“The person who doesn’t know where his next dollar is coming from usually doesn’t know where his last one went” is a financial saying that has been printed on many images. “It is almost invariably the case that the person who doesn’t know where his next dollar is coming from also doesn’t know where his last one went” was printed in “Paragraphically Speaking” by Olin Miller, in the Paducah (KY) Sun-Democrat on April 20, 1954.
 
Olin Miller (1894-1981) wrote for a newspaper in Thomaston, Georgia. His syndicated daily feature entitled “Dixie Dewdrops” appeared in many other newspapers, and his lines were frequently quoted by others.
     
       
20 April 1954, Paducah (KY) Sun-Democrat, “Paragraphically Speaking” by Olin Miller, pg. 4, col. 1:
It is almost invariably the case that the person who doesn’t know where his next dollar is coming from also doesn’t know where his last one went.
 
29 July 1954, The Times Recorder (Zanesville, OH), Earl Wilson syndicated entertainment column, pg. 4, col. 5:
“THE FELLOW WHO DOESN’T KNOW where his next dollar’s coming from,” noted Richard Barstow, “is usually the one who doesn’t know where the last dollar went.”
     
24 February 1959, Chicago (IL) Daily Tribune, pt. 4, pg. 1, col. 2:
The man who doesn’t know where his next dollar is coming from should ask his wife who also knows where it’s going.
—Joseph Charles Salak
 
30 March 1960, Greensboro (NC) Record, “Hi Nabor” by Olin Miller, pg. 1, col. 1:
The man who doesn’t know where his next dollar is coming from does not know where his last one went.
 
Google Books
The Contractor
Associated Builders and Contractors
Volumes 12-14
1963
Pg. 9:
The person who doesn’t know where his next dollar is coming from usually doesn’t know where his last one went. —Grit
 
7 March 1964, Logan (UT) Daily News, “Laurelville Rt. 2 News” by Mrs. Merle Fiume, pg. 4, col. 7:
The person who doesn’t know where his next dollar is coming from usually doesn’t know where his last dollar went.
       
Google Books
Complete Speaker’s and Toastmaster’s Library
By Jacob Morton Braude
Englewood Cliffs, NJ: Prentice-Hall
1965
Pg. 51:
The person who doesn’t know where his next dollar is coming from usually doesn’t know where his last dollar went.
     
Google Books
Social Media and Networking:
Concepts, Methodologies, Tools, and Applications
Edited by Management Association, Information Resources
Hershey, PA: Information Science Reference
2016
Pg. 194:
“The person who doesn’t know where his next dollar is coming from usually doesn’t know where his last dollar went.” Anonymous
 
Twitter
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“The person who doesn’t know where his next dollar is coming from usually doesn’t know where his last dollar went.” - Unknown
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1:45 PM · Apr 21, 2019 · Hootsuite Inc.
 
Inc.
July 22, 2019
17 Quotes About Money That Will Also Change Your Attitude About Life
Sure—money isn’t everything, but it can sure help.
By Peter EconomyThe Leadership Guy@bizzwriter
(...)
11. “The person who doesn’t know where his next dollar is coming from usually doesn’t know where his last dollar went.”—Unknown