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I would suggest that anyone (seniors or otherwise) considering starting their own small home business go to the closest Small Business Development Center (SBDC) -- you can do a search online for all the offices in your state. Most will offer free workshops on "How to Start a Small Business" several times a year. They can also help you create a start-up business plan. If you follow it, you will have a greater chance of succeeding. There are other places too -- SCORE (Senior Corps of Retired Executives), which also offers free consultations.
A business plan is really important when you're trying to develop a home-based or other small business. It's a "road map" of where you are and where you are heading. Following that map will insure you don't get sidetracked and veer from your goals, no matter how big or small they may be.
These small personal efforts to generate income are what will be fueling personal economic recovery for a lot of people during these tough times. We can never again expect big businesses to be what they were (and that's not the fault of any politician, no matter what kind of nonsense we hear from the media).
We cannot expect to be called back to work, especially if we're at or nearing what was the normal retirement age. There are too many new college graduates out there looking for work, and they'll work for far less than experienced workers. That puts young people at an advantage in that they are not only full of energy, new ideas, and familiar with all the latest technology, but they're also more affordable..... big business has been living beyond its means --padding everything from its inventory to its personnel for years in order to look prosperous. What we're now seeing is the result of that. They now have no choice but to "trim the fat" and operate at the level where they should have been operating all along.
So while some of us may be lucky enough to have someone give that resume' or interview a 2nd look based on the fact that they are specifically looking for experience, some will not get those interviews. But you DO have something to offer -- don't doubt that for a moment! Make a list of all your experiences: work, volunteer, hobbies ..... note those things that you are especially good at it and get to work finding a place to "sell" those skills and send them a resume' that reflects them. If there are no companies nearby where you will be a good fit, then give the home-based business idea a try.
As for your insurance -- don't worry about it. Employers can't ask how old you are, but they can figure out without much difficulty ..... have you ever filled out a job application that didn't ask for your date of birth? And knowing that you're on Medicare and don't need insurance may even be considered a plus if you and "the other guy" are equal in all else ..... you're one less person they need to pay insurance for! Sell THAT as a positive!