The Bob Dylan song “Blowin’ in the Wind” (1962) begins:
 
“How many roads must a man walk down
Before you call him a man?”
       
“How many roads must a man walk down before he admits he’s lost?” is a jocular variation that has been printed on many images. “How many roads must a man walk down before he admits he’s lost?” was posted on the newsgroup alt.org.promisekeepers on February 15, 1996.
   
   
Wikipedia: Blowin’ in the Wind
“Blowin’ in the Wind” is a song written by Bob Dylan in 1962 and released as a single and on his album The Freewheelin’ Bob Dylan in 1963. Although it has been described as a protest song, it poses a series of rhetorical questions about peace, war, and freedom. The refrain “The answer, my friend, is blowin’ in the wind” has been described as “impenetrably ambiguous: either the answer is so obvious it is right in your face, or the answer is as intangible as the wind”.
 
In 1994, the song was inducted into the Grammy Hall of Fame. In 2004, it was ranked number 14 on Rolling Stone magazine’s list of the “500 Greatest Songs of All Time”.
             
Google Groups: alt.org.promisekeepers
Why are churches and PK anti-single???
Rob Buckman
2/15/96
(...) 
... How many roads must a man walk down before he admits he’s lost?
 
Google Groups: rec.humor
[TAGLINES] Dumb Questions
Dave Harper
6/21/96
(...)
How many roads must a man walk down, before he admits he’s lost?
 
Google Groups: rec.music.dylan
How Many Roads bumper sticker
NewSource2
3/27/00
Yesterday I saw a bumper sticker that asked:
     
“How many roads must a man walk down
Before he admits that he’s lost?”
 
I assume the car belonged to a woman.
   
Google Books
1,001 Smiles
By Marion Kaplinsky
San Francisco, CA: Chronicle Books
2005
Pg. 245:
To quote that song
How many roads must a man walk down ... before he admits he is lost?
 
11 December 2005, The People (London, UK), “Scrawl the best ; A look at the best graffiti on the world’s walls” by Rachael Bletchly, pg. 8:
HOW many roads must a man walk down before he admits that he’s lost?
     
30 September 2007, The Advertiser (Adelaide, Australia), “Mouthing Off” by Marty Smith, pg. 20:
Question in need of an answer: How many roads must a man walk down before he admits he is lost?
 
Twitter
Mike Folsom‏
@MikeF_says
“How Many Roads Must A Man Walk Down Before He Admits He’s lost?”
3:00 AM - 5 Mar 2009
 
Twitter
Michael Goodwin‏
@bumblsbounce
“How many roads must a man walk down before he admits he’s lost and asks for directions.” - Bob Dylan
3:02 PM - 7 Feb 2018