Endowment effect

McKeown recommends evaluating possessions and opportunities as if one did not already have them.

“the idea is to trick your brain into putting it in the position where you don't own the thing, where you don't have the opportunity”

The Tim Ferriss Show: #885: How to Simplify Your Life — Tips from Oliver Burkeman, Chip Conley, Elizabeth Gilbert, and More (Oct 2, 2026) · Listen from 19:45

McKeown says many people pursue outdated goals and opportunities, which he calls 'stormtroopers,' simply because they already hold them.

“I think a lot of people have a lot of stormtroopers in their life. And so it's not about the closet”

The Tim Ferriss Show: #885: How to Simplify Your Life — Tips from Oliver Burkeman, Chip Conley, Elizabeth Gilbert, and More (Oct 2, 2026) · Listen from 16:05

McKeown argues the endowment effect becomes harmful when it causes people to overvalue things they should discard.

“It's a positive phenomenon until and unless we overvalue something that we really ought not to have in the closet at all”

The Tim Ferriss Show: #885: How to Simplify Your Life — Tips from Oliver Burkeman, Chip Conley, Elizabeth Gilbert, and More (Oct 2, 2026) · Listen from 15:37

Ferriss notes a business version of the reframe, attributed to Andy Grove, of asking whether a company would enter its current line of business afresh.

“if we were not already in this line of business, how much would we pay to pursue it or would we pursue it in the first place”

The Tim Ferriss Show: #885: How to Simplify Your Life — Tips from Oliver Burkeman, Chip Conley, Elizabeth Gilbert, and More (Oct 2, 2026) · Listen from 19:20