Why would anyone pay to run 26.2 miles through a city they could walk around for free?
On Sunday, 11 October, more than 55,000 people did exactly that at the 48th Bank of America Chicago Marathon. They started and finished in Grant Park, ran through 29 of the city’s neighbourhoods, and did it in temperatures that climbed into the 70s Fahrenheit, which is lovely for a picnic and considerably less lovely for mile twenty.
The Race Itself
Kenya’s Amos Kipruto won the men’s race in 2:01:09, a personal best. What makes his win special is what came before it. He finished third in Chicago in 2024 and second in 2025. This year, he finally crossed the line first. Ethiopia’s Hawi Feysa defended her women’s title in 2:13:33, also a personal best. Switzerland’s Catherine Debrunner set a world record in the women’s wheelchair race and her compatriot Marcel Hug set a course record in the men’s.
Third, then second, then first. If you ever need a picture of patience, that is it.
Follow the Money
Now for the part I could not stop thinking about. Kipruto and Feysa each took home $100,000, and the total prize purse across the divisions came to $900,000, according to NBC Chicago. That is a very good day’s work.
Then look at the city. An independent study found that last year’s marathon pumped nearly $756 million into the Chicago economy, 7.5% more than the year before, and supported more than 5,000 full-time equivalent jobs. The biggest drivers were visitor spending on hotels, food and entertainment. Runners also raised a record $47.1 million for charity in 2025, and around a third of this year’s field signed up to run for an official charity.
Put those numbers side by side, and the shape of it is obvious. The runners did the suffering. The prize money, generous as it is, was a rounding error. The real money went to whoever was standing beside the course with a hotel room, a table for four, or a tray of bagels.
The Lesson Is About Position
Effort and reward are related, but they aren’t the same thing. Position decides how much of your effort turns into money. The hotels did not train for months. They did not ice their knees or learn to eat energy gels on the move. They stood in the right place on the right weekend, and the money came to them.
I find this one of the most useful ideas in personal finance, and it applies far beyond running. Two people can work equally hard and end up in very different places, simply because one of them is standing where the money flows. Moving your position is often worth more than adding more effort.
And Yet They Ran Anyway
Here is the other side, and it matters just as much. Fifty thousand of those runners knew perfectly well they would not win $100,000. They paid to enter, trained through dark mornings, and gave up weekends for months. They did it because some things cannot be bought, only built: the fitness, the discipline, the friendships made on long runs, and the moment you cross a line you once thought was impossible.
My own running career is best described as a series of promising Januaries. I am a much more reliable walker, and I have made the case before that walking may be the most underrated exercise there is. But I understand the pull. A quality life is not only about where the money goes. It is also about what you are willing to pay for, and why.
What I Took Home
Chicago gave me two lessons in one weekend. The first is financial: put yourself where the money flows, because effort alone rarely gets you there. The second is personal: some of the most valuable things you will ever own were paid for in sweat, not cash.
The best lives, I think, manage both. And if it takes a few attempts- third, then second, then first- that is not failure. That is just how the race is run.
The Jacqueline Brand: knowledge builds confidence; confidence builds wealth.
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