Before I start reminiscing about mechanical problems over the years, I want to link to this amazing post about an 88 year old man who recently became the oldest person to complete Lejog. Unlike Amber and I, he rough rode it instead of being catered too. That means he carried camping gear and all his own equipment. I'm so impressed.
I've had numerous mechanical problems occur during my rides - some I overcame, some overcame me.
I have had two front derailleur cables break. The first time I wrapped the cable around my top tube and cinched it tight to force the derailleur into the middle ring. This was a mistake because the tension put gouges into the top tube. The second time was on a 600k. I removed the broken cable and adjusted the set screw in the derailleur to push the chain onto the middle ring. A much better solution.
Once my rear derailleur fell apart. I lost the screw holding the lower jockey wheel and bits just went flying everywhere. I looked all over and could not find the lost screw. In the end I used my chain tool to shorten the chain and make my bike a single speed. It's really difficult to make a chain tight enough and the rear dropout on a non single speed bike doesn't allow you to add any tension so I ended up adding an extra link and then carefully moving the chain onto a larger sprocket by hand.
In San Clemente, climbing a hill, my chain broke. I'd just had it replaced and I could see the mechanic had not quite put the pin in all the way. Fortunately I carry a chain tool so I fixed it. Then I took it back to the shop and made them replace the chain for free, which they did because they're a good bike store.
More recently, I had a saddle bolt break during a ride. It's a Botranger adjustable saddle with forward and back bolts so the nose just shot up into the air. I'm lucky I didn't go down. I had no solution to that one but fortunately I was riding with Amber and she rode back and got her truck. I carry a spare bolt now.
I had a Vittoria Randonneur tire with a bad bead weld ruin one of my 600ks. The weld on the bead failed and the bead punctured my tire. Unfortunately it took three flats in 10 miles before I realized what was causing them. I had to ride 15 miles in the wrong direction on a flat tire to the nearest bike shop where I could buy a new tire. Unfortunately we were now three hours behind schedule and it was obvious we were not going to make the time limit so I abandoned. Those were the last Vittoria tires I ever bought.
I had a problem with a pedal that wouldn't stay in the crank arm. It kept coming lose no matter how hard I tightened it (yes, I had a pedal wrench with me!). I'd stand on the pedal wrench but the pedal was so loose five miles later that I could hand tighten it. It was a long ride home and I simply replaced the pedals.
Probably the worst was after I had major work done on the front end of my bike including new fork and stem. On the next ride I was turning a corner and the front brakes came off - the mechanic had not put the nut on the bolt that attaches them to the frame. I was unhurt and the brakes did not fall into the wheel. Imagine if I had been flying down hill and the brakes had gone into the spokes. That was the last time I ever went to that bike shop and I told the manager exactly what I thought of his mechanic.
The latest was a broken spoke last Friday evening. I carry a spoke wrench but I was unable to stop the wheel rubbing completely so I turned around and rode back to the car. Fortunately it was only five miles and I was able to get to my bike shop before they closed.