Sundown & Survival: The Dark Side of Entrepreneurship

Whether it’s a song or a setback, life doesn’t stop for us to catch our breath. Here’s how Sundown by Gordan Lightfoot mirrored my journey as an entrepreneur.

Ever had a song that brings back memories the moment it starts?

For me, that’s Sundown by Gordon Lightfoot. It hit the radio when I was only three in 1974, but it stayed with me, echoing those tough nights, big regrets, and the times life seemed to hit hardest.

Lightfoot wrote Sundown about a complicated relationship with a woman who left him feeling jealous and alone. For me, it wasn’t about someone sneaking around.

It was the nights I was left alone, with just my own thoughts, a drink, and the feeling that every time I was close to winning, I’d get pushed back to the start.

Running a business hasn’t been easy. I’ve been cheated by a business partner who walked away with $100,000 and MY company. I’ve gone through a tough divorce. And some nights, alcohol felt like the only thing that could numb the pain.

The next morning?
Reality is still there, but worse.

Lightfoot wrote Sundown with his heart wide open, showing his mistakes and regrets. And that’s why I connect with it so much.

Life knocks you down, over and over.

  • Get back up.

  • Learn from the pain

  • Keep going

  • Even though it seems hopeless.

Each time I rebuild, I get a little stronger.

I don’t know what keeps me going sometimes—maybe just the fact that I don’t have another choice.

The scars are still there, but they tell my story. Lightfoot found healing through his music; I find it in building things. Whether it’s a song, a business, or life itself, it’s all about creating something real out of the struggle.

Here’s to the battles, the scars, and to Sundown—a reminder that when life creeps in, you stand your ground and keep fighting.

Talk soon!
Keith

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