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🚀 Play Chess in Your Career, Not Checkers (Issue #574)

🚀 Play Chess in Your Career, Not Checkers (Issue #574)

How to be more strategic at work

“I’m putting in long hours and working harder than ever. Why am I not getting promoted?”

Do you know how many times I’ve heard that complaint?

Sure, working harder than your peers can get you promoted during the early years of your career. But you will soon find that what got you where you are today won’t get you where you want to be tomorrow.

Most people play checkers with their careers. They hop around the board, marching ahead, step by step, and don’t think more than one step ahead.

The game board looks similar. In the early days of your career, you and the other pieces are making the same moves—trying to get head, space by space. But you eventually find out that strategy won’t cut it.

Your career growth is limited when you behave like a checker piece on the corporate chess game board. Unfortunately, many people experience that. They think more of the same will continue to move them ahead.

  • Working harder

  • Working longer hours

  • Taking on more work

Sadly, that is the path to stagnation and abuse. Yes, abuse. I’ve watched many people get used by their employers. Many managers love dumping work on the people who work hard, don’t complain, and never ask for raises or promotions.

So, if you want to avoid being stuck in checker mode, there are five things you must do:

  1. Become a valuable chess piece

  2. Use strategic long-term planning

  3. Leverage pattern recognition

  4. Make sacrificial moves when necessary

  5. Play leadership chess, too

1. Become a valuable chess piece

If you want to play chess, you must qualitatively change how you work and transform the value you deliver. Leaders don’t get promoted because they work harder than their peers. They get promoted because they think differently, add unique value, get results, and know how to make 1+1=3.

World-class chess players don’t randomly flail away moving pieces on the board. They never think one step ahead and hope things work out.

So, stop behaving like an interchangeable checker piece. In the game of checkers, every individual piece has the same capabilities (i.e., hopping one space forward). You can easily be replaced if you are a commodity with the same skills as everyone else. Heck, maybe they can even find a cheaper piece to replace you! And if they can do that, they will.

I watched that happen many times over the decades of my career. A senior employee was often replaced with a more affordable junior employee who could do the same work.

I remember an executive saying, “Why should we pay this much for a U.S. employee? I can hire three designers in country XYZ for that salary.”

A basic U.S. checker piece was often replaced with more affordable international pieces. Basic pieces were also frequently put on the inevitable layoff lists about every six months.

However, the employees who had leveled up to provide unique strategic value were never replaced. Their cost was never questioned. Instead, they were assigned the best and most challenging projects. They were the ones promoted when the review cycles rolled around every year.

I often ran into the unfortunately common belief that tenure will eventually lead to a promotion. Some employees thought they would keep moving up the career ladder if they stayed with the company long enough. I’m sorry, but higher-level promotions simply don’t work that way.

A pawn that has been with the company for 5 years—but still acts and performs like a pawn—won’t be promoted to knight simply because of tenure. Level up and transform yourself, or be stuck where you are forever.

2. Use strategic long-term planning

Professionals who end up succeeding in their careers are thinking many, many steps ahead. They aren’t simply focused on their next career move. They have a vision for where they want to be several years from now—sometimes even decades. Every move they make is intentional and sets them up for the next move and the next.

They use strategic thinking instead of scattered and mindless hopping.

One of my old colleagues and friends had a clear vision for where they wanted to end their career—as a C-level executive in a public company. Every move they made was deliberately planned to help them advance toward that goal.

  • New projects

  • New connection in their network

  • New skills and experiences

  • New domains

  • New jobs with the right employers

  • Seizing new opportunities when they appeared

Over the years, I watched them make smart moves until they finally did land that C-level role. It was definitely a clever game of corporate chess, not checkers.

📞 Schedule a free strategy call with me if you’d like to work on your long-term career plan.

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3. Leverage pattern recognition

My grad school advisor was really into chess, and I mean really. He was an excellent player, but he was also a psychologist who researched expert players.

Great chess players have a stronger conceptual knowledge of the game and are better at recognizing familiar patterns. Similarly, successful professionals master the rules of the “corporate game” and start to recognize familiar patterns in company dynamics, organizational politics, and individual behavior.

Leveling up your corporate “chess game” beyond checkers requires deeply learning corporate rules, how organizations function, and individual motivations. The more experience you gain, the more you should start recognizing patterns and how to quickly and successfully navigate them.

4. Make sacrificial moves when necessary

With a long-term vision and strategy, you can focus on the big prize instead of being distracted by the short-term benefits. If you've ever hiked to a mountain top, you know it's never a straight and obvious shot to get there. The nearby moves may seem counterintuitive. You move sideways. You move downslope to transfer to other trails.

For example, one job might pay more immediately, but another might set you up for later promotions and better long-term earning potential. I often discuss how this is essential to searching for your next job. How do competing employers compare in terms of factors like:

  • Better leadership

  • More supportive management

  • More challenging projects

  • Learning a new technology

  • Gaining more powerful skills

  • Access to talented people

  • Building relationships with movers and shakers

  • Creating a stronger professional reputation

You can become a more powerful piece on the professional chessboard of life instead of being stuck in checker mode forever.

5. Play leadership chess, too

If and when you move into leadership roles, the chess vs. checkers strategy comes into play again. It’s about recognizing that your team members are not simple checker pieces to be placed willy-nilly on the board. Each person has unique talents, experience, and goals. For example, you don’t want to treat a queen like a pawn and give that person a project that doesn’t leverage their strengths. You also don’t want to overload a pawn with a complex project far beyond their capabilities.

Also, playing chess means understanding that people are not interchangeable checker pieces. You must learn who to invest in retaining and growing, who will benefit from mentoring and coaching, and who isn’t playing well with the other pieces on the board. You can’t simply swap in a new person and expect them to behave and perform like everyone else.

Finally, successful leadership does require strategic vision and planning several moves ahead. You must start recognizing behavior patterns in other leaders to anticipate their next moves, plan your move, and survive the inevitable politics of playing at that level. Leaders who play the corporate game like checkers (e.g., only focused on executing the next move) don’t tend to last long.

Start playing chess

If you’re happy with your job, don’t care about promotions, and focus more on work-life balance, there’s nothing wrong with playing checkers at work. Do good work, get paid, and go home to your friends and family to enjoy your personal life.

Believe me, I get that! That’s why I left the corporate world behind in 2010 to build a lifestyle business.

However, if you are ambitious and you really want to get ahead at work, move up the career ladder, and reach your biggest goals, then learn the rules of the corporate chess game. Become more powerful and more valuable. Play strategically and be prepared for how hard your colleagues/competitors will play.

Those top leadership positions become increasingly rare as you advance in the organization. Playing checkers won’t put you in those seats, but playing a clever game of corporate chess just might.


By the way, I recently refreshed my Invincible Career community and have started rebuilding it from scratch on my Discord server (instead of Slack). If you’re interested in joining a friendly, supportive community of ambitious peers, upgrade your newsletter subscription so I can send you an invitation!

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I’m Larry Cornett, a Freedom Coach who works with you to optimize your career, business, and life. My mission is to help you become a more "Invincible You" so you can live your life on your terms instead of being controlled by someone else's rules. I live in Northern California near Lake Tahoe with my wife and our Great Dane.

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Invincible Career®
Invincible Career - Claim your power and regain your freedom
Claim your power, regain your freedom, and become invincible in your work and life! I share professional advice, challenges, and tips to help you create your Invincible Career®.