[BiggsHoson]

The first one (of many) that comes to mind is not looking to the future when I started life on my own. Had someone told me when I was in my 20s that a day would come much sooner than retirement age when I would be sick of my career (and had I listened--not at all a given) I would have been much farther ahead in my life now. If I had started investing right from the start, especially as the stock market was booming back then, I could have retired some time ago.

Related to that, I wish I'd found and fostered some sort side gig that would have allowed me to eventually ditch the 9-to-5 work life.

I wish I had realized how important it is to find some place you enjoy living (for whatever reason--friends, recreation opportunities, favorable weather, etc.), and then doing what you can to make a life there. Instead, I pursued jobs wherever they took me and I think my family paid a price for that instability. I didn't realize for a long time, but I think that I, too, paid a price for all those relocations in pursuit of the next job.

And then related to that, I wish I had not been so optimistic about my jobs. I should have realized that no matter how convincing the dream being sold to me, it was never going to be that good. I should gave treated my jobs as paychecks, as means to another end, not something into which I should pour the best of my attention and purpose of life.

Wow. I have never told anyone all this.