What I Learned From Kenny Rogers and The Gambler About Making Money
Why you shouldn’t obsess about constantly checking your stats.
The year was 1979, and Kenny Rogers’ The Gambler was a big hit. I was managing a Pizza Hut at the NW edge of Chicago. Cross the Devon Ave, and you’d be in Lincolnwood. Lucy had just started working there as a waitress (remember when Pizza Hut used to be a full-service sit-down restaurant?) for a couple of days per week to earn extra income.
Have you ever worked as a server in a restaurant? You receive a token hourly pay from the restaurant. Your real income is dependent on the tips you receive from the people you serve. I have for many years, and I prefer that over managing a restaurant.
Lucy would always count her tips throughout her shift, and her worries would multiply because she wasn’t making enough money.
“You never count your money when you’re sitting at the table, There’ll be time enough for counting when the dealing’s done.”
I explained to her that when you’re continually counting your tips, it affects your attitude, and as a result, the quality of your service you provide. You worry when you’re not making enough tips, and that gives out a negative vibe, making your customers feel that you’re not happy to take care of them. However, if you reach your goal early, you may not feel like being there anymore, and again you’re giving out the same vibe.
I told her that if she’d simply focus on taking care of the customer without being concerned about how much she was making from each individual table, she’ll be surprised at the end of the shift with how much she made. I told her that if she gets tempted to count her tips, remember the wise words of The Gambler in the Kenny Rogers song. “You never count our money when you’re sitting at the table.”
She suddenly stopped working there after a couple of weeks. I never knew why.
I finally got tired of managing restaurants and started working as a waiter. I am a people person, and I enjoy taking care of them, and consequently, I made a good living as a server. As I said, the restaurants pay a token wage to the servers, their real income is from tips, and a good server makes almost as much as a manager, if not more. I should know I have done both.

These days, I enjoy working as a balloon twister, and I earn more than a decent living, collecting tips, and whenever I am having an off day, I remind myself of the wisdom from The Gambler.
As writers on Medium, our situation is not much different. I have heard ample bitching and moaning about the pittance that we receive as payment. I have been guilty of constantly checking my stats, and I know how it impacts my attitude and my writing. Most of us write because we want to write. We enjoy writing and painting word pictures. Yes, we want to get paid, and we want to get paid handsomely.
I honestly believe that people who write consistently regardless of how much or even if they get paid are the ones that end up making the most money in the long run. When you get in the flow, enjoying the process, your writing has a quality that reflects that ease and joy. The Universe will find a way to compensate you well, so you can keep spreading that joy.
Ask anyone successful, and they’ll tell you that it takes years to be an overnight success. I am shooting to be an overnight success, and I am willing to enjoy working for it for years. The Joy of Writing is its own reward, the money is a bonus, and I expect a hefty one.
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I am a self-proclaimed weirdo, Jack of Many Trades and Master of Some. I live the Freedom Lifestyle — life on my terms, and help those who are interested in doing the same.
My perspective on life is somewhat unconventional, and I write from that point of view, mostly from personal experience of what I’ve learned from life and my interpretation of the world as I see it.
“You can let others tell you what it means to be successful, or you can decide it for yourself.”






