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Greetings!
For years, I thought I was winning. Then I realized I had been playing the wrong game.
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When we’re young, careers like music, sports, and acting look like the ultimate jackpot — fame, fortune, and endless applause. Millions chase that dream. Yet even among world-class performers, most earn less than a solid middle manager. It’s not a career path; it’s the world’s most expensive lottery ticket, and nearly everyone loses.
Life as a Series of Games
Let’s say your career is a game. The question is: which one are you playing — dice, checkers, chess, or poker?
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Dice
There are nearly two million rideshare drivers in the U.S., and not one of them studied to become an Uber driver. They, like many in the gig economy, take what they can find. Earnings depend mostly on timing and luck — in other words, they’re playing dice.
Some careers fall into this category too. Project management, for instance, is nicknamed “the accidental profession” because few planned for it. They just rolled into it out of necessity.
If you find yourself hopping jobs constantly, hoping the next one finally “clicks,” you’re probably rolling dice as well.
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Checkers
A traditional career ladder looks a lot like a game of checkers: you move forward, one square at a time, until you reach the far end and get “kinged.”
Military, academia, and government careers all follow this linear climb. Most corporate paths do, too. One move, one promotion, one rung at a time — until, hopefully, you reach the corner office, the general’s stars, or tenure. Congratulations, you’re king.
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Chess
Chess is far more complex and — thankfully — more interesting. The tech world is full of chess players. Specialization, strategy, and flexibility rule the board.
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Here, careers aren’t linear. Engineers migrate into sales, marketers pivot to product, and admins find themselves in operations or enablement. Roles are constantly evolving, and so are the players.
But chess has limits. No matter how sharp your strategy, you can only win one game at a time. Which brings us to something entirely different: poker..
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Poker
Unlike checkers or chess, poker thrives on incomplete information. Nobody knows your hand. That’s why you can’t bluff in chess — but in poker (and business), bluffing is critically important.
Poker is a game of probabilities and discipline. A great hand can lose, a bad hand can win — but play the odds consistently, and over time, you come out ahead.
Entrepreneurs are poker players at heart. They make bets — some bad, some brilliant. They hire the wrong person, pick the wrong market, or launch the wrong product… and sometimes still hit it big. Why? Because while each hand is uncertain, long-term smart betting pays off.
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Short & Long Term Choices
Early in life, quick-money jobs can look like victory laps. Bartenders and servers can earn more in their twenties than fresh law or med school grads who are buried under tuition debt.
But that flips by their thirties — the professionals skyrocket while the service earnings plateau. It’s not about who wins early; it’s about who’s still playing well later.
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| Investor Scott Galloway tells a story about his experience as a student at UCLA. He tried to be the star athlete but couldn’t make the team. Instead, he took the finance and entrepreneur track. Some of his athlete classmates went on to qualify for the Olympics and even brought home some medals. Two years later, they were out of work and begging him for a job. | |
Are you Playing the Right Game?
The people I admire most aren’t necessarily smarter, harder working, or more talented than others. What sets them apart? They bet on themselves. They stopped waiting for promotions and started creating opportunities. They aren’t climbing ladders — they’re playing poker, and they’ve learned to bet on themselves when the odds are right.
So, what about you? Are you climbing a ladder, rolling dice… or putting chips in the pot?
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Mike Schmidtmann coaches business owners and sales leaders across the USA. He works to drive results in sales recruiting, new business development, and profitability.
Mike led sales for Inacom Communications for ten years. then founded and built a $30 Million business unit for SPS.
Mike produces the award-winning Trans4mers webinar series on IT sales and management subjects. He is a frequent public speaker on business topics.
He lives on a farm in Northern Virginia with his family and assorted horses, alpacas, goats and dogs.
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Mike Schmidtmann
(703) 408 - 9103
Mike@Trans4mers.net
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