“It’s easier to get to the top than it is to stay there” is a popular saying in entertainment, sports and business. “It is much easier to reach the top of the ladder than it is to stay there” was printed in the Chicago (IL) News in December 1901 and reprinted in many newspapers.
 
“It’s easier to get to the top than it is to stay there when you are there” was said by a stage performer in 1921. “It’s easier to climb to the top than it is to stay there!” was said by a swimmer in 1927. “I have always heard that it is easier to get to the top than it is to stay there, but heretofore I did not know it could be proved with figures” was printed in a 1929 newspaper article titled “A Business Man’s Philosophy.”
 
   
11 December 1901, The Daily Northwestern (Oshkosh, WI), pg. 1, col. 3:
It is much easier to reach the top of the ladder than it is to stay there.
 
13 December 1901, The Daily News (Denver, CO), “Short Stops” (Chicago News), pg. 4, col. 5:
It is much easier to reach the top of the ladder than it is to stay there.
 
Chronicling America
19 December 1901, The Central Record (Lancaster, KY), pg. 4, col. 3:
It is much easier to reach the top of the ladder than it is to stay there.
 
Google Books
February 1921, The American Magazine, “Frank Tinney’s Job Is To Make People Laugh” by Mary B. Mullett, pg. 123, col. 2:
The difference is “It’s easier to get to the top than it is to stay there when you are there,” he went on. “You can get to the top in almost any line of work if you concentrate on it. I know because I’ve proved it.”
 
23 February 1922, Cleveland (OH) Plain Dealer, “Film Players Who Are to be Seen in Neighborhood Houses: Thomas Conkey,” pg. 12, col. 2:
“It is easier to get to the top than to stay there.”
 
Old Fulton NY Post Cards
6 June 1927, The Newtown Ray, (Newtown High School, Newtown, NY), “Our Champion: Agnes Geraghty, Champion World’s-Record Breaker,” pg. 1, col. 4:
There Agnes retained her Indoor title. “It’s easier to climb to the top than it is to stay there!” she explained.
 
Old Fulton NY Post Cards
8 June 1929, New York (NY) Evening Post, “A Business Man’s Philosophy” by William Feather, pg. E3, col. 6:
I have always heard that it is easier to get to the top than it is to stay there, but heretofore I did not know it could be proved with figures.
 
25 June 1944, The Sunday Star (Washington, DC), “For a Composer, Opening Nights Never End” by Lawrence Perry, pg. C-8, col. 5:
“Irving Berlin,” Mr. (Kurt—ed.) Weill remarked as he and this writer took seats in the recesses of a box at the Alvin Theater, “once said to me, ‘Never rely on your reputation. It is easier to get to the top that to stay there. So keep an eye on your music always.”
 
20 December 1977, San Diego (CA) Union, “Face of Collegiate Basketball Unchanged As Rich Get Richer” by Bill Finley, pg. C-6, col. 1:
There is a saying in athletics that it is easier to get to the top than it is to stay there.
 
Google News Archive
9 December 1981, Reading (PA) Eagle, “Eagles Learning What Cowboys Know,” pg. 41, col. 1:
DALLAS (UPI) — Whoever first made the observation that it is easier to get to the top than it is to stay there was likely a professional football coach.
 
16 December 1981, Augusta (GA) Chronicle, “Downside of success” by Sydney J. Harris, pg. 4-A, col. 5:
IT IS AN old axiom in show business that it is easier to get to the top than to stay there, and I suspect it is just as true in any other business or endeavor.
   
FOX Sports
Still Perfect: Q&A with Don Shula
Aaron Torres
JAN 08, 2015 11:53 p ET
(...)
So I guess I’d ask you: What are the new challenges in Year 1 versus Year 2, because as the old adage goes ‘It’s easier to get to the top, than stay there.’