Wow, interesting question. Over the past 5 years I've gone through a relationship breakdown, lost contact with friends, and I'm on my third job in this exact period. I'd like to say that I love my current job and have no intention of leaving, yet those other two points I wish that I had never screwed up. Also, if I count back 20 years, I do have several regrets that I wish I had done differently: - Pay attention at school, rather than mucking about with friends who I had absolutely minimal contact with after I finished. I'd perhaps be in a much better career. - Stand up for myself, I've suffered virtually my whole life with this (currently 31). I've always been a somewhat shy timid individual, and I wish I could state my opinion far more often rather than leave it bottled up inside. I have gone the opposite way obviously, however these are things that I believe I could improve on for 20 years into the future. I'm still relatively young (although I seem to think I'm old lol), so I've still got plenty of years ahead of me to get my life sorted, back on track, and to actually feel proud of myself and what I've achieved.