As you've all illustrated, our work exists on a continuum from the "fun and games, keeping my own stuff running and staying stimulated by learning new things", through work for an employer and/or customer, to mission-critical/man-rated, where mistakes have the most serious consequences. As fate has had it, I've never been involved in the latter, and some of the very best programmers I've ever worked with have been categorical about not wanting that kind of responsibility. My career has been in the middle, and often as a contractor, where those mistakes sometimes came out of my own pocket.
But back at the lighter end of the scale, here's another learning-on-the-fly boner move:
For the longest time I had a persistent - and increasingly severe - drivetrain vibration in my old beater '91 Dakota 4x4. At one point I was so frustrated I was determined to just start disconnecting things until something changed. So off came the front driveshaft. No change. Then one front drive axle - I pulled it out and took it for a spin. No change. Then the other drive axle. I headed out our driveway and about a quarter mile down the access road to the secondary highway (we're out in the country). As I pulled out onto the highway, both front bearings (without the axles supporting the load) gave out, planting the front end on the pavement with the wheels splayed out like in a cartoon, or a newborn colt that can't quite stand up yet. I wish I'd had a camera - as I stood back and looked at it I just couldn't stop laughing. Then I trudged home, got the jacks and tools, and sorta wedged it all back together again well enough to limp back to the garage. To cap it, while I was fetching the tools, my girls' school bus driver passed by the poor thing, so the story got around.
As my former business partner and I say: We know it's built right because we did it six times.