What the World Cup teaches us about tax planning

Every four years, the World Cup gives us something familiar: a structured game, clear rules, and a single objective. Win. 

But anyone who follows the tournament knows that what looks simple on the surface is actually anything but. Every decision, every adjustment, and every small advantage can change the outcome. Taxes are much the same way. 

Jump to ↓

Choosing the field you play on

The rules haven’t changed. The (tax) review has.

The game is always moving 

What the scoreboard doesn’t show

Small margins matter — on the field and in tax planning

How does timing affect tax planning?

Choosing the field you play on 

In international soccer, some players have a choice. Dual nationality allows them to represent more than one country, and that decision is rarely as simple as picking the highest-ranked team.  

Some choose a traditional powerhouse with a chance to compete for a championship. Others choose a smaller country where they’re more likely to earn playing time and have a meaningful role. That decision isn’t always about which team is “better,” but about finding the best fit. 

Business owners face similar choices when it comes to taxes. Many assume there is one correct entity structure or one perfect tax strategy. In reality, there are usually several reasonable options, each with advantages and disadvantages. One approach may reduce taxes today but limit flexibility later. Another may create more administrative work while opening the door to future opportunities. 

The best answer depends less on theory and more on how your business actually operates.

The rules haven’t changed. The (tax) review has. 

For years, what looked like a goal in real time would stand as a goal; then video-assisted review (VAR) came along. What appears to be a clean score can be reviewed from multiple angles, measured down to inches, and occasionally overturned. Offside decisions that once would have gone unnoticed are now examined with remarkable precision. 

Tax analysis has followed a similar path. The tax code hasn’t been rewritten from scratch, but technology has dramatically increased the IRS’s ability to verify information, compare data, and identify inconsistencies. Positions that once might have escaped notice are now much easier to examine. 

Just because something appeared acceptable in real time doesn’t necessarily mean it will survive closer scrutiny.

The game is always moving 

Soccer has a defined structure. The field is the same size. The rules are established. The clock runs the same way every match. Within that structure, however, every game unfolds differently. Momentum shifts. Coaches adjust tactics. Players make decisions under pressure, often with incomplete information. 

Taxes work the same way. The tax code provides the framework, but your results depend on the decisions you make throughout the year. This is where you really start to see how timing affects tax planning. When you recognize income, purchase equipment, hire employees, make retirement contributions, or change your entity structure can all influence the final outcome. 

The framework stays relatively consistent. The decisions within that framework, and the timing behind them, determine the result. 

What the scoreboard doesn’t show 

When the final whistle blows, the scoreboard tells everyone the final outcome. What it doesn’t show are the countless decisions to produce that result. A missed opportunity in the first half, a substitution in the seventieth minute, or a single defensive mistake may have been far more important than the final score suggests. 

A tax return is much the same. It displays the final numbers, but it doesn’t reveal the planning that happened months earlier. It doesn’t show the structure that was chosen, the deductions that were documented correctly, the timing decisions that were made, or the opportunities that were missed. 

By the time the return is filed, the game is largely over. The return simply records the outcome.

Small margins matter — on the field and in tax planning 

One of the biggest changes VAR introduced wasn’t a new set of rules. It simply made the margins smaller. Inches matter. Timing matters. Positioning matters. 

It’s similar to how timing affects tax planning. Small differences in entity selection, documentation, timing, or the order in which decisions are made can produce very different financial results. The margin between a good outcome and a great one is often much smaller than people realize — and more often than not, timing is the margin. 

How does timing affect tax planning? 

No World Cup team expects the rules to change in its favor. Successful teams learn the rules, understand their strengths, and build a strategy that gives them the best opportunity to succeed. Tax planning requires the same mindset; and so much of that strategy comes down to timing. 

You don’t control Congress. You don’t control the IRS. But you do control how you organize your business, when you make important decisions, and whether you plan before the return is due.  

That’s the real answer to how timing affects tax planning: it’s rarely one big move, and much more often the cumulative effect of dozens of smaller decisions made at the right moment. 

Like the World Cup, success isn’t usually determined by one dramatic moment. More often, it’s the result of dozens of thoughtful decisions — many of them about timing — made long before anyone is keeping score.