Richard Pierce Thomas

Leadership and Small Business Consultant

Often when I ask young entrepreneurs what they most hope to learn in their career, the responses typically have to do with how to get rich by starting and selling a successful business.               

Conversely, when I ask seasoned leaders who have achieved success what they have learned that has been most valuable in their business achievements, their answers are usually along the lines of learning to deal with 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 then, the challenge becomes learning how to respond in the face of failure. It is how you respond which 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 was repeatedly frustrated with their lack of willingness to take the Confederate Army head on. Rather than leading to win, they were trying to not lose which resulted in prolonged inaction in prosecuting the war. It wasn’t until Lincoln consolidated control of the Union Army under General Grant, who played to win, did the tide begin to turn for the Union Army. What do we draw from this example then?

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!

Start out by creating lab time – time and space where you can safely experiment by using daily routines as an easy place to start. For example, if you always drive to and from work the same way, try a different route. If you dress putting the pants on first, then start with your shirt first. Shave the same way? Yes, even that too. You’ll find that as you tackle the easy stuff, larger opportunities will seem easier for you. 

Perhaps it will be the morning pep talk with the team that always ends on a flat note. Take a chance and change the conversation. Lead by asking a question rather than a statement, and observe how the outcome changes. If you fail, try something else. In all of this, however, it’s important to remind yourself that failure is an indication of learning and unless you are repeatedly committing the same mistake, you will eventually find success.

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.

Rick Thomas is a Principal and Director of Human Capital at Pilot Wealth Management, a registered investment advisor in Oregon state. Leading their focus on the human component of building wealth, he consults and speaks to organizations across the country, focusing on individual and organizational achievement.