Country music legend Kenny Rogers passed away on March 20, 2020. He left a hole in the heart of Nashville as one of the frontrunners of country music. However, what he left behind are life lessons that every person can learn something from, regardless of their age.

15 Life Lessons From “The Gambler” Kenny Rogers

On a hot August day in Houston, TX, Kenneth Donald Rogers made his debut. That summer day in 1939 would change the world. At the age of 20, he released his first song entitled “The Poor Little Doggie.” He was voted one of the best-selling music artists of all time. He sold more than 100 million albums across the globe.

What was so special about Rogers, and what did he teach the masses that can help those who have a dream and want to be successful in life? Here are some of the most important lessons he leaves with fans.

1. “Friendships come and go, but families are forever.”

Rogers was married five times. He had a child in 1982, but at that time he was in the thick of his career and didn’t get to be there for him. He had three other children from his other marriages. However, when he met Wanda and married her in 1997, his life was indeed fulfilled.

He had twin boys that were 15 years old at the time of his death. It bothered him that he may not be there to see then graduate. He made them a top priority. His goal was to show them the world and spend as much time with them as he could until he passed.

His children and grandchildren took center stage in his golden years. He lived a full and happy life, but as he aged, he wanted more than anything to be known as a father.

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2. “I feel like I learn something from everything I do.”

While most might think that Rogers was an “A” student with tons of accolades, they might be surprised to find he was just average in the schoolhouse. He never expected his children to be on the honor roll. All he asked was that they do their best. He proved that it’s okay to be average in a world that expects perfection.

3. “You gotta know when to hold ’em, know when to fold ’em, know when to walk away, know when to run.”

While Rogers was known for a lucrative career, he also had his fair share of failures in life. When he was asked to advise others about his life, he was incredibly blessed, and he wouldn’t change one thing. He was grateful for both the ups and downs. And the key is in having the wisdom to know when enough is enough. Sometimes, you’ve got to regroup.

4. “You can’t make old friends. You either have them, or you don’t.”

Most would think that being a huge superstar like Rogers came with bragging rights. While he was proud of his accomplishments, he also looked up to other stars. He adored greats like Waylon Jennings, Willie Nelson, and Johnny Cash. He thought their music was unique because they used good stories, something so many songs today lack. These were his mentors and lifelong friends.

5. “If you want people to know what your message is, just sing it.”

Kenny Rogers didn’t feel the need to step on a few people on the way to the top. He said he never wanted to be like anyone else. He wanted to bring something unique to the industry and wanted people to like him for his distinctive music, and he certainly accomplished this goal through his unique voice and powerful lyrics.

6. “You know, I’ve always said, I’ve never felt I was a particularly good singer, but I’ve always thought I had a great knack for picking hit songs.”

When Kenny Rogers wrote or performed a song, he would only do the ones that others could sing along with him. He believed that you had to get people excited and what to join in. When he was asked about his hit “The Gambler,” he said the key is to have a song that everyone can sing. It was an easy song to memorize, and the story the song told was relatable.

7. “Islands in the stream; that is what we are. No one in between. How can we be wrong. Sail away with me to another world.  And we rely on each other, ah-ha. From one lover to another, ah-ha.”

There were always tons of rumors about Rogers and Dolly Parton. However, one life lesson he taught his fans was that it was okay to have fun and flirt, but you didn’t have to be intimate to be good friends. Though they often teased about their relationship and romance, they were never anything other than the best of friends.

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Read 23 inspirational quotes from Kenny’s good friend, Dolly Parton.

8. “I think when you’re in the public eye, you feel a pressure to stay younger looking.”

After some plastic surgery in the 2000s, Kenny Rogers became almost unrecognizable to his fans. He felt the need to be younger looking since his wife was younger and he had young twin boys. However, when asked about plastic surgery later, he told people that he would never do it again. He wished he left his face as it was before he had surgery.

9. “You know, I think the greatest gift in the world is a good employee, you know, or people who can do your work for you and do it well the way you’d like to have it done. And I’ve always been able to surround myself with really good people.”

Throughout the years, Rogers sold so many albums that his estimated net worth was $250 million at the time of his death. He believed that you never spent everything you had. When it came time for payday, his philosophy was that you pay the taxman, and put 20 percent back for a rainy day. He was one of the few stars that were never reported to have financial trouble over his career. Rogers often extolled the skills of his staff for always looking out for him, contributing to his success and wealth.

10. “My mom loved to sing. And I’ll go on record to say she was the worst singer ever. I’d get up and move away from her!”

Rogers was fond of his mother, Lucille. He listened to her when she gave him advice on life and his career. He stated that the best advice she ever gave him was to learn to be happy wherever you are in life. It’s easy to be happy when you are at the mountain top, but learning to be happy down in the valleys takes some real work. Regardless of being perhaps a bit tone-deaf, it sounds like Lucille was a wise woman!

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11. “There is a trade-off. As you grow older, you gain wisdom, but you lose spontaneity.”

Rogers was friendly and likable. However, his long career made him wary of letting too many people become overly close to him. Though Rogers had many friends and people who wanted to be in his inner circle, he let very few get close to him. He lived by the motto that his father, Edward, taught him. You must always be friendly to everyone. However, you only develop friendships with a few.

12. “I just hope I can spread some of the happiness that’s been coming my way.”

Kenny Rogers’s last performance in Nashville was in 2017 with his dear friend Dolly Parton. After that performance, he hung up his hat. He focused all his energy on spending time with his family. After his farewell concert, he went into seclusion to live out his final years in peace, enjoying time with his youngest children and relaxing.

13. “Youth is a frame of mind. If you get out there and enjoy it, you can have it at any time of your life.”

Kenny Rogers had many loves over his long-spanning career, but he proved that age was just a number when it came to his last wife. They were married for 22 years, but she was a shocking 28 years younger than he. When he met Wanda Miller, his entire life changed for the better. He proved that age didn’t matter, but it’s what’s inside that counts.

14. “It won’t mean you’re weak if you turn the other cheek.”

Few people knew that Rogers had something to fall back on should his singing career fizzle. And when he set out to Nashville, he knew that he had a talent in case he failed. Kenny Rogers, surprisingly to many, was a pro-level tennis player. He was great on the courts, and he dabbled in many things other than singing. Best yet, he taught people that if your first career choice didn’t work out, then you should always have a backup plan. And it does not make you weak!

15. “With all my heart and all my soul, I will love you till the winds don’t blow. Until the oceans turn to stone, my love is yours and yours alone. My love is forever until forever’s gone.”

One of the most important life lessons Rogers taught his fans was that in the end, a family is all that matters. Roger had many health problems that left him in frail health. As he entered this world, he was surrounded by his loving family, and when he left this world, he was with his family too. His wife and children were with him as he peacefully slipped from this world to the next.

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Final Thoughts: Kenny Rogers Lived A Legendary Life

There’s been a lot of country greats that have graced the stage at the Grand Ole Opry over the years. Perhaps, Kenny Rogers was one of the best. He had his ups and downs in life and his career, but he remained centered and focused on what mattered most.

As in life as in death, he taught his fans and those around him about what was necessary. He left life lessons behind to help those who idolized him put things about this world and your very existence into perspective.