I suspect that this is an interesting dilemma for many boomers today! As a fellow boomer that has reinvented himself - I can say that the prospect as well as the actual undertaking creates more panic in the ones that depend upon your continued success (that they have become accustomed too) - than it does in yourself. At least that was my experience.
After 35 years of sales - and one quad bypass surgery - I started a videography and video production business. There have been lots of twists, turns and disappointments but the rewards are really starting to come forth. Have a long way to go but now have a solid footing from home - with a great deal more enjoyment, reward and satisfaction
Saxmansteve,
Once you have learned the art of the sale, the negotiation and the close you will always make a great living and acheive a great deal of personal satisfaction. There are always the cold calls, the people that will not take your calls and the gate keepers, but that is all part of the art of selling. Maybe I should produce a video on the art of selling for our fellow SuN yougsters (ha, ha).
When I had quad bypass surgery three years ago (August) it gave me time to really do some self analysis regarding what legacy I was leaving behind for my kids and grandkids. I realized at that time that I had a legacy that I wanted to leave
and I started researching and planning an approach to fullfill my wish. As a salesperson of high end personal products (translated - Million Dollar RVs) to my generation of business owners and successful baby boomers, I realized that everyone has a life story and that most of them had not made any provisions to actually tell it. You might be able to spend your children`s inheritance if you choose, but you can not rob them of their legacy, which is your life and accomplishments, that they may choose to model themselves after. Therefore, I analyzed my present resources and talent and realized that my interview techniques that I had honed so well as a saleperson, allowed me to get people to open up and discuss their life stories, given the right forum and setting. I put the talents I had developed to work on what I consider a much higher calling, recording and producing individuals life stories, in a specific format that is appropriate for distribution to the individuals family members and freinds, before or even after the subject dies.
I also found, by studying and analyzing the questions, responses and forums of my fellow SuN members, as well as other on-line resources, and them making inquiry to additional prospective clients, that I could stay busy producing similar products for other people. industries and events and decided that I will undertake to my present business.
And so there really is a saleman out there that actually is looking for a response to those many qualifying questions that are asked when you are thinking about about a purchase, and it may not relate to what you has really anticipated.
Thanks for asking.
LifeStoryBob
It is said that during the course of any conversation or negotiation that you will reach a point (if you are listening) where the next one that speaks loses! (I prefer to say commits rather than loses)
You`re right Bob... Like I said above, knowing when to shut up is a key factor.
Sometimes, the best answer in that situation is to just give a little sympathetic smile... and politely wait. (Yeah, I know a few seconds waiting time can seem like hours, but it WILL pay off... I promise.) 
Nick