4 Reasons Why It’s So Hard to Cut Yourself Slack

How to go from self-critic to self-coach

Jack Calhoun
Forge

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Photo: Westend61/Getty Images

I recently watched a 2018 Netflix special with David Letterman and Jerry Seinfeld in which the two legendary entertainers took turns interviewing each other on stage. What struck me most was how much the two differed in their approach to compliments: Seinfeld was gracious and appreciative whenever Letterman noted his incredible career success while Letterman rejected or downplayed any positive comment Seinfeld made about his career.

It came off more as self-loathing than modesty. “I should have left [the show] 10 years ago,” Letterman said at one point, “because then I could have taken some of that energy and focus and applied it to actually doing something good for humans.”

I should note here that Letterman has been trending lately and not in a good way: The host has been in the crosshairs over several upsetting interviews he did with female celebrities on his Late Night With David Letterman show, including a 2007 interview in which he badgered Paris Hilton about her time in jail and a 2012 conversation with Lindsay Lohan in which he pressed the actress about her upcoming stay in a rehab facility.

By the end of the Netflix special, one thing was abundantly clear: The lack of compassion he displayed in those past…

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Jack Calhoun
Forge
Writer for

20+ years as managing principal of a wealth advisory firm. I write about the principles of sound investing, the solopreneur life and the wisdom of experience.