Crashing at Mile 20: What a Century Ride Taught Me About Financial Planning

I was 20 miles into a 100-mile race, pacing with a family friend — a Marine — cruising at over 20 mph. Confident. Locked in.

Then came a sharp 90-degree turn. I should’ve slowed down. I didn’t.
I held speed, misjudged the line, and shot wide off course.

My front tire hit the shoulder. My body followed.
Still clipped into the pedals, I went head over heels into a four-foot ditch.
The handlebars bent. Road rash lit up my arm. I was bleeding. Stunned.

I sat there, staring at the mess, and got back up.
Bent the bars straight. Climbed on.
Pedaled the next 80 miles, bruised, bleeding, and humbled.

That crash has stuck with me — not just physically, but mentally.
And over time, I realized it wasn’t just a lesson in pride or pacing.
It was a lesson in planning.

Because financial plans are built the same way long races are ridden:

Not for when everything goes right.
But for when everything doesn’t.

We build these carefully constructed strategies — investment portfolios, tax plans, retirement roadmaps — all assuming a straight road and clear skies. But real life throws you off course. It might be a market crash. A layoff. A health scare. A divorce. A phone call that changes everything.

And when that happens, your financial plan either holds or it breaks.
Just like the bike.
Just like the turn.

The point of financial planning isn’t to avoid every crash. It’s to make sure you can get back on the bike.

To make sure the bars are bent but the frame is intact.
To make sure the ride continues — even if it’s slower, messier, or harder than you thought.

I finished the race that day. Slower than I wanted. Humbled.
But stronger in a different way — the kind that only comes from hitting the ground and getting back up.

That’s what a real financial plan is for.
Not perfection.
But resilience.

And if your plan doesn’t include room for crashes — it’s not really a plan. It’s a hope.