Reddit mentions of Searching for Meaning: Idealism, Bright Minds, Disillusionment, and Hope

https://www.amazon.com/gp/aw/d/1935067222/ref=ox_sc_act_image_3?smid=A1WJGQY6PQPADF&psc=1 searching for meaning

I would recommend this book, maybe for both you and him to read:

Searching for Meaning: Idealism, Bright Minds, Disillusionment, and Hope by James Webb.

>Many bright idealists find themselves disillusioned in today's world, and they may experience existential depression as they examine their lives and search for meaningfulness. This book will help such individuals to understand themselves and their struggles. It also includes helpful information and suggestions for actions that disillusioned idealists can use to better manage their feelings and thoughts in ways that will nurture their idealism and provide a sense of satisfaction and contentment. People with existential depression need more than medications. It is fundamentally more important for those with existential depression to become aware that others have had similar experiences and to realize that someone truly understands their idealism, disillusionment, and anger that things are not as they"should be." Searching for Meaning bridges this gap and provides a safety net of sorts for those floating in the abyss of concentrated disillusionment. This book offers guidance and support in taking the first steps toward renewed perspective and helps to promote a solid foundation to prevent future relapses.
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>https://www.amazon.com/gp/product/1935067222/

I've gone through something like this in the last little while. Each person is different, has different circumstances, and different expectations. So I can't really say much in the general realm besides that he's probably feeling like he has to "keep up with the Joneses" without realizing that sometimes luck has a big part to play in the people you meet and the business situations you are offered. Your own efforts can increase the chances but by no means guarantee an outcome.