1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.
2. I wish I didn’t work so hard.
3. I wish I’d had the courage to express my feelings.
4. I wish I had stayed in touch with my friends.
5. I wish that I had let myself be happier.
#3 has never been a problem for me, #1 I thought I had whipped, but when you really sit down and think about what you are doing and why...well it might not be as true as you thought. At least that was the case for me. #4 is a toss up, since if I have let people slide from my life it is probably for good reason. #2 is the one I really needed to work on, but not in the traditional sense. The context here is for your typical male worker of a generation that preceded the Internet. Someone who was away from home and family. I by comparison don't think working hard has to be bad, if you can do something that is fulfilling and especially if you can do it with your spouse.
And that leaves #5. That has been the hardest. It's not that I am unhappy, it is more that I don't seek happiness but rather fulfillment. Sometimes I will #2 and not take the time to #5. I'm working on it.