Business Decisions as Games

When do you stay patient, when do you go all in, and when do you walk away? 

Running a business forces you to make these decisions, but you can master them from games you might play long before you ever face them in the boardroom.

1. Staying in the game: The art of “pushing” in tennis

In recreational tennis, there's a player everyone hates and nobody wants to face. The pusher. They don't hit winners. They don't try to end the point in two shots. They just get the ball back, one more time, and then one more time after that. They let you beat yourself. And more often than not, you do. 

This was me when I played tennis, mostly out of fear at messing up the point, but I now see the benefit looking back.

Pushing may seem passive, but often isn’t. It can be a disciplined decision to keep the rally alive instead of forcing an outcome that isn't there yet.

A lot of deal-making works exactly this way. Picture a business owner negotiating the sale of their company. The buyer comes in early with a low offer and a tight deadline, hoping pressure forces a quick answer. The instinct is to fire back hard or to cave. The pusher does neither. They keep the conversation going, ask for the buyer's diligence list, request clarification on the earnout, and let time and information do the work. Weeks later, the buyer who created the false urgency is still at the table, and the terms have moved.

The same is true in a commercial lease renewal, or a vendor dispute where one side is betting you'll get frustrated and concede. Sometimes the strongest position is simply being the person who is still calmly hitting the ball back when the other side runs out of patience. You don't win these by overpowering anyone. You win by not making an unforced error.

2. Going for it: When the moment demands a winner

Pushing has a failure mode. If that's the only gear you have, you lose to anyone who can wait you out, and you leave real opportunities on the table because you were too cautious to take the shot.

Poker is a good teacher here. A disciplined poker player folds most hands and waits. But when they finally get the cards and read the table right, they don't slow-play it into nothing. They push their stack in. The whole point of all that patience is to be ready to commit fully when the right hand finally comes. Hesitating in that moment is its own kind of mistake.

Business has these moments too, and they're easy to miss because they don't announce themselves. A competitor unexpectedly puts a strategic asset up for sale, and you have a narrow window to make a clean, aggressive offer before someone else does. A key piece of commercial real estate comes available in a market you've wanted to enter for years. A founder gets a term sheet from an investor and realizes this is the round that actually lets them scale, so they commit rather than keep shopping for a marginally better valuation.

In each of these, the patient, get-the-ball-back approach would cost you the opportunity entirely. The skill isn't knowing how to go for it. Most people can do that. The skill is recognizing which moments actually call for it, so you spend your aggression on the hands worth playing.

3. Knowing when to resign: The hardest lesson in chess

Then there's the decision nobody likes to talk about. When to stop.

Chess has a built-in mechanism for it that I find genuinely useful: resignation. A strong player, deep in a losing position, doesn't play it out to the bitter end out of pride or hope. They see that the position is lost, they extend a hand, and they move on to the next game with their energy intact. Beginners almost never resign. They play every losing position to checkmate because stopping feels like giving up. Strong players understand that refusing to resign a lost game just costs you the energy you'll need for the next one.

This is the decision I see business owners struggle with most, and I understand why. You've put money, time, and ego into something. Walking away feels like admitting failure.

But the lesson holds. There's the acquisition where diligence keeps surfacing problems, the price keeps climbing, and at some point the deal you wanted no longer exists. There's the partnership that's quietly costing you more in conflict than it ever returned in value. There's the litigation-bound dispute where the smart move is a clean settlement, because the cost of “winning” outweighs the win itself. Knowing when to resign isn't weakness. It's protecting your capital, your time, and your attention so they're available for the game that's actually worth playing.

The hardest part is that resigning well requires you to be honest about a position you badly want to be better than it is. A good advisor earns their keep right here, by telling you the position is lost before you've spent everything finding out the hard way.

Reading the game

If there's a thread running through all three approaches, it's this: the strategy isn't the hard part. Patience, aggression, and walking away are all learnable. The hard part is diagnosis. Looking at the situation in front of you and correctly naming which kind of moment it is.

Most of the costly mistakes we see aren't a failure of execution. They're a failure of diagnosis. Someone went for a winner when they should have kept the rally going. Someone kept patiently hitting the ball back when the opportunity of the decade was sitting right there. Someone refused to resign a deal that was lost three months ago.

That's a lot of what good legal counsel actually does. Not just executing the move, but helping you read the game first.

Candidly, Kalaria Law