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In the history of sports and in our ‘winning is everything’ culture, I’m not aware of anyone who ever won every game, or every event, or every championship they competed for. Roger Federer, the great tennis player who some call the greatest of all time, has won a record seventeen Grand Slam titles. Yet, he has competed in more than sixty Grand Slam events. Thus, perhaps the greatest tennis player ever failed more than two-thirds of the time. While we don’t think of him as a failure, but rather as a champion, the plain fact is, he failed much more than he succeeded on this measure, and that’s generally the way things are for anyone. Failure precedes success. Simply accept that failure is part of the process and get on with it."

Identity Design: Design the Identity You Need to get the Life You Want By Judge Frank Szymanski

I assume it refers to 'the greatest tennis player ever failed more than two-thirds of the time' but what does 'measure' mean? Does it mean 'a measured quantity'?

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To determine the meaning of this measure in the paragraph, you need to backtrack and find the relevant sentence(s):

Roger Federer, the great tennis player who some call the greatest of all time, has won a record seventeen Grand Slam titles. Yet, he has competed in more than sixty Grand Slam events. Thus, perhaps the greatest tennis player ever failed more than two-thirds of the time.

This measure refers to the number of times he has competed in the events and how many times he has lost those events. Mathematically, if you find that easier, the measure refers to the ratio (lost)/(played), which, as the author states, is more than 2/3. This in turn implies he won less than 1/3 of all Grand Slam tournaments he played in. The author says that by this measure, Federer "failed much more than he succeeded"; this comment just summarizes the above-quoted material.

To address your question specifically, measure is defined by Merriam Webster's dictionary as:

a basis or standard of comparison : wealth is not a measure of happiness

Thus, in the context of sports, a measure is the means by which we judge or evaluate a player's performance (e.g. Freder).

The author is trying to suggest that many athletes whom we deem exceptional ("the greatest tennis player who some call the greatest of all time") are just as human as we are, and they are by no means perfect. Thus, they've very likely lost more championships than they've won.

  • Nitpick: It implies that he won less than 1/3 of all grand slam tournaments that he competed in, not games. (In fact he reached the quarters, semis, or finals at most of them, giving him a match win/loss ratio more in the range of 5:1, or 83% success rate since it takes 7 match wins to win the tournament.) – Hellion Jun 15 '17 at 17:35
  • @Hellion Right, that's what I meant by games :) Edited for clarity. – AleksandrH Jun 15 '17 at 17:52
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'measure'refers to a comparison of the number of times he has appeared in the grand slam and the number of times he had won.He participated in 60 and won 17 only.

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