"What would you regret not doing?"



The hospice nurse's question wasn't directed at me. I was visiting my mentor, who'd built a multi-million dollar empire.

His answer shocked me:

"I regret not playing catch with my son more."

Here was a man who'd achieved everything by conventional business standards. Impressive financial performance. Multiple successful exits. Financial freedom.

But on his deathbed, he wasn't thinking about profit margins or revenue growth.

He was thinking about moments.

That conversation haunted me for weeks.

I realized I was following the same path—building business success while sacrificing life satisfaction.

Working late instead of reading bedtime stories. Missing family dinners for client calls. Canceling weekend plans for "urgent" projects.

I was optimizing everything except what would matter on my deathbed.

That revelation sparked a complete business philosophy transformation:

Principle 1: Moment Optimization I started measuring success by meaningful moments created, not just money earned.

Principle 2: Regret Prevention Before saying yes to any business opportunity, I asked: "Will I regret missing life for this?"

Principle 3: Legacy Design I redesigned my business to support the life I wanted to be remembered for.

Principle 4: Present Value I invested in experiences and relationships that would matter decades later.

The changes were profound:

My working hours decreased dramatically. Our business efficiency improved because I focused on high-impact activities. My relationships deepened significantly.

Most importantly, I started living a life I wouldn't regret on my deathbed.

Your business should enable the life you want to be remembered for—not prevent you from living it.

Bottom line growth means nothing if you're not growing the parts of life that actually matter.

What would you regret not doing?