What's the costliest single mistake you've ever made, and how much did it cost you?

I was in an Air Force Officer Training Program, called ROTC (Reserve Officer Training Corp). Basically, while you're in college, doing your classes, you take a day or two out of the week to do some military training. You graduate college and commission as an officer on the same day, so it's a sweet deal. Go through school, have a guaranteed job straight out of graduation. It's 3-4 year program, depending on when you joined. Finally, the program is primarily run by the trainees, which we call cadets- but there is oversight by a few officers. Oh, and an important note- the Air Force program in particular does not hand out many scholarships, as many people believe. You pretty much need to major in engineering or foreign language to earn one.

Story time: Last month of college, last month of ROTC. It's been 4 long years of training. As with any program, I've grown very close with many of these men and women. I've got my job assignment, I've got a date to report in, and I've got my security clearance. At this time, the Cadet Wing Commander (guy in charge of all cadets) is a close friend of mine. I was his superior at one point, and we got along very well. He was a diligent man, very willing and able to carry out task. Had a good heart, and was just an overall nice person. When his mom passed because of cancer, I would call him up to check on him, to see how he was coping. Go out to dinner with him, hang out when we could.

Now what happens next is a very long, very convoluted story, so I'm just going to sum it up. I told one of my subordinates to lie. It didn't involve drugs, violence, or anything that would had serious consequence. It was over a door being left open. But that doesn't matter. Fact is, I fucked up and told a subordinate to lie. I confessed this to the cadet Wing Commander, told him how sorry I was. He is so frustrated, so upset at it, he turns me over to the officers. 6 long months later, after graduation, and a lengthy investigation, I get disenrolled for lack of integrity, lying, possible security violation, and so on. No job in the Air Force, no career to look forward to. Those 4 years were for nothing, and now I have thousands to pay back in student loans with no job prospect. My "friend" claims he had no idea this was going to happen when he turned me in. Said he was sorry, that he would not have done it if it led me to losing everything.

Cost of mistake: Thousands in student loans, and no career prospect.

/r/AskReddit Thread