--- title: To Win You Must Be Willing To Lose description: To win you must be playing the game, and when the game is on the line, and the risk is at its highest, the entrepreneur with a winning mindset demands the opportunity to carry the ball. image: https://www.tonycaldwell.net/hubfs/Imported_Blog_Media/7_2_19-1030x604.jpg --- [![Logo - TC](https://www.tonycaldwell.net/hubfs/Tony%20Caldwell/Logo%20-%20TC.png) ](https://www.tonycaldwell.net) - Type - Topic July 02, 2019 # To Win You Must Be Willing To Lose Blog, strategy - [**](https://www.facebook.com/sharer/sharer.php?u=https://www.tonycaldwell.net/blog/to-win-you-must-be-willing-to-lose) - [**](https://twitter.com/intent/tweet?source=https://www.tonycaldwell.net/blog/to-win-you-must-be-willing-to-lose&text=To%20Win%20You%20Must%20Be%20Willing%20To%20Lose) - [**](https://www.linkedin.com/shareArticle?mini=true&url=https://www.tonycaldwell.net/blog/to-win-you-must-be-willing-to-lose&title=&summary=&source=) - [**](mailto:?&subject=https://www.tonycaldwell.net/blog/to-win-you-must-be-willing-to-lose&body=https://www.tonycaldwell.net/blog/to-win-you-must-be-willing-to-lose) During breakfast this morning with a friend and successful entrepreneur, we talked as we often do about sports.  We’re both former college athletes and share a competitive mindset.  We agreed that championship sports teams are always those who are willing to risk everything, including humiliating defeat, to win. I recalled deciding in 1973 that I wanted to be a national karate champion in the sport of Tae Kwon Do.  Upon telling my teacher (a former national champion) of my goal, he promptly beat me severely in the ring; multiple times.  He saw to it in the coming months that others beat me regularly.  In losing I learned to maximize my capabilities, I honed my determination to win and I gained a lot of bruises, a broken bone and hands that would be disfigured later in life.  Nevertheless, by being willing to lose, I learned how to win. ![Professional Suited Man with american football ball on blue banner background.](https://www.tonycaldwell.net/hs-fs/hubfs/Imported_Blog_Media/7_2_19-1030x604.jpg?width=300&name=7_2_19-1030x604.jpg)Ultimately, I came in second in the national championships because of stupidly losing my temper, (which is the subject for another blog) but the lessons of what it takes to be successful, including the willingness to dream big dreams and take risks have stayed with me a lifetime. I notice that many talented business owners fail to maximize their own potential because they aren’t willing to risk what they have already achieved.  To lose what they’ve gained is more psychically fearsome than the prospect of winning.  When someone gets in this position they have already lost. I find it fascinating that people who never played a sport can become rabid fans.  They cheer when their team wins, and often hurl criticism at them when they lose, but it is the athlete who is playing the game.  The champions are the ones who, in moments of maximum risk, and when the game is on the line, want the ball in their hands. It is the same in business.  To win you must be playing the game, and when the game is on the line, and the risk is at its highest, the entrepreneur with a winning mindset demands the opportunity to carry the ball.  He knows he may lose; perhaps everything he has worked for up until now.  It’s not that he’s fearless.  He is full of fear, but fear doesn’t stop him; it empowers him.  Having lost before he understands the consequences of losing. Sports champions and successful entrepreneurs learn in similar ways and they behave in the same ways too.  They have sacrificed to be where they are.  They have lost many times before.  They have learned that to win they have to play the game.  They can’t just cheer from the sidelines and that by playing they risk losing, but that is the price of winning! [Tony Caldwell Tony Caldwell is a modern “renaissance man,” who is not only immensely successful in the field of insurance, but is also a writer, children’s advocate, mentor and even a licensed pilot. Always keen on helping others make their dreams come true, Tony and his team have helped independent agents grow into more than 250 independent agencies. This has made OAA the number one ranked Strategic Master Agency of SIAA for the last 5 years, and one of Oklahoma's 25 Best Companies to Work for. Tony loves to share his knowledge, insight and wisdom through his bestselling books as well as in free mediums including podcasts and blogs. Tony and his family are members of Crossings Community Church, and he is very active in community initiatives: he’s chairman of It’s My Community Initiative, Inc., a nonprofit working with disadvantaged people in Oklahoma City; and chairman of the Oklahoma Board of Juvenile Affairs., and he has served through many other organizations including the Salvation Army, Last Frontier Council of the Boy Scouts of America, and the Rotary Club. In his spare time, Tony enjoys time with his family. He’s also an active outdoorsman and instrument-rated commercial pilot. ](https://www.tonycaldwell.net/blog/author/tony-caldwell) 2 minute read ## Recent Posts ### [Plant The Garden You Won't Live to See](https://www.tonycaldwell.net/blog/plant-the-garden-you-wont-live-to-see) Plant the Garden You Won't Live to See What Le Notre Knew About Building Institutions That Outlast Their Founders Here is a question most builders never ask themselves out loud. ... ### [Overcoming Insurance Industry Challenges](https://www.tonycaldwell.net/blog/insurance-industry-challenges) Those of us who own insurance agencies are no strangers to industry challenges. The COVID-19 pandemic brought several of the latest issues racing to the forefront as individuals ... ### [The Future of Digital Trends in the Insurance Industry](https://www.tonycaldwell.net/blog/digital-trends-in-insurance-industry) The times, as they say, they are a’changing! 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