Are You Playing to Win, Or Trying Not to Lose

President Lincoln, shown here with his generals after the battle of Antitetam in 1862. Antietam, located in Sharpsburg, Maryland was the bloodiest single-day battle in American history with over 23,000 Confederate and Union soldiers casualties. Most of the generals pictured; Burnside, Hooker, McDowell, McLellan, and Pope would be eventually fired due to their inability to commit to a winning strategy which required an all-in approach. While the battle technically concluded in a draw, General Lee accomplished this with half of the troops than of the Union Army and use of a more aggressive and 'playing to win' strategy.

By Nick Fisher, Portfolio Manager and Rick Thomas, Business Advisor


Often, when I ask young entrepreneurs what they most hope to learn in their career, their responses have to do with how to get rich by starting a successful business. Conversely, when I ask successful business owners what has been their most valuable lesson, the answers are usually along the lines of learning to overcome setbacks and failure.

The difference in the answers illustrates the truth that is lurking behind every successful journey in business -- failure is a reality.

It’s not a matter of if you will fail, but when failure will be upon you. Knowing this, the challenge then becomes learning how to respond in the face of failure. How you respond in the face of challenge and failure will define your character and whether you succeed, or not. But getting past the failure to get to success? There are no shortcuts. Nor are there any guarantees that you will eventually “get it.”

The upside, however, is there are plenty of examples to learn from these days as the headlines are filled with stories of leaders who continually fail to learn from their mistakes; not because they aren’t smart nor lack the necessary ethics, but because their response in the face of failure lacks the courage and willpower to see them through it.

This is illustrated in history by the numerous failures of the Union Army generals at the outset of the Civil War. President Lincoln, as shown in this photo from1862, rarely visited the battlefield and relied on his generals to carry out the objectives of the war. Yet Lincoln was repeatedly frustrated with their lack of initiative and courage to face the Confederate Army head on.

His frustration was most pointed with General George McClellan who represented the supposed best that West Point could produce, but in the face of battlefield action failed to muster any significant advance against the Confederacy. Generals McDowell, Pope, Burnside and Hooker also were ineffective and suffered humiliating defeats.

It wasn’t until Lincoln consolidated control of the Union Army under General Grant did the tide begin to turn for the Union Army. Rather than leading to win the war, the Union Generals (save for Grant and a small handful of others) they were trying to not lose.

What can we draw from this example then in how we lead our businesses? If you are an aspiring leader, or even a seasoned leader that plays not to lose, it is time to take a hard look in the mirror and decide if success is truly important to you. If so, then you have also decided you are truly willing to begin learning, and one of the quickest ways to get there is as a good friend once advised, “double your mistake rate.”

The wisdom of this is that for many, repeated decisive actions even if wrong, will bring about success much more quickly than a safe and over-cautious approach. This will also help develop a key leadership trait that is fundamental to sustaining success once you achieve it -- humility.

As Jim Collins describes in his seminal business book, Good to Great, humility is the highest and most important quality in a Level 5 leader, and is a necessary trait for a leader to sustain business success over time. And nothing develops humility quicker than having to face your failures in front of your team!

Learning in the face of failure is a mindset that is built over time and amongst your many failures you will have successes that will keep you going. With commitment and perseverance you will eventually be able to share your hard-earned wisdom with the next generation and temper their enthusiasm with the reality of the journey.