Green’s Dictionary of Slang

(US) a problematic, demanding situation; hard times.

1839		Vermont Mercury (Rutland, VT) 8 Nov. 2/1: Business men are very apt in good times and in good sledding to take on heavy loads [...] but when there is a spot of bare ground, then comes the rub, it is hard sledding.
1871		New England Farmer (Boston, MA) 20 May 1/5: As usual, it has been hard sleding with farmers.
1889		Hickory Press (NC) 3 Oct. 4/3: He had tried to serve God [...] for forty years, but he had found it mighty hard sledding.
1894		Sun. News (Wilkes-Barre, PA) 19 Aug. 12/1: Scranton’s vain, self-important post-master, has had plenty hard sledding the past week.
1909		H. Green Mr. Jackson 180: Since you quit the game [...] I ain’t been runnin’ with no topliners, ’Frisco. It’s kind o’ hard sleddin’.
1912		H. Green Vaudevillians in Omaha Dly Bee (NE) 19 Dec. 9/5: When you’re married the hard sleddin’ begins .
1921		O.O. McIntyre New York Day by Day 12 Jan. [synd. col.] The slump in the moving picture industry is going to make it hard sledding for many authors this winter.
1935		(con. 1920s) J.T. Farrell Judgement Day in Studs Lonigan (1936) 716: It’s going to be tough sledding.
1936		(con. 1920s) Dos Passos Big Money in USA (1966) 801: It was heavy sledding because Merrit was [...] trying to size up Charley.
1941		D. Burley N.Y. Amsterdam Star-News 12 Apr. 13: You chicks are in for some hard sledding unless you’re hipped.
1949		Rocky Mt. Teleg. (NC) 21 Nov. 6/5: Both the winners and runners-up face tough sleddng this week.
1953		W. Brown Monkey On My Back (1954) 183: Charlie had taken the cure. It was tough sledding, though, when he got out.
1955		B. Schulberg On the Waterfront (1964) 150: That’s why this waterfront investigation is having such tough sledding.
1964		Chicago Trib. 25 Dec. 6/7: Turmoil and ‘years of tough sledding’ still remain.
1975		Indianapolis News (IN) 29 May 10/4: Many employers are having hard sledding now because of economic recession.
1985		Hartford Courant (CT) 19 Mar. 71/3: ‘Im told we will have hard sledding’.
1995		J. Stahl Permanent Midnight 69: The pay’s swell, but it’s tough sledding for the hard-core delusional intent on maintaining the facade of free will.
2005		J. Stahl I, Fatty 220: I’m generally inclined to compassion [...] but in Virginia’s case I found it tough sledding.
2008		Dly Jrnl (Franklin, IN) 29 Aug. 2/1: There will be heavy sledding for the US economy during the next couple of quarters.
2014		Central N.J. Home News (New Brunswick, NJ) 17 Dec. PC3/1: It may prove to be tough sledding again.