Biggest regret was a business decision. Trusted some "good church folk" when they wanted to sell us their business. Within a year, found they had not been honest with the numbers. Contacted legal counsel about suing for fraud. Cost of going after them would be enormous. Decided to make every attempt to rescue the business and move forward. Closed the business two years later, having seen our life savings gone... disappeared. Woke up the morning of our 35th wedding anniversary and did not have a dime to our name. The bank held a second mortgage on our home. Things were pretty bleak.
Spent the next 14 years living on the road to make the "big money". Over 2,000 nights in hotels, missing grandkids births and events. Came back to where we could retire earlier this year at age 70. Financial advisor says we should be okay until age 92. Still would not be good to meet the couple on the street. Would probably say thing that would be less than gentlemanly and lower myself to their level.
Certainly, raising our children and going through almost 51 years of marriage there are some things one might want "do-overs" on. My wife and I have promised never to go to bed angry. The speed bumps we've hit have been met and crossed and we are only looking forward.