The hulk of a man with a beer in his hand he looked like a drunk old fool
And I knew if I hit him right why I could knock him off of that stool
But everybody they said watch out hey that’s the Tiger Man McCool
He’s had the whole lotta fights and he’s always come out winner yeah he’s a winner
But I had myself about five too many and I walked up tall and proud
I faced his back and I faced the fact that he had never stooped or bowed
I said Tiger Man you’re a pussycat and a hush fell on the crowd
I said lets you and me go outside and see who’s the winner.

Bobby Bare – The Winner – 1973

1997 was a year of transition for me.  By then I finally figured out what I wanted to do with the rest of my life, which was start my own business creating better bosses.  I still had about 18 months left in the Navy, but I was already out the door.  I had recently completed my MA degree.  I was teaching some college classes in the evening.  I was even dressing differently.  Nice clothes.  A tie.  I carried a briefcase.  The old boxy kind like your grandpa carried.

I was also teaching some workshops in the Navy on process improvement.  The Command sent me and a couple of other guys from Bremerton, WA to Bethesda, MD to do a train-the-trainer class.  I remember boarding the plane in nice civilian clothes, carrying my briefcase.  On the flight over, I imagined I was living this life full time. Air travel to go to client sites all over the world to do management training.  It was exhilarating!  I saw myself as special.  A winner! When I was little, I pretended I was in the military.  Now in the military I was pretending I was a civilian.

A few years later, I met an old trainer on a project I was working on.  He was in his mid-60s.  I was still in that euphoria of my new career.  When I commented how lucky he was to be flying around the country doing training, I was surprised at his answer.

“I hate it,” he said.  “I wish I could quit and do something different.”

I couldn’t believe it.  This life was what I dreamed about.  Why would he want to quit?

And yet today, I think I understand.  I love what I do, but the glory of flying and travel?  No thanks!

In the song above, the guy who’s about to call out Tiger Man McCool thinks he wants to be The Winner.  He wants the respect.  The accolades.  The reputation.  The only way he gets it is to take out The Winner.

But in an unexpected turn, Tiger Man simply educates him on what it took to be The Winner and what it costs him today.  The respect is great, but when he considers what it took to get there, he simply said,

Now you remind me a lotta my younger days with your knuckles a clenchin’ white
But boy I’m gonna sit right here and sip this beer all night
And if there’s somethin’ that you gotta gain to prove by winnin’ some silly fight
Well okay I quit.  I lose. You’re the winner.

This post isn’t meant to take to shine off your dream.  It’s simply an FYI.  I don’t regret my career choice one bit.  But as for the lifestyle?  Yeah, that was great at first. It was everything I imagined on the plane back in 1997 and more.  I’ve done workshops in 43 of the 50 states and in China, Poland, Germany, Ireland, Italy, the UK, Canada, and Puerto Rico. I used to stack up my hotel room keys at the end of every year and take a photo of it for Facebook to brag to my friends.  I saw more of the world outside of the Navy.  But like that old trainer, I’m real tired of it.

Dreams are massive.  When we try to divide and compartmentalize them, it often seems like it leads to disappointment and failure.  But if you remember WHY you wanted this dream, you might find it happens but looks a little different.  The travel was eventually a drag, but helping managers become better bosses?  Well, it doesn’t get much better than that!

Keep dreaming. The Winner looks different for all of us.  It’s up to you to define The Win.