“A pessimist sees the difficulty in every opportunity; an optimist sees the opportunity in every difficulty” – Winston Churchill

Those who know me recognize my affinity for Sir Winston Churchill. His leadership, while cantankerous and arguably self-serving, may well be the very reason the allies were victorious during World War II. What’s most interesting about Winston Churchill is to understand the history that forged both his style and his philosophies on leadership. Bear with me as I share highlights of his life and the connection to the quote above.

Born of nobility in Great Britain in the late 1800’s, one could argue he was given all the opportunity necessary for success. Despite this privileged status, he had an interesting and somewhat rocky childhood. Raised largely by his nanny, his interaction with his parents was fairly removed and arguably of limited influence.

Churchill struggled mightily during his formative years. A young, stocky red headed boy (I can relate to that), he spoke with both a stutter and a lisp (something that plagued him most his life). In and out of 3 different schools, Churchill’s early academic record was quite poor. And while excelling in certain subjects (Mathematics, History, and English), he was generally thought of as “a poor student”.  Continue reading →