We can only make decisions based on the (usually flawed or incomplete) data we have at the time.
I too have been struggling with the idea that I make bad decisions. A friend reminded me of this poem, which really helped me:
The Road Not Taken
ROBERT FROST
Two roads diverged in a yellow wood,
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth;
Then took the other, as just as fair,
And having perhaps the better claim,
Because it was grassy and wanted wear;
Though as for that the passing there
Had worn them really about the same,
And both that morning equally lay
In leaves no step had trodden black.
Oh, I kept the first for another day!
Yet knowing how way leads on to way,
I doubted if I should ever come back.
I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.
His choice of the two roads was actually arbitrary. He could see only so far down both, and in the end took a less known one. That might imply courage, but it might be more banal than that. When he says "I shall be telling this with a sigh", I think we get to the nub of it. It’s how we interpret things that matter. The stories we tell ourselves about our lives and our choices - they matter. Because “I always make bad choices” is a fairly dreadful way to view one’s life. Whereas “things always work out ok” is much kinder to oneself.
How we tell the story of our lives makes all the difference, actually. Tell a kinder story about yourself, and remember there are always more forks in the road, more chances for things to turn out ok.