When we get older we do not regret the things we have tried or have done. We regret the things we didn't do.
When a friend was considering doing something she had always wanted to do, but had not, I quoted the above saying. Another friend, looking back at things she could've done and did not do, for the most part, is glad she didn't do them because she thinks she would have regretted them.
I agree that there are many things in a person's life that they may well regret if they do them, but I believe the quote refers to those things that we do not do even though we feel we will always regret it if we don't take the risk.
I have always made my decisions on that basis. I acknowledge that the chosen path may not work out, but if I don't try, I will always regret the road not taken. I also look down both roads as far as I can, contemplate both the best and the worst that could happen, and determine if I could survive the worst. The result is never the best or worst that can happen, but will probably be somewhere in the middle. If I feel that I can deal with the worst and still feel I would regret not acting on the opportunity, I jump into the deep end and swim like he**.
As a teenager, I knew an elderly couple who had lived a very full life, with all the trials and tribulations that come with such a life. In their twilight years, in the summers, they sat on the porch in their rockers, side by side until the sun set and darkness came. They would then go into the kitchen, light a lamp and make a snack before going to bed. They were not filled with regrets and bitterness. They were content. I want to achieve that contentment while waiting for the boatman.
My greatest leaps of faith have been to divorce an abusive husband, enter into a second marriage that no one expected to last a year, and drag my family, including parents-in-law, half way across the country to begin a life that would prove to be better in every way. I have not regretted any of those decisions, and I'm sneaking up to the rocker on the front porch with few regrets.
I wish such an ending to all.