maier Vincent’s full executive profile here →