Maybe because I saw pieces of myself in Jeff Kikel’s story, or maybe because it reminded me how fragile the whole idea of “security” really is, but I felt an immediate kinship to this entrepreneur.
Luckily I never went through the same demoralizing treatment he received.
The Novelist Who Ended Up in Finance
Jeff told me he wanted to be a novelist when he was young. Not a financial planner (I was the opposite). He said, “I wanted to write novels. I thought I was going to be the next Hemingway.” And I could picture that version of him, probably with a stack of books on his nightstand and some half formed idea about what a writer’s life might look like.
Then life did what life does. It nudged him sideways. He drifted into advertising. Then into finance. Not because he planned it, but because the bills showed up first. But isn’t that how life goes?
Seven Tries and One Brutal Review
A lot of us who’ve started businesses have failed with at least one of them. He burned through seven of them. I’ve been there. Its hared when a business is threatening your very ability to pay for life’s necessities.
There’s one story though that I couldn’t help laughing at, though it was no laughing matter at the time. It was about this one performance review he experienced. It was the thing that actaully got him started on the path he’s on now.
His boss looked him in the eye and said, “You are the worst employee we’ve ever had.”
I had to laugh for a second because the way Jeff tells it, he wasn’t even surprised. He knew he didn’t fit the mold. He was too independent. Too willing to just go do things without asking permission. The exact traits that make someone a creator were the traits that made him a terrible employee.
Jumping Without a Net
He quit without a plan or parachute. Just a man who finally realized he couldn’t keep trying to fit into a system that didn’t want what he naturally brought to the table.
And the next few years were rough. He told me they almost lost their house. They burned through retirement savings. They lived in that tight, breathless space where you’re not sure if you’re building something or destroying everything.
But he didn’t go back. That part matters. He could have. He had the resume. He had the experience. But once you see the truth, it’s hard to unsee it. A job can fire you faster than you can save yourself.
A Bucket List in the Middle of Nowhere
Later in his journey, he ended up at a resort in California for a work event. Alone. No distractions. Just time. They handed him a bucket list journal. He didn’t plan to use it. But he did. And what came out surprised him.
He didn’t write down yachts or mansions. He wrote down experiences. Things that moved or flew or floated. A Lamborghini at the F1 track. A WWII bomber flight. A speedboat straight out of Miami Vice.
And he realized most of them cost about five hundred dollars. That number became a turning point. He asked himself, “What can I do to create five hundred dollars a month?”
The Five Hundred Dollar Shift
Jeff decided he would generate five hundred dollars a month and use it to check off one bucket list item every month for a year. Twelve months. Twelve experiences. Twelve reminders that he could create income on demand.
That year rewired him. It taught him something he didn’t learn in finance. Something he didn’t learn in corporate life. Something he didn’t learn in any of those seven failed businesses.
He learned how to make money. Not earn it. That skill became the foundation of his Freedom Day.
Where This Lands for Me
Talking with Jeff reminded me of something I keep relearning in my own life. The moment you stop trying to fit into a system that was never built for you is the moment you start building something real.
It doesn’t happen all at once. It doesn’t feel clean or cinematic. It feels like late nights and doubt and tiny sparks of clarity that show up when you least expect them.
Freedom doesn’t start with a giant leap. It starts with a small number that suddenly makes sense. Five hundred dollars. One experiment. One moment where you decide to create instead of wait.
Learn more about how Jeff’s Freedom Day Method can help you at: http://www.freedomdaymethod.com/
Check out the whole podcast at: https://brentxp.podbean.com/e/lightminded-arts-29-the-job-that-couldn-t-save-him-jeff-kikel/?token=d69449df8cdb4e31217ff1c888498ee1
And as always, if you want to support me and this channel, just check out my books and leave a review.
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