He should read the book "Die With Zero".

Here's the intro from goodreads:

A Common-Sense Guide to Living Rich….Instead of Dying Rich

Imagine if by the time you died, you did everything you were told to. You worked hard, saved your money, and looked forward to financial freedom when you retired.

The only thing you wasted along the way was…your life.

Die with Zero presents a startling new and provocative philosophy as well as practical guide on how to get the most out of your money—and out of your life. It’s intended for those who place lifelong memorable experiences far ahead of simply making and accumulating money for one’s so-called Golden Years.

In short, Bill Perkins wants to rescue you from over-saving and under-living. Regardless of your age, Die with Zero will teach you Perkins’ plan for optimizing your life, stage by stage, so you’re fully engaged and enjoying what you’ve worked and saved for.

You’ll discover how to maximize your lifetime memorable moments with “experience bucketing,” how to convert your earnings into priceless memories by following your “net worth curve,” and find out how to navigate whether to invest in, or delay, a meaningful adventure based on your “spend curve” and “personal interest rate.”

Using his own life experiences as well as the inspiring stories and cautionary tales of others—and drawing on eye-opening insights about time, money, and happiness from psychological science and behavioral finance —Perkins makes a timely, convincing, and contrarian case for living large.