You made your bed, that's where you lie...
I regret every decision I've ever made. Even the ones that worked out - I figure I probably could have made a better one, or that something could still go wrong.
The problem is that I don't like myself all that much. So I don't really trust my judgment. Especially about myself.
Every major decision I've ever made I find myself second guessing. Jobs. Major purchases. Education.
The latest thing I've been agonizing over was a job opening that was open at the school I work in another department. I actually had my eye on the job before it was open - I though for years if the person in the position ever left, it would be a great opportunity for me.
And then the person actually did leave. And I looked at the position. I was going to apply, and then I looked at what they were looking for - experience managing web development teams, managing databases, doing all kinds of stuff I never did.
This caused some odd conversations with people. Everyone I mentioned this to thought I should apply for the job anyway, because that was just a "wish list". I don't understand the logic of this - to me, if someone knows what they want in a candidate, why would they hire someone who lacks all those things? I mean, I hope the next time I see a doctor, that he or she got the job based on qualifications, not on "hey, I've never performed surgery, but people like me and they figured I could learn".
So I was going to apply anyway. Then I saw that it required references, and I was reluctant to use people I'd work with. I figured that using someone you currently work for is not terribly informative - a boss who likes an employee may lie and say they suck, so they don't leave, while a boss who wants to get rid of an employee may lie and say they rock so they can get rid of them.
Once again, this makes perfect sense to me, but doesn't seem to make any sense to anyone else in the rest of the world.
But I started to think about it some more, and I couldn't see it working out - I didn't have experience, the job didn't really have any potential - it would be a promotion, but there wouldn't be anywhere to go after that, I would be working alone so I wouldn't have anyone to lean on for help, and I'm not sure I would really enjoy the work. So I did the easiest thing - nothing - and didn't apply.
And now I'm wondering if I should have. I actually checked the HR website today to see if I could still apply for it, but the job listing is gone, so it's too late.
The problem with making decisions is that it often takes years to know if you made the right decision. Part of my logic was that if I remained where I am, another position might open up that's more like what I want to do - something more towards management (but more technical than the other position) or system administration. If something like that does open up and I get it, then I'm a genius. If not, and I'm still carting monitors and removing viruses 5 years from now, then I'm an idiot.
The same is true about other decisions - I won't know if buying my house was a good move until it comes time to sell. I won't know if buying my truck was a good move until it starts breaking down. But since I don't have a lot of faith in my decision making, I figure there is a good possibility that it's wrong, and so I worry.
I've often defended the Iraq invasion on the grounds that it was a reasonable decision at the time, with the information available - Saddam was acting like someone with weapons, and there was no way to be sure, so we made a rational decision based on the info we had at the time. But I can never seem to convince myself of the same logic for my own personal decisions.