I am admitting now that I have not read all replies just giving my own experience. I sold my business in July as I realized that the one thing I can’t buy more of is time. Having each day belong to my wife and I to do whatever we want is priceless. There came a point, at least for me, where more work/money wasn’t going to change or enhance my current lifestyle so it was time. It has been amazing every day. Now money concerns are a very real thing but if you are comfortable with your financial situation you will not regret it. I have always said if you get bored in retirement then you don’t have enough interests. My wife and I are trying to figure out how we used to fit work into our lives because LIVING the way we are now is full time fun!!