“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”. 

His enrollment in the military academy might well have been a turning point in his life. And yet even at that point few would see his promise as a future leader of such significance. And there are numerous stories of his early military career – some included near death experiences; others as a military prisoner.

Even as an early politician, Churchill wasn’t always viewed in a positive light. At one point he was actually fired as First Lord of the Admiralty, having been blamed for leading a failed attack on Turkey early in World War I. Nonetheless, these experiences galvanized Churchill to find a way to overcome any obstacle.

This history doesn’t necessary reflect what you would expect of a leader that might well be one of the greatest in recent history. As Prime Minister of Great Britain during World War II, he held together both a country and an alliance for the express purpose of protecting his homeland, restoring freedom to Europe, and liberating the oppressed from a brutal regime. I do not believe I am exaggerating when I say this.

My point is not to debate the virtues of Churchill’s leadership. There are plenty who would take that argument. What I do want to stress is that every situation offers each of us a choice – and how we approach it may well shape the final outcome. In Churchill’s case, early challenges with academics didn’t prevent him with becoming and accomplished leader. A lifetime battle with a stutter and lisp didn’t prevent him from becoming an orator. Near death experiences and imprisonment didn’t prevent him from finding a way to live through it. And losing his job as First Lord of the Admiralty didn’t prevent him from ultimately becoming the Prime Minister of Great Britain.

How often do we look at our circumstance and find difficulty in every opportunity. How often do we convince ourselves that the challenges of today will forever shape our future? How often do we allow setbacks to discourage – or better yet – define us?

A pessimist sees difficulty in every opportunity; an optimist sees opportunity in every difficulty. What do you see?