Leadership Lessons from My Dad: You Learn More from Losing than Winning

March 3, 2023

I played volleyball in high school and I loved it. We had some good years and we had some bad years, some good coaching and some not-so-great coaching; but I loved it enough to stick with it.

Looking back, I was learning a lot about myself and my life during that time. I learned how to win and how to lose, and I learned the importance of practice and perseverance. I also learned about leadership and what it means to be part of a team, and I definitely learned that I don’t like losing.

I knew in my brain that playing sports was more about learning valuable life lessons, but losing was incredibly frustrating. (That’s why I was also learning about grace, how to accept it, and the importance of giving it.) 

I remember after each match, my father and I would debrief the game. We would talk through what went wrong and what went right, which would lead me to think about what I needed to do differently for the next match. And he would regularly remind me of this:

“You learn more from losing than winning.”

This wasn’t always what I wanted to hear, but I knew in my heart that he was right. It is in the losing that we learn perseverance, forgiveness, and grace. It’s where we learn what works and what doesn’t, and it can give us the courage to take risks and try new things. In these ways, losing becomes a big part of winning. Yet it never feels good and it doesn’t make it any easier. 

Mark 8:34-35 – Then he called the crowd to him along with his disciples and said: “Whoever wants to be my disciple must deny themselves and take up their cross and follow me. 35 For whoever wants to save their life will lose it, but whoever loses their life for me and for the gospel will save it. 

Jesus understood just how much we hate losing and love to win. (I wonder if he ever sat at a foot race or a wrestling match and watched his created people be poor losers or gracious winners?) He understood our distaste for losing so deeply that he uses it to make a point that, even today, makes us cringe.

“Whoever wants to be my disciple must deny themselves and take up their cross and follow me. Whoever wants to save their life will lose it, but whoever loses their life for me and for the gospel will save it.”

Has that verse ever made you think twice about following Jesus?

Jesus could have painted a nicer picture of what life with Him would be like…but He wants us to know what we’re getting into. He wants us to know what it takes to get the big win he offers. And these two verses perfectly portray what it takes to follow Jesus.

It takes losing what we think matters most in this world. It takes losing the right and the desire to win at this life. It takes giving up the “win at all costs” mentality for a “lose here so I can gain there” one. And sometimes, it means we have to literally lose our life for His gospel. There’s no nice picture in any of that.

In leadership, we want what we are leading to succeed. We want those that are following us to win at whatever we are leading them toward. So if we go back to the idea of making sure we’re leading those that follow us toward gospel goodness, it would seem that we should be leading people to…lose?

That doesn’t seem right. Losing isn’t usually something we say we want to be a leader of! 

But to win in Jesus’ eyes requires losing what this world says is important. We have to lose our selfish ambitions, our pride, our desire for more, more, more; we need to lose whatever it is that stands between us and Jesus, and those are usually things that mean a lot to us. 

This is hard work. It’s hard to do in our own lives, let alone be a leader for others. It requires practice, perseverance, following the right examples, forgiveness for ourselves and others, and a whole lot of grace to withstand the pressure of wanting to win and get the glory of this world. It will take courage to live and lead differently than what this world expects and all of that is going to take Jesus or it won’t happen. 

But in the end, our lives will have eternal implications for those that follow us. In the end, we will see God’s face and know the best kind of win. And that’s the most important thing my parents taught me… that in this world, I will gain far more from losing than I ever will from winning. 


Written by Trudy Ash

Regional Catalyzer – USA Midwest

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