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Checkmate: The Parallels of Chess and Business Strategy

There are striking parallels between chess and entrepreneurship that can help you gain insights into strategy, resilience, and success and empower you as a dynamic business leader.

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Chess is often considered the archetypal thinking person's game, but this intellectual pursuit can also offer some significant object lessons for those delving into the entrepreneurial world.

Referencing chess as a strategy game only scratches the surface because there are many nuanced layers to overcoming an opponent that can only be fully appreciated with the experience of having played hundreds of times. On one level, the basic rules of chess are relatively straightforward, but applying the discretion to carry them out in the most effective manner possible is an acquired skill. The fact that each player in a game has a king, a queen, two bishops, two knights, two rooks, and eight pawns creates a genuinely level playing field. It's up to the individual player to carve out a distinctive approach that can provide a winning edge to eliminate the competition.

An irony of chess is that some uninformed observers lump the game into the same category as checkers. Because the boards used by both games are comprised of sixty-four squares in an 8x8 grid, the temptation can exist to consider chess and checkers as variations on the same basic theme. Nothing could be further from the truth, for although Checkers does contain an element of strategy in its gameplay, the pieces on the board are all equal, with no differentiation in appearance or capabilities. Contrast this with the chessboard, whose pieces are distinctive in what they represent, how they move, and what role they play in the overall unfolding of the game.

Another unique aspect of chess pieces is that they begin each game by occupying concrete squares on the board. The rigid setup requirements for play imply that there are only a limited number of options for how a game might unfold. Still, the reality is that the movement variations embodied in the pieces can play out in ways that lead to a seemingly endless number of possible combinations. Further influenced by each player's individual experience and strategy, the result is a tremendous variety of scenarios demanding careful attention to resolve them successfully.

The underlying goal is to place the opponent's king in "checkmate" – a situation in which the king is threatened with capture and is unable to escape. In this case, there's nowhere the king can move to be out of harm's way, and there are no available pieces able to intercede on his behalf. The king can initially be in "check," a condition where he faces the possibility of capture. However, he can still find a remedy to the problem by moving into a space out of range or by another piece being able to capture the attacker. Check is a threat, but checkmate is a game-ender.

The entrepreneur in the process of launching a new endeavor in many ways mirrors chess pieces set up at the start of a match. There are specific prerequisites for starting a business that can't be overlooked or substituted for, so all new owners will find themselves in the same spot everyone else begins from. From obtaining a business license to procuring office space, hiring staff, and getting insurance coverage, each entity will launch from a similar point of origin. But it's the next steps that make the difference, and, just as chess pieces have different abilities, each business owner will possess talents and ideas that will differentiate them from everyone else just getting started.

Money, resources, and market connections are certainly things that any new business owner looks to as the great solutions to problems standing in the way of entrepreneurial success. A sole proprietorship trying to launch on a dime might feel incredibly ill-equipped for the many tasks at hand, and there is always the temptation to believe that there's simply no way to compete against established successful businesses. But humble beginnings shouldn't be despised simply because they're humble, and even the youngest and smallest of businesses can hold tremendous promise when vision, innovation, and purpose fuel the journey.

On October 17, 1956, a 13-year-old chess player named Bobby Fischer soundly defeated a leading American master named Donald Byrne. Fischer later became a Grandmaster and is generally ranked at the top of the list of the best players in the game's history. Onlookers may have initially scoffed at his age and lack of relative experience with the game when compared to Byrne, but Fischer had more to offer than most truly understood, and his commitment to how he played the game enabled him to achieve tremendous success before he was even old enough to drive. Fischer is credited with single-handedly launching a renaissance of chess in the early 1970s, an event which never would have occurred had he allowed himself to be intimidated at the thought of facing older, more seasoned opponents.

The pawns are the least celebrated pieces in the chess realm, yet they play a crucial role in unfolding the player's overall strategy. Able to move only a square at a time, and without the ability to move backward, the pawn's movement can seem plodding and uneventful. But a pawn who can cross the entire board to reach a square on the opposite end from where he started can be exchanged for a previously captured piece, allowing a more powerful one to re-enter the game. Some actions we take in launching a new business can seem as monotonous and fruitless as a lumbering pawn. However, perseverance can yield to establishing solid structures for how we do things that we never would have understood had we simply moved forward full-tilt.

Bishops are pieces with an exclusively diagonal movement pattern, forward or back, but always running corner to corner from one square to the next. This type of movement can be challenging; although they can cross through open spaces for the full extent of the board, their intended path can sometimes be blocked as an opponent's pieces move. We can encounter a similar scenario in our businesses when a bottleneck of obstacles can choke out what we thought was the easy path to success. This deterrent can drag everything to a grinding halt, so we must search for alternate routes or take concrete steps to analyze and circumvent whatever lies in our way.

Rooks can only move in a straight line but can cover the entire board length, providing that all intervening spaces are vacant. This great freedom of movement can be deceptive because it can lead to situations in which the rook ends up perhaps too far into enemy territory, only to be blocked from escape during the opponent's next turn. Entrepreneurs can sometimes adopt a similar approach, fixating on a shining goal and moving full steam ahead, only too late realizing that they're overextending themselves and stepping into something unsustainable. Easy paths to success usually lead anywhere, but where we think they will, so it really comes down to being judicious. There can be tremendous value in moving quickly and striking while the iron is hot but do so only after you've made a moderate, thoughtful appraisal of where you're heading.

The movement of the knight is sometimes the most perplexing for new players. Comprising an "L" shape, the knight's trajectory is two squares horizontally and one vertically, or two squares vertically and one horizontally. The most exciting aspect of the knight is that it's the only piece capable of moving over other pieces. Even though a row of eight pawns stands directly in front of it at the start of the game, the knight can jump over them to move rather than wait for them to get out of the way. In business, we sometimes need to adopt strategies that allow us to overcome obstacles rather than merely sitting back and hoping that they magically disappear. The effort requires us to elevate beyond our circumstances, and just as the knight combines forward and lateral movement, we, too, have to recognize that not all the steps we take in entrepreneurship will move us in a truly straight line.

The queen is the most powerful piece in the assemblage of the chess armies, capable of moving forward, backward, left, right, or diagonally any number of open squares. This tremendous ability can threaten the opponent when adequately handled and lure a player into the foolhardy position of placing the queen in great peril. Nothing is beyond our grasp once we've gained a little traction with our businesses. Momentum and enthusiasm are of great value, but taking a risky approach can undo all the meticulous work we've done establishing our business and send us on a reckless course toward disaster.

The king is ironic – the piece around which the entire game is built, yet the weakest and most ineffectual component. Because challenging an opponent's piece can often end up placing the king in danger ("check"), the bulk of the game sees him being protected and preserved by the other pieces, often at their own expense. The purpose behind our businesses – the motivation and underlying reason we undertook the enterprise in the first place – is what all our efforts center around. Like the king, our purpose has to be protected and cared for. It's the essence of why we're doing what we do, but in and of itself, it doesn't truly contribute to the work required to succeed.

Moving chess pieces from their original starting places to other squares on the board is called "developing the pieces." We start one spot in our businesses, then take steps into uncharted territory to develop, grow, and mature into something better that's poised for true success. Just as chess players have to learn from the moves their opponents make, so must we observe our business competition, adjust to what they're doing, and ultimately carve out a unique strategy that ensures us a winning advantage.


Ready to level up your business strategy in 2024? Take the first step by scheduling a Power Hour with ValorExcel. Our expert team will help you apply your goals and objectives to a concrete plan for success. Visit, to book your session. Or, you can email us at, or call 240-329-9387. Then, don't forget to check our recent videos on YouTube by clicking HERE. #BusinessStrategy #ChessToSuccess #ValorExcelPowerHour

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