THE TRUTH BEHIND “THINKING ABOUT LEAVING” – THE SONG THAT ALMOST NEVER WAS
In the mid-1980s, as country music leaned into commercial polish, Dwight Yoakam arrived like a ghost from Bakersfield’s golden past. With his silver hat, tight jeans, and unmistakable honky-tonk voice, he became the poet of quiet heartbreaks and silent departures.
One song that perfectly captures that spirit is “Thinking About Leaving,” from his debut album Guitars, Cadillacs, Etc., Etc. released in 1986. While it was never a chart-topper, the song has quietly become a favorite for longtime fans – because it feels less like a hit and more like a private confession.
“I Don’t Wanna Be That Man… But I’m Thinking About Leaving.”
There’s no dramatic crescendo here. No pleas, no tears. Just a stark realization – the kind that comes in the middle of the night, whispered into the darkness.
The narrator isn’t cruel. He isn’t bitter. He’s just… distant. He loves, perhaps, but he no longer feels alive in that love. And so, he considers leaving – not out of anger, but out of emotional absence.
Dwight delivers the lyrics in that laid-back drawl that feels like an old friend talking honestly for the first time in years.
Based on a Real Moment in Dwight’s Life?
Few fans know that, in 1985, just before his big break, Dwight almost walked away from music entirely. He felt lost in Los Angeles – disconnected from the industry, ignored by labels, and creatively misunderstood.
In a rare 1989 interview, he admitted:
“There was a time I thought I’d go back to Kentucky and work at my dad’s horse farm. I loved music, but I wasn’t sure it loved me back.”
That silent crossroads – stay or leave – gave birth to “Thinking About Leaving.”
For the Ones Who Left Quietly
Some goodbyes don’t come with slam doors or loud arguments. Some happen in silence – one packed suitcase at a time. “Thinking About Leaving” is for those quiet exits. That’s why it never became a stadium anthem – but has remained a deeply personal song for those who truly listened.
The Performance That Silenced a Theater
During a 2005 concert at the Ryman Auditorium, Dwight stunned fans by performing the song again after years of absence. That night, the theater fell into a hush. No applause mid-song. Just his voice, echoing through dim lights, and the weight of every unspoken goodbye hanging in the air.
One fan later wrote:
“It felt like Dwight was singing just for me. I don’t know how he did it – but I’ll never forget that night.”
The Goodbye That Was Never Sent
Dwight Yoakam never left country music. He stayed – not for charts or awards, but because music was the only place he could truly tell the truth.
“Thinking About Leaving” isn’t just a song. It’s a quiet letter to the self. One that many of us have written, even if we never sent it.