The block of pine whittled into the shape of approaching that of a 4 wheeled vehicle sat perched atop the hilltop created by the wooden track. Someone blew a whistle, someone else started a stopwatch, a third someone dropped the pins holding back the blocks of pine. The Pinewood Derby, a mainstay to this day in Cub Scouting, was underway!

I never won The Derby. I remember coming close but my memory doesn’t extend to remembering how many places down the leaderboard I considered close back when my age could be expressed in single digits. But I definitely remember not winning. I remember that because each year I tried to do better. I think I did. I do remember the dads saying how much faster everyone got this year.

I also remember we didn’t have any juggernauts in the wood race car circuit. No one was a perennial powerhouse. Someone new always took home the big trophy. (I have no recollection of this at all other than my intuition but I’m pretty sure that big trophy stood about 3, maybe 4 inches high.)

The pinewood derby isn’t the only thing I never won. It heralded in a lifetime of losing. I don’t mind. Sometimes it gets old never getting to take home the big trophy. But along the way I’ve amassed an impressive number of little trophies, plaques, and certificates.

There were losses in Little League baseball, high school baseball and basketball, college bowling, gun club skeet shooting, and car club rallying. Actually, at the car club I do have a few first-place plaques but only in the novice division rallies. There too the big trophies eluded me.

Another set of competitions I’ve proudly lost at have been speech contests. Going back to high school forensics competitions I’ve only ever come tantalizingly close to a trophy I’d have to readjust the shelves in the bookcase to display. Even today, after countless attempts at Toastmasters International World Series of Public Speaking I’ve never broken past the district level, leaving me only halfway to the international stage and the really big trophy.

I’m happy with my life of loserdom. Each time I didn’t win, or won only to put me back into a more competitive position, I learned something about myself, what got me that far, what I need to go farther. Toastmasters has a rule, if you ever win the WSOP, you cannot compete again, not even all the way back at the club level contests. You’re one and done. I think it’s a sound system.

We looked at winning, losing, and learning, in this week’s Uplift, Run the Good Life. We said, “Winning isn’t everything. Not quitting is! Run the race so you get the most out of life,” and much, much more. Go on, take a look.