Kenny Rogers: Leadership Lessons from the Gambler

Grammy award-winner and Country Music Hall of Fame Member Kenny Rogers was a cultural icon and changed the way modern country music was produced and enjoyed around the world. In honor of Rogers, who passed away this past month, Refresh Leadership decided to extract some lessons from the gambler himself by breaking down one of his most celebrated and award-winning tunes: The Gambler.

The story line of the song follows the narrator who encounters an individual who made a living playing cards and gambling. Check out these lessons we can learn from the characters in the song.

Take Advice from Others

In the beginning of the song, the narrator is urged to take advice from a person who had made a living gambling. Regardless of your trade, good advice is universal and can be applied to most aspects of life and business. While the narrator most likely wasn’t a gambler, the advice given was applicable to his current situation.

From seasoned veterans to experienced workers, learning from others’ successes and failures is a great way to develop leadership skills and knowledge. Consider finding a mentor who can help you navigate your current situation. Sometimes it takes an outside perspective to show you “I can see you’re out of aces … I’ll give you advice.”

Learn to Read the Room

One of the most important traits a leader can have is empathy. Truly understanding where people are coming from, what they need, and how to read them is imperative to leading with compassion and conviction. The gambler in the story has “made a life out of reading people’s faces, knowing what the cards were by the way they held their eyes.”

Most people may only offer a partial picture of how their life or workflow is going. Try to develop empathy skills to determine how your employees are handling their work, as well as the anxieties of life. Understand that not everyone is on the same page as you, so it’s imperative to learn to read the room and lead accordingly.

Lead with Integrity

While it may seem like a stretch to extract the virtue of integrity from a song about gambling, it is built into the structure of the song. Regardless of your industry or role, it is important to play by the rules and lead with all aspects of your values, goals, and purpose integrated into one common resolve.

As the gambler put it, “if you’re gonna play the game, boy, you gotta learn to play it right.” Understand what needs to be done, how to do it, who you need to accomplish the goal, and when to implement specific actions to drive everything forward.

“Know When to Hold them, Know When to Fold Them”

The most iconic advice in the song is found in The Gambler’s chorus.

You’ve got to know when to hold ’em
Know when to fold ’em
Know when to walk away
And know when to run
You never count your money
When you’re sitting at the table
There’ll be time enough for counting
When the dealing’s done

Sometimes, business leaders double down on a specific play, when all along, they should just fold and move on to the next game. The only failure is when a leader is pot heavy, or has invested too much, and doesn’t know when to give up. Consider all outcomes when developing a plan for your team. If the risk outweighs the reward, then maybe it’s time to not just walk away, but to run.

Roger’s classic is chock full of advice, and if implemented, it takes the pressure off winning and losing. “The secret to surviving is knowing what to throw away and knowing what to keep … ’cause every hand’s a winner and every hand’s a loser.” Every leader will experience wins and losses in life, but it’s what they do with the cards they have that determines whether they are successful or not.

What’s your favorite Kenny Rogers’ song? What lyrical wisdom have you pulled from his music? Let us know in the comments section below!

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5 Responses to Kenny Rogers: Leadership Lessons from the Gambler

  1. Debbie Lowery May 5, 2020 at 8:56 am #

    The Gambler is a very iconic song and you have definitely integrated into a means by which people can learn something in the work force. The empathy a boss has towards his or her employees is very important to understanding what their employees are experiencing in both their work families and personal families. An employee appreciates a boss who will be understanding of the work environment whether it is toxic or encourages a better work environment. It also takes a good boss to realize when some employees need to be weaned from the team and replace them with people who will be a better fit for the team. Learn when to hold ’em and when to fold ’em!!

  2. James May 5, 2020 at 9:01 am #

    Kenny Rogers had a lot of great songs, The Gambler was probably one of my favorite and this article really hits the points well for life lessons. Many songs are about life lessons if you pay attention to the words. Another great song by Kenny was Coward of the County.

    Thanks for a great article and story about Kenny!

    • Lita May 8, 2020 at 4:43 pm #

      My thoughts exactly!

  3. Shauna May 5, 2020 at 9:39 am #

    I really enjoyed this piece.

    20 years ago
    All my memories from those days come gather round me
    What I’d give if they could take me back in time
    It almost seems like yesterday
    Where do the good times go?
    Life was so much easier twenty years ago.

    I guess I should stop by Mr. Johnson’s hardware store
    His only son was my friend Joe
    But he joined the army back in 1964
    How could we know he would never come back
    Twenty years ago

    I was not born yet in 1964 and we can’t see into the future but we do look back. Remember that your current days are the “good times”. Twenty years ago seemed easier but at the time they weren’t. Enjoy now, tomorrow isn’t promised but do go back in your memory and to places where you found joy and comfort. Remembrances can make the current days a little easier to bear.

  4. Gary May 6, 2020 at 10:22 pm #

    Some leaders spend enormous amounts of time and energy keeping a dead horse alive–barely–when the humane thing to do would be to let the poor thing die. Of course, I am talking about a company that is no longer viable or doing what it was intended to do. That is especially true of not-for-profits. Sometimes businesses just outlive their usefulness.

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