When I was a kid, I used to do a lot of bicycle road racing.

That was before Lance Armstrong even straddled a bike. He’s a year younger than me, but I guess I missed my opportunity to fly down to Texas, get him out of bed as a 14 year old, and beat him silly up the nearest mountain. But I’ll be honest. By the time he was 14, I had been racing for two years, and he hadn’t discovered his freaky gift. So that would have been it: my single window.

To say that I didn’t have Armstrong-esque talent would be an understatement. But I used to visualize beating tougher riders through bizarre circumstances. I visualized success before visualization became popular:

A dog would run in front of the lead pack of ten riders in a 100km race. The lead rider hit the dog, and we’d go down like dominos. I, like Rocky Balboa, looked across at the Apollo Creed’s laying across the road. The finish line would be just 500 meters in front. Who could get back on their bike first? Yes, it was me—not yet nursing my concussion, but pressing on the pedals while screaming, beautiful women urged me to victory.

No, that wasn’t just something I made up now. I made that up in 1985. And if I couldn’t honestly visualize beating stronger opponents, I’d concoct a story like this, and daydream in class while on my way to earning high school report cards that looked like old Russian hockey jerseys: CCCP, CCCP. The “P” stood for “please”. I’ll pass your sorry dreaming ass if you “please” never enrol in one of my classes again. Fair enough.

I’m probably too old to have those kinds of daydreams today (at least that’s what I’m admitting) but last month, one of those old fantasies came to life.

I entered a 10K running race in Singapore. It was about 32 degrees, and we faced 10,000 meters of asphalt and path, with about 1000 other runners, in 100% humidity. Settling into a decent pace, I found myself among the top 25 runners after the second kilometre. There was no real hope of winning.

Then the guy directly in front of me cut off the path and onto a lower trail heading counter-clockwise around a lake. There were a few other guys who did the same thing before him. And there were a few guys, behind me, who got tired of staring at my skinny wet ass, and swerved right as well.

Now, I’m not the most astute guy when my lungs are burning, my eyes are bleeding and I’m wishing I was listening to a time-share salesman instead of torturing myself. But I knew that those others guys were heading the wrong way.

Long story short. I ran alone for most of the race, before getting caught in the final 500 meters. I figured I was going to be 10th, or 15th. But later, I found that I had been leading the race, up until the final half kilometre. I wasn’t among the fastest runners there, but I took home the hardware for second place: about $600 worth of prizes.

Perhaps we always need to be optimistic about our odds of success. Perhaps Captain Kirk was right when he used to say that there’s no such thing as a “no win situation”.

There’s a lesson to be learned here, related to investing, as well. You get it, right?