I am not meaning to patronize you but, really, if you believe that the worst mistake you ever made was leaving behind a vacuum cleaner, it would be a much bigger mistake to think you’ve not done well.
I do have something. When I was at my old job, I glossed over (okay, let’s face it, lied) about a situation that under ideal circumstances should have destroyed the careers of the people who were doing it, but I did what I did because I knew that the situation would be turned around and made out to be my fault, because one of the perpetrators was Our Department’s Little Golden Boy Who Could Do No Wrong. Srsly, this guy was totally exempt from disciplinary action, and everyone who worked there knew about it.
We’re talking about a situation that may have led to deaths. And no, when the truth was revealed, they didn’t get in any kind of trouble for it, either. Nor did I, but I did explain why I made the decision I did.
Marrying my second ex. Hands down, the biggest screwup of my life, bar none.
my worst mistake is not learning from all my previous mistakes.
Oh believe me, I’ve made far worse and far bigger mistakes, but I prefer to think of them as “learning experiences.” I just wanted to bring something less depressing to the thread.
I couldn’t begin to list all the screw-ups in my life between age 17 and 30, when I finally got all my shit together.
You married a designated hitter? Cool.
Reading through this cranky old zombie and thinking about my own mistakes, I have one thought.
Those really old people who say they have no regrets? They’re either lying, have no memory of their lives, or are complete sociopaths.
Maybe there’s something to be said for Alzheimers…
Being born in America… the mistake of my parents I guess. 
I smashed my finger in a car door.
That really was a good vacuum cleaner.
On a broad life-altering level, I should have gotten therapy so I could have finished college. But if I’d done that, I wouldn’t have met my current boyfriend and I would be an entirely different person. I kinda like my boyfriend and the person I am now, so I can’t say it’s my biggest mistake. Honestly, I have more regrets about the first (and last) time I got blackout drunk. I woke up at 6am with puke on my sleeve and had no idea what happened the night before. Didn’t even know whether it was my puke. I was among friendly members of a club I was in, so nothing bad likely happened. But I was so paranoid that I embarrassed myself that I never talked to any of them (or went back to a meeting) ever again.
On the plus side, I scaled my drinking waaaay back after that. Now I drink a couple times a month at the most.
Not joining the Air Force after my stint in the Marine Corps.
The Air Force told me I couldn’t pick my exact occupation (had to give them several choices, out of which they decided), and for a year I’d be on a 1-week notice to go to whatever not-boot-camp they give to prior service.
I thought that sucked, so I said never mind.
Now I kick myself because surely, I could have come up with 5 things I would have been willing to do, that would have actually given me some skills and experience for when I decided to leave.
And, I could have retired in two or three years.
Ahhh where do I begin?
Like others have said, I made a lot of conscious and just plain stupidly unconscious mistakes when I was younger. Ok, up until the last 7 years really. Finally I learned to just get over myself and take accountability/do the hard thing even if it was inconvenient for me. Mainly this was a result of being married to a wonderful man who stuck by me. Good thing I woke up and didnt lose him too.
But I mostly regret not appreciating my parents while they were alive and not spending more time with them telling them I love them. Man it feels good to get that off my chest.