More like you might say “I wish I had spent more time with my kids and less time at work” but you won't remember the anxiety of planning for the future. In hindsight you managed to saved enough for retirement but it didn't always looked that way when you were laid off for the second time in 4 years in the middle of an economic crisis. Your kids grew without life changing injuries but you didn't know that and you didn't have to battle a cancer.
So at the twilight of your life you might say that you wish you hadn't worked overtime for that startup or spent your weekends on side projects but at the time you were worried about paying your rent or a dead-end career path and you had to try to work harder because you had no way of knowing things would turn out fine. And maybe they turned out fine because of your efforts.
Hindsight is 20/20 and this is just as true for your future self judging your current self.
So at the twilight of your life you might say that you wish you hadn't worked overtime for that startup or spent your weekends on side projects but at the time you were worried about paying your rent or a dead-end career path and you had to try to work harder because you had no way of knowing things would turn out fine. And maybe they turned out fine because of your efforts.
Hindsight is 20/20 and this is just as true for your future self judging your current self.