About once a year I try to get my dose of humility … you know, the kind that makes you question your manliness; the kind that tests your skills beyond their limits and strips your confidence to the core of your naked worthless soul.

That’s right, once a year I go snowmobiling with Bret Rasmussen.

Now riding with Bret may not sound all that bad. If fact, it’s rather unique. He is familiar with the terrain, he understands snow conditions and he knows the snowmobiles. He knows what can be done, what can’t be done and what probably shouldn’t be done. He has the ability to quickly assess the riding capability of those in the group … and sets a riding pace that will challenge everyone without excluding anyone. However, he does take everyone to their breaking point.

The secret to riding with Bret is you don’t want to be the “least” talented of the group … nor the “most” talented. If you are the least, it’s going to be one long day. If you are the most … well, Bret will eventually find somewhere that takes you past your threshold of ability. And that “somewhere” is most likely going to be somewhere you wish you had never gone … and will leave you wondering if it’s somewhere from which you will never return.

This past winter I made a colossal mistake … I was both the most and the least. I was the only one riding with Bret. He was able to devote his full attention to taking me to the point of breaking.

What made matters worse was that it was mid-April—spring riding. For those who don’t get out in the mountains in the spring, this is all you need to know: Mistakes are magnified 10-fold in the spring. The snow changes with the temperatures—from concrete to mash potatoes. You can climb anything … but when you start your descent, you’re riding a 500-pound chunk of metal down a sheet of ice—there is no braking, there is no steering; you only stop when the mountain stops … or when an unmovable object gets in your path.

When Bret and I left Copenhagen parking lot (between Preston and Montpelier at about 7,400 elevation) and headed south toward Bloomington Lakes, we didn’t spend much time on the trail. It was up one ridge, down the next. The good thing about the ride was that we were on 2010 Arctic Cat M8s. The bad thing was that these prototype sleds are usually a little more expensive and replacement parts haven’t been made yet. So I was under just a little more pressure to make sure the sled returned in a similar condition to what it began in.

It didn’t take Bret seven miles to figure out where my abilities ended … and nearly my life. Cutting up a steep tree-covered slope, making tight zigs and zags, Bret cut a line around a tree and up to the ridge. My line wasn’t quite as crisp and exact. In fact, instead of zigging, I zagged, shooting me up over a knob and into the bows of a huge pine. This sudden change in slope angle left me high-sided by my sled. The pine bows served as a giant brush, scraping me off balance.

As gravity took control of the sled and pulled it over on its side, I was trapped in a dilemma … do I ditch this expensive sled to save myself or do I try to keep it somewhat under control and use my body to stop it from tumbling down the mountain?

Being the courageous person I am … I thought “Heck with the sled, every man for himself.” However, as the snowmobile came over the top, my backpack got caught up between the tunnel and the track, sucking me into the sled and wrapping me up with the fate of the snowmobile.

Perhaps it was fortunate that the huge pine stopped my descent … and fortunate for the snowmobile that my body cushioned its crash into the huge pine. But when the snowdust cleared, I was pinned against the tree with the entire sled resting on the length of my body … with the motor idling.

I could move my right arm a little, but not enough to push the sled up the hill. And the tree and my bruised butt prevented the sled from rolling down the hill. So there we were, stacked upside-down and downside-up. I was trapped, left for dead and waiting for the bears to come out of hibernation and feast on my rotting carcass.

Okay, so perhaps I wasn’t going to die. I knew Bret would soon be coming back down looking for where he scraped me off … and it was going to be tough coming up with some lame excuse for why a snowmobile was still riding me like a two-bit whore.

Although the minutes seemed like hours, the good news was when Bret finally turned off my snowmobile and asked me if I was okay, there was a tinge of concern in his voice. I think he may have actually thought I was dead. The better news is that he was able to roll the sled up the hill just enough for me to get my backpack out of the track and to slide out from under its crushing weight. The best news was that nobody else was around to take photos.

For the next 10 miles, Bret took it easy on me, making sure I was always behind him and that there were no apparent injuries that could affect my riding. But once he was assured that I was back to normal, the terrain got steeper and the lines got tougher. Fortunately, I became smarter. I stayed close enough to pick up his lines and his direction, but far enough back to select my own lines. It’s not that I quit following him. I just made sure that I had a little more terrain to make adjustments in.

In fact, it wasn’t until late in the ride that Bret found another opportunity to test my mettle again. This time it was coming down a steep narrow drainage.

Visually, it sort of resembled a luge course … with huge trees disrupting the natural flow of gravity. It was a steep drainage where once you started down you were committed. All I could do was try to manage my speed with a combination of braking, swerving and hitting stuff.

With only two miles left before the parking lot, I knew I had to make this final descent. However, near the bottom of the luge, there were two trees (exactly 46 inches apart) that blocked the natural flow of the terrain. I couldn’t get above them, and I didn’t get below them. The best I could hope for was to shoot between them. Oh, and did I mention that there was a third tree involved, though it was much smaller, squarely between the two large trees?

With little time to think or react, I had to grab the throttle to power myself directly between the trees, and then grab my brake and hope the third (5-inch thick) tree could stop me before crashing into a vertical wall of the drainage.

Again, fortunately I hit my mark, with the skis’ outer edge just scraping between the huge trees. And that third middle tree did its job of stopping me … well, at least stopping my sled. For me, it was over the bars and into the bank. This time, when Bret returned to see his handiwork, there was a slight smirk to his face—satisfaction that he was able to drop me one last time before the end of the ride.

In all, it was a great ride. My sled finished out the day looking as good as when it started. Bret finished the day knowing that he was able to school me yet again. And I finished the day wondering if I would be able to hide the bruises on my body or would have to explain them to my wife.

I can hardly wait until next season’s ride with Bret.