The Remarkable Fools Letter

The Remarkable Fools Letter

five words to folly

how hard could it be?

Jim Dalling's avatar
Jim Dalling
Jun 12, 2025
∙ Paid

What five words cause men the most trouble?

How hard could it be?

Five words. That’s it.

They express the peak of folly - optimism, overconfidence and underestimation all wrapped up in an eggshell of impulsiveness.

Nothing good comes from beginning a task with the phrase how hard could it be, and yet, that’s how I began my ride on Sunday

It was only a hundred kilometers. I’d ridden much further in both April and May

How hard could it be?

There were six of us on the ride. Camaraderie! Support!

How hard could it be?

I knew the route - sure we were doing it ‘backwards but I knew the area

How hard could it be?

I was riding my favorite bike with a brand new derailleur and shifter - THE XT MODEL!

How hard could it be?

Well lemmie tell ya dear reader, it was hard. Much harder than I anticipated.

Sure it was only a hundred kilometers - but those other rides? They were mostly flat and smooth. Given the rocks and baby heads on this ride the hills were covered in hills.

Sure there were downhill sections but …

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