On Winning

What is "On Winning" about?

Building on his recurring theme that life consists of endless, parallel games, Gilad focuses on the uncomfortable truths embedded in the word 'game' itself: games have rules, constraints, winners, losers, and definite endings, some arriving gradually through neglect and others abruptly without warning, with timing that isn't negotiable. The piece pushes readers to confront whether they are actually winning in the specific areas of life that matter most to them, rather than assuming general busyness or effort equates to success. Gilad guides a concrete exercise: listing the three most important areas of one's life, honestly assessing whether one is currently winning in each, and then vividly describing—as if narrated in a documentary—what genuine winning in those areas would actually look like in detail. He then has readers quantify the gap between their current state and that vision on a 1–10 scale, before committing to three specific actions per area for the coming week designed to move the needle by just one notch. The essay's core message is that meaningful progress in life's most important games comes from small, deliberate, immediate weekly action rather than sweeping aspiration.

In brief

What are the key takeaways?

1. 01Life's games have real endings, rules, and stakes—evaluate your three most important areas and ask if you're actually winning.
2. 02Vividly define what true winning looks like in those areas, then rate your current gap on a 1–10 scale.
3. 03Commit to three specific actions per key area each week to move the needle by just one notch rather than aiming for a sweeping overhaul.