From Software to Storytelling: What Winston Churchill Can Teach Us Today

I had the great privilege of being interviewed about my project by Ron Pruett, Managing Partner at The Boston Associates. As Ron mentions in his introduction just below, he is my cousin.

Did you ever think about quitting your job to pursue a passion project, travel the world or maybe write a book? Well Bill Whiteside did all three. He grew up in the Philadelphia suburbs, the oldest of 6 kids, and graduated from the University of Notre Dame with a degree in Management. In addition to a wonderful wife and two children, Bill also had a thriving software sales company for over thirty years. Yet one day, Bill decided he'd had enough. It was time to truly dedicate himself to going deep on a continuously developing fascination with Winston Churchill, one that had now grown into an obsession. It was time to take a new journey, a book writing one. This is Bill's story about how he went from software to storytelling, what lessons he learned along the way, and what we can all learn from one of the most inspirational leaders of all time. (I should note that Bill is my cousin so I was as interested in what he was doing as I trust you will be).

How did your career develop and what led to making a change?

My career is a good example of luck, timing, and rational self-confidence. My first job out of college was at Mrs. Paul’s. After marketing fish sticks and onion rings in Philadelphia for 10 years, a blind letter from a recruiter led to a job marketing ice cream in Lancaster County, PA. I left that job after four years to start my own business to sell a sales forecasting software package that I had purchased for the dairy. I wrote on a regular basis for work, and my writing ability added value to every job I ever had. I carried a vague thought that I might write a book one day, but had nothing in the way of a plan – or even a topic to write about. After reading multiple biographies of Winston Churchill though, I became fascinated with a deadly confrontation between the British and French fleets during Churchill’s second month as prime minister. I started researching and loosely writing about that as a mental-health diversion while I traveled for work. As I dug deeper into the story and learned more of the details about the clashes of personalities and honor that preceded the fighting, I quit my job and became a full-time writer to finish the book.

How and when did your fascination for Winston Churchill begin?

I loved to read from an early age, and some of the best stories were in the history books my mom encouraged me to read. She never stopped feeding my interest and gave me the middle volume of William Manchester’s The Last Lion trilogy one Christmas when I was in my thirties. I quickly recognized that Churchill was not just a great man, but he was a man whose life was the stuff of some of the very best stories.

The book sounds like a passion project. How did this passion ignite?

There are a number of parallels to my last job. I mentioned that I bought a sales forecasting software package for the ice cream company where I was director of marketing. I was so excited about the ability of the software to help companies save money and transform chaos into profitability that I quit that job to sell the software solely on a commission basis. I had never sold a thing in my life, and the owner of the software company told me I was “a complete idiot” to think I could make a living by selling his software. He happened to be right for my first two years, but I truly believed in myself and in his software, and over the next 28 years I built a successful business with the help of some incredibly talented colleagues. If I hadn’t taken that leap I would have always regretted it and would have wondered what might have been.

If I hadn’t taken that leap I would have always regretted it and would have wondered what might have been.

My book snowballed in a similar way. Starting with my fascination with Winston Churchill, I then became obsessed with learning every detail around his decision to ensure that the French fleet would not end up under Hitler’s control. As I learned more about that conflict, and about some of the other fascinating personalities who played important roles, I became consumed with the conviction that “people need to hear this story.” As I started accumulating research and outlining a possible book, it became a story that I just had to write. I know I would always regret if I didn’t finish this project.

How did you organize such an intense research and discovery project?

I used to give a presentation titled “Keeping Track and Keeping Score.” Metrics have always been important to me. At one point I even quantified how the harder and smarter I worked, the more money I made. That being said, I was all over the place when I started working on this book, especially since I was working full time. One of the first things that helped was when I diagrammed all of the different facets of this process. That helped ensure I did all of the right things. It also helped resolve “What do I do next?” or “What should I be doing more of?” during moments of uncertainty.

Then I started my typical maniacal score-keeping – with tables and graphs in which I tracked the number of pages transcribed, the number of lines in my first Excel outline, the number of pages in my Word outline, the number of words in my first draft, etc. The practice of keeping score helped me maintain progress, and it also worked as a visual incentive to make sure that I avoided not making progress (if that makes sense). 

When I completed my first draft and started polishing what I had written, I began to subjectively grade each chapter on the basis of quality. I use a 5-point quality scale, ranging from 5: “Absolute slop” to 1: “I can’t wait for someone else to read this.”

What business skills did you bring to the project?

A big revelation was that in some respects, researching, writing, and publishing a book is like managing a business.

