30 Days of Greatness- Day 2 Sir Winston Churchill

May 2. 2014

Day 2 of 30 Days of Greatness. Today Sir Winston Churchill.

If there was ever an example of “Cometh the Hour, Cometh the Man” Churchill was it!.

As Margaret Thatcher once said “He needs his moment to fulfil himself, before he became prime minister he had made some terrible political and military mistakes.” Churchill’s story is that of extreme public failure and yet rising again and again into the pages of history. A lesson for us all.

30 Biggest lessons from Sir Winston Churchill


  1. Never Never Never Give in!

  2. He was a great reactionary leader. He needed a challenge to rise to the occasion. War Gave that to him- What is your FIGHT?

  3. He, like us all, need only a moment of to fulfil themselves. When that moment come- seize it!

  4. When his strong views aligned with the needs of the people then he was a towering figure of greatness, when they didn’t he was cast out.

  5. Despite an upperclass upbringing he always remained connected to the people and accessible as a leader during the war

  6. He failed 3 times to join the military, before he got in. Again I repeat point 1

  7. Serve your apprenticeship it will serve you later in life- Churchill Served in 3 wars before leading England in WWII, these experiences shaped his views about military strategy and warfare.

  8. By 23 he wrote his first book- start writing!

  9. He escaped prison during the boer war twice.

  10. You need a charger to guide you into battle!

  11. His impatience in 1915 cost over 100,000 lives. He lost his cabinet position and immediately joined the front line of the battle as a lieutenant . Not something he forgot in the later years.

  12. He was a terrible singer (me to)

  13. During the “Blitz” Churchill would walk the streets at night to see first hand what was happening to the country and understand the battle. Something more leaders need to do- connect with your people on the front line.

  14. He kept a journal and would record his daily thoughts.

  15. Keep a strict schedule- Churchill would take a 2 hour nap at 6pm before working until the early part of the morning.

  16. Consider Life as an adventure- Churchill loved to travel, connect and make relationships

  17. Build Partnerships- It was Winston’s ability to woo then President of the United States Theodore Roosevelt that saved England and Europe during the war.

  18. Trust in yourself and Back yourself 100%- Churchill faced opposition at home and away in the fight against the Nazi’s. Hi adamant belief was that there was no negotiating with Hitler and as such Britain needed to fight. That belief saved Europe.

  19. Use your failures to grow and develop- Churchill spend years in “the Wilderness” a political exile after some huge mistakes.

  20. He believed that he was born at this time for a specific purpose.- The night Churchill was appointed Prime Minsiter of England he wrote in his journal:

    • “I was conscious of a profound sense of relief. I felt as I was though I was walking with destiny. That all my past life had been but a preparation for this trial, I was sure I should not fail.”

  21. He had an enormous faith that he was being guided and protected, on evening whilst walking during the Biltz a bomb landed a few hundred meters from Churchill and his bodyguard. His bodyguard then urged Churchill to come inside the bunker for protection, fearing that another may fall at any moment. Churchill replied:When in the midst of a storm (Business, Political, Relationship) always be sure to reaffirm the vision and destination even when you can’t see it and it looks like you’ll never make it. “Let us move forward, together, stead fast into the storm.”

    • “There’s someone else looking after me besides you. I have a mission to perform and that person intends to see that it is performed”

  22. Be daring and don’t be afraid to fail.

  23. It’s never a question of resources its always a question of resourcefulness. Churchill recalled the british expedition force some 21 thousand men and women across the english channel using everything from war ships to tug boats.

  24. He had absolute certainty when addressing the public of a resounding victory He was the first British Prime minister to receive a Nobel Prize and Became an honorary citizen of the united states.

    •  “Is it possible that they do not realise that we shall never cease to persevere against them until they have been taught a lesson that they and the rest of the world will never forget!”

  25. You can’t connect the dots looking forward!- A re-quote from Steve Jobs, Churchill found himself in Berlin a few years before the war began and had the opportunity to meet Hitler. Rumour has it that Hitler came to the hotel for the meeting but didn’t have to courage to go ahead with the meeting so left. 

  26. As a communicator, Churchill was barely paralleled in his time. His passion and authenticity when addressing parliament and the public are the traits for which he is most warmly remembered.

  27. Stay true to your core beliefs and ideals- These served Churchill under the enormous weight of a nation at war

  28. Focus on Key details not every detail! Churchill was excellent and finding and actioning the key things that would make the difference.

  29. Passion and Certainty are essential leadership ingredients

  30. Leave a legacy!

There are few people in this world who will have a greater impact on the world that Sir Winston Churchill. He will afterall be remebered as the man who saved Britain and the world from Nazi Germany.

I leave you with his most famous words…

Calvin “Never Give In” Coyles

Never Give In