To go “from the outhouse to the penthouse” is to climb up the ladder, to go from worst to first. The saying is popular in sports and in business. “From the penthouse to the outhouse” is the reverse process.
 
“In pro football, ‘the jump from the penthouse to the outhouse is a quick one’” was cited in print in 1955. “The Crims’ short journey back from the ‘outhouse’  to the ‘penthouse’ on Friday night’s victory over Tucson” was cited in 1959.
 
 
27 September 1955, The Independent (Long Beach, CA), “Sanders,” pg. 17, col. 6:
But he (Sid Gillman, football coach of the Los Angeles Rams—ed.) warned both his players and the Rams followers not to expect a parade of such “miracle” victories, declaring that in pro football, “the jump from the penthouse to the outhouse is a quick one.”
 
12 October 1959, Lexington (KY) Leader, “LSU Coach Recalls Debut And 19-7 Win Over UK” by Paul Dietzel (LSU Football Coach), pg. 7, cols. 2-3:
On Thursday Coach George Blackburn (a close buddy) sent me the following telegram: “Congratulations, but remember: It’s a quick trip from the penthouse to the outhouse.”
 
26 October 1959, The Sun (Yuma, AZ), “Crims Hit Peak Against Badgers” by John Lindblom, pg. 6, col. 1:
High coach Jlarv Rosengarten credited peak-season performances by both his offense and defense as major factors in the Crims’ short journey back from the “outhouse” to the “penthouse” on Friday night’s victory over Tucson.
 
23 December 1963, Aberdeen (SD) American-News, “Denver Falls To Chargers 58 To 20” by Mike Rathet (AP), pg. 22, col. 2:
“IT’S LIKE going from the outhouse to the penthouse.”
 
That was the cogent comment of San Diego line coach Joe Madro after the Chargers compelted an amazing flip-flop y overwhelming Denver 58-20 Sunday and clinching their third Western Division title in the four-year history of the American Football League.
 
OCLC WorldCat record
Finding some life after housework ; Image, from outhouse to penthouse
Author: Don Aslett
Publisher: Pocatello, ID : D. Aslett, 1982.
Edition/Format:   Audiobook on Cassette : Cassette recording : English
 
OCLC WorldCat record
From the outhouse to the penthouse : a memoir for family
Author: Ernest E Cragg
Publisher: Wilmington, Del. : Cragg Enterprises of Delaware, ©1994.
Edition/Format:   Print book : Biography : English : 1st ed
 
OCLC WorldCat record
The Pontiac Press : from the outhouse to the penthouse and back
Author: Bruno L Kearns
Publisher: [New Port Richey, FL] : [The Author], [1999]
Series: Episodes of life, Press., book 6.
Edition/Format:   Print book : Biography : English
 
OCLC WorldCat record
Turning Points From the Outhouse to the Penthouse.
Author: Brown, B. Dean
Publisher: West Bow Pr 2014.
Edition/Format:   Print book : English
 
Twitter
Chris Orlando
‏@chrisorlando11
From the penthouse to the outhouse Cowboys! To funny cowgirls #FlyEaglesFly
6:29 PM - 25 Oct 2015