I’ve got plenty to worry about as I prepare to bikepack the Great Divide. Brutal climbs. Foul weather. Saddle sores. Limited oxygen.

But my biggest fear is that I’ll make some colossal blunder that turns my vacation into a nightmare. These trepidations are justified by my checkered history of missteps. “You’re like an absent-minded professor!” my grade school teacher told me more than 30 years ago.

Einstein: bicyclist, absent-minded professor

Examine my GPAs, SATs, and GREs and you’d conclude I’m pretty smart guy. But judge me by the number of items I’ve lost/destroyed or the number of insurance claims I’ve filed or contemplated and you’d conclude that I’m still in need of adult supervision.

The die was cast early, when I was around two years old. I was visiting my grandparents’ house in upstate New York, running across their yard, and—whoosh!—I disappeared into the lawn, which was saturated from recent rains. Luckily, my mom was there to pull me out by my ankles and save me drowning in the subterranean cesspool (some may say I’ve been full of shit ever since then).

With the hope of immunizing myself against more expensive and embarrassing goofs, I’ve decided to codify my carelessness with this list of my top-10 fuck ups.

10. Driving into the garage with my bike on the roof (times two). The first time, the impact cracked the front tube of my Specialized Stumpjumper and fatally injured the bike. The bright side was that it forced me to buy a new bike, but a few years later, I did the same exact thing with my Specialized Epic Comp—the bike I’ll be riding on the Great Divide Mountain Bike Route. In this case, I only busted the front fork, but the collision caused my bike to cart-wheel around the back of my Subaru Forester and smash through the hatchback window. (If you’re keeping score at home, I destroyed yet another suspension fork a few months ago while leaving a remote campsite on the North Rim of the Grand Canyon, after my handlebar snagged a juniper branch and was ripped off my roof rack.)

9. Dropping a $799 lens off a cliff. I was backpacking in Aravaipa Canyon, near Tucson, and decided to climb the surrounding cliffs to snap some photos of the emerald riparian corridor flanked by desert and stately saguaros. As I was switching to a new lens, it slipped out of my hands, bounced off my foot, and rolled off a 200-foot precipice. The mournful cry of “Noooooooo!” echoed through the empty canyon.

8. Leaving my iPhone atop my car. On a work trip to Northwest Colorado, I heard a noise coming from my roof rack and pulled over to check it out (see #10 and #2). As I adjusted my bike, I rested my iPhone on the roof, then got back into the car without it and sped off on I-70. It only took a short while to realize my mistake and I circled back on the highway. My phone was scattered across the asphalt and I got to see an 18-wheeler run over the biggest piece.

7. Losing my sunglasses (times 78). My sunglasses (and loaners from Ginette) have a life expectancy of a few months, at best. Accordingly, I never spend more than $30 on a new pair (likewise, I always replace my front forks with low-end models, knowing they won’t last long on my bike.)

6. Impaling my car in Telluride. While on book tour a few years ago, I drove out to Telluride to give a talk (approximately three people showed up). The next morning, while leaving the hotel parking lot, a terrible chain reaction transpired in a matter of seconds: I sprayed my windshield to clear off the ice, the sun blinded me as I was turning out of the parking space, and I drove into a guardrail at around 3 mph. Perfectly placed, the rod-shaped guardrail harpooned my right headlight and lodged itself halfway into the engine compartment. This prompted a 127-mile tow-truck ride to Grand Junction, several thousand dollars in repairs (thank god for deductibles!), renting a car to drive back to Denver, and then taking a Greyhound back to Grand Junction to fetch my car a few weeks later.

5. Dropping my laptop at the Denver airport. Knowing how likely I am to drop stuff, I protect my MacBook and iPad with padded, neoprene sleeves. But these things only work if they’re zipped up. Such was not the case as I unloaded my possessions onto the conveyor belt at the security checkpoint. My laptop slipped out and the sound of metal meeting concrete echoed throughout the cavernous white tent that serves as the terminal. The fall caused the machine to make a horrible whirring noise but the guy at the Apple Store managed to fix it for free (I now buy SquareTrade warranties for my pricier gadgets—totally worth the peace of mind).

4. Paying $500 to a plumber after snapping a 10-cent screw. The shower in my house in Tucson was a little leaky and I decided to fix it myself to save a little money. While tightening a screw in the faucet handle, the head snapped off, which necessitated hiring a plumber to bust through the shower tile in my other bathroom, on the opposing side of the wall, to access the pipe and fixture (don’t ask). Easier to visualize is my immediate reaction to breaking the screw:  I punched a hole in the drywall of my bedroom, which I kept hidden for years by putting a picture in front of the damage.

3. Trashing the U-haul truck. When Ginette and I moved from Tucson to Berkeley, we made the mistake of renting a U-Haul truck. Ninety minutes into the trip, the truck died on I-8, in the middle of the Sonoran Desert, on a triple-digit day in August. Nearly two hours later, a mobile mechanic came out and replaced the alternator, but this was just the beginning of the adventure. The next day, we came within a few yards of running out of gas in the Mojave Desert after the truck’s gas gauge went from ¼ full to empty in about 30 seconds as we climbed a mountain pass. While pulling into a gas station, I ran into yet another metal post (see #6) and dented the side. While parking in Berkeley, I ran over and flattened a stop sign—nothing a little duct tape couldn’t fix. Good thing I had the full-coverage, no-fault insurance coverage from U-Haul!

2. Showering my camping gear onto I-70 near Golden. Ginette and I were driving to the Grand Canyon (see #10) and it was ferociously windy as we left Denver. Near Golden, the Yakima box on our roof flew open and expelled a bunch of our camping gear (apparently I hadn’t locked it correctly). In my rear-view mirror I could see the stuff sack with my sleeping bag bouncing down the middle lane of I-70 (see #8) and I had to wait for a break in the traffic to dash out and retrieve it. Miraculously, the only harm done was a tiny hole in the air mattress that I was able to fix with patches for bicycle tubes.

1. Breaking my hand in a hotel bathroom. I was in a San Francisco hotel room the night that I submitted my manuscript for Endangered to my publisher. Relieved (and stone cold sober), I went to bed, woke up in the middle of the night, tripped in the bathroom, jammed my hand against the shower wall, and broke my middle metacarpal bone, which put me in a cast for six weeks. After five years of working on the book, I guess my body was telling me to stop typing.

I think these episodes offer a number of lessons. For starters, you should never loan me your sunglasses or let me put your bike on the roof of my car. Another is that insurance can be money well spent. Even more important, my history of costly mess-ups means that I really need to be more mindful and focus on the here and now. That goes for this trip, and for life in general.