From Deals to Destiny: How Entrepreneurs Can Use any Meal to Design Their Legacy

Weekends and holidays aren’t just about connection and reflection. For high achievers—especially those in business or finance—they’re also one of the few natural pauses to slow down over a great lunch or dinner. A chance to step away from precision and power and consider something often not talked about in society or life: your legacy.

The problem? Most legacy conversations feel cold. They’re reduced to tax strategies, estate transfers, or philanthropic structures. Important, yes—but not the whole story as we are human beings. If your legacy were only about balance sheets, heirs wouldn’t be failing at alarming rates and influential lives wouldn’t fade without resonance.

That’s why meal tables matter, especially when the pace slows down over a weekend or a holiday. A holiday or any special meal, prepared with warmth and for reflection, can become the perfect stage for the real questions—the ones that move beyond money to meaning.

The Stakes: Why It Matters

If you don’t define your legacy, someone else will. Your name becomes a line item, your story reduced to numbers. For an entrepreneur, especially one in finance or business, that’s not just a risk—it’s a waste of influence.

Legacy isn’t just about what you leave behind. It’s about who you become while you’re here, and the essence you transfer beyond financial wealth.

Framework: A Lunch or Dinner Conversation Arc

Think of this as a flow, not a script. Each stage gently builds trust and depth, moving from light reflection to profound clarity.

1. Appetizers — Start with Reflection

Begin lightly. Invite stories, not strategy.

• What’s a highlight from this year you’d relive?

• Who inspired you most recently?

• What are you most proud of outside of work?

This eases everyone into openness without pressure.

2. Main Course — Values and Vision

Now move toward identity and meaning.

• When people describe you, what words (values) should they know about or capture as to your essence?

• Which lessons from childhood deserve to be passed on—or rewritten?

• If money weren’t a factor, how would you spend your time?

This shifts the spotlight from deals made to the life designed.

3. Wine or Tea/Coffee Pause — Power and Stewardship

Here, explore influence and responsibility.

• Do you see yourself as a guardian, builder, or catalyst?

• Who benefits most from your influence today—and who should tomorrow?

• If your wealth could “teach” a lesson, what would it be?

Entrepreneurs, especially those that work with numbers, thrive on control; this reframes one's capital in all its forms (i.e. emotional, intellectual, spiritual, etc,) as stewardship, not possession. Do you know the five forms of capital and your relationship to them?

4. Dessert — Mortality and Immortality

Once trust deepens, open the legacy conversation further.

• If one building, project, or idea carried your name, what would or should it represent?

• What would surprise people about what you really want to be remembered for?

• Is legacy about what you leave—or who you become?

These questions give permission to wrestle with mortality without losing hope.

5. Digestif (End of Meal Beverage) — Gratitude and Hope

Always end light, inspiring, and future-facing.

• What are you most grateful for right now?

• What hope feels bigger than yourself for the year(s) ahead?

The goal is not to solve everything at the table. It’s to seed clarity—so the real work of your legacy design can begin while you are still here.

The Transformation: From 'Talking About Just The Money' to Designing A Life Legacy

You’ve mastered designing deals. The next frontier is designing your legacy.

The lunch or dinner table is where this journey can begin—not in a boardroom, not with spreadsheets, but in conversations that reveal your essence. Because at the end of the day, your life isn’t just financial capital—it’s other forms of capital, contribution, and continuity.

So the next chance when there is space to speak deeply over a lunch or a dinner, perhaps on a weekend or a holiday when the pace is slower, raise a glass. And ask the question that matters most: What part of you do I want to live beyond your life?