Biggest regret

I'd have to say not having the right priorities with my time spent with family. I grew up in a family where work was everything. While my work ethic and dedication to what needed to be done made me very successful in that part of my life, I was (still am a social retard). I missed out on a lot of time I could have spent with my Dad (ironically it's his dedication to work that molded that in me) and a lot of time with my own family. I did finally change careers in my 40s (bad financial decision) and my wife got me to spend a lot more time with my kids but I still missed out on a lot of time with my dad.

TM

Not taking my hockey career to the next level after high school…Notre Dame.

My biggest regret; should've got out of Active Duty Air Force and went Guard or Reserve when my first wife died. That way I could've still did my time for Uncle Sam, but have time to mourn, plus take care of my (at the time) three month old daughter. 

regret not investing more in my 20's, I blew a lot of cash doing dumb but very fun things, 

also regret not asking a girl out that I liked when I was 18,