In addition to whatever writing ability I might have - along with the discipline to manage the different pieces of this project, and my use of metrics to help ensure steady progress - I’ve had to learn about the business side of writing and publishing. To be successful, a writer has to be willing and able to market and sell his own work. I’m counting on my background in marketing to help immensely in this area. These days I spend as much time working on my platform – things like the website for my book, plus social media and email activities – as I spend writing. This might seem like drudge work for some writers, but I absolutely enjoy it.

A big revelation was that in some respects, researching, writing, and publishing a book is like managing a business.

If necessary, I will self-publish, but I would like to take a shot at finding an established publisher. In order to sign with a publisher, I need to first entice an agent to represent me to publishers. Lately, the process of finding an agent feels very similar to selling software – except instead of selling someone else’s product, I’m selling myself. And just as every software customer has unique interests and requirements, so does every agent.

How has book writing impacted you?

This process has helped make me a better writer and also a more confident writer.

I knew I could write, but I realized that to write a book - especially one of this magnitude - I needed to become a better writer. So I worked on that. I continued to read the works of great nonfiction authors. (Rick Atkinson, Laura Hillenbrand and Michael Lewis are my favorites). I studied the craft of writing (including Good Writing by Stephen King, Story Craft by Jack Hart, and Good Prose: The Art of Nonfiction by Tracy Kidder and Richard Todd). Most importantly I spent many hours writing and rewriting during times when “the other kids were out playing.” While I can’t quantify this, I know my writing has improved along the way. My first draft of just about everything is still every bit as horrid as my first drafts have ever been, but I now have a very high degree of confidence that I will eventually turn it into something pretty good.

On the downside, I see signs that I might be evolving into “that guy” … who jumps in whenever he hears a suspect Winston Churchill story or quote.

What leadership lessons can we learn from Churchill today?

First, you must have convictions, and then you must have the courage to stick with your convictions. Here’s a great example from the story I’m writing. In the first two years of World War II, Churchill’s most important goal was for Britain to survive until the United States eventually entered the war. When the French Government signed its armistice with Germany in June 1940, Churchill would not accept any possible risk that France’s Navy would join with Germany’s Kriegsmarine. He refused to accept any form of weak compromise. The potential threat to his island nation was just unthinkable. So, despite the fact that Churchill loved France, despite multiple assurances from France’s Admiral of the Fleet that no French ship would ever sail under a swastika, and despite heartfelt pleas from a number of Royal Navy admirals and commanders to trust the word of their former allies, Churchill insisted that the French fleet be removed from action – and he advocated deadly force if necessary. In the immediate aftermath of the British attack, he told a colleague “This is heartbreaking for me.” But he stood fast with his convictions.

First, you must have convictions, and then you must have the courage to stick with your convictions.

One other thing – it would require a long essay (or even a book) to do justice to this, but Churchill’s first Cabinet as Prime Minister has parallels to Abraham Lincoln’s team of rivals.

Are our circumstances today similar to those of Churchill?

On the day that Winston Churchill was named Prime Minister, Germany invaded Belgium, Holland, and Luxembourg. They entered French territory the next day. The German armed forces had significant advantages in equipment, manpower, imagination, and momentum. Churchill started out with two major allies: Belgium and France. Belgium surrendered after just 18 days. France signed an armistice with just Germany just 5 weeks later. Churchill had to organize Britain’s war effort as it fought alone, and he had to inspire the British public to not lose hope and to not give in.

Especially in terms of how Britain stood as an isolated target for annihilation, as bleak as life might seem at times today, I believe that Churchill led his country through more perilous circumstances.

Are we overlooking great leaders like Churchill today? 

No. No one comes close.

What Churchill traits are the most ever-lasting?

It’s no wonder that some leaders wish to compare themselves with Churchill. He led his country through a very dark time against incredibly tough odds. He did so in part by writing and speaking some of the most memorable phrases in history. He had a quick wit and was a master of the written and spoken word. He was resolute in his beliefs.

Many of us carry the mental image of Churchill with a twinkle in his eye, a cigar in hand, and glass of whiskey or champagne within reach. But there was the substance of a long and successful public life behind the caricature. He succeeded in achieving his ambitions, he did not waver from his beliefs, he enjoyed life to the hilt, and he enriched the lives of those around him. 

I didn’t really answer your question, did I? For me at least, his mastery of language, his sense of humor, and the strength of his character are his most ever-lasting traits.

How will you measure the success of this project and the book?

I will exhale and smile and consider this project a success when I can hand hardcover copies of my book to my dad, my wife and my two kids. My dream level of satisfaction would be to walk through an airport or on the beach in Ocean City, NJ and spot someone reading my book.