I don't regret foolish decisions I made before I knew it was foolish - I think thats being too hard on one's self. However, I would have a tough time knowingly making a foolish decision. Which category do your foolish decisions fall in to?
I've noticed I feel better when I create opportunity for myself. For example, I'd probably feel very bad if I spent money on short-term enjoyment because that money would be gone forever. However, if I can consistently put in hours towards a project, I can reflect on those hours with pride.
"Which category do your foolish decisions fall in to?"
Moving abroad for my first job.
Quitting my extremely well paying engineer job to become a pro photographer ("how can you quit???"). I earned approximately 8 times less, for 8 years.
Asking the amazing woman out... We're happy together, it was 3.5 years ago.
Returning to a better paying job, in spite of some success and reputation as photographer ("how can you quit???"). It was in february.
Deciding to move abroad again... in october this year if all goes as planned, I'll start a digital nomad life, working remotely for a startup.
Also I had a cerebral infarct when I was 32. It was 10 years ago. Please don't wait for such an event before you realize it's time to take your life where you want it.
One thing that might help you: recently, I heard a Ted talk about intelligence. In a word: the clever choice is often the one which will maximize the choices you have further down the road.
When you feel like you're stuck, almost any move will do. Standing still will not.
I've noticed I feel better when I create opportunity for myself. For example, I'd probably feel very bad if I spent money on short-term enjoyment because that money would be gone forever. However, if I can consistently put in hours towards a project, I can reflect on those hours with pride.