What are some ways of reaching people who are in career transition?

Try ex-brokers. I am serious (as well as having fun): see this article about JumpStart NYC

Believe it or not, I think a lot of people are actually putting something in their Linked In profiles about how their careers are in transition right now. There are so many people out there who have been working in one industry for years, and now can’t find jobs – and they need to make it clear to potential employers that they’re interested in jobs outside of their fields.

Try getting on Linked In and doing a search on “in transition” or “transitioning career” – you might be surprised at what you find.

Soup kitchens in Greenwich. I expect you’ll find plenty of people transitioning there.

Also, look at yacht or private plane sales. The sellers have probably taken a serious financial hit recently. Or, withdrawals from private schools.

I have some initial ideas:

Craigslist, I know that is silly but seriously.
The employment ads in the newspaper.
Low-Income Housing Units.
Fair Ground Bulletin Board (especially in the summer).
Local College/University.
Of course the local employment and unemployment offices.