His father, Alfred Hastings, was a solicitor, although he failed to establish much of a law practice and was perennially involved in spurious business schemes. "Bankruptcy in my family was not a misfortune, it was a habit," Hastings wrote later in life, according to Hyde. Hastings was often present at late-night parties during which his father and friends, fueled with strong drink, railed over financial matters and various legal woes. The youthful Hastings listened, and privately reasoned that the mens' flimsy arguments would likely never stand the scrutiny of a court of law.
Sent to boarding school at the age of ten, Hastings disliked school's harsh discipline and was physically beset by asthma. He attended the Charterhouse School next, a well-known private academy for boys in England. Such schools were considered training ground for a career in politics or the military, or as a preliminary to an elite education, and were infamous for their insularity and unspoken codes of behavior. Again, at Charterhouse he endured a miserable few years and left the school at age 16. Then, on the heels of another financial blunder by his father, with his older brother Archie and his mother, Hastings went to Europe.
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