Greatest challenge I've had to face. My first obstacle was believing this was going to be more difficult than the last time. The bosses keep getting younger, but that has never been a problem for me unless they weren't capable of doing their job, of course. It's those HR people who make this hard.
Most HR people I've encountered have been fresh out of college trained. Even if they have been working for 10 years, they have only been in the HR hiring position and don't show a true understanding for on the job skills. I've only been looking for temporary assignments this time, not even temp-to-hire, and my years are proving to be a serious detriment. My computer testing consistently yields 100% scores in all the MS Office programs and should open the door into any Executive Assistant position where the boss is high demand. But, not one door has shown itself. Imagine that, an Executive Assistant who can spell, write a coherent sentence, understands business, marketing, professionalism, and can accomplish the work of 3 people in a day. If she's over 50, few are willing to turn the desk outside their plush office over to her, though.
I have two good friends who are in their late 30's/earliest 40's. We often find ourselves applying for the same jobs. Neither one can type accurately, intuitively figure out new computer programs, polish the etiquette elements of a Board meeting, or head off potential problems by thinking ahead of them. Yet, both are beautiful to look at, and each has gotten at least one job over me. It took those shallow bosses about 3 months of working with them to literally grow to hate the sight of them before they got fired for an inability to accomplish the work they were hired to do. I'd bet you all saw that coming, though.
My skills and confidence have finally come full circle and I have decided this belief in my own talents, love for success, and strength in business protocols are far more suited to being in business for myself. Who can I possibly trust more than me to take care of me? My personal success lies in me doing what is most satisfying to me professionally.
Keep in touch, and I'll keep you posted on my business growth and the positive (or negative) elements of detaching myself from the corporate control monster. My business is focused in that other passion of the over 50 set, too. Retaining the appearance of our more youthful days!
If you want more information, post your questions in comments and I'll reply as soon as possible.