The Working Wisdom of Winston Churchill

By Sarah Nord

I don’t go to the movies very often these days. Perhaps I’m cheap (the tickets have gotten silly expensive) or maybe I just can’t sit still that long. At any rate, it’s been a year or two since I last set foot in a theater, but recently, my husband and I broke tradition and went out to see Darkest Hour. This film depicts Winston Churchill’s early days as Prime Minister of the United Kingdom, set at the outset of WWII. It’s simply excellent.

Actor Gary Oldman is nearly unrecognizable as Winston Churchill. In fact, I’ve never seen an actor transform so completely into a historical figure. (Not even Daniel Day-Lewis as Lincoln!) If you haven’t seen Darkest Hour yet, do. I can’t get it out of my head—particularly Churchill’s wise and witty quotes, sprinkled throughout the film.

As I typically do when obsession strikes me, I began Googling Churchill to learn more. My search led me to “50 Sir Winston Churchill Quotes to Live By,” published by BBC America. It’s a goldmine of insight for our personal and professional lives.

Here are a few of the quotes that struck me as particularly relevant for us “working folk”:

“To improve is to change, so to be perfect is to change often.”

In my profession, I can hardly keep up with the rapid pace of change, and I sometimes feel discouraged by everything I don’t know. But like it or not, change is inevitable. It’s the reality of our professional lives. As Churchill reminds us, it’s all a quest for improvement. If we stop changing, we might as well power down for good.

“Men occasionally stumble over the truth, but most of them pick themselves up and hurry off as if nothing ever happened.”

This applies to women, as well. :) How often do we miss the truth when it’s staring us in the face? How often do we shy away from data that doesn’t tell the story we want to see? This Churchill quote challenges us to stop, pay attention and consider ideas and perspectives that may differ from our own. Let’s not be so quick to hurry off in the opposite direction.

“Success is the ability to go from one failure to another with no loss of enthusiasm.”

If you pay attention to the startup ecosystem, your ears are probably ringing with the phrase, “Fail Fast.” It’s a cringe-worthy expression for anyone (myself included) who is used to striving for success at all costs. Failure is a bogeyman to be avoided, right? No, not entirely. Just like change, failure is inevitable. It’s going to happen, and those who are able to rebound are the ones who have a fighting chance at success.

“It is a mistake to try to look too far ahead. The chain of destiny can only be grasped one link at a time.”

As we dive into the new year, this Churchill quote struck me as timely. Like many of my colleagues, I’m a planner, and I love to make predictions about the outcomes of my work. I want to know what’s coming so I can be ready for it! But if history is any indicator, my plans will almost never come to fruition just as I expect. (Circling back to that first quote), change is coming. Perhaps I should plan for that.

“Personally I’m always ready to learn, although I do not always like being taught.”

Ah, another Churchill quote that stings a little. I consider myself a person with a thirst for knowledge, but I like to consume that knowledge in my own time and on my own terms. I hate to admit it, but I sometimes bristle when a friend or colleague tries to “school me.” Maybe it’s that fear of failure creeping in. Or maybe I just don’t want to look foolish. But here’s the reality: The people we work with day by day are our best teachers. These folks walk the same road we walk, and they may have insights that completely transform the way we think and operate. Resisting knowledge, just because we don’t want to hear it from a certain person, is truly the height of foolishness.

“Courage is what it takes to stand up and speak. It’s also what it takes to sit down and listen.”

We are inundated with information and opinions, and I think it’s human nature to respond. We’re compelled to have our say and take a stand. We want to be known as problem solvers who can think on our feet. But as Churchill reminds us, sometimes we need to just sit down and listen. We don’t always need to be the first or loudest voice in the room. We don’t always need to post that comment. In a world that gets noisier by the second, a little silent reflection may be just what we need the most.

And now for one final Churchill quote. This one needs no commentary:

“Every day you may make progress. Every step may be fruitful. Yet there will stretch out before you an ever-lengthening, ever-ascending, ever-improving path. You know you will never get to the end of the journey. But this, so far from discouraging, only adds to the joy and glory of the climb.”

Like What You’ve Read? Subscribe for More

Join the Onspring Insights newsletter for monthly updates from our blog. You may unsubscribe at any time.

NOTE: By submitting this form, you confirm that you agree to our Privacy Policy.