"The best time to start thinking about your…

“The best time to start thinking about your retirement is before the boss does” is a jocular saying about retirement that has been included in many quotation collections. The saying possibly was first used by the syndicated comic strip “Little Liz” in June 1958.

Google Books
The Office Economist
Volumes 38-42
1956 (The Google Books date may be incorrect—ed.)
Pg. 14:
The best time to start thinking about your retirement is before the boss does.

Google News Archive
30 June 1958, Portsmouth (OH) Times, “Little Liz,” pg. 2, col. 2:
The best time to start thinking about your retirement is before the boss does.

17 January 1992, Marietta (GA) Daily Journal, pg. 5B, col. 1:
Yesterday’s Cryptoquote: THE BEST TIME TO START THINKING ABOUT YOUR RETIREMENT IS BEFORE THE BOSS DOES.—AUTHOR UNKNOWN.

Google Books
Phillips’ Book of Great Thoughts, Funny Sayings:
A stupendous collection of quotes, quips, epigrams, witticisms, and humorous comments
By Bob Phillips
Wheaton, IL: Tyndale House
1993
Pg. 273:
The best time to start thinking about your retirement is before the boss does. Anonymous

Google Books
The Quote Manual:
Wisdom and Wit of the Ages:
A fifty-year collection of inspirational and thought provoking quotes
By Robert G. Moscatelli
Bloomington, IN: Authorhouse
2005
Pg. 202:
“The best time to start thinking about your retirement is before the boss does.” Unknown

Google Books
Getting Ready for Retirement:
Preparing for a Quality of Life for the Rest of Your Life
By Tina Manion
Lincoln, NE: iUniverse
2008
Pg. 104:
“The best time to start thinking about your retirement is before the boss does.”
Source unknown