How to Reclaim Your Initiative: Lessons from the Chessboard of Life

In the world of chess, there is a specific type of player that coaches often warn against: the "hope player." This is the person who makes a move not because it is objectively the best, but because they hope their opponent won't see the threat, or because they want to keep the game "polite" and avoid conflict on the board.

In life, we often play the role of the hope player. We move through our social circles and professional lives making "appeasement moves." We say yes to projects we don't have time for, nod in agreement with opinions we find distasteful, and suppress our own needs to ensure the "engine" of the relationship keeps running smoothly. We do this for the immediate dopamine hit of approval—the smile of an opponent who thinks you’ve made a mistake, or the warmth of a friend who thinks you are "so easy-going."

But much like a chess game where you consistently make sub-optimal moves to please the crowd, your "position" in life eventually collapses.

The Middle Game of Resentment

When you play chess to please others—perhaps by playing an opening you don't like because your mentor prefers it—you lose your initiative. In chess, the initiative is the ability to dictate the flow of the game. When you live for approval, you hand your initiative over to everyone else. You are no longer playing your game; you are reacting to theirs.

Consider the "Gambit of Identity." In chess, a gambit is the sacrifice of a pawn for a perceived advantage. People-pleasers perform a social gambit every day: they sacrifice a piece of their authentic self (a pawn of truth) to gain the "advantage" of being liked. However, a real gambit is supposed to lead to a stronger attack. The people-pleaser's gambit leads to a hollowed-out center.

In the short term, being a "people-pleaser" feels like winning. You are well-liked, you avoid the discomfort of a "check," and you keep the peace. However, a chess board is a closed system of logic. You cannot ignore the structural weaknesses you’ve created forever. Every time you say "yes" when you mean "no," you create a "hole" in your position—a square that you can no longer defend.

Eventually, these holes accumulate. You look at the board of your life and realize your pieces (your time, energy, and talents) are scattered and disorganized. They are serving everyone else’s strategy but your own. This is where resentment enters the endgame. Resentment is the feeling of being trapped in a losing position that you built with your own hands. You feel angry at your opponent for "taking" your pieces, forgetting that you offered them up freely in exchange for a momentary nod of acceptance.

The Overworked "Queen" Syndrome

In many people-pleasing dynamics, we treat our energy like the Queen on the board. We believe that because we are "powerful" or "capable," we should be everywhere at once, defending every square and satisfying every demand.

• At work: You take on the extra shift because your boss looks stressed, even though your own "King" (your mental health) is under direct attack.

• In relationships: You play the "support piece," constantly adjusting your diagonal to fit your partner’s needs, until you realize you’ve been pinned against the edge of the board with no moves left.

The Queen is the most powerful piece, but even she can be smothered. When you act out of guilt or the need for approval, you are essentially "overworking" your pieces. In chess theory, an overworked piece is one that is required to defend too many things at once. Eventually, the opponent (in this case, life’s demands) will strike one of those targets, and your entire defense will crumble.

Reclaiming the Center: The "Self-First" Strategy

To stop losing yourself, you must learn to "play the board," not the person sitting across from you. This doesn't mean becoming a selfish or "aggressive" player who ignores others. In fact, the strongest grandmasters are those who understand that they must first secure their own King before they can effectively engage with the rest of the world.

Pleasing yourself first is not an act of narcissism; it is an act of positional integrity. In chess, if your King is exposed, any "gift" or help you try to offer your team of pieces is useless. You are one checkmate away from the game being over. By prioritizing your own well-being, values, and boundaries, you are "castling"—tucking your King into safety so that you can operate from a place of strength.

When you move based on conscious choice rather than guilt, the quality of your "giving" changes:

• Authenticity over Performance: You give because you have an abundance of "material," not because you are trying to buy safety.

• Sustainability: You won't "flag" (run out of time) because you aren't wasting mental clock cycles wondering if people like your moves.

• Respect: Interestingly, the players who are most respected on the circuit are not those who give away pieces, but those who play a principled, honest game.

The Grandmaster’s Choice

Imagine standing at the board and making a move simply because it is the truth of the position. You aren't looking at your opponent to see if they approve. You aren't worried about the spectators. You make the move because it aligns with your strategy and protects your center.

When you live this way, you find that you actually have more to give. Because you aren't drained by the constant calculation of "what will they think?", you have the energy to be a truly great partner, friend, and human. You give to others not as a bribe for their love, but as a deliberate gambit—a sacrifice made from a position of total control and joy.

In the endgame of life, the final score isn't based on how many people liked your style of play. It is based on whether you stayed true to the rules of your own heart. Don't spend your life playing for a draw just to keep people happy. Play your best game. The right people will stay to watch the beauty of a match well-played, and more importantly, you will be able to look at the board at the end of the night and recognize the person who played the pieces