If you want to see a bunch of happy retirees, come to Southwest Florida.

At least a few times a week I hear someone praising the good weather and the wonderful opportunities for leisure fun. Personally, I do that every day.But for the past six months, I've been hearing a new sentiment: I should have waited longer to retire. And I've been hearing it from those I never thought would run into money problems.Two well-heeled retired male friends (or so I thought) in the boating community have sold their boats. One has his home up for sale because he says he has to downsize. The other friend is even begging his much-younger wife to get a job to help with expenses.They are upfront about their urgent need to cut back on expenses."If I had it to do all over again, I would have waited until I was 70 retire," said one of the guys who retired early, thinking he had enough saved. He was wrong, he says.I have been hearing this refrain a lot lately: "If I would have known the economy would tank like this, I would have worked longer."As it is, many people seem to be in the same boat. We sit there with a pencil and paper, adding up the expenses, looking to see where we can cut.Several of my friends have stopped getting the newspaper and have changed their cable plan to basic only. They cut off every frill.Some are trying to get back into the job market. They are willing to take anything. One 70-year-old retired librarian is working at a paint store because she said her meager pension isn't keeping up with the cost of insurance and other expenses.Another older woman who said her retirement funds "dwindled to almost nothing" is working as a waitress, hard work for anyone and harder yet for someone her age. She's says she's doing what she has to do to survive.A local beautician who had her hours cut because fewer are spending the money for salon services found a different way to survive. She is sharing her house with a boarder. He's old, sickly and cranky, and he needs help with everything. But the income helps her stay in her home, she says.The first five years I was here, I seldom heard anyone talk about money. Those who did were whiners who whine about everything. But as the economy keeps tanking and costs keep escalating, money woes are being discussed by people who previously "never talked money."When I was paying my insurance bill this week, a friend who was with me told the agent she should have worked longer because she's not making it. She's normally a very private person and I was surprised to hear her discussing her money woes with a stranger. I think when she heard about the big jump she was facing in her house insurance, it was the final straw.After we left we had a long discussion about a relevant question:Should you work as long as you can?Or, should you retire as soon as you can?I've been telling my working friends to stay on the job as long as they can. No one who is presently enjoying health benefits from their employer can anticipate how much they will have to pay for these benefits once they retire.I was one of those financially conservative people who "worked the numbers" long and hard before I retired. Now, when I look at what I projected I would spend, I can see that I wasn't even close.Should I have waited longer to retire? Maybe. On the other hand, these retirement years have been some of the happiest times of my life. Every day is a joy.When we are facing our last sunset, will we say, "Oh, if only I would have worked longer?"For me, these are the soft years I prayed for. I never expected retirement to be so much fun. In the long run, I made the right decision to retire when I did.Eventually, many people have to find their own answer to the question of timing retirement. Should they retire as soon as they can? Or, should they work as long as they can?I tell people who are still debating those questions to seriously consider what kind of life they are retiring to.Most of all, I caution them before they jump into retirement's waters, to make sure they can swim. The waters are rougher than they might have thought.