“Now is always the most difficult time to invest” is an investment adage, with the joke being that it is always “now” and always a difficult time. Charles Welles Buek, an investment banker with the United States Trust Company, might have popularized the saying from about 1959.
 
 
Investment Trivia/ Stock Market Trivia/ Wall Street Trivia
More Famous Investment Quotations
“Now is always the most difficult time to invest.” Anonymous
 
New York (NY) Times
Charles Buek, 76, A Former Chairman Of the U.S. Trust Co.
By ALFONSO A. NARVAEZ
Published: July 20, 1988
Charles Welles Buek, an investment banker and former chairman of the United States Trust Company, died of heart failure Monday at his home in Darien, Conn. He was 76 years old.
 
Mr. Buek joined United States Trust in 1933 as a research analyst in the investment division and remained with the company until his retirement in 1976.
       
Google Books
The Trust Bulletin
By American Bankers Association. Trust Division
v. 38 - 1958 (It appears that 1858 is correct—ed.)
Pg. ?:
NOW Is Always the Most Difficult Time to Invest…Charles W. Buek
     
Google Books
Trusts and Estates
By Banking Publicity Assn. of the United States
v. 100 - 1961
Pg. 1018:
It is axiomatic that the most difficult time to invest is now but those in attendance heard from Charles W. Buek. first vice president, United States Trust Co. of New York, some common-sense suggestions which may…
 
Google News Archive
19 July 1983, Reading (PA) Eagle, “Investment expert confident,” pg. 19, col. 3:
When is the best time to invest in stocks? Stovall (Robert H. Stovall—ed.) said the best answer is “now.”
 
“There is an old saying on Wall Street that ‘Now is the most difficult time to invest.’” he said, adding that “now” can be anytime.
 
14 September 1998, Chicago (IL) Tribune, “Obey Your Signal” by Charles A. Jaffe, “Your Money” section, pg. 1:
There’s an old investment adage that says “Now is the most difficult time to invest.”
 
Google Books
Smartbounce:
3 Action Steps to Portfolio Recovery
By Keith G. Richards
Toronto: BPS Books
2009
Pg. 15:
“Now is always the most difficult time to invest.”
—Anonymous
     
Kitco
Gold Outlook for 2010: Gold Resuming its Historical Monetary Role - as the Anti-Currency
By Nick Barisheff    
Jan 11 2010 4:25PM
(...)
There is a famous investment axiom that states, “Now is always the most difficult time to invest.”  To that I would add, “But now is also the best time to insure the wealth we have accumulated is protected through the ownership of gold.”