Well, Sooz, I've been self-employed full time as an entertainer and music therapist, primarily for senior facilities, since early 1994.

Funny you should mention the "business side" of this type of work.  Some folks seem to think that if you "play" music--especially for senior or non-profit facilities--you should do it gratis or for peanuts. But for every hour I'm actually performing or doing a therapy gig, I spend an average of about 1.5 hours of other work (commuting, equipment set up and breakdown, tax accounting, and phone calls, letters, and faxes for publicity/booking/billing). With some clients, getting paid can be like pulling teeth.  And there are others who book you a year or more ahead of time but who may double book or forget they booked you if you don't remind them every couple of months.  (One problem peculiar to the retirement/assisted living/senior center/nursing home industry is the frequent and unpredictable change of activity directors.  One AD books you and then leaves the facility with no notice to you.  Usually the management and the new AD feel no obligation to honor commitments made by the erstwhile AD--even if you have a signed contract.  If they honor it, it's often just for convenience.  Often when the AD leaves, no one knows what bookings they have made.)

Oh, and I forgot to mention the time I spend doing research and rehearsal to learn songs that the clients want to hear.  And the extra NSAIDS and asthma inhalers I have to buy to get through a day in which I may play and sing for 4 to 7 hours.  (Some days like St. Patrick's, Cinco de Mayo, Christmas Eve, and Valentine's Day I may have 6 bookings (some 90 minutes) that day alone.)  Osteoarthritis, if you are prone to it, is an occupational hazard for folks who play a lot in any given day, and mine developed in my left hand when I began doing music as a regular job.

I've been known to make a 2-hour round trip to get to a 1-hour $25 gig.  To paraphrase your workshop presenter, you do what you know will get <i>and maintain</i> your clients.  If I have four jobs lined up in a suburb 30 miles away and all but one of them cancel, I'm probably not going to cancel the 4th one--especially if it's a regular client.  I'd rather have a regular, frequent gig that pays $25 for an hour than have one that pays $75 but for which I have to spend $3 and 3 hours in phone calls and faxes to get and confirm the booking and then not be able to count on the client not to double book or cancel at the last minute.

I do manage to make a very modest living doing this sort of thing (though I have some other income from investment interest).  I look at my gig slots much the way a store looks at merchandise. You sell what you can at "list price," which for me is $60 for an hour program.  You discount the rest PRN, with the goal being to make the profit you seek for the whole lot, not on a particular item.  This means occasionally some of the time spots will be sold for less than cost.  In other cases, I look at a $25 job a mile and a half from another gig and at a time that's not in high demand as icing on the cake.  An hour between two other gigs is not worth a lot to me unless I'm in a place where I can make productive use of it, and that's usually not the case if I'm not at home.

Lest you think this is a terrible way to try to make a living, let me point out that I've become a better singere, a much better guitarist and a far better entertainer  -- not to mention increasing my performance repertoire by about 50% -- since I started doing this full time.  Also, when I'm actually singing and playing the guitar--whether jogging the memories and stirring the emotions of cognitively impaired residents in a nursing home, doing a sing-along and sharing stories with very sharp senior citizens in an upscale retirement community, or doing a special concert of international music for a party with a mulit-generation audience--it's all worth it.  Very few jobs I've had (including college prof, fitness instructor, and mental health counselor) have had this kind of payoff for me.

Genie

PS, Susan, thanks for starting the thread.  I'm very interested in other folks' music business stories.