Many business owners spend decades building a thriving company, providing for their families, and earning the freedom they once dreamed about.

But eventually, a different question emerges:

Now what?

In this conversation, David sits down with longtime friend, attorney, entrepreneur, and author Ben Glass to explore what it means to intentionally design the second half of life.

Rather than viewing an exit as the finish line, Ben shares why the greatest opportunity may be to shift from building a business to building people—passing on wisdom, cultivating deeper relationships, and creating a life defined by purpose instead of professional identity.

Together, they discuss why happiness comes from having choices, how to prepare for life beyond your primary career years before you ever step away, and why the most valuable asset you can build isn't simply wealth—it's the freedom to decide how you'll spend your time.

This conversation isn't really about retirement.

It's about becoming the kind of person whose greatest contribution may still be ahead.

Because financial freedom isn't the end goal.

It's the opportunity to design a life that becomes more meaningful with every passing year.

Episode Links:
Ben Glass Law: https://benglasslaw.com
Lunch with Ben: https://lunchwithben.com

Get David Phelps' Exit Optional Playbook: https://exitoptional.com

Timecodes:
00:00 – Building a Life, Not Just a Resume
05:04 – Doing More of What Gives You Energy
10:27 – Letting Go & Finding Your Next Chapter
16:37 – Creating Meaningful Friendships
20:19 – Succession Planning Done Right
26:25 – Happiness Comes From Choices
30:45 – Give Yourself Permission to Lead
35:24 – Thriving in the Age of AI
38:38 – Principles for a Meaningful Life
43:02 – How to Connect with Ben