Leadership is sometimes a lonely and humbling endeavor. Many of us strive to lead in our careers while others have it thrust on us. Some of us fail at it, others flourish, and we all do some of both at times. There certainly is always room for improvement. So how can we become better leaders? And where do leaders go when they need insight and guidance?


When I need inspiration, advice, or a sounding board, I turn to my “personal board of advisors”—inspired by Thinkertoys: A Handbook of Creative-Thinking Techniques by Michael Michalko—and solicit their wisdom, or at least what I think they would offer me as advice. Abraham Lincoln, one of the greatest leaders in U.S. history, is one of those advisors.

I relate to Lincoln a great deal. If you read articles or books about him, you’ll find that Lincoln was a bit of a tortured soul. He thought he was a failure at many things: He lost his job, he failed in business, his sweetheart died, he had a nervous breakdown, and he was defeated for a number of positions, including in the House of Representatives, in the U.S. Senate, and as vice president, all before he was elected President. Even as President, Lincoln struggled greatly with decisions and, at times, considered himself a failure. Great leaders usually have great confidence internally and exude it, but sometimes they privately feel like they can never do enough so are always striving to do more and lead better. Albert Einstein was very much this way as well—repeatedly failing to get to a successful result and never really being happy along the way. Leadership takes a strong heart, a strong mind, and a boatload of perseverance.


I rose pretty quickly through the various ranks of a couple of companies—mostly in finance and accounting positions in high-tech manufacturing and consulting—and had been in leadership roles for some time. About 12 years into my career, I was given the opportunity to take advanced leadership development training, and I thought, “Great, let’s sharpen the saw on a couple of points and become better.”

But I didn’t realize what I was in for. It was a week-long, small-cohort leadership development course that had collected input from my boss, peers, and subordinates to focus on my leadership styles and performance. It was clear on the first day of this program that many of us had faced a multitude of challenges but really hadn’t encountered failure yet in our careers. We were all fairly successful leaders, and our companies were investing in us to get to the next level. Our arrogance is what made the next couple of days very difficult. My cohort and I got feedback on our leadership styles, some good and some “constructive.” Many of us were hard-charging executors. We knew how to get stuff done, and that was largely why we were successful. But at what cost were we achieving this success?

After the first day of the program, and after my cohort and I spent a night commiserating about some of the constructive feedback we had just received, it was clearly time to roll up our sleeves and make some changes. We needed to continue to achieve results but to ensure we weren’t leaving burned trails behind us. We needed to lead more holistically and command and control less.


What led me to consider a change in leadership style was a conversation between me and the mentor I had during that training week. He unearthed my love of boating and told me this analogy about leadership, which I have never forgotten:

“Patrick, you like boats, right? Well, think of yourself as driving a powerboat—a twin-prop, turbo, gas-guzzling boat—ripping up the waters of life and business to get to your destination. You are getting to your end result quickly, you can do it yourself, and you have had some success. But when you land the powerboat, turn around and look at the wake you’ve left behind. On land we call those ‘burned trails.’ You achieved success and reached your destination, but at what cost? Going forward, I want you to think of yourself as captain of the America, the 19th-Century racing yacht and first winner of the America’s Cup international sailing trophy. Similar to your powerboat, the America is very fast and will get to its destination quickly as well, but the only way it will achieve that goal is with great leadership and a team that works together. Sailing is definitely a team sport, and one that requires strong leadership by the captain.

“The captain lays the plan of action via the sailing plan, outlining how the crew plans to navigate and perform according to the weather conditions and other factors. With that plan, the crew works together to execute and make decisions on how to implement adjustments in the midst of the race. The captain leads, and the crew follows. They work together. Then, after you reach your destination, turn around and look back. No burned trails, no large wake. As a matter of fact, your crew likely cheers and celebrates the team victory! Yes, sometimes business and life require individual efforts, but many times they require team efforts. I want you to think of how you can be the best captain of the America and lead your team to victory!”

Yes, sometimes I revert to powerboating to get certain tasks done and to achieve the goal that may be required at the time. But in more circumstances than not, business requires me to be a strong leader—the captain—to get the team to work together so we can all achieve the goal. To remind me of this anecdote, I proudly display a replica of the 1851 America in my office. I look at its design, its sails, its beauty, and I think about how the crew function together to make that boat fly through the water. In full disclosure, I did make one modification to my replica, though: I glued the engine of a toy car to the back of it, just in case I need to fire up those engines once in a while to help my team cross the finish line!

Consider how you lead and what you leave behind you when getting those results. Burned trails and a gigantic wake or a cheering crew? Be the captain, and lead the team to victory!

About the Authors