Job Hunting Over 40

I’ve always hated looking for a job and it hasn’t gotten any easier now that I’m over 50.  About a year ago I left my job because I had an unsupportive boss who made my life miserable.  I “retired” early, perhaps way too soon, since as soon as I left, the stock market tanked, gas went through the roof along with everything else we spend our limited income on.

So here’s the problem:  I have x number of years doing y but I don’t want to do y anymore.  The only jobs I’m getting interviewed for are the y type jobs and I’m having difficulty convincing employers that much of my experience is transferrable.  Has anyone else successfully made the leap, and if so, how?  I need all the help I can get!