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Life Lessons: Winning by losing Thumbnail

Life Lessons: Winning by losing

Growing up I was never a ‘sports guy.’ My experiences with competitive sports were not good. My first foray was in sixth grade when I was on my elementary school basketball team. My school principal, Mr. Schillinger, encouraged me to play I think because I was one of the taller kids in my class. I was a lanky and pretty uncoordinated kid. I spent a lot of time on the bench watching games until the town finals.

Then, during town playoffs, my coach decided to put me in at the end of a game where our team was up by a lot. In other words, there would be little that I could do to screw up the win for our team. While I appreciated the opportunity to play, strangely I didn’t feel that I had earned it. It was the “Let’s give every kid a chance to play as long as we don’t lose” strategy.

As a parent we want our kids to excel at everything they do. It’s even better when they can outperform us. That can make us proud but somewhat selfish parents. But, never losing can be a problem. Life is full of disappointment—at work, in relationships, and in life.

When I think about the times when I have learned the most, it’s always been when I failed. There is something about losing that is a great teacher.

Mind you, I am not complaining about my life. I feel extremely fortunate to have gone to great schools, have a wonderful wife, family, & friends, and a job that I love. Am I lucky? I think not. I think most of my successes go back to the hard lessons that I learned by losing.

This past weekend my wife, son and I traveled to Atlantic City, NJ for my son’s club volleyball tournament (I’ll write about Atlantic City and the casino industry in another blog). These 16 year-old boys came from several different towns in Boston’s MetroWest. They were still getting to know each other and how to work together as a team. Coming into the tournament they were far from the best but not the worst either.

On Saturday they lost most of their matches except one against a top ceded 16s team from New Jersey. On Sunday they had more losses but battled back to play that same team in the very last set of the tournament. It was the best 2 out of 3 games to win the bracket. They lost their first game by a few points but fought hard in the second to win by the required 2 point margin, making them eligible for the third, shortened game. It was a tight game but they lost by 2 points.

What could have been missed in all of this was how they really came together to play better individually and also as a team. They were no longer the team fumbling the ball on easy plays. They improved their overall level of play. They won by losing.

Since we like to draw parallels to financial planning, I’ll say that this relates to the long game of planning. Too often money decisions focus on short term needs, wants and decisions. While meditation teaches us to try to live each day in the moment (we should), we must also lay the groundwork so that our future turns out the way we expect. Living in the moment does not mean ignoring the future.

Hopefully this tells you how we think about your goals and finances. It’s always about the long game and better long term outcomes.

Have questions about your long game? Give us a call. We’re here to help.


Lyman H. Jackson




Financial Planning Solutions, LLC (FPS) is a Registered Investment Advisor. FPS provides this blog for informational and educational purposes only. Nothing in this blog should be considered investment, tax, or legal advice. FPS only renders personalized advice to each client after entering into an advisory relationship. Information herein includes opinions and forward-looking statements that may not come to pass. Information is derived from sources believed to be reliable. Information is at a point in time and subject to change without notice. Such information may not be independently verified by FPS. Please see important disclosures link at the bottom of this page.

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