Your true reputation is not what you project, but the sum of stories people tell about you when you're not in the room or after you've left an organization. This "legacy" narrative is the ultimate litmus test of your integrity and impact.

For Ed Helms, traditional metrics of success like fame and money have lost their meaning. He now evaluates his work based on whether it's something his children can be proud of as they get older—a project with intrinsic value that reflects him putting his heart into something worthwhile.

An empire is built for personal gain, name recognition, or familial wealth and will eventually crumble. A legacy is built on values and beliefs that benefit everyone and spread long after the founder is gone. A leader must consciously choose one path, as they are mutually exclusive.

Gary Vaynerchuk recounts how building his father's business from $3M to $60M, despite low pay, remains his greatest accomplishment. This foundation of patience and dedication to a family legacy provided a level of fulfillment that even his future, larger successes cannot replicate.

When eulogized, a person's career accomplishments are footnotes. The core of their legacy is their character—how they behaved and treated others—and their service. This reality should inform how we prioritize our daily actions, focusing on behavior over status or material success.

At the end of life, people don't reminisce about grand accomplishments but long for simple, ordinary pleasures like sharing a meal with loved ones. This suggests that a meaningful life is built in the quiet, everyday moments, not just the major milestones like promotions or awards.

The initial goal of building a company that endures can be misplaced. A more meaningful and lasting legacy is created through the people you train and empower. The corporate entity may fade, but the skills and values instilled in your team will ripple outwards for decades through their own ventures and leadership.

In final conversations, wealthy individuals consistently prioritize legacy, values, and family relationships over financial matters like tax savings. This highlights the need to focus on the "softer side" of estate planning from the very beginning.

A driving force for the American revolutionaries was a profound sense of posterity—the idea that their sacrifices were for future generations, not immediate personal gain. This long-term, selfless perspective explains their willingness to risk everything